CMLS / Cumulus Media Inc. - SEC Filings, Annual Report, Proxy Statement

Cumulus Media Inc.
US ˙ OTCPK ˙ US2310828015

Basic Stats
LEI 549300OW8SUYVNKSAC51
CIK 1058623
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Cumulus Media Inc.
SEC Filings (Chronological Order)
This page provides a complete, chronological list of SEC Filings, excluding ownership filings which we provide elsewhere.
August 7, 2025 EX-10.1

Fifth Amendment to Employment Agreement, dated June 10, 2025, by and between Cumulus Media Inc. and Richard S. Denning.

FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fifth Amendment to Employment Agreement (“Fifth Amendment”) is made by and between Richard S.

August 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 00

August 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 7, 2025 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 7, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 7, 2025 EX-99.1

Cumulus Media Reports Operating Results for the Second Quarter 2025

Cumulus Media Reports Operating Results for the Second Quarter 2025 ATLANTA, GA — August 7, 2025: Cumulus Media Inc.

May 30, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 30, 2025 CUMULUS MEDIA INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 30, 2025 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Nu

May 1, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 0

May 1, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 1, 2025 Cumulus Media Inc. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 1, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 1, 2025 EX-99.1

Cumulus Media Reports Operating Results for the First Quarter 2025

Cumulus Media Reports Operating Results for the First Quarter 2025 ATLANTA, GA — May 1, 2025: Cumulus Media Inc.

April 25, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to § 240.

April 23, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 23, 2025 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 23, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

March 10, 2025 EX-3.1

Third Amended and Restated Bylaws of Cumulus Media Inc.

SECONDTHIRD AMENDED AND RESTATED BYLAWS OF CUMULUS MEDIA INC. ARTICLE I OFFICES; BOOKS AND RECORDS Section 1.1 Registered Office and Agent. Cumulus Media Inc. (hereinafter called the “Corporation”) shall at all times maintain a registered office in the State of Delaware and a registered agent in the State of Delaware, as required by the Delaware General Corporation Law (the “DGCL”), but may have s

March 10, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 4, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File N

March 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 6, 2025 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 6, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File N

February 27, 2025 EX-19.1

CUMULUS MEDIA INC. Prohibitions on the Use of Inside Information in Connection with Trading Company Securities

CUMULUS MEDIA INC. Prohibitions on the Use of Inside Information in Connection with Trading Company Securities I. General Rule The U.S. securities laws regulate the sale and purchase of securities in the interest of protecting the investing public. U.S. securities laws give the company, its officers and directors, and other employees the responsibility to ensure that information about the company

February 27, 2025 EX-21.1

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivab

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivables Funding LLC Delaware CMP Houston-KC, LLC Delaware CMP KC LLC Delaware CMP Susquehanna LLC Delaware CMP Susquehanna Radio Holdings LLC Delaware Con

February 27, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumulus Med

February 27, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 27, 2025 EX-99.1

Cumulus Media Reports Operating Results for 2024

Cumulus Media Reports Operating Results for 2024 ATLANTA, GA — February 27, 2025: Cumulus Media Inc.

February 26, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 26, 2025 Cumulus Media I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 26, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

January 22, 2025 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 22, 2025 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

January 22, 2025 EX-99.1

Cumulus Media Appoints a Top Shareholder Steven M. Galbraith to Board of Directors

Cumulus Media Appoints a Top Shareholder Steven M. Galbraith to Board of Directors ATLANTA, GA — January 22, 2025: Cumulus Media Inc. (NASDAQ: CMLS) today announced the appointment of Steven M. Galbraith to its Board of Directors. "We are thrilled to welcome Steve to our board," said Chairman Andrew W. Hobson. "As a longtime shareholder in the Company, Steve has demonstrated a deep commitment to t

December 20, 2024 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 16, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

November 1, 2024 EX-99.1

Cumulus Media Reports Operating Results for the Third Quarter 2024 Increased Digital Marketing Services Revenue by 38%, Total Digital Revenue by 8% Reported Q3 Total Revenue of $204 Million, Down 1.8%, in Line with Pacing Guidance

Cumulus Media Reports Operating Results for the Third Quarter 2024 Increased Digital Marketing Services Revenue by 38%, Total Digital Revenue by 8% Reported Q3 Total Revenue of $204 Million, Down 1.

November 1, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file numbe

November 1, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

August 2, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 2, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 2, 2024 EX-99.1

Cumulus Media Reports Operating Results for the Second Quarter 2024 Completed Highly Successful Debt Exchange That Reduced Our Debt Obligations Under Our Debt Instruments by Approximately $33 Million, Extended Maturities to 2029, Obtained Favorable I

Cumulus Media Reports Operating Results for the Second Quarter 2024 Completed Highly Successful Debt Exchange That Reduced Our Debt Obligations Under Our Debt Instruments by Approximately $33 Million, Extended Maturities to 2029, Obtained Favorable Interest Rates, and Preserved Structure Free of Financial Maintenance Covenants Upsized ABL Facility by 25% to $125 Million and Extended Maturity to 2029 Reported Q2 Total Revenue of $205 Million, Down 2.

August 2, 2024 EX-10.9

Eighth Amendment to Employment Agreement, dated June 14, 2024, by and between Cumulus Media Inc. and Dave Milner.

EIGHTH AMENDMENT TO EMPLOYMENT AGREEMENT This EIGHTH AMENDMENT TO EMPLOYMENT AGREEMENT (“Eighth Amendment”) is made and entered into this 14th day of June, 2024 (“Effective Date”), by and between Cumulus Media Inc.

August 2, 2024 EX-10.7

Sixth Amendment to Employment Agreement, dated June 18, 2024, by and between Cumulus Media Inc. and Robert J. Walker.

SIXTH AMENDMENT TO EMPLOYMENT AGREEMENT This SIXTH AMENDMENT TO EMPLOYMENT AGREEMENT (“Sixth Amendment”) is made and entered into this 18th day of June, 2024 (“Effective Date”), by and between Cumulus Media Inc.

August 2, 2024 EX-10.6

Fifth Amendment to Employment Agreement, dated April 25, 2022, by and between Cumulus Media Inc. and Robert J. Walker.

FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT This FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT (“Fifth Amendment”) is made and entered into this 25th day of April, 2022 (“Effective Date”), by and between Cumulus Media Inc.

August 2, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 00

August 2, 2024 EX-10.8

Seventh Amendment to Employment Agreement, dated April 25, 2022, by and between Cumulus Media Inc. and Dave Milner.

SEVENTH AMENDMENT TO EMPLOYMENT AGREEMENT This SEVENTH AMENDMENT TO EMPLOYMENT AGREEMENT (“Seventh Amendment”) is made and entered into this 25th day of April, 2022 (“Effective Date”), by and between Cumulus Media Inc.

June 13, 2024 CORRESP

780 Johnson Ferry Road NE Suite 500

780 Johnson Ferry Road NE Suite 500 Atlanta, GA 30342 June 13, 2024 CORRESPONDENCE FILING VIA EDGAR U.

June 10, 2024 CORRESP

June 10, 2024

June 10, 2024 CORRESPONDENCE FILING VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.E. Washington, D.C. 20549 Attention: Inessa Kessman Robert Littlepage Re: Cumulus Media Inc. Form 10-K for the Fiscal Year Ended December 31, 2023 File No. 001-38108 Ladies and Gentlemen: Cumulus Media Inc., a Delaware corporation (the “Company”

May 3, 2024 EX-10.4

Sixth Amendment to the ABL Credit Agreement, dated as of May 2, 2024, entered into by and among Cumulus Media Intermediate Inc., Cumulus Media New Holdings Inc., each of the restricted subsidiaries of Cumulus Media New Holdings Inc. signatory thereto, Fifth Third Bank, National Association, as the administrative agent for the lenders and collateral agent for the secured parties, and the other lenders from time to time party thereto

Exhibit 10.4 SIXTH AMENDMENT TO ABL CREDIT AGREEMENT This Sixth Amendment to ABL Credit Agreement (this “Amendment”), dated as of May 2, 2024, is entered into by and among CUMULUS MEDIA INTERMEDIATE INC., a Delaware corporation (“Intermediate Holdings”), CUMULUS MEDIA NEW HOLDINGS INC., a Delaware corporation (“New Holdings”), each of the Restricted Subsidiaries of New Holdings signatory hereto as

May 3, 2024 EX-4.3

First Supplemental Indenture, dated as of May 2, 2024, between Cumulus Media New Holdings Inc. and U.S. Bank Trust Company, National Association, as trustee

Exhibit 4.3 SUPPLEMENTAL INDENTURE THIS FIRST SUPPLEMENTAL INDENTURE, dated as of May 2, 2024 (this “Supplemental Indenture”), between Cumulus Media New Holdings Inc., a Delaware corporation (the “Issuer”) and U.S. Bank Trust Company, National Association (as successor to U.S. Bank National Association), as trustee under the Indenture referred to below (in such capacity, the “Trustee”) and as note

May 3, 2024 EX-99.1

Cumulus Media Announces Expiration and Final Results of Exchange Offer and Consent Solicitation

Exhibit 99.1 Cumulus Media Announces Expiration and Final Results of Exchange Offer and Consent Solicitation ATLANTA, GA — May 2, 2024 – Cumulus Media Inc. (NASDAQ: CMLS) (the “Company” or “Cumulus”) today announced the expiration and final results of its subsidiary’s, Cumulus Media New Holdings Inc. (the “Issuer”), previously announced offer to exchange (as amended, the “Exchange Offer”) any and

May 3, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 0

May 3, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 3, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 3, 2024 EX-4.1

Indenture dated as of May 2, 2024, among Cumulus Media New Holdings Inc., the Guarantors (as defined therein) and U.S. Bank Trust Company, National Association, as trustee

Exhibit 4.1 CUMULUS MEDIA NEW HOLDINGS INC., as Issuer THE GUARANTORS NAMED ON THE SIGNATURE PAGES HERETO and U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, as Trustee and Notes Collateral Agent INDENTURE Dated as of May 2, 2024 8.000% SENIOR SECURED FIRST-LIEN NOTES DUE 2029 TABLE OF CONTENTS Page ARTICLE 1 DEFINITIONS AND INCORPORATION BY REFERENCE 1 Section 1.01. Definitions 1 Section 1.02. Oth

May 3, 2024 EX-10.1

Amended Credit Agreement, reflecting amendments to that certain Credit Agreement, dated as of September 26, 2019, entered into by and among Cumulus Media Intermediate Inc., Cumulus Media New Holdings Inc., each of the restricted subsidiaries of Cumulus Media New Holdings Inc. signatory thereto, and Bank of America, N.A., as administrative agent (included as Exhibit A to Exhibit 10.2 hereto).

Exhibit 10.1 TERM LOAN EXCHANGE AGREEMENT This TERM LOAN EXCHANGE AGREEMENT (this “Agreement”) is made as of May 2, 2024, by and among CUMULUS MEDIA NEW HOLDINGS INC., a Delaware corporation (the “Borrower Agent”), CUMULUS MEDIA INTERMEDIATE INC., a Delaware corporation (“Intermediate Holdings”), the other Borrowers and Guarantors party hereto, the Consenting Lenders (as defined below), Bank of Am

May 3, 2024 EX-99.1

Cumulus Media Reports Operating Results for the First Quarter 2024; Refinances its Capital Structure to Secure Five-Year Maturities Through Successful Debt Exchange and ABL Facility Upsize and Extension –Completed Successful Debt Exchange That Reduce

Cumulus Media Reports Operating Results for the First Quarter 2024; Refinances its Capital Structure to Secure Five-Year Maturities Through Successful Debt Exchange and ABL Facility Upsize and Extension –Completed Successful Debt Exchange That Reduced Principal by Approximately $33 Million, Extended Maturities to 2029, Obtained Favorable Interest Rates and Preserved Structure Free of Financial Maintenance Covenants; Exceeded Expectations with Approximately 97% Aggregate Participation –Upsized ABL Facility by 25% to $125 Million and Extended Maturity to 2029 –Reported Q1 Total Revenue of $200 million, Down 2.

May 3, 2024 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 2, 2024 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 2, 2024 8-K

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 2, 2024 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

April 19, 2024 EX-99.1

Cumulus Announces Selected Preliminary Operating Results for First Quarter 2024

Cumulus Announces Selected Preliminary Operating Results for First Quarter 2024 ATLANTA, GA — April 18, 2024: Cumulus Media Inc.

April 19, 2024 EX-99.1

Cumulus Media Announces Amendment and Extension of Withdrawal Deadline and Expiration Time for Exchange Offer and Consent Solicitation

Exhibit 99.1 Cumulus Media Announces Amendment and Extension of Withdrawal Deadline and Expiration Time for Exchange Offer and Consent Solicitation ATLANTA, GA — April 18, 2024 – Cumulus Media Inc. (NASDAQ: CMLS) (the “Company” or “Cumulus”) today announced that its subsidiary, Cumulus Media New Holdings Inc. (the “Issuer”), has amended its previously announced offer to exchange (as so amended, th

April 19, 2024 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 18, 2024 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 19, 2024 EX-10.1

Transaction Support Agreement, dated as of April 18, 2024, by and among Cumulus Media Inc., Cumulus Media New Holdings Inc. and the Ad-Hoc Group

Exhibit 10.1 THIS TRANSACTION SUPPORT AGREEMENT IS NOT AN OFFER OR ACCEPTANCE WITH RESPECT TO ANY SECURITIES. ANY SUCH OFFER OR SOLICITATION WILL COMPLY WITH ALL APPLICABLE SECURITIES LAWS. Nothing contained in thIS TRANSACTION SUPPORT AGREEMENT shall be an admission of fact or liability OR, UNTIL THE OCCURRENCE OF THE AGREEMENT EFFECTIVE DATE ON THE TERMS DESCRIBED HEREIN, DEEMED BINDING ON ANY O

April 19, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 18, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 18, 2024 EX-99.1

Cumulus Media Announces Further Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Further Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

April 18, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 18, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 17, 2024 EX-99.1

Cumulus Media Announces Further Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Further Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

April 17, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 17, 2024 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 17, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 15, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 15, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 15, 2024 EX-99.1

Cumulus Media Announces Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Additional Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

April 10, 2024 EX-99.1

Cumulus Media Announces New Further Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces New Further Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

April 10, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 10, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 3, 2024 EX-99.1

Cumulus Media Announces Further Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Further Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

April 3, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 3, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File N

March 29, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to § 240.

March 27, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2024 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

March 27, 2024 EX-99.1

Cumulus Media Announces Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Extension of Expiration Time in Exchange Offer and Consent Solicitation Relating to 6.

March 12, 2024 EX-99.1

Cumulus Media Announces Extension of Early Tender Time in Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Extension of Early Tender Time in Exchange Offer and Consent Solicitation Relating to 6.

March 12, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 12, 2024 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 12, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

February 27, 2024 EX-10.31

EMPLOYMENT AGREEMENT

EXECUTION VERSION EMPLOYMENT AGREEMENT This EMPLOYMENT AGREEMENT (the “Agreement”) is made and entered into as of the 29th day of November, 2023 (the “Execution Date”), by and between Cumulus Media New Holdings Inc.

February 27, 2024 EX-4.6

Description of Securities of Cumulus Media Inc.

Exhibit 4.6 Description of Securities of Cumulus Media Inc. General, Authorized Stock Cumulus Media Inc. (the “Company”) has one class of securities, our Class A Common Stock, par value $0.0000001 per share, registered under Section 12 of the Securities Exchange Act of 1934, as amended. Our authorized capital stock consists of 100,000,000 shares of Class A common stock, 100,000,000 shares of Class

February 27, 2024 EX-97.1

Cumulus Media Inc. Compensation Clawback Policy Effective November 1, 2023

Cumulus Media Inc. Compensation Clawback Policy Effective November 1, 2023 Purpose As required pursuant to the listing standards of The Nasdaq Stock Market (the “Stock Exchange”), Section 10D of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 10D-1 under the Exchange Act, the Board of Directors (the “Board”) of Cumulus Media Inc. (the “Company”) has adopted this Comp

February 27, 2024 EX-21.1

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivab

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivables Funding LLC Delaware CMP Houston-KC, LLC Delaware CMP KC LLC Delaware CMP Susquehanna LLC Delaware CMP Susquehanna Radio Holdings LLC Delaware Con

February 27, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2024 Cumulus Media I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 27, 2024 EX-10.5

Cumulus Media Inc. Description of 2023 Quarterly Incentive Plan

Cumulus Media Inc. Description of 2023 Quarterly Incentive Plan Awards to executive officers under Cumulus Media Inc.’s (the “Company”) annual executive incentive plan for certain officers of the Company, which operates as a quarterly incentive plan for 2023 (the “2023 QIP”), will be based on the Company achieving budgeted adjusted earnings before interest, taxes, depreciation and amortization ("E

February 27, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2024 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 27, 2024 EX-99.1

Cumulus Media Reports Operating Results for 2023 Launches Debt Exchange for Senior Notes and Term Loan

Cumulus Media Reports Operating Results for 2023 Launches Debt Exchange for Senior Notes and Term Loan ATLANTA, GA — February 27, 2024: Cumulus Media Inc.

February 27, 2024 EX-10.25

EX-10.25

milner1stamendment

February 27, 2024 EX-10.26

EX-10.26

milneragreementsecondame

February 27, 2024 EX-10.13

EX-10.13

richarddenningagreement2

February 27, 2024 EX-99.1

Cumulus Media Announces Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026

Cumulus Media Announces Exchange Offer and Consent Solicitation Relating to 6.750% Senior Secured First-Lien Notes due 2026 ATLANTA, GA — February 27, 2024 – Cumulus Media Inc. (NASDAQ: CMLS) (the "Company" or “Cumulus”) today announced that its subsidiary, Cumulus Media New Holdings Inc. (the "Issuer"), has commenced an offer to exchange (the "Exchange Offer") any and all of the Issuer’s outstand

February 27, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumulus Med

February 22, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 21, 2024 CUMULUS MEDIA INC

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 21, 2024 CUMULUS MEDIA INC.

February 22, 2024 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES Pursuant to Section 12(b) or (g) of the Securities Exchange Act of 1934 CUMULUS MEDIA INC. (Exact name of registrant as s

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES Pursuant to Section 12(b) or (g) of the Securities Exchange Act of 1934 CUMULUS MEDIA INC.

February 22, 2024 EX-99.1

Cumulus Media Inc. Adopts Limited-Duration Shareholder Rights Plan

Exhibit 99.1 Cumulus Media Inc. Adopts Limited-Duration Shareholder Rights Plan ATLANTA, February 22, 2024 – Cumulus Media Inc. (NASDAQ: CMLS) (“Cumulus Media” or the “Company”) today announced that its Board of Directors (the “Board”) has adopted a limited-duration shareholder rights plan (“Rights Plan”) to protect the best interests of all Cumulus Media shareholders. The Rights Plan is effective

February 22, 2024 EX-4.1

Stockholder Rights Agreement, dated as of February 21, 2024, by and between Cumulus Media Inc. and Continental Stock Transfer & Trust Company (incorporated by reference to Exhibit 4.1 to Cumulus Media Inc.’s Current Report on Form 8-K filed with the SEC on February 22, 2024).

Exhibit 4.1 EXECUTION VERSION STOCKHOLDER RIGHTS AGREEMENT DATED AS OF FEBRUARY 21, 2024, BY AND BETWEEN CUMULUS MEDIA INC. AND CONTINENTAL STOCK TRANSFER & TRUST COMPANY AS RIGHTS AGENT TABLE OF CONTENTS Page 1. Certain Definitions 1 2. Appointment of Rights Agent 6 3. Issuance of Right Certificates 6 4. Form of Right Certificates 8 5. Countersignature and Registration 8 6. Transfer, Split Up, Co

January 29, 2024 SC 13G

CMLS / Cumulus Media Inc. / SEAPORT GLOBAL ASSET MANAGEMENT LLC - SC 13G Passive Investment

SC 13G 1 d610356dsc13g.htm SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.  )* Cumulus Media Inc. (Name of Issuer) Class A Common Stock, $0.0000001 par value per share (Title of Class of Securities) 231082801 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) C

January 24, 2024 SC 13D

CMLS / Cumulus Media Inc. / Renew Group Private Ltd Activist Investment

SC 13D 1 renewcumulus13d.htm CUSIP No. 231082801 Page 1 of 5 Pages UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 CUMULUS MEDIA INC. (Name of Issuer) Class A Common Stock, par value $0.0000001 per share (Title of Class of Securities) 231082801 (CUSIP Number) Ravinder Sajwan 463 MacPherson Road Singapore 368181 +65 6587

October 27, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 27, 2023 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

October 27, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file numbe

October 27, 2023 EX-99.1

Cumulus Media Reports Operating Results for the Third Quarter 2023

Cumulus Media Reports Operating Results for the Third Quarter 2023 ATLANTA, GA — October 27, 2023: Cumulus Media Inc.

September 21, 2023 8-K/A

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 27, 2023 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporatio

July 28, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 00

July 28, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 28, 2023 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File N

July 28, 2023 EX-99.1

Cumulus Media Reports Operating Results for the Second Quarter 2023

Cumulus Media Reports Operating Results for the Second Quarter 2023 ATLANTA, GA — July 28, 2023: Cumulus Media Inc.

July 28, 2023 SC 13G

CMLS / Cumulus Media Inc. - Class A / Renew Group Private Ltd Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. ) Cumulus Media Inc. (Name of Issuer) Class A Common Stock, par value $0.0000001 per share (Title of Class of Securities) 231082801 (CUSIP Number) July 21, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate th

July 28, 2023 SC 13D

CMLS / Cumulus Media Inc. - Class A / Renew Group Private Ltd Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. ) Cumulus Media Inc. (Name of Issuer) Class A Common Stock, par value $0.0000001 per share (Title of Class of Securities) 231082801 (CUSIP Number) July 21, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate th

June 14, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

June 14, 2023 EX-99.(A)(5)(C)

Press Release issued by the Company on June 14, 2023

Cumulus Media Announces Final Results of Tender Offer ATLANTA, GA — June 14, 2023 – Cumulus Media Inc.

June 14, 2023 SC TO-I/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO

SC TO-I/A 1 cmlsscheduletoamendmentno.htm SC TO-I/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (RULE 14d-100) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2) Cumulus Media Inc. (Name of Subject Company (Issuer)) Cumulus Media Inc. (Names of Filing Persons (Offeror)) Class A common stock, par

June 13, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 9, 2023 CUMULUS MEDIA INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 9, 2023 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Nu

June 13, 2023 EX-10.1

Second Amendment to the Credit Agreement, dated as of June 9, 2023, entered into by and among Cumulus Media Intermediate Inc., Cumulus Media New Holdings Inc. (“Holdings”), each of the restricted subsidiaries of Holdings signatory thereto, and Bank of America, N.A., as administrative agent.

Execution Version AMENDMENT NO. 2 TO CREDIT AGREEMENT THIS AMENDMENT NO. 2 TO CREDIT AGREEMENT (this “Agreement”), dated as of June 9, 2023, is entered into among CUMULUS MEDIA NEW HOLDINGS INC., a Delaware corporation (the “Borrower Agent”), each of the Restricted Subsidiaries of the Borrower Agent party hereto (together with the Borrower Agent, the “Borrowers”), CUMULUS MEDIA INTERMEDIATE INC.,

June 12, 2023 EX-99.(A)(5)(C)

Press Release issued by the Company on June 12, 2023

Exhibit (a)(5)(C) Exhibit (a)(5)(C) Cumulus Media Announces Preliminary Results of Tender Offer ATLANTA, GA — June 12, 2023 – Cumulus Media Inc.

June 12, 2023 EX-FILING FEES

Filing Fee Table

EX-FILING FEES Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

June 12, 2023 SC TO-I/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (RULE 14d-100) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) Cumulus Media Inc. (Name of Subject

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (RULE 14d-100) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1) Cumulus Media Inc. (Name of Subject Company (Issuer)) Cumulus Media Inc. (Names of Filing Persons (Offeror)) Class A common stock, par value $0.0000001 per share (Title of Class of Secur

May 12, 2023 EX-99.(A)(1)(C)

Notice of Guaranteed Delivery

EX-99.(a)(1)(C) Exhibit (a)(1)(C) NOTICE OF GUARANTEED DELIVERY To Tender Shares of Class A Common Stock of CUMULUS MEDIA INC. Pursuant to its Offer to Purchase For Cash up to $10,000,000 of shares of its Class A Common Stock At a Purchase Price Not Greater Than $3.25 Per Share and Not Less Than $2.85 Per Share THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END

May 12, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

May 12, 2023 SC TO-I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (RULE 14d-100) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Cumulus Media Inc. (Name of Subject C

SC TO-I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (RULE 14d-100) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. ) Cumulus Media Inc. (Name of Subject Company (Issuer)) Cumulus Media Inc. (Names of Filing Persons (Offeror)) Class A common stock, par value $0.0000001 per share (Title of Class o

May 12, 2023 EX-99.(A)(1)(E)

Letter to Clients for use by Brokers, Dealers, Banks, Trust Companies and Other Nominees

EX-99.(A)(1)(E) 6 d421905dex99a1e.htm EX-99.(A)(1)(E) Exhibit (a)(1)(E) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $10,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $3.25 PER SHARE AND NOT LESS THAN $2.85 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 9, 2023, UNLESS THE OFFER IS EXTENDE

May 12, 2023 EX-99.(A)(1)(D)

Letter to Brokers, Dealers, Banks, Trust Companies and Other Nominees

EX-99.(A)(1)(D) 5 d421905dex99a1d.htm EX-99.(A)(1)(D) Exhibit (a)(1)(D) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $10,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $3.25 PER SHARE AND NOT LESS THAN $2.85 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 9, 2023, UNLESS THE OFFER IS EXTENDE

May 12, 2023 EX-99.(A)(1)(B)

Letter of Transmittal (including IRS Form W-9)

EX-99.(a)(1)(B) Exhibit (a)(1)(B) Letter of Transmittal To Tender Shares of Class A Common Stock of CUMULUS MEDIA INC. Pursuant to its Offer to Purchase For Cash up to $10,000,000 of Shares of its Class A Common Stock At a Purchase Price Not Greater Than $3.25 Per Share and Not Less Than $2.85 Per Share. The undersigned represents that I (we) have full authority to tender without restriction the c

May 12, 2023 EX-99.(A)(5)(B)

Press Release issued by the Company on May 12, 2023

EX-99.(a)(5)(b) Exhibit (a)(5)(B) Cumulus Media Announces Modified Dutch Auction Tender Offer to Purchase up to $10 Million of its Outstanding Class A Common Stock ATLANTA, GA — May 12, 2023 – Cumulus Media Inc. (NASDAQ: CMLS) (the “Company” or “Cumulus”) today announced that it commenced a “modified Dutch auction” tender offer to purchase up to $10 million of shares of its Class A common stock, o

May 12, 2023 EX-99.(A)(5)(A)

Summary Advertisement, dated May 12, 2023

EX-99.(a)(5)(A) Exhibit (a)(5)(A) This announcement is neither an offer to purchase nor a solicitation of an offer to sell Shares (as defined below). The Offer (as defined below) is made solely pursuant to the Offer to Purchase dated May 12, 2023 and the related Letter of Transmittal, as they may be amended or supplemented from time to time. The Offer is not being made to, nor will tenders be acce

May 12, 2023 EX-99.(A)(1)(A)

Offer to Purchase, dated May 12, 2023

EX-99.(a)(1)(A) Table of Contents Exhibit (a)(1)(A) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $10,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $3.25 PER SHARE AND NOT LESS THAN $2.85 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 9, 2023, UNLESS THE OFFER IS EXTENDED (SUCH DATE AND TIM

April 27, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 27, 2023 Cumulus Media Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 27, 2023 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 27, 2023 EX-99.1

Cumulus Media Reports Operating Results for the First Quarter 2023

Cumulus Media Reports Operating Results for the First Quarter 2023 ATLANTA, GA — April 27, 2023: Cumulus Media Inc.

April 27, 2023 S-8

As filed with the Securities and Exchange Commission on April 27, 2023

As filed with the Securities and Exchange Commission on April 27, 2023 Registration No.

April 27, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark one) ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 0

April 27, 2023 EX-24.1

Power of Attorney.

Exhibit 24.1 POWERS OF ATTORNEY KNOW ALL BY THESE PRESENTS, that each of the undersigned directors and officers of Cumulus Media Inc., a Delaware corporation (the “Company”), does hereby constitute and appoint each of Richard S. Denning and Francisco J. Lopez-Balboa, or any of them, each acting alone, as the true and lawful attorney-in-fact or attorneys-in-fact for each of the undersigned, with fu

April 27, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 27, 2023 CUMULUS MEDIA INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 27, 2023 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

April 27, 2023 EX-FILING FEES

Calculation of Filing Fee Tables.

EXHIBIT 107 Calculation of Filing Fee Table Form S-8 (Form Type) Cumulus Media Inc.

April 27, 2023 EX-10.1

2020 Equity and Incentive Compensation Plan (Amended and Restated Effective April 26, 2023) (incorporated by reference to Exhibit 10.1 to Cumulus Media Inc.’s Current Report on Form 8-K filed with the SEC on April 27, 2023)

CUMULUS MEDIA INC. 2020 EQUITY AND INCENTIVE COMPENSATION PLAN (Amended and Restated Effective April 26, 2023) 1. Purpose. The purpose of this Plan is to permit award grants to non-employee Directors, officers and other employees of the Company and its Subsidiaries, and certain consultants to the Company and its Subsidiaries, and to provide to such persons incentives and rewards for service and/or

March 23, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

March 23, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEF 14A Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Pursuant to § 240.

March 7, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 3, 2023 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File N

February 23, 2023 EX-10.8

Form of Restricted Stock Unit Agreement (Senior Executive) (incorporated by reference to Exhibit 10.8 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT (this “Agreement”) is made effective (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and name (the “Recipient”). WHEREAS, the Company has granted to the Recipient an award of Restricted Stock Units under Section 7 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the “Plan

February 23, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2023 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 23, 2023 EX-10.10

Form of Restricted Stock Unit Agreement (Director) (incorporated by reference to Exhibit 10.10 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

EX-10.10 6 directorrsuagreement.htm EX-10.10 CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT is made effective (the “Grant Date”),1 between Cumulus Media Inc., a Delaware corporation (the “Company”), and (the “Recipient”). WHEREAS, the Company desires to grant to the Recipient an award denominated in units (the “Restricted Stock Units”) of its Class A common capital stock (the “C

February 23, 2023 EX-10.21

FIRST AMENDMENT TO EMPLOYMENT AGREEMENT

FIRST AMENDMENT TO EMPLOYMENT AGREEMENT This First Amendment to Employment Agreement (“First Amendment”) is made by and between Robert J.

February 23, 2023 EX-10.24

FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT

FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fourth Amendment to Employment Agreement (“Fourth Amendment”) is made by and between Robert J.

February 23, 2023 EX-21.1

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivab

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivables Funding LLC Delaware CMP Houston-KC, LLC Delaware CMP KC LLC Delaware CMP Susquehanna LLC Delaware CMP Susquehanna Radio Holdings LLC Delaware Con

February 23, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumulus Med

February 23, 2023 EX-10.9

Form of Stock Option Agreement (incorporated by reference to Exhibit 10.9 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

EX-10.9 5 february2020cumulus-stocko.htm EX-10.9 CUMULUS MEDIA INC. NONSTATUTORY STOCK OPTION AGREEMENT THIS AGREEMENT is made this day of (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and (the “Optionee”). WHEREAS, the Company desires to grant to the Optionee an option to purchase shares of Class A common stock (the “Shares”) under the Company’s Long-Term

February 23, 2023 EX-10.7

Form of Restricted Stock Unit Agreement (Non-Senior Executive) (incorporated by reference to Exhibit 10.7 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT (this “Agreement”) is made effective (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and name (the “Recipient”). WHEREAS, the Company has granted to the Recipient an award of Restricted Stock Units under Section 7 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the “Plan

February 23, 2023 EX-10.22

SECOND AMENDMENT TO EMPLOYMENT AGREEMENT

SECOND AMENDMENT TO EMPLOYMENT AGREEMENT This Second Amendment to Employment Agreement (“Second Amendment”) is made by and between Robert J.

February 23, 2023 EX-10.23

THIRD AMENDMENT TO EMPLOYMENT AGREEMENT

THIRD AMENDMENT TO EMPLOYMENT AGREEMENT This Third Amendment to Employment Agreement (“Third Amendment”) is made by and between Robert J.

February 23, 2023 EX-10.25

EMPLOYMENT AGREEMENT Senior Vice President – Western Region

EMPLOYMENT AGREEMENT Senior Vice President – Western Region This EMPLOYMENT AGREEMENT (the “Agreement”) is made and entered into as of the 21st day of July, 2014 (the “Effective Date”), by and between Cumulus Radio Corp.

February 23, 2023 EX-10.28

FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT

FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fifth Amendment to Employment Agreement (“Fourth Amendment”) is made by and between David Milner (“Employee”) and Cumulus Media New Holdings Inc.

February 23, 2023 EX-99.1

FY 2022 Investor Update February 2023 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 an

FY 2022 Investor Update February 2023 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

February 23, 2023 EX-10.27

FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT

FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fourth Amendment to Employment Agreement (“Fourth Amendment”) is made by and between David Milner (“Employee”) and Cumulus Media Inc.

February 23, 2023 EX-10.6

Description of 2022 Quarterly Incentive Plan (incorporated by reference to Exhibit 10.6 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

Cumulus Media Inc. Description of 2022 Quarterly Incentive Plan Awards to executive officers under Cumulus Media Inc.’s (the “Company”) annual executive incentive plan for certain officers of the Company, which operates as a quarterly incentive plan for 2022 (the “2022 QIP”), will be based on the Company achieving budgeted adjusted earnings before interest, taxes, depreciation and amortization (“E

February 23, 2023 EX-10.11

Form of Stock Option Agreement (Director) (incorporated by reference to Exhibit 10.11 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

CUMULUS MEDIA INC. NONSTATUTORY STOCK OPTION AGREEMENT THIS AGREEMENT is made this day of (the “Grant Date”),1 between Cumulus Media Inc., a Delaware corporation (the “Company”), and (the “Optionee”). WHEREAS, the Company desires to grant to the Optionee an option to purchase shares of Class A common stock (the “Shares”) under the Company’s Long-Term Incentive Plan (the “Plan”); and WHEREAS, the C

February 23, 2023 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2023 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 23, 2023 EX-10.20

EMPLOYMENT AGREEMENT Senior Vice President

EMPLOYMENT AGREEMENT Senior Vice President This EMPLOYMENT AGREEMENT (the “Agreement”) is made and entered into as of the 1st day of January, 2015 (the “Effective Date”), by and between Cumulus Media Inc.

February 23, 2023 EX-10.29

SIXTH AMENDMENT TO EMPLOYMENT AGREEMENT

SIXTH AMENDMENT TO EMPLOYMENT AGREEMENT This Sixth Amendment to Employment Agreement (“Sixth Amendment”) is made by and between David Milner (“Employee”) and Cumulus Media Inc.

February 23, 2023 EX-10.12

Form of Cash Based Performance Unit Agreement (Non-Senior Executive) (incorporated by reference to Exhibit 10.12 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

CUMULUS MEDIA INC. CASH-BASED PERFORMANCE UNIT AGREEMENT THIS AGREEMENT (this “Agreement”) is made effective (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and (the “Recipient”). WHEREAS, the Company has granted to the Recipient a Cash Incentive Award under Section 8 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the “Plan”); and WHE

February 23, 2023 EX-10.13

Form of Cash Based Performance Unit Agreement (Senior Executive) (incorporated by reference to Exhibit 10.13 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2023)

CUMULUS MEDIA INC. CASH-BASED PERFORMANCE UNIT AGREEMENT THIS AGREEMENT (this “Agreement”) is made effective (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and (the “Recipient”). WHEREAS, the Company has granted to the Recipient a Cash Incentive Award under Section 8 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the “Plan”); and WHE

February 23, 2023 EX-99.1

Cumulus Media Reports Operating Results for 2022 Total Revenue of $953.5 Million, Up 4% Year-Over-Year Digital Revenue of More Than $142 Million, Up 12% Year-Over-Year Net Income of $16.2 Million, Down 6% Year-Over-Year Adjusted EBITDA of $166.0 Mill

Cumulus Media Reports Operating Results for 2022 Total Revenue of $953.5 Million, Up 4% Year-Over-Year Digital Revenue of More Than $142 Million, Up 12% Year-Over-Year Net Income of $16.2 Million, Down 6% Year-Over-Year Adjusted EBITDA of $166.0 Million, Up 23% Year-Over-Year ATLANTA, GA — February 23, 2023: Cumulus Media Inc. (NASDAQ: CMLS) (the “Company,” "Cumulus Media," “we,” “us,” or “our”) t

February 23, 2023 EX-10.26

THIRD AMENDMENT TO EMPLOYMENT AGREEMENT

THIRD AMENDMENT TO EMPLOYMENT AGREEMENT This Third Amendment to Employment Agreement (“Third Amendment”) is made by and between David Milner (“Employee”) and Cumulus Media Inc.

February 14, 2023 EX-99.A

AGREEMENT REGARDING THE JOINT FILING OF SCHEDULE 13G

EX-99.A 2 d413743dex99a.htm EX-99.A Exhibit A AGREEMENT REGARDING THE JOINT FILING OF SCHEDULE 13G The undersigned hereby agree as follows: (i) Each of them is individually eligible to use the Schedule 13G to which this Exhibit is attached, and such Schedule 13G is filed on behalf of each of them; and (ii) Each of them is responsible for the timely filing of such Schedule 13G and any amendments th

February 14, 2023 SC 13G/A

CMLS / Cumulus Media Inc / Sp Signal Manager, Llc - SC 13G/A Passive Investment

SC 13G/A 1 d413743dsc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to Rules 13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to Rule 13d-2(b) (Amendment No. 2)* Cumulus Media Inc. (Name of Issuer) Class A Common Stock, par value $0.0000001 per share (Title of Cla

February 13, 2023 SC 13G/A

CMLS / Cumulus Media Inc / Capital World Investors - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Cumulus Media Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 231082801 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to

February 9, 2023 SC 13G/A

CMLS / Cumulus Media Inc / Beach Point Capital Management LP - SC 13G/A Passive Investment

SC 13G/A 1 brhc10047889sc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* CUMULUS MEDIA INC. (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0000001 PER SHARE (Title of Class of Securities) 231082801 (CUSIP Number) December 31, 2022 (Date of Event which Requires Filing of this Sta

October 28, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

October 28, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 ☐ TRANSITION REPORT PURSUANT

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108

October 28, 2022 EX-99.1

Q3 2022 Investor Update October 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and

Q3 2022 Investor Update October 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

October 28, 2022 EX-99.1

Cumulus Media Reports Operating Results for the Third Quarter 2022

Cumulus Media Reports Operating Results for the Third Quarter 2022 ATLANTA, GA ? October 28, 2022: Cumulus Media Inc.

October 28, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

September 30, 2022 SC 13G/A

CMLS / Cumulus Media Inc / Standard General L.P. Passive Investment

SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Cumulus Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 231082801 (CUSIP Number) September 30, 2022** (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is filed: [ ] Rule 13d-1(b) [x] Rule 13d-1(c) [ ] Rule

August 22, 2022 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 17, 2022 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 22, 2022 EX-99.1

Cumulus Media Appoints Deborah Farrington to Board of Directors

Cumulus Media Appoints Deborah Farrington to Board of Directors ATLANTA, GA, August 22, 2022 ? Cumulus Media Inc.

August 10, 2022 CORRESP

Re:

CORRESP 1 filename1.htm 780 Johnson Ferry Road NE Suite 500 Atlanta, GA 30342 August 10, 2022 Ms. Inessa Kessman and Mr. Robert Littlepage Securities and Exchange Commission Division of Corporation Finance Office of Manufacturing 100 F Street, N.E. Washington, D.C. 20549 Re: Cumulus Media Inc. Form 10-K for the Fiscal Year Ended December 31, 2021 Form 10-Q for the Fiscal Quarter Ended March 31, 20

August 3, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 3, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 3, 2022 EX-99.1

Q2 2022 Earnings Update August 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and

Q2 2022 Earnings Update August 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

August 3, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 ☐ TRANSITION REPORT PURSUANT TO S

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumu

August 3, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 3, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 3, 2022 EX-99.1

Cumulus Media Reports Operating Results for the Second Quarter 2022 Delivers Strong Results with Total Revenue Up 5% Led by Digital Revenue Growth of 20% Recorded Net Income of $8.7 Million (+247%) and EBITDA of $45.5 Million (+23%) Completed $25 Mil

Cumulus Media Reports Operating Results for the Second Quarter 2022 Delivers Strong Results with Total Revenue Up 5% Led by Digital Revenue Growth of 20% Recorded Net Income of $8.

June 9, 2022 EX-99.(A)(5)(D)

Press Release issued by the Company on June 9, 2022.

Cumulus Media Announces Final Results of Tender Offer ATLANTA, GA - June 9, 2022 - Cumulus Media Inc.

June 9, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

June 9, 2022 SC TO-I/A

_________________________________________________________________________ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (Amendment No. 2) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securitie

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (Amendment No. 2) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Cumulus Media Inc. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A common stock, par value $0.0000001 (Title of Class of Securities) 231082801 (CUSIP Number of Class of Securitie

June 8, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 3, 2022 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Nu

June 8, 2022 EX-10.1

FIFTH AMENDMENT TO ABL CREDIT AGREEMENT

FIFTH AMENDMENT TO ABL CREDIT AGREEMENT This Fifth Amendment to ABL Credit Agreement (this ?Amendment?), dated as of June 3, 2022, is entered into by and among CUMULUS MEDIA INTERMEDIATE INC.

June 6, 2022 EX-99.(A)(5)(C)

Press Release issued by the Company on June 6, 2022.

Cumulus Media Announces Preliminary Results of Tender Offer ATLANTA, GA ? June 6, 2022 ? Cumulus Media Inc.

June 6, 2022 SC TO-I/A

_________________________________________________________________________ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (Amendment No. 1) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securitie

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO (Amendment No. 1) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Cumulus Media Inc. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A common stock, par value $0.0000001 (Title of Class of Securities) 231082801 (CUSIP Number of Class of Securitie

June 6, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

May 6, 2022 EX-99.(A)(1)(C)

Notice of Guaranteed Delivery

Exhibit (a)(1)(C) NOTICE OF GUARANTEED DELIVERY To Tender Shares of Class A Common Stock of CUMULUS MEDIA INC.

May 6, 2022 EX-99.(A)(1)(A)

Offer to Purchase, dated May 6, 2022

Exhibit (a)(1)(A) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $25,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $16.50 PER SHARE AND NOT LESS THAN $14.50 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 3, 2022, UNLESS THE OFFER IS EXTENDED (SUCH DATE AND TIME, AS THEY MAY BE EXTENDED, THE

May 6, 2022 SC TO-I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Cumulus Media Inc. (Name of Subject Company (Issuer) and Filing Perso

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Cumulus Media Inc. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A common stock, par value $0.0000001 (Title of Class of Securities) 231082801 (CUSIP Number of Class of Securities) Richard S. Denn

May 6, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Cumulus Media Inc.

May 6, 2022 EX-99.(A)(1)(D)

Letter to Brokers, Dealers, Banks, Trust Companies and Other Nominees

Exhibit (a)(1)(D) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $25,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $16.50 PER SHARE AND NOT LESS THAN $14.50 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 3, 2022, UNLESS THE OFFER IS EXTENDED (SUCH DATE AND TIME, AS THEY MAY BE EXTENDED, THE

May 6, 2022 EX-99.(A)(1)(B)

Letter of Transmittal (including IRS Form W-9)

Exhibit (a)(1)(B) Letter of Transmittal To Tender Shares of Class A Common Stock of CUMULUS MEDIA INC.

May 6, 2022 EX-99.(A)(5)(A)

Summary Advertisement, dated May 6, 2022

Exhibit (a)(5)(a) This announcement is neither an offer to purchase nor a solicitation of an offer to sell Shares (as defined below).

May 6, 2022 EX-99.(A)(1)(E)

Letter to Clients for use by Brokers, Dealers, Banks, Trust Companies and Other Nominees

Exhibit (a)(1)(E) OFFER TO PURCHASE FOR CASH BY CUMULUS MEDIA INC. OF UP TO $25,000,000 OF ITS CLASS A COMMON STOCK AT A PURCHASE PRICE NOT GREATER THAN $16.50 PER SHARE AND NOT LESS THAN $14.50 PER SHARE THE OFFER AND WITHDRAWAL RIGHTS WILL EXPIRE AT MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON JUNE 3, 2022, UNLESS THE OFFER IS EXTENDED (SUCH DATE AND TIME, AS THEY MAY BE EXTENDED, THE

May 5, 2022 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2022 (May 3, 2022) CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commi

May 5, 2022 EX-99.1

Cumulus Media Announces Modified Dutch Auction Tender Offer to Purchase up to $25 Million of its Outstanding Class A Common Stock

Cumulus Media Announces Modified Dutch Auction Tender Offer to Purchase up to $25 Million of its Outstanding Class A Common Stock ATLANTA, GA ? May 5, 2022 ? Cumulus Media Inc.

May 5, 2022 SC TO-C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2022 Cumulus Media Inc. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 5, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 5, 2022 EX-99.1

Cumulus Media Announces Modified Dutch Auction Tender Offer to Purchase up to $25 Million of its Outstanding Class A Common Stock

Cumulus Media Announces Modified Dutch Auction Tender Offer to Purchase up to $25 Million of its Outstanding Class A Common Stock ATLANTA, GA ? May 5, 2022 ? Cumulus Media Inc.

May 4, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 4, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 4, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 4, 2022 Cumulus Media Inc. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

May 4, 2022 EX-99.1

Cumulus Media Sends Letter to Shareholders Regarding Strong Financial Results and Outlook, New Capital Return Program and Response to Unsolicited Indication of Interest Delivers Strong Q1 Earnings Results with Total Revenue Up 15% Led by Digital Reve

Cumulus Media Sends Letter to Shareholders Regarding Strong Financial Results and Outlook, New Capital Return Program and Response to Unsolicited Indication of Interest Delivers Strong Q1 Earnings Results with Total Revenue Up 15% Led by Digital Revenue Growth of 18% Achieves Lowest Net Leverage Ratio in More Than a Decade and Best Among Peers Reiterating 2022 EBITDA Guidance Range of $175-200 Million Announcing $50 Million Share Repurchase Program Board Determined Unsolicited, Non-Binding, Highly Conditional Indication of Interest Significantly Undervalues Cumulus Media and is Not in the Best Interests of Shareholders ATLANTA, GA ? May 4, 2022: Cumulus Media Inc.

May 4, 2022 EX-99.1

Cumulus Media Reports Operating Results for the First Quarter 2022 Delivers Strong Q1 Earnings Results with Total Revenue Up 15% Led by Digital Revenue Growth of 18% Achieves Lowest Net Leverage Ratio in More Than a Decade and Best Among Peers Announ

Cumulus Media Reports Operating Results for the First Quarter 2022 Delivers Strong Q1 Earnings Results with Total Revenue Up 15% Led by Digital Revenue Growth of 18% Achieves Lowest Net Leverage Ratio in More Than a Decade and Best Among Peers Announcing $50 Million Share Repurchase Program ATLANTA, GA ? May 4, 2022: Cumulus Media Inc.

May 4, 2022 EX-99.2

Q1 2022 Earnings Update May 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and oth

Q1 2022 Earnings Update May 2022 SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

May 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT PURSUANT TO

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cum

March 28, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEF 14A 1 a51570.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ý Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for

February 23, 2022 EX-10.28

Fifth Amendment to Employment Agreement, dated December 10, 2018, by and between Cumulus Media Inc. and Dave Milner (incorporated by reference to Exhibit 10.28 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EX-10.28 18 milneramendment5.htm EX-10.28 FIFTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fifth Amendment to Employment Agreement (“Fourth Amendment”) is made by and between David Milner (“Employee”) and Cumulus Media New Holdings Inc. (“Company”), successor-in-interest to Cumulus Media Inc., on this 10 day of December, 2018. WHEREAS, Employee and Company are parties to that certain Employment Agreem

February 23, 2022 EX-10.10

Form of Restricted Stock Unit Agreement (Director) (incorporated by reference to Exhibit 10.10 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT is made effective (the ?Grant Date?),1 between Cumulus Media Inc., a Delaware corporation (the ?Company?), and (the ?Recipient?). WHEREAS, the Company desires to grant to the Recipient an award denominated in units (the ?Restricted Stock Units?) of its Class A common capital stock (the ?Common Stock?); and WHEREAS, the Restricted St

February 23, 2022 EX-10.13

Form of Cash Based Performance Unit Agreement (Senior Executive) (incorporated by reference to Exhibit 10.13 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. CASH-BASED PERFORMANCE UNIT AGREEMENT THIS AGREEMENT (this ?Agreement?) is made effective (the ?Grant Date?), between Cumulus Media Inc., a Delaware corporation (the ?Company?), and (the ?Recipient?). WHEREAS, the Company has granted to the Recipient a Cash Incentive Award under Section 8 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the ?Plan?); and WHE

February 23, 2022 EX-10.21

First Amendment to Employment Agreement, dated February 19, 2016, by and between Cumulus Media Inc. and Robert J. Walker (incorporated by reference to Exhibit 10.21 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

FIRST AMENDMENT TO EMPLOYMENT AGREEMENT This First Amendment to Employment Agreement (?First Amendment?) is made by and between Robert J.

February 23, 2022 EX-10.23

Third Amendment to Employment Agreement, dated September 26, 2017, by and between Cumulus Media Inc. and Robert J. Walker (incorporated by reference to Exhibit 10.23 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EX-10.23 13 thirdamendmenttoemployment.htm EX-10.23 THIRD AMENDMENT TO EMPLOYMENT AGREEMENT This Third Amendment to Employment Agreement (“Third Amendment”) is made by and between Robert J. Walker (“Employee”) and Cumulus Media Inc. (“Company”) on this 26th day of September, 2017. WHEREAS, Employee and Company are parties to that certain Employment Agreement dated January 1, 2015, and as amended b

February 23, 2022 EX-10.6

Description of 2022 Quarterly Incentive Plan (incorporated by reference to Exhibit 10.6 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

Cumulus Media Inc. Description of 2022 Quarterly Incentive Plan Awards to executive officers under Cumulus Media Inc.?s (the ?Company?) annual executive incentive plan for certain officers of the Company, which operates as a quarterly incentive plan for 2022 (the ?2022 QIP?), will be based on the Company achieving budgeted adjusted earnings before interest, taxes, depreciation and amortization (?E

February 23, 2022 EX-99.2

Investor February 2022 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and

Investor February 2022 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

February 23, 2022 EX-10.7

Form of Restricted Stock Unit Agreement (Non-Senior Executive) (incorporated by reference to Exhibit 10.7 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EX-10.7 3 a2022rsuawardagreement-tema.htm EX-10.7 CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT (this “Agreement”) is made effective (the “Grant Date”), between Cumulus Media Inc., a Delaware corporation (the “Company”), and name (the “Recipient”). WHEREAS, the Company has granted to the Recipient an award of Restricted Stock Units under Section 7 of the Cumulus Media Inc. 2020

February 23, 2022 EX-10.20

Employment Agreement, dated as of January 1, 2015, by and between Cumulus Media Inc. and Robert J. Walker (incorporated by reference to Exhibit 10.20 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EMPLOYMENT AGREEMENT Senior Vice President This EMPLOYMENT AGREEMENT (the ?Agreement?) is made and entered into as of the 1st day of January, 2015 (the ?Effective Date?), by and between Cumulus Media Inc.

February 23, 2022 EX-10.22

Second Amendment to Employment Agreement, dated August 26, 2016, by and between Cumulus Media Inc. and Robert J. Walker (incorporated by reference to Exhibit 10.22 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

SECOND AMENDMENT TO EMPLOYMENT AGREEMENT This Second Amendment to Employment Agreement (?Second Amendment?) is made by and between Robert J.

February 23, 2022 EX-10.8

Form of Restricted Stock Unit Agreement (Senior Executive) (incorporated by reference to Exhibit 10.8 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. RESTRICTED STOCK UNIT AGREEMENT THIS AGREEMENT (this ?Agreement?) is made effective (the ?Grant Date?), between Cumulus Media Inc., a Delaware corporation (the ?Company?), and name (the ?Recipient?). WHEREAS, the Company has granted to the Recipient an award of Restricted Stock Units under Section 7 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the ?Plan

February 23, 2022 EX-10.9

Form of Stock Option Agreement (incorporated by reference to Exhibit 10.9 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. NONSTATUTORY STOCK OPTION AGREEMENT THIS AGREEMENT is made this day of (the ?Grant Date?), between Cumulus Media Inc., a Delaware corporation (the ?Company?), and (the ?Optionee?). WHEREAS, the Company desires to grant to the Optionee an option to purchase shares of Class A common stock (the ?Shares?) under the Company?s Long-Term Incentive Plan (the ?Plan?); and WHEREAS, the Co

February 23, 2022 EX-10.24

Fourth Amendment to Employment Agreement, dated July 1, 2021, by and between Cumulus Media Inc. and Robert J. Walker (incorporated by reference to Exhibit 10.24 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EX-10.24 14 fourthamendmenttoemploymen.htm EX-10.24 FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fourth Amendment to Employment Agreement (“Fourth Amendment”) is made by and between Robert J. Walker (“Employee”) and Cumulus Media Inc. (“Company”) on this 1st day of July, 2021. WHEREAS, Employee and Company are parties to that certain Employment Agreement dated January 1, 2015, and as amended by t

February 23, 2022 EX-10.12

Form of Cash Based Performance Unit Agreement (Non-Senior Executive) (incorporated by reference to Exhibit 10.12 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. CASH-BASED PERFORMANCE UNIT AGREEMENT THIS AGREEMENT (this ?Agreement?) is made effective (the ?Grant Date?), between Cumulus Media Inc., a Delaware corporation (the ?Company?), and (the ?Recipient?). WHEREAS, the Company has granted to the Recipient a Cash Incentive Award under Section 8 of the Cumulus Media Inc. 2020 Equity and Incentive Compensation Plan (the ?Plan?); and WHE

February 23, 2022 EX-99.1

Cumulus Media Reports Operating Results for 2021 Total Revenue of $916.5 Million, Up 12% Year-Over-Year Digital Revenue of More Than $125 Million, Up 48% Year-Over-Year Net Income of $17.3 Million vs. 2020 Net Loss of $59.7 Million EBITDA of $134.9 M

EX-99.1 2 cmls20211231earningsrelease.htm EX-99.1 PRESS RELEASE Cumulus Media Reports Operating Results for 2021 Total Revenue of $916.5 Million, Up 12% Year-Over-Year Digital Revenue of More Than $125 Million, Up 48% Year-Over-Year Net Income of $17.3 Million vs. 2020 Net Loss of $59.7 Million EBITDA of $134.9 Million, Up 66% Year-Over-Year ATLANTA, GA — February 23, 2022: Cumulus Media Inc. (NAS

February 23, 2022 EX-10.25

Employment Agreement, dated as of July 21, 2014, by and between Cumulus Media Inc. and Dave Milner (incorporated by reference to Exhibit 10.25 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

EX-10.25 15 davemilneremploymentagreem.htm EX-10.25 EMPLOYMENT AGREEMENT Senior Vice President – Western Region This EMPLOYMENT AGREEMENT (the “Agreement”) is made and entered into as of the 21st day of July, 2014 (the “Effective Date”), by and between Cumulus Radio Corp. (the “Company”), and David Milner (the “Employee”) (collectively the “Parties” and individually a “Party”). WHEREAS the Company

February 23, 2022 EX-10.26

Third Amendment to Employment Agreement, dated August 12, 2016, by and between Cumulus Media Inc. and Dave Milner (incorporated by reference to Exhibit 10.26 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

THIRD AMENDMENT TO EMPLOYMENT AGREEMENT This Third Amendment to Employment Agreement (?Third Amendment?) is made by and between David Milner (?Employee?) and Cumulus Media Inc.

February 23, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2022 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 23, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumulus Med

February 23, 2022 EX-10.11

Form of Stock Option Agreement (Director) (incorporated by reference to Exhibit 10.11 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

CUMULUS MEDIA INC. NONSTATUTORY STOCK OPTION AGREEMENT THIS AGREEMENT is made this day of (the ?Grant Date?),1 between Cumulus Media Inc., a Delaware corporation (the ?Company?), and (the ?Optionee?). WHEREAS, the Company desires to grant to the Optionee an option to purchase shares of Class A common stock (the ?Shares?) under the Company?s Long-Term Incentive Plan (the ?Plan?); and WHEREAS, the C

February 23, 2022 EX-10.27

Fourth Amendment to Employment Agreement, dated September 1, 2017, by and between Cumulus Media Inc. and Dave Milner (incorporated by reference to Exhibit 10.27 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

FOURTH AMENDMENT TO EMPLOYMENT AGREEMENT This Fourth Amendment to Employment Agreement (?Fourth Amendment?) is made by and between David Milner (?Employee?) and Cumulus Media Inc.

February 23, 2022 EX-10.29

Sixth Amendment to Employment Agreement, dated July 1, 2021, by and between Cumulus Media Inc. and Dave Milner (incorporated by reference to Exhibit 10.29 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2022)

SIXTH AMENDMENT TO EMPLOYMENT AGREEMENT This Sixth Amendment to Employment Agreement (?Sixth Amendment?) is made by and between David Milner (?Employee?) and Cumulus Media Inc.

February 23, 2022 EX-21.1

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivab

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivables Funding LLC Delaware CMP Houston-KC, LLC Delaware CMP KC LLC Delaware CMP Susquehanna LLC Delaware CMP Susquehanna Radio Holdings LLC Delaware Con

February 14, 2022 SC 13G/A

CMLS / Cumulus Media Inc / Cetus Capital VI, L.P. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Cumulus Media Inc. (Name of Issuer) Class A common stock, par value $0.0000001 per share (Title of Class of Securities) 231082801 (CUSIP Number) Cetus Capital VI, L.P. OFM II, L.P. 8 Sound Shore Drive Suite 303 Greenwich, CT 06830 (203) 552-3500 Copy to:

February 11, 2022 SC 13G/A

CMLS / Cumulus Media Inc / Standard General L.P. Passive Investment

SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Cumulus Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 231082801 (CUSIP Number) December 31, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is filed: [ ] Rule 13d-1(b) [x] Rule 13d-1(c) [ ] Rule 13d

February 8, 2022 SC 13G

CMLS / Cumulus Media Inc / Beach Point Capital Management LP Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* CUMULUS MEDIA INC. (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0000001 PER SHARE (Title of Class of Securities) 231082801 (CUSIP Number) December 31, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designa

February 8, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 8, 2022 (February 3, 2022) CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporati

November 3, 2021 EX-3.1

Second Amended and Restated Bylaws of Cumulus Media Inc. (incorporated by reference to Exhibit 3.1 to the Registrant’s Quarterly Report on Form 10-Q filed with the SEC on November 3, 2021).

AS AMENDED THROUGH AUGUST 3, 2021 SECOND AMENDED AND RESTATED BYLAWS OF CUMULUS MEDIA INC.

November 3, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 3, 2021 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

November 3, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPORT PURSUANT

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108

November 3, 2021 EX-99.2

Investor November 2021 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and

Investor November 2021 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

November 3, 2021 EX-99.1

CUMULUS MEDIA Reports Operating Results for the Third Quarter 2021

CUMULUS MEDIA Reports Operating Results for the Third Quarter 2021 ATLANTA, GA ? November 3, 2021: Cumulus Media Inc.

September 20, 2021 EX-99.1

CUMULUS MEDIA Releases New Investor Presentation Announces Participation in Deutsche Bank 29th Annual Leveraged Finance Conference

CUMULUS MEDIA Releases New Investor Presentation Announces Participation in Deutsche Bank 29th Annual Leveraged Finance Conference ATLANTA, GA ? September 20, 2021: Cumulus Media Inc.

September 20, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 20, 2021 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission F

September 20, 2021 EX-99.2

Investor September 2021 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute “forward-looking” statements within the meaning of the Private Securities Litigation Reform Act of 1995 and

Investor September 2021 Presentation SAFE HARBOR STATEMENTS Forward-Looking Statements: Certain statements in this presentation may constitute ?forward-looking? statements within the meaning of the Private Securities Litigation Reform Act of 1995 and other federal securities laws.

August 16, 2021 SC 13G

CMLS / Cumulus Media Inc / Standard General L.P. Passive Investment

SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Cumulus Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 231082801 (CUSIP Number) August 5, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedule is filed: [ ] Rule 13d-1(b) [x] Rule 13d-1(c) [ ] Rule 13d-1(d

August 16, 2021 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT This Joint Filing Agreement, dated as of August 16, 2021 is by and among Standard General L.P. and Soohyung Kim (the foregoing are collectively referred to herein as the ?Filers?). Each of the Filers may be required to file with the United States Securities and Exchange Commission a statement on Schedule 13D and/or 13G with respect to Class A Common Stock, of Cu

August 4, 2021 EX-3.1

SECOND AMENDED AND RESTATED BYLAWS OF CUMULUS MEDIA INC. ARTICLE I OFFICES; BOOKS AND RECORDS

EX-3.1 2 cmls06302021ex31.htm EX-3.1 AS AMENDED THROUGH AUGUST 3, 2021 SECOND AMENDED AND RESTATED BYLAWS OF CUMULUS MEDIA INC. ARTICLE I OFFICES; BOOKS AND RECORDS Section 1.1 Registered Office and Agent. Cumulus Media Inc. (hereinafter called the “Corporation”) shall at all times maintain a registered office in the State of Delaware and a registered agent in the State of Delaware, as required by

August 4, 2021 EX-99.1

CUMULUS MEDIA Reports Operating Results for the Second Quarter 2021

CUMULUS MEDIA Reports Operating Results for the Second Quarter 2021 ATLANTA, GA ? August 4, 2021: Cumulus Media Inc.

August 4, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 4, 2021 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File

August 4, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ☐ TRANSITION REPORT PURSUANT TO S

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumu

June 29, 2021 SC 13G

CMLS / Cumulus Media Inc / Cetus Capital VI, L.P. - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Cumulus Media Inc. (Name of Issuer) Class A common stock, par value $0.0000001 per share (Title of Class of Securities) 231082801 (CUSIP Number) Cetus Capital VI, L.P. OFM II, L.P. 8 Sound Shore Drive Suite 303 Greenwich, CT 06830 (203) 552-3500 Copy to:

May 5, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cum

May 5, 2021 EX-99.1

CUMULUS MEDIA Reports Operating Results for the First Quarter 2021

EX-99.1 2 cmls2021331earningsrelease.htm EX-99.1 CUMULUS MEDIA Reports Operating Results for the First Quarter 2021 ATLANTA, GA — May 5, 2021: Cumulus Media Inc. (NASDAQ: CMLS) (the “Company,” "CUMULUS MEDIA," “we,” “us,” or “our”) today announced operating results for the three months ended March 31, 2021. Mary G. Berner, President and Chief Executive Officer of CUMULUS MEDIA, said, "Our first qu

May 5, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2021 (May 4, 2021) CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commi

May 5, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 5, 2021 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission File Num

March 29, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material Pursuant to ? 240.

February 23, 2021 EX-99.1

CUMULUS MEDIA Reports Operating Results for 2020

CUMULUS MEDIA Reports Operating Results for 2020 ATLANTA, GA — February 23, 2021: Cumulus Media Inc.

February 23, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2021 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fi

February 23, 2021 EX-10.20

Description of 2021 Quarterly Incentive Plan (incorporated by reference to Exhibit 10.20 to Cumulus Media Inc.’s Annual Report on Form 10-K filed with the SEC on February 23, 2021)

Cumulus Media Inc. Description of 2021 Quarterly Incentive Plan Awards to executive officers under Cumulus Media Inc.?s (the ?Company?) annual executive incentive plan for certain officers of the Company, which operates as a quarterly incentive plan for 2021 (the ?2021 QIP?), will be based on the Company achieving budgeted adjusted earnings before interest, taxes, depreciation and amortization (?E

February 23, 2021 EX-21.1

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivab

Subsidiaries of Cumulus Media, Inc. 2-L Corporation Louisiana Atlanta Radio, LLC Delaware Broadcast Software International LLC Delaware Catalyst Media, LLC Delaware Chicago FM Radio Assets, LLC Delaware Chicago Radio Assets, LLC Delaware CMI Receivables Funding LLC Delaware CMP Houston-KC, LLC Delaware CMP KC LLC Delaware CMP Susquehanna LLC Delaware CMP Susquehanna Radio Holdings LLC Delaware Con

February 23, 2021 10-K

Annual Report - 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108 Cumulus Med

February 16, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5)*

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

February 11, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 11, 2021 (February 5, 2021) CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporat

January 20, 2021 SC 13G

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities & Exchange Act of 1934 (Amendment No. )* Cumulus Media Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 231082801 (CUSIP number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate

November 5, 2020 EX-99.1

CUMULUS MEDIA Reports Operating Results for the Third Quarter 2020

CUMULUS MEDIA Reports Operating Results for the Third Quarter 2020 ATLANTA, GA — November 5, 2020: Cumulus Media Inc.

November 5, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38108

November 5, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 5, 2020 CUMULUS MEDIA INC. (Exact name of registrant as specified in its charter) Delaware 001-38108 82-5134717 (State or other jurisdiction of incorporation) (Commission Fil

November 5, 2020 EX-10.2

MASTER AGREEMENT CUMULUS MEDIA NEW HOLDINGS INC., VERTICAL BRIDGE REIT, LLC, VB NIMBUS, LLC DATED AS OF AUGUST 7, 2020

Exhibit 10.2 MASTER AGREEMENT AMONG CUMULUS MEDIA NEW HOLDINGS INC., VERTICAL BRIDGE REIT, LLC, AND VB NIMBUS, LLC DATED AS OF AUGUST 7, 2020 1 Table of Contents Page ARTICLE 1 DEFINITIONS 2 Section 1.1 Certain Defined Terms 2 Section 1.2 Construction 21 Section 1.3 Assignments; Transfers of Certain Assets and Liabilities 21 ARTICLE 2 CONTRIBUTION, CONVEYANCE/GRANT OF LEASEHOLD, SUBLEASEHOLD OR OT

October 1, 2020 EX-99.1

CUMULUS MEDIA Completes Initial Closing of Tower Portfolio Monetization Transaction for $208 Million

CUMULUS MEDIA Completes Initial Closing of Tower Portfolio Monetization Transaction for $208 Million ATLANTA, GA — October 1, 2020: Cumulus Media Inc.

Fintel data has been cited in the following publications:
Daily Mail Fox Business Business Insider Wall Street Journal The Washington Post Bloomberg Financial Times Globe and Mail
NASDAQ.com Reuters The Guardian Associated Press FactCheck.org Snopes Politifact
Federal Register The Intercept Forbes Fortune Magazine TheStreet Time Magazine Canadian Broadcasting Corporation International Business Times
Cambridge University Press Investopedia MarketWatch NY Daily News Entrepreneur Newsweek Barron's El Economista