Document:

exv10w40

Exhibit 10.40

LEASE NOVATION AGREEMENT (CAC [     ]), dated as of December 15, 2010 (this “Agreement”), among
WELLS FARGO BANK NORTHWEST, NATIONAL ASSOCIATION, a US national banking association, not in its
individual capacity but solely as Owner Trustee (“Existing Lessor”), THUNDERBIRD [   ] LEASING
LIMITED, a Mauritius company (“New Lessor”), and SOUTH AFRICAN AIRWAYS (PTY) LTD., a South African
private limited liability company (“Lessee”).

RECITALS

Pursuant to Lease Agreement (CAC [     ]), dated as of December 16, 2009 (as previously amended
and supplemented, the “Lease Agreement”), between Existing Lessor, as lessor, and Lessee, as
lessee, in respect of one Airbus A330-200 aircraft with manufacturer’s CAC [   ] and
manufacturer’s serial number [     ] (the “Aircraft”), Existing Lessor agreed to lease and Lessee
agreed to take on lease the Aircraft upon the terms and conditions set out therein.

Existing Lessor and New Lessor desire that Existing Lessor transfer to New Lessor by novation the
Lease Agreement, and Lessee is willing to agree to such novation, in each case upon the terms and
conditions contained herein.

AGREEMENT

In consideration of the foregoing premise, and for other good and valuable consideration the
adequacy and receipt of which are hereby acknowledged, the parties hereto agree as follows:

1. DEFINITIONS AND CONSTRUCTION

The capitalized terms used in this Agreement shall have the respective meanings ascribed
thereto below:

“Effective Time” means the acceptance of the Aircraft by Lessee from New Lessor, as
evidenced by Lessee’s execution of the Acceptance Certificate.

“Novated Lease” means the Lease Agreement as novated and amended by this Agreement.

Capitalized terms used, but not defined, in this Agreement shall have the respective
meanings assigned to them in the Lease Agreement.

The provisions of Part II of Schedule 1 to the Lease Agreement shall apply to this Agreement
as if set out herein in full and as if references therein to “this Agreement” were
references to this Agreement.

2. NOVATION

As and with effect from the Effective Time:

	 	(1)	 	Lessee releases Existing Lessor from Existing Lessor’s obligations, duties and
liabilities to Lessee under the Lease Documents to the extent related to the period,
and which arise, after the Effective Time;
	 
	 	(2)	 	Existing Lessor releases Lessee from Lessee’s obligations, duties and
liabilities to Existing Lessor under the Lease Documents and Existing Lessor agrees
that it has no further rights under the Lease Documents, in each case, to the extent
related to the period, and which arise, after the Effective Time;
	 
	 	(3)	 	New Lessor agrees with Lessee to assume the rights, obligations, duties and
liabilities of Existing Lessor under the Lease Documents, to the extent related to the
period, and which arise, after the Effective Time;

 

 

	 	(4)	 	Lessee consents to and accepts the assumption by New Lessor of Existing
Lessor’s rights, obligations, duties and liabilities under the Lease Documents;
	 
	 	(5)	 	Lessee agrees that it will not assert against New Lessor any claim or defense
that it may have or have had against Existing Lessor under the Lease Documents related
to the period or arising prior to the Effective Time; and
	 
	 	(6)	 	Lessee agrees with New Lessor to perform its obligations under the Lease
Documents (as amended and supplemented by this Agreement) in favor of New Lessor,

each of the foregoing events and agreements being conditional on, and taking effect
simultaneously with, the others.

The Existing Lessor, New Lessor and Lessee accordingly agree that, as and with effect from
the Effective Time (subject to the satisfaction, or the waiver in accordance with Section
5.3, of the conditions precedent set out in Sections 5.1 and 5.2), the Lease Agreement shall
be novated to New Lessor with the effect of constituting a new agreement in the form of the
Novated Lease between New Lessor, as lessor and Lessee, as lessee.

Without prejudice to the rights of New Lessor or Lessee hereunder or under the Novated
Lease, Lessee and Existing Lessor agree that, in respect only of any losses, liabilities or
claims suffered or incurred by either of them in respect of the part of the Lease Period
prior to the Effective Time, each shall have the same rights and remedies against each other
as it would have had if Existing Lessor had remained the “Lessor” under the Lease Documents
and this Agreement had not been executed. The New Lessor shall not be responsible to Lessee
in respect of any such losses, liabilities or claims nor shall Lessee exercise any set off
or counterclaim against New Lessor in respect of any such losses, liabilities or claims.

3. NEW LESSOR’S AGREEMENTS

Prior to the earlier of (x) the Effective Time and (y) January 31, 2011, New Lessor will
deliver to Lessee:

	 	(1)	 	A guarantee issued by Aircastle Holding Corporation Limited in the same form as
delivered by Aircastle Holding Corporation Limited to Lessee on December 16, 2009, but
guaranteeing the obligations of New Lessor;
	 
	 	(2)	 	An officer’s certificate certifying that (a) Aircastle Holding Corporation
Limited has a net worth of at least $US$30,000,000 and (b) the accuracy of an attached
balance sheet for Aircastle Holding Corporation Limited, which attached balance sheet
will show that Aircastle Holding Corporation Limited has a tangible net worth of at
least $US$30,000,000.

Further, New Lessor confirms to Lessee that:

	 	(1)	 	So long as no Event of Default shall have occurred and be continuing, none of
Owner, New Lessor or any Person validly claiming by or through Owner or New Lessor
shall violate Lessee’s quiet enjoyment of the use, operation and possession of the
Aircraft and rights thereto under this Lease Agreement;
	 
	 	(2)	 	Lessee’s obligations under the Operative Documents shall not, as measured at
the Effective Time, increase as a consequence of the novation contemplated hereby
(other than in respect of Taxes, which are addressed in Schedule 6 to the Lease
Agreement) and Lessee’s rights and benefits under the Operative Documents shall not, as
measured at the Effective Time, be diminished as a consequence of the novation
contemplated hereby. Neither a change in the Person or Persons to whom, or for whose
benefit, Lessee performs its obligations under the Operative Documents, nor an increase
in the number of, or change in the nature of, beneficiaries under any indemnification,
insurance or other obligation shall, in each case, constitute by itself or in the
aggregate an increase in the obligations of Lessee under the Operative Documents; and

 

 

	 	(3)	 	New Lessor shall reimburse (or cause to be reimbursed) to Lessee promptly upon
invoice Lessee’s reasonable out-of-pocket expenses actually incurred in connection with
co-operating with Existing Lessor and New Lessor in relation to any such transfer or
proposed transfer referred to in this Agreement (such costs to include the fees and
expenses of Skadden and, if any, Lessee’s Mauritius counsel), provided that such
expenses are substantiated to New Lessor’s reasonable satisfaction and provided further
that no Event of Default has occurred and is continuing.
	 
	 	(4)	 	Other than the execution and delivery of this Agreement, and the performance of
the obligations set forth herein, Existing Lessor and New Lessor do not require Lessee
to execute or deliver any other documents or assurances, or take any other action, in
each case pursuant to Section 14.1 of the Lease Agreement, to establish or protect the
rights and remedies created or intended to be created in favor of the New Lessor.

3. LEASE AMENDMENT

As of, and with effect from, the Effective Time the Lease Agreement, as novated hereby, will
be amended as follows:

	 	(1)	 	the expression “Lessor” wherever it appears in each of the Lease Documents will
be treated as though it referred to New Lessor to the exclusion of Existing Lessor;
	 
	 	(2)	 	where the context so permits, the expression “this Agreement” wherever it
appears in the Lease Agreement will be treated as though it referred to the Lease
Agreement as novated and amended hereby;
	 
	 	(3)	 	clause (a) of Section 5.1(1) will be amended and restated as follows:
	 
	 	 	 	(a) is a company duly organized under the Laws of the Lessor Jurisdiction
	 
	 	(4)	 	the definition of “Business Day” in Part I of Schedule 1 will be amended and
restated as follows:
	 
	 	 	 	“Business Day” means a day (other than a Saturday or Sunday) on which banks are open
for business in Johannesburg, New York and Port Louis.
	 
	 	(5)	 	the definition of “Lessor Jurisdiction” in Part I of Schedule 1 will be amended
and restated as follows:
	 
	 	 	 	“Lessor Jurisdiction” means Mauritius.
	 
	 	(6)	 	the definition of “Other Aircraft” in Part I of Schedule 1 will be amended and
restated as follows:
	 
	 	 	 	“Other A330 Aircraft” means the other five A330-200 aircraft (CAC [      ],
CAC [     ], CAC [      ], CAC [      ], CAC [      ]) subject to lease agreements, dated as
of the date hereof, between Lessee and Affiliates of Lessor.
	 
	 	(7)	 	the definition of “Indemnified Party” in Part I of Schedule 1 will be amended
and restated as follows:
	 
	 	 	 	“Indemnified Party” means Lessor, Owner, Remarketing Servicers, Administrative Agent,
any backup remarketing servicer, each Financing Party, Manufacturing Inspector and
the successors and permitted transferees and assigns of each of the foregoing, and
the directors, officers, corporate stockholders, partners, employees, contractors,
servants and agents of each of the foregoing.
	 
	 	(8)	 	Section 1.6 of Schedule 2 will be amended and restated as follows:

	 	(1)	 	In the case of the Airframe, in the upper sill of the left-hand
forward entry door, adjacent to Airframe Manufacturer’s plate, “THIS AIRCRAFT IS
OWNED BY THUNDERBIRD [ ]

 

 

	 	 	 	LEASING LIMITED AND IS HELD UNDER LEASE BY SOUTH AFRICAN AIRWAYS (PTY) LTD.”
	 
	 	(2)	 	In the case of each Engine, in a clearly visible place in close
proximity to the manufacturer’s plate, “THIS ENGINE IS OWNED BY THUNDERBIRD [ ]
LEASING LIMITED AND IS HELD UNDER LEASE BY SOUTH AFRICAN AIRWAYS (PTY) LTD.”

	 	(9)	 	the Lessor’s notice details in Schedule 5 will be amended and restated as
follows:

Thunderbird [ ] Leasing Limited

c/o Aircastle Advisor LLC

300 First Stamford Place

Fifth Floor

Stamford CT 06902 USA

Fax: +1 (917) 591-9106

Attention: Lease Management

4. REPRESENTATIONS AND WARRANTIES

4.1 Lessee’s Representations to New Lessor

Lessee represents and warrants to New Lessor as of the Effective Time that Lessee’s
representations and warranties in Section 5.2 of the Lease Agreement are true and correct
including with respect to the Lease Agreement as amended hereby and with this Agreement as
an Operative Document.

4.2 New Lessor’s Representations

New Lessor represents and warrants to Lessee as of the Effective Time that the
representations and warranties in Section 5.1 of the Lease Agreement are true and correct
including with respect to the Lease Agreement as amended hereby and with this Agreement as
an Operative Document.

5. MISCELLANEOUS

THIS AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF ENGLAND AND
WALES.

The provisions of Sections 16, 17, 18.2 to 18.4, and 19 of the Lease Agreement shall apply
to this Agreement mutatis mutandis.

This Agreement is an “Operative Document” for purposes of the Lease Agreement.

IN WITNESS whereof the parties hereto or their duly authorized representatives have executed this
Agreement on the date written above.

 

 

WELLS FARGO BANK NORTHWEST, NATIONAL ASSOCIATION,

as Owner Trustee

	 	 	 	 	 

	By:
	 	 	 	 
	 

	 	 

Name:
	 	 
	 

	 	Title:	 	 
	 
	 	 	 	 
	THUNDERBIRD [ ] LEASING LIMITED	 	 
	 
	 	 	 	 
	By:
	 	 	 	 
	 

	 	 

Name:
	 	 
	 

	 	Title:	 	 
	 
	 	 	 	 
	SOUTH AFRICAN AIRWAYS (PTY) LTD.	 	 
	 
	 	 	 	 
	By:
	 	 	 	 
	 

	 	 

Name:
	 	 
	 

	 	Title:	 	 
	 
	 	 	 	 
	By:
	 	 	 	 
	 

	 	 

Name:
	 	 
	 

	 	Title:	 	 
	 
	 	 	 	 
	By:
	 	 	 	 
	 

	 	 

Name:
	 	 
	 

	 	Title:exv10w1

Exhibit 10.1

 

 

INVESTMENT AGREEMENT

Dated as of March 9, 2011

by and among

CUMULUS MEDIA INC.

and

THE INVESTORS PARTY HERETO

 

 

 

 

TABLE OF CONTENTS

	 	 	 	 	 
	 	 	Page	 
	ARTICLE I DEFINITIONS
	 	 	2	 
	 
	1.1 Definitions
	 	 	2	 
	 
	ARTICLE II PURCHASE; INVESTMENT CLOSING
	 	 	5	 
	 
	2.1 Purchase
	 	 	5	 
	2.2 Crestview Investor Warrants
	 	 	7	 
	2.3 Investment Closing
	 	 	7	 
	2.4 Parent Deliveries
	 	 	7	 
	2.5 Investor Deliveries
	 	 	8	 
	2.6 Independent Nature of Investors’ Obligations and Rights
	 	 	9	 
	 
	ARTICLE III REPRESENTATIONS AND WARRANTIES
	 	 	9	 
	 
	3.1 Representations and Warranties of Parent
	 	 	9	 
	3.2 Representations and Warranties of the Investors
	 	 	10	 
	 
	ARTICLE IV COVENANTS
	 	 	12	 
	 
	4.1 Conduct of Business Prior to the Investment Closing
	 	 	12	 
	4.2 Parent Forbearances
	 	 	12	 
	4.3 Regulatory Matters; Third Party Consents
	 	 	12	 
	4.4 Access to Information
	 	 	14	 
	4.5 Advice of Changes
	 	 	15	 
	 
	ARTICLE V ADDITIONAL AGREEMENTS
	 	 	15	 
	 
	5.1 Cumulus Media Partners
	 	 	15	 
	5.2 Certain Transactions
	 	 	16	 
	5.3 Nasdaq Stock Market Listing
	 	 	16	 
	5.4 Monitoring Fee
	 	 	16	 
	5.5 Registration Rights Agreement
	 	 	16	 
	5.6 Stockholders Agreement
	 	 	16	 
	5.7 Shareholder Rights Plan
	 	 	16	 
	5.8 Employee Incentive Plan
	 	 	16	 
	5.9 Debt Commitments
	 	 	17	 
	5.10 Actions under this Agreement and the Merger Agreement
	 	 	18	 
	5.11 Withdrawing Investor
	 	 	18	 

i

 

	 	 	 	 	 
	 	 	Page	 
	5.12 Contribution With Respect to Sponsor Guarantees
	 	 	19	 
	5.13 Cross Indemnification
	 	 	19	 
	5.14 Notice of Closing
	 	 	20	 
	5.15 Macquarie Investor Syndication
	 	 	21	 
	5.16 Termination Fee
	 	 	22	 
	 
	ARTICLE VI INVESTMENT CLOSING CONDITIONS
	 	 	23	 
	 
	6.1 Conditions of Each Party to Investment Closing
	 	 	23	 
	6.2 Conditions of Parent to Investment Closing
	 	 	23	 
	6.3 Conditions of each Investor to the Investment Closing
	 	 	24	 
	 
	ARTICLE VII TERMINATION
	 	 	25	 
	 
	7.1 Termination
	 	 	25	 
	7.2 Effects of Termination
	 	 	26	 
	 
	ARTICLE VIII MISCELLANEOUS
	 	 	26	 
	 
	8.1 Survival of Representations, Warranties and Covenants; Indemnification
	 	 	26	 
	8.2 Expenses
	 	 	26	 
	8.3 Post-Closing Third-Party Claims
	 	 	27	 
	8.4 Notices
	 	 	27	 
	8.5 Counterparts
	 	 	27	 
	8.6 Entire Agreement
	 	 	28	 
	8.7 Governing Law
	 	 	28	 
	8.8 Jurisdiction
	 	 	28	 
	8.9 Publicity
	 	 	29	 
	8.10 Assignment
	 	 	29	 
	8.11 Remedies
	 	 	30	 
	8.12 Amendment
	 	 	31	 
	8.13 Waivers
	 	 	32	 
	8.14 No Duty to Other Investors
	 	 	32	 
	8.15 Severability
	 	 	32	 
	8.16 Interpretation
	 	 	32	 
	8.17 Rules of Construction
	 	 	34	 

ii

 

EXHIBITS, ANNEXES AND SCHEDULES

	 	 	 

	EXHIBITS
	 	 
	 
	 	 
	Exhibit A:

	 	Class B Warrant Term Sheet
	Exhibit B:

	 	Class A Warrant Term Sheet
	Exhibit C:

	 	Registration Rights Agreement Term Sheet
	Exhibit D:

	 	Stockholders Agreement Term Sheet
	Exhibit E:

	 	Terms of Parent Straight Preferred
	Exhibit F:

	 	Form of Monitoring Fee Agreement
	Exhibit G:

	 	Shareholder Rights Plan Term Sheet
	Exhibit H:

	 	Employee Incentive Plan Term Sheet
	Exhibit I:

	 	Parent Series C Convertible Preferred Stock Terms
	Exhibit J:

	 	Letter Agreement by and among the Crestview Investor, Parent and certain of the Parent
Significant Stockholders
	 
	 	 
	ANNEXES
	 	 
	 
	 	 
	Annex A: 

Annex B:

	 	Crestview Funds

Investor Investment Amounts

iii

 

INDEX OF DEFINED TERMS

	 	 	 
	Term	 	Section
	6.13(d) Expenses
	 	5.12
	Actual Investment Amount
	 	2.1(a)
	Agreement
	 	Preamble
	Aliens
	 	1.1(s)
	Beneficial Ownership
	 	1.1(a)
	Beneficially Own
	 	1.1(a)
	Blackstone Group
	 	1.1(b)
	BOA Stockholders
	 	1.1(c)
	Cadet Portion
	 	1.1(d)
	Claims
	 	8.3
	Class A Warrants
	 	Recitals
	Class B Warrants
	 	Recitals
	Class B Warrant Shares
	 	Recitals
	Communications Act
	 	1.1(e)
	Continuing Investor
	 	5.11
	Crestview Equity Commitment Letter
	 	3.2(d)
	Crestview Funds
	 	Recitals
	Crestview Indemnifiable Losses
	 	5.13(a)
	Crestview Investment Commitment
	 	3.2(d)
	Crestview Investor
	 	Preamble
	Dickey Stockholder Group
	 	1.1(f)
	Exchange Agreement
	 	5.1
	Failing Investor
	 	5.10
	FCC
	 	1.1(g)
	FCC Applications
	 	1.1(h)
	FCC Regulations
	 	1.1(i)
	Funding Investor
	 	5.10
	Initial Order
	 	1.1(j)
	Investment Amount
	 	1.1(k)
	Investment Closing
	 	2.3
	Investment Closing Date
	 	2.3
	Investment HSR Clearance
	 	1.1(l)
	Investment Percentage
	 	1.1(m)
	Investment Transactions
	 	Recitals
	Investor Liability Cap
	 	8.11(c)
	Investor Party
	 	1.1(n)
	Investor Warrants
	 	1.1(o)
	Investors
	 	Preamble
	Issued Securities
	 	Recitals
	Losses
	 	8.1(b)
	Macquarie Capital
	 	5.15
	Macquarie Equity Commitment Fee
	 	1.1(p)

iv

 

	 	 	 
	Term	 	Section
	Macquarie Indemnifiable Losses
	 	5.13(b)
	Macquarie Investor
	 	Preamble
	Macquarie Investor Syndication
	 	5.15
	Macquarie Syndication Fee
	 	1.1(q)
	Macquarie Syndication Risk Fee
	 	1.1(r)
	Merger Agreement
	 	Recitals
	Merger Closing Conditions
	 	5.10
	Monitoring Agreement
	 	5.4
	New Incentive Plan
	 	5.8
	Non-U.S. Person
	 	1.1(s)
	Offering Documents
	 	5.15
	Parent
	 	Preamble
	Parent Straight Preferred
	 	Recitals
	Parent Series C Preferred
	 	1.1(t)
	Parent Significant Stockholders
	 	1.1(u)
	Parent Stockholder Consent
	 	Recitals
	Parties
	 	1.1(v)
	Price Per Share
	 	2.1(a)
	Registration Rights Agreement
	 	Recitals
	Rejected Portion
	 	1.1(w)
	Stockholders Agreement
	 	Recitals
	Straight Preferred Certificate of Designations
	 	2.1(a)
	Syndication Portion
	 	1.1(x)
	Transfer
	 	1.1(y)
	Withdrawing Investor
	 	5.11

v

 

     INVESTMENT AGREEMENT, dated as of March 9, 2011 (this “Agreement”), by and
among Cumulus Media Inc., a Delaware corporation (“Parent”), Crestview Radio Investors,
LLC, a Delaware limited liability company (the “Crestview Investor”), and MIHI LLC, a
Delaware limited liability company (the “Macquarie Investor”; the Macquarie Investor and
the Crestview Investor each being sometimes referred to herein as an “Investor” and,
together, as the “Investors”).

RECITALS:

     WHEREAS, Parent intends to issue and sell to the Crestview Investor, and the Crestview
Investor intends to purchase from Parent at the Investment Closing, as an investment in Parent,
shares of Parent Class A Common Stock;

     WHEREAS, Parent intends to issue and sell to the Macquarie Investor, and the Macquarie
Investor intends to purchase from Parent at the Investment Closing, as an investment in Parent,
warrants, substantially upon the terms set forth on Exhibit A, to purchase shares of Parent
Class B Common Stock (the “Class B Warrants” and the shares of Parent Class B Common Stock
for which the Class B Warrants are exercisable being referred to herein as “Class B Warrant
Shares”), or in lieu thereof, shares of Parent Series A Preferred Stock, par value $0.01 per
share, of Parent (“Parent Straight Preferred”), provided that the securities sold pursuant
to the Syndication Portion (as hereinafter defined) may be issued in the form of Parent Series C
Preferred (as hereinafter defined), all as more fully set forth herein;

     WHEREAS, at the Investment Closing, Parent will pay a commitment fee in cash to each Investor
and issue to the Crestview Investor, for no additional consideration, warrants, substantially upon
the terms set forth on Exhibit B, to purchase shares of Parent Class A Common Stock (the
“Class A Warrants” and, together with the shares of Parent Class A Common Stock issued to
the Crestview Investor, and shares of Parent Straight Preferred, shares of Parent Series C
Preferred and Class B Warrants issued to the Macquarie Investor pursuant hereto, the “Issued
Securities”);

     WHEREAS, Parent has incorporated Holdco as a wholly-owned, direct subsidiary of Parent, and,
prior to the Investment Closing Date, will contribute to Holdco all of the equity interests in
Parent’s other direct subsidiaries;

     WHEREAS, in connection with the execution and delivery of this Agreement, Parent has entered
into that certain Agreement and Plan of Merger, dated as of the date hereof (the “Merger
Agreement”), by and among Parent, Holdco, Merger Sub and the Company, pursuant to which Merger
Sub will merge with and into the Company, with the Company continuing as the surviving corporation
of the merger and a wholly-owned, direct subsidiary of Holdco;

     WHEREAS, the Parent Board has recommended that this Agreement and the Merger Agreement and the
transactions contemplated hereby and thereby (the “Investment Transactions”) are in the
best interests of Parent and its stockholders and has previously approved this Agreement and the
Investment Transactions;

 

 

     WHEREAS, as a condition and inducement to Parent entering into this Agreement, concurrent with
the execution and delivery of this Agreement, each of the Affiliated funds of the Crestview
Investor listed on Annex A (the “Crestview Funds”) and the Macquarie Investor, has
entered into a limited guarantee with the Company, dated as of the date hereof, to and in favor of
the Company;

     WHEREAS, as a condition and inducement to each Investor entering into this Agreement, prior to
execution of this Agreement, the requisite stockholders of Parent who hold in the aggregate
approximately 54% of the outstanding voting control of Parent, have delivered to Parent a written
consent (the “Parent Stockholder Consent”) in lieu of a stockholders meeting in accordance
with Section 228 of the DGCL approving the Parent Charter Amendment and the Share Issuance,
constituting the approval of such matters by the stockholders of Parent;

     WHEREAS, at the Investment Closing, the Parties will enter into a registration rights
agreement, substantially upon the terms set forth on Exhibit C (the “Registration
Rights Agreement”), pursuant to which, among other things, Parent will agree to register the
Parent Class A Common Stock included in the Issued Securities or for which the Class A Warrants may
be exercised, or obtainable upon conversion of the Class B Warrant Shares or upon conversion or
exchange of Parent Series C Preferred, subject to the terms and conditions set forth therein; and

     WHEREAS, the independent members of the Parent Board have approved, effective as of the
Investment Closing, the appointment of a director designated by the Crestview Investor as lead
director and, at the Investment Closing, each of the Parent Significant Stockholders and Parent
will enter into a stockholders agreement substantially upon the terms set forth on Exhibit
D (the “Stockholders Agreement”), pursuant to which, among other things, as of the
Investment Closing, two (2) directors designated by the Crestview Investor will be appointed to the
Parent Board, one (1) of which will be so appointed as the lead director of the Parent Board.

     NOW, THEREFORE, in consideration of the premises, and of the representations, warranties,
covenants and agreements set forth herein, Parent and each Investor agrees as follows:

ARTICLE I

DEFINITIONS

     1.1 Definitions. Terms used but not defined in this Agreement shall have the
meanings: set forth in the Merger Agreement. In addition, the following terms shall have the
following meanings:

          (a) “Beneficially Own” means, with respect to ownership of securities by any Person,
such securities as to which such Person is the “Beneficial Owner” under Rule 13d-3 of the Exchange
Act. “Beneficial Ownership” shall have the correlative meaning.

2

 

          (b) “Blackstone Group” means, collectively, Blackstone FC Communications Partners
L.P., Blackstone FC Capital Partners IV, L.P., Blackstone FC Capital Partners IV-A L.P., Blackstone
Family FCC L.L.C., Blackstone Participation FCC L.L.C. and Blackstone Communications FCC L.L.C.

          (c) “BOA Stockholders” means, together, BA Capital Company, L.P. and Banc of America
Capital Investors SBIC, L.P.

          (d) “Cadet Portion” means, with respect to the Investment Amount of the Macquarie
Investor, a portion of such Investment Amount equal to $125,000,000.

          (e) “Communications Act” means the Communications Act of 1934, as amended.

          (f) “Dickey Stockholder Group” means, collectively, Lewis W. Dickey, Jr., John W.
Dickey, David W. Dickey, Michael W. Dickey, Lewis W. Dickey, Sr. and DBBC, L.L.C.

          (g) “FCC” means the Federal Communications Commission.

          (h) “FCC Applications” means those applications for assignment and/or for transfer of
control that Parent will file, or will cause to be filed, with the FCC for its consent to the
transactions contemplated by the Merger Agreement, which applications will, to the extent required
by FCC Regulations, seek consent for the transactions contemplated by this Agreement as well.

          (i) “FCC Regulations” means the rules, regulations, published decisions, published
orders, and policies promulgated by the FCC and in effect from time to time.

          (j) “Initial Order” means, collectively, those orders by the FCC (including action
duly taken by the FCC’s staff pursuant to delegated authority) granting the FCC Applications.

          (k) “Investment Amount” means, with respect to each Investor, the amount set forth
opposite such Investor’s name on Annex B to this Agreement.

          (l) “Investment HSR Clearance” means HSR Clearance in respect of the purchase and sale
of the Issued Securities pursuant to this Agreement.

          (m) “Investment Percentage” means, (1) in the case of the Crestview Investor, 39.6%,
(2) in the case of the Macquarie Investor, 15.0%, and (3) in the case of Parent, 45.4%. For the
avoidance of doubt, the Investment Percentages set forth in this definition shall not be amended or
modified as a result of any sell-down by the Macquarie Investor as provided in Section 5.15.

3

 

          (n) “Investor Party” means, with respect to any Investor, each of such Investor and
any of such Investor’s former, current or future equity holders, controlling persons, directors,
officers, employees, agents, general or limited partners, managers, management companies, members,
stockholders, Affiliates or assignees and any and all former, current or future equity holders,
controlling persons, directors, officers, employees, agents, general or limited partners, managers,
management companies, members, stockholders, Affiliates or assignees of any of the foregoing, and
any and all former, current or future heirs, executors, administrators, trustees, successors or
assigns of any of the foregoing.

          (o) “Investor Warrants” means the Class A Warrants and the Class B Warrants.

          (p) “Macquarie Equity Commitment Fee” means an amount, calculated on a daily basis,
equal to 3.1% per annum on the dollar amount of the Cadet Portion of the Macquarie Investor’s
Investment Amount outstanding from time to time between the date of this Agreement and the
Investment Closing and not terminated by Parent; provided, however, if the
Investment Closing does not occur on or prior to the one year anniversary of this Agreement, the
foregoing rate, solely with respect to the period following such one year anniversary, shall
increase to 6.2% per annum.

          (q) “Macquarie Syndication Fee” means an amount, calculated on a daily basis, equal to
3.1% per annum on the dollar amount of the Syndication Portion of the Macquarie Investor’s
Investment Amount outstanding from time to time between the date of this Agreement and the
Investment Closing that has not, as of any date of calculation, either been syndicated or included
in the Rejected Portion as of such date; provided, no Macquarie Syndication Fee shall
payable if the Syndication Portion is fully syndicated on or before March 16, 2011.

          (r) “Macquarie Syndication Risk Fee” means an amount equal to four percent (4%) of the
dollar amount of the Syndication Portion that has not either been syndicated or become a part of
the Rejected Portion, in each case, as of the earlier of (A) the final date on which Company
shareholders have made (or are deemed to have made) their election as to the form of consideration
to be received by them in the Merger and (B) July 8, 2011.

          (s) “Non-U.S. Person” means any Person that, for purposes of the Communications Act
(including Section 310(b) of the Communications Act) and the FCC Regulations, is an alien, or a
representative of an alien, or a foreign government or representative thereof, or a corporation
organized under the laws of a foreign country (each an “Alien” and collectively,
“Aliens”), or any other entity (1) that is subject to or deemed to be subject to control by
Aliens or (2) the majority of the equity of which is owned, controlled on a de jure or de facto
basis by, voted by, or held for the benefit of, Aliens.

4

 

          (t) “Parent Series C Preferred” means the Series C Convertible and Exchangeable
Preferred Stock of Parent having substantially the terms set forth on Exhibit I to this
Agreement.

          (u) “Parent Significant Stockholders” means each of the Crestview Investor, the Dickey
Stockholder Group, the Blackstone Group, the BOA Stockholders and, if the Macquarie Investor
purchases at the Investment Closing Class B Warrants initially exercisable for at least 11,520,737
shares of Parent Class B Common Stock, the Macquarie Investor.

          (v) “Parties” means Parent and each of the Investors.

          (w) “Rejected Portion” means, as of any date, the total amount of bona fide
unconditional offers to purchase the obligations of the Macquarie Investor under this Agreement at
a price of not less than the equivalent of $4.34 per share of Parent Class A Common Stock or Class
B Warrant Shares, as the case may be, and on terms and conditions and with a counterparty
acceptable to the Macquarie Investor in its sole and absolute discretion, which offers have been
declined in writing by the Macquarie Investor on or prior to such date.

          (x) “Syndication Portion” means, with respect to the Investment Amount of the
Macquarie Investor, a portion of such Investment Amount equal to $125,000,000.

          (y) “Transfer” shall mean a transfer, sale, assignment, hypothecation or other
disposition.

ARTICLE II

PURCHASE; INVESTMENT CLOSING

     2.1 Purchase.

          (a) On the terms and subject to the conditions set forth herein, at the Investment Closing,
Parent shall issue and sell (1) to the Crestview Investor, a number of shares of Parent Class A
Common Stock equal to the quotient obtained by dividing (A) the Investment Amount (as each
Investor’s Investment Amount may be reduced pursuant to Section 2.1(b) (such amount, the
“Actual Investment Amount”)) by (B) Four Dollars Thirty-Four Cents ($4.34) (the “Price
Per Share”) and (2) subject to the limitations contained in the Communications Act and FCC
Regulations as to ownership and voting of securities of an entity regulated by the FCC, to the
Macquarie Investor, Class B Warrants initially exercisable for a number of shares of Parent Class B
Common Stock equal to the quotient obtained by dividing (A) the Macquarie Investor’s Actual
Investment Amount (as such amount shall be reduced in the case of, and to the extent of, any
sell-downs by the Macquarie Investor pursuant to Section 5.15) by (B) the Price Per Share;
provided, that the Macquarie Investor may, in lieu thereof, elect in its discretion to receive
shares of Parent Straight Preferred having an aggregate initial liquidation value

5

 

equal to the
Macquarie Investor’s Actual Investment Amount. Such election (which may be made in whole or in
part) shall be made by the Macquarie Investor by irrevocable written notice to Parent and the
Crestview Investor not less than eight (8) Business Days prior to the Investment Closing. The
terms of the Parent Straight Preferred shall be set forth in a certificate of designations relating
to the Parent Straight Preferred upon the terms set forth on Exhibit E (the “Straight
Preferred Certificate of Designations”).

          (b) If, as of the Election Deadline, the aggregate number of Company Shares and Company
Warrants that the holders thereof elect to have converted at the Effective Time into Parent Shares
pursuant to the Merger Agreement exceeds the aggregate number of Company Shares and Company
Warrants that would be converted at the Effective Time into Parent Shares in the “Max Cash”
scenario in which the aggregate Cash Consideration is equal to the Cash Consideration Cap, the
Investment Amount of the Crestview Investor and the Cadet Portion of the Investment Amount of the
Macquarie Investor shall be automatically reduced by an aggregate amount equal to the product of
(1) such excess aggregate number of Company Shares and Company Warrants and (2) $37.00. Such
reduction shall be applied to the Investment Amounts of the Investors as follows: (A) first (but
only as to the first $50,000,000 of such reduction), to the Investment Amount of the Crestview
Investor, on the one hand, and the Cadet Portion of the Investment Amount of the Macquarie
Investor, on the other, 50/50, on a dollar-for-dollar basis, and (B) second (as to amounts in
excess of $50,000,000), to the Cadet Portion of the Investment Amount of the Macquarie Investor,
but not less than zero. Notwithstanding anything in this Agreement to the contrary: (i) the
minimum Investment Amount of the Crestview Investor will be $225,000,000 and, even if the
Investment Amount of the Crestview Investor would not be reduced by operation of the preceding
sentence by virtue of Company shareholder elections, Parent may reduce the Investment Amount of the
Crestview Investor to $225,000,000 upon written notice to the Crestview Investor not later than the
earlier of (x) 20 Business Days prior to the Investment Closing and (y) 5 Business Days after the
Election Deadline; (ii) Parent will have the right to terminate the Cadet Portion of the Macquarie
Investor’s Investment Amount, in whole or in part, at any time prior to the Investment Closing upon
written notice to the Macquarie Investor, provided any such termination, once made, is irrevocable;
(iii) in the event that Parent either sells more equity or Holdco borrows more money under the Debt
Financing than is reflected in the “Max Cash” scenario of the Sources and Uses in the form provided
by Parent to the Investors contemporaneously with the execution of this Agreement, with the result
that Parent does not, as determined by Parent in its sole and absolute discretion, require the full
Investment Amount of the Macquarie Investor to consummate the transactions contemplated by the
Merger Agreement, then Parent shall notify the Macquarie Investor not later than eight (8) Business
Days prior to the Investment Closing of the amount of the Macquarie Investor’s Investment Amount
that is as a result thereof not required and the Macquarie Investor may elect to reduce its
Investment Amount in its sole discretion to the extent not so needed by Parent, by written notice
to Parent not more than six (6) Business Days after such notice from Parent, provided that once
made, such reduction is irrevocable; and (iv) Parent may, by written notice, request that the
Syndication Portion of the Macquarie Investor’s Investment Amount be reduced, in whole or in part,
at any time prior to the Investment Closing; provided any such reduction shall be made at the
Macquarie Investor’s sole discretion

6

 

and, once made, such reduction is irrevocable. Parent shall
promptly provide to the Investors information that it receives regarding the election by Company
shareholders of the consideration to be received under the Merger Agreement.

     2.2 Crestview Investor Warrants. On the terms and subject to the conditions set forth
herein, at the Investment Closing, Parent shall issue to the Crestview Investor for no additional
consideration, and the Crestview Investor shall receive from Parent, Class A Warrants to purchase
Seven Million Seven Hundred Seventy-Six Thousand Four Hundred Ninety Eight (7,776,498) shares of
Parent Class A Common Stock at an exercise price of Four Dollars Thirty-Four Cents ($4.34) per
share.

     2.3 Investment Closing. Subject to the satisfaction or waiver of the conditions set
forth in this Agreement (other than those conditions that by their nature are to be satisfied by
actions taken at the Investment Closing, but subject to the satisfaction or waiver of those
conditions), the closing of the issuance and sale of the Issued Securities to the Investors
pursuant hereto (the “Investment Closing”) shall occur concurrently with and at the same
location as the Closing under the Merger Agreement. The date the Investment Closing occurs is
referred to as the “Investment Closing Date.”

     2.4 Parent Deliveries. At the Investment Closing, Parent shall deliver, or cause to be
delivered:

          (a) (1) to the Crestview Investor, a stock certificate representing the applicable number of
shares of Parent Class A Common Stock being purchased by it as calculated in accordance with
Section 2.1(a) and (2) to the Macquarie Investor, Class B Warrants to purchase a number of shares
of Parent Class B Common Stock and/or a stock certificate representing the applicable number of
shares of Parent Straight Preferred, each as calculated in accordance with Section 2.1(a), in each
case, free and clear of all Liens;

          (b) to each Investor, payment of an equity commitment fee equal to Ten Million Dollars
($10,000,000) by wire transfer(s) of immediately available funds to bank accounts designated by the
Macquarie Investor and the Crestview Investor, respectively, no less than two (2) Business Days
prior to the Investment Closing (which equity commitment fee, for the avoidance of doubt, will not
be reduced in the event the Macquarie Investor syndicates a portion of its Investment Amount as
provided in Section 5.15);

          (c) to the Crestview Investor, Class A Warrants to purchase, at an exercise price of Four
Dollars Thirty-Four Cents ($4.34) per share, the number of shares of Parent Class A Common Stock
set forth in Section 2.2;

          (d) to the Macquarie Investor, payment by wire transfer of immediately available funds to a
bank account designated by the Macquarie Investor no less than two (2) Business Days prior to the
Investment Closing of an amount equal to the aggregate of the Macquarie Syndication Risk Fee, the
Macquarie Syndication Fee and the Macquarie Equity Commitment Fee;

7

 

          (e) to the Crestview Investor, the Monitoring Agreement, duly executed by Parent;

          (f) to each Investor, the Registration Rights Agreement, duly executed by Parent;

          (g) to each Investor that is a Parent Significant Stockholder, the Stockholders Agreement,
duly executed by Parent and the Parent Significant Stockholders;

          (h) to the Crestview Investor, evidence of the appointment of two (2) directors (one (1) of
whom shall be Jeffrey Marcus and the other of whom shall be Tom Murphy, Barry Volpert or Brian
Cassidy or, in each case, any other individual reasonably acceptable to Parent) designated by the
Crestview Investor to the Parent Board, including the appointment of Jeffrey Marcus as the lead
director of the Parent Board;

          (i) to each Investor, a certificate, dated as of the Investment Closing Date, signed on behalf
of Parent by the Chief Executive Officer or the Chief Financial Officer of Parent, certifying as to
the fulfillment of the conditions set forth in Sections 6.3(a) and (b);

          (j) to the Macquarie Investor, evidence of the filing of the Straight Preferred Certificate of
Designations with the Delaware Secretary of State (to the extent applicable in accordance with
Section 2.1(a)) and such other agreements implementing the terms of Exhibit E duly executed by
Parent and Holdco, to the extent such terms are not otherwise provided for in the Straight
Preferred Certificate of Designations; and

          (k) to each Investor, a copy of (1) the amended and restated certificate of incorporation of
Parent, as amended by the Parent Charter Amendment, and (2) a copy of the bylaws of Parent (which
shall not have been amended since the date hereof), in each case, as in effect as of the Investment
Closing Date.

     2.5 Investor Deliveries. At the Investment Closing, each Investor (or, in the case of
Section 2.5(b), the Crestview Investor) shall deliver, or cause to be delivered, to Parent:

          (a) payment by such Investor of an amount equal to its Actual Investment Amount by wire
transfer(s) of immediately available funds to a bank account designated by Parent no less than two
Business Days prior to the Investment Closing;

          (b) the Monitoring Agreement, duly executed by the Crestview Investor;

          (c) the Registration Rights Agreement, duly executed by such Investor;

8

 

          (d) the Stockholders Agreement, to the extent such Investor is a Parent Significant
Stockholder, duly executed by such Investor; and

          (e) a certificate, dated as of the Investment Closing Date, signed on behalf of such Investor
by an authorized signatory of such Investor, certifying as to the fulfillment of the conditions set
forth in Sections 6.2(a) and (b) by such Investor.

     2.6 Independent Nature of Investors’ Obligations and Rights. The obligations of each
Investor under this Agreement are several and not joint with the obligations of the other
Investors, and no Investor shall be responsible in any way for the performance of the obligations
of the other Investor under this Agreement. Nothing contained herein, and no action taken by any
Investor pursuant hereto, shall be deemed to constitute the Investors as a partnership, an
association, a joint venture or any other kind of entity, or create a presumption that the
Investors are in any way acting in concert or as a group with respect to such obligations or the
Investment Transactions. Each Investor shall be entitled to independently protect and enforce its
rights, including the rights arising out of this Agreement, and it shall not be necessary for any
other Investor to be joined as an additional party in any proceeding for such purpose.

ARTICLE III

REPRESENTATIONS AND WARRANTIES

     3.1 Representations and Warranties of Parent. Parent hereby represents and warrants
to each Investor as follows:

          (a) Valid Issuance. The Issued Securities to be issued pursuant to this Agreement
will be duly authorized and validly issued and, at the Investment Closing, all such Issued
Securities will be fully paid, nonassessable and free of preemptive rights, with no personal
liability attaching to the ownership thereof, and will be free and clear of all Liens..

          (b) Corporate Existence; Authority; No Violation.

               (1) Parent is a corporation validly existing under the Laws of the jurisdiction of its
organization. Parent has the corporate power and authority to own or lease all of its properties
and assets and to carry on its business as it is now being conducted.

               (2) Parent has the corporate power and authority to execute and deliver this Agreement and to
consummate the Investment Transactions. The execution and delivery of this Agreement and the
consummation of the Investment Transactions (other than approval of the New Incentive Plan) have
been duly and validly approved by the Parent Board. The Parent Board has determined that this
Agreement, the Investment Transactions and the Parent Charter Amendment are advisable to and are in
the best interests of Parent and its stockholders and, except for the Parent Stockholder Consent
and the Consent Right Holder Consent (each of which has been obtained

9

 

contemporaneously with the
execution of this Agreement and provided to each Investor), no other corporate proceedings on the
part of Parent are necessary to approve this Agreement and to consummate the Investment
Transactions (other than approval of the New Incentive Plan). This Agreement has been duly and
validly executed and delivered by Parent and (assuming the due authorization, execution and
delivery by the Investors) constitutes the valid and binding obligation of Parent.

               (3) Neither the execution and delivery of this Agreement by Parent, nor the consummation of
the Investment Transactions, nor compliance by Parent with any of the terms or provisions of this
Agreement, will violate any provision of the Parent Charter or the Parent Bylaws.

          (c) Parent Reports. Except as would not have a Material Adverse Effect on Parent,
(1) none of the Parent Reports filed by Parent since December 31, 2007, as of the date of such
Parent Report (or, if amended prior to the date hereof, as of the date of the last amendment and
filing thereof), contained any untrue statement of a material fact or omitted to state a material
fact required to be stated therein or necessary in order to make the statements made therein, in
the light of circumstances under which they were made, not misleading and (2) Parent has timely
filed all Parent Reports that were required to be filed by Parent since December 31, 2007 and has
complied as to form in all material respects with the published rules and regulations of the SEC
with respect thereto.

          (d) Debt Financing. Parent has delivered to each Investor true, correct and complete
copies, as of the date of this Agreement, of an executed Debt Commitment Letter to provide, subject
to the terms and conditions therein, Debt Financing. As of the date hereof, the Debt Commitment
Letter has not been amended or modified and the commitment contained in such letter has not been
withdrawn or rescinded in any respect. Parent or Holdco has fully paid or is paying, or has caused
or is causing to be fully paid, substantially contemporaneously with the execution and delivery of
this Agreement, any and all commitment fees or other fees in connection with the Debt Commitment
Letter that are payable on or prior to the date hereof. The net proceeds contemplated by the Debt
Commitment Letter, together with the net proceeds contemplated by the Crestview Equity Commitment
and the equity commitment of the Macquarie Investor hereunder and cash and cash equivalents
available to Parent, will, in the aggregate, be sufficient to consummate the Transactions upon and
in accordance with the terms and conditions contemplated by the Merger Agreement and this
Agreement.

     3.2 Representations and Warranties of the Investors. Each Investor, severally and not
jointly, hereby represents and warrants to Parent solely with respect to itself that:

          (a) Organization. Such Investor is duly organized, validly existing and in good
standing under the Laws of the jurisdiction of its organization. Such Investor has corporate or
other power and authority to own or lease all of its properties and assets and to carry on its
business as it is now being conducted.

10

 

          (b) Authority; No Violation.

               (1) Such Investor has the corporate or other power and authority to execute and deliver this
Agreement and to consummate the Investment Transactions. The execution and delivery of this
Agreement by such Investor and the consummation of the Investment Transactions have been duly and
validly approved by the board of directors or other governing body of such Investor and no other
corporate or other proceedings on the part of such Investor are necessary to approve this Agreement
and to consummate the Investment Transactions. This Agreement has been duly and validly executed
and delivered by such Investor and (assuming due authorization, execution and delivery by Parent
and the other Investor) constitutes the valid and binding obligations of such Investor.

               (2) Assuming the truth and accuracy of the representations and warranties of Parent contained
in Section 3.1(b)(3), neither the execution and delivery of this Agreement by such Investor, nor
the consummation of the Investment Transactions, nor compliance by such Investor with any of the
terms or provisions of this Agreement, will violate any provision of the organizational or
governing documents of such Investor.

          (c) Purchase for Investment. Such Investor acknowledges that the Securities have not
been registered under the Securities Act or under any state securities Laws. Such Investor (1) is
acquiring the Securities pursuant to an exemption from registration under the Securities Act solely
for investment with no present intention to distribute any of the Securities to any Person,
(2) acknowledges that it shall be prohibited from selling or otherwise disposing of any of the
Securities except in compliance with the registration requirements or exemption provisions of the
Securities Act and any other applicable securities Laws, (3) has such knowledge and experience in
financial and business matters and in investments of this type that it is capable of evaluating the
merits and risks of its investment in the Securities and of making an informed investment decision
and (4) is an “accredited investor” (as that term is defined by Rule 501 of the Securities Act).

          (d) Financial Capability. With respect to the Crestview Investor: (i) such Investor
has delivered to Parent a true, correct and complete copy, as of the date of this Agreement, of an
executed equity commitment letter from the Crestview Funds (the “Crestview Equity Commitment
Letter”), pursuant to which the Crestview Funds have committed, subject to the terms and
conditions therein, to invest the cash amounts set forth therein (the “Crestview Investment
Commitment”); and (ii) as of the date of this Agreement, the Crestview Equity Commitment Letter
has not been amended or modified and the Crestview Investment Commitment contained in such letter
has not been withdrawn or rescinded in any respect.

          (e) Non-U.S. Person Status. The Crestview Investor represents and warrants that it is
not a Non-U.S. Person. The Macquarie Investor represents and warrants that it is a Non-U.S.
Person.

11

 

ARTICLE IV

COVENANTS

     4.1 Conduct of Business Prior to the Investment Closing. During the period from the
date of this Agreement to the Investment Closing, except as expressly contemplated or permitted by
this Agreement or a provision of Section 5.3 of the Parent Disclosure Letter delivered pursuant to
the Merger Agreement, Parent will, and will cause each of the Parent Subsidiaries to, (a) use
commercially reasonable efforts to maintain and preserve in all material respects intact its
business organization, Employees and advantageous business relationships and retain the services of
its key officers and key Employees and (b) use reasonable best efforts to comply in all material
respects with the Communications Act and FCC Regulations in the operation of its businesses
regulated by the FCC.

     4.2 Parent Forbearances. During the period from the date of this Agreement to the
Investment Closing, except as expressly contemplated or permitted by this Agreement or Section 5.3
of the Parent Disclosure Letter delivered pursuant to the Merger Agreement, Parent will not, and
Parent will not permit any of the Parent Subsidiaries to, without the prior written consent of the
Crestview Investor (in its reasonable discretion) and the Macquarie Investor (in its reasonable
discretion), take any of the actions set forth in Sections 5.3(a) through (i) of the Merger
Agreement.

     4.3 Regulatory Matters; Third Party Consents.

          (a) Parent will promptly prepare and file with the SEC the Joint Proxy/Information Statement
and Parent will promptly prepare and file with the SEC the Form S-4 in which the Joint
Proxy/Information Statement will be included as a prospectus. Parent will use its commercially
reasonable efforts to have the Form S-4 declared effective under the Securities Act as promptly as
practicable after such filing, and thereafter mail or deliver the Joint Proxy/Information Statement
to its respective stockholders.

          (b) Parent, on the one hand, and each Investor, on the other hand, will cooperate with each
other and use their respective commercially reasonable efforts to promptly prepare and file, or
cooperate in the filing of, all necessary documentation, including all applications, notices,
reports and petitions, to obtain as promptly as practicable all permits, consents, approvals and
authorizations of all third parties and Governmental Entities that are necessary or advisable to
consummate the Merger Agreement and the Investment Transactions and to comply in all material
respects with the terms and conditions of all such permits, consents, approvals and authorizations
of all such Governmental Entities. Parent, on the one hand, and each Investor, on the other hand,
will have the right to review in advance, and, to the extent practicable, each will consult the
other on, in each case subject to applicable Laws relating to the exchange of information, all the
information relating to Parent or such Investor, as the case may be, and any of their respective
Subsidiaries, which appear in any filing made with, or written materials submitted to, any third
party or any

12

 

Governmental Entity in connection with the Merger Agreement or the Investment
Transactions. In exercising the foregoing right, Parent, on the one hand, and each Investor, on
the other hand, will act reasonably and as promptly as practicable. Parent, on the one hand, and
each Investor, on the other hand, will consult with each other with respect to the efforts to
obtain of all permits, consents, approvals and authorizations of all third parties and Governmental
Entities necessary or advisable to consummate the Merger Agreement and the Investment Transactions,
and each party will keep the other apprised of the status of those efforts.

          (c) Parent, on the one hand, and each Investor, on the other hand, will, upon request, furnish
to the other Parties all information concerning itself, its Subsidiaries, directors, officers and
stockholders and such other matters as may be reasonably necessary or advisable in connection with
the Joint Proxy/Information Statement, the Form S-4 or any other statement, filing, notice or
application made by or on behalf of Parent, such Investor or any of their respective Subsidiaries
to any Governmental Entity in connection with the Investment Transactions. Parent shall promptly
notify each Investor of the receipt of any comments of the SEC staff with respect to the Joint
Proxy/Information Statement and of any requests by the SEC for any amendment or supplement thereto
or for additional information and shall provide to such Investor, as promptly as reasonably
practicable, copies of all written correspondence between Parent or any of its Representatives and
the SEC with respect to the Joint Proxy/Information Statement. If comments are received from the
SEC staff with respect to the preliminary Proxy Statement, Parent shall use its commercially
reasonable efforts to respond as promptly as reasonably practicable to such comments. Parent shall
provide each Investor and its legal counsel with a reasonable opportunity to review any amendment
or supplement to each of the preliminary and the definitive Joint Proxy/Information Statement prior
to filing with the SEC and shall cooperate with each Investor with respect to additions, deletions
or changes suggested by such Investor in connection therewith. Each Investor shall promptly
provide Parent with such information as may be required to be included in the Joint
Proxy/Information Statement or as may be reasonably required to respond to any comment of the SEC
staff.

          (d) Parent, on the one hand, and each Investor, on the other hand, will promptly advise the
other Parties upon receiving any communication from any Governmental Entity relating to any consent
or approval which is required for consummation of the Merger Agreement or the Investment
Transactions, including the Merger Closing Conditions.

          (e) Each Investor will promptly take, all commercially reasonable actions necessary (1) to
secure the Investment HSR Clearance and/or to resolve any objections asserted by any Governmental
Entity with respect to the Investment Transactions under any antitrust Law and (2) to prevent the
entry of, and to have vacated, lifted, reversed or overturned, any decree, judgment, Injunction or
other order that would prevent, prohibit, restrict or delay the consummation of the Investment
Transactions; provided, that no Investor shall be required by this Section 4.3(e) to take or agree
to undertake any action, including entering into any consent decree, hold separate order or other
arrangement, that would, in the reasonable judgment of such Investor,

13

 

materially impact the value
or benefits to such Investor of the transactions contemplated hereby.

          (f) Parent, on the one hand, and each Investor, on the other hand, will (A) diligently take,
or cooperate in the taking of, all necessary, desirable, proper and commercially reasonable
actions, and provide any additional information, reasonably required or requested by the FCC with
respect to the FCC Applications, (B) keep the other informed of any material communications
(including any meeting, conference or telephonic call) and will provide the other copies of all
correspondence, including electronic correspondence, between it (or its advisors) and the FCC with
respect to the FCC Applications, (C) permit the other to review any material communication relating
to the FCC Applications to be given by it to the FCC, (D) use reasonable efforts to notify the
other in the event it becomes aware of any other facts, actions, communications or occurrences that
might directly or indirectly adversely affect the FCC’s timely approval of the FCC Applications;
(E) cooperate in the preparation and filing of oppositions to any petitions to deny or other
objections filed with respect to the FCC Applications and any requests for reconsideration or
judicial review of the Initial Order, and (F) not take any action that would reasonably be expected
to materially delay, materially impede or prevent receipt of approval of the Initial Order.
Parent shall be permitted to execute or agree (orally or otherwise) to any settlements,
undertakings, consent decrees, stipulations or other agreements in respect of any Investor or any
FCC Application without such Investor’s prior written consent (not to be unreasonably withheld);
provided, that prior written consent of such Investor to any such settlement, undertaking, consent
decree, stipulation or other agreement shall be required to the extent that such settlement,
undertaking, consent decree, stipulation or other agreement would reasonably be expected to
materially and adversely diminish the benefits expected to be derived by such Investor from the
transactions contemplated hereby (whether by reason of impact on such Investor’s existing
businesses or assets or on Parent’s business or assets).

     4.4 Access to Information.

          (a) Upon reasonable notice and subject to applicable Laws relating to the exchange of
information, Parent will, and will cause each of its Subsidiaries to, afford to each Investor and
its Representatives, reasonable access, during normal business hours during the period prior to the
Investment Closing Date, to all its personnel, properties, books, Contracts, commitments and
records, and, during such period, the Parties will, and will cause its Subsidiaries to, make
available to the other party (1) a copy of each report, schedule, registration statement and other
document filed or received by it during such period pursuant to the requirements of federal or
state securities Laws (other than reports or documents that such party is not permitted to disclose
under applicable Law) and (2) all other information concerning its business, properties and
personnel as the other may reasonably request. Neither Parent nor any of its Subsidiaries will be
required to provide access to or to disclose information where such access or disclosure would
jeopardize the attorney-client privilege of Parent or its Subsidiaries or contravene any Law, rule,
regulation, order, judgment, decree, fiduciary duty or binding agreement entered into prior to the
date of this Agreement. The Parties

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will make appropriate substitute disclosure arrangements under
circumstances in which the restrictions of the preceding sentence apply. In addition to the
foregoing, from the period beginning immediately after the receipt of Investment HSR Clearance
until the Investment Closing Date, Parent will use its reasonable best efforts to (A) afford each
Investor and its authorized Representatives full and free access, during regular business hours, to
Parent’s personnel and allow such Investor to hold meetings with such personnel; (B) afford each
Investor the right to visit and inspect Parent’s properties; and (C) provide each Investor with
copies of Parent’s weekly pacing reports and monthly P&L reports on a market basis and any other
reports reasonably requested by such Investor.

          (b) From and after the Investment Closing Date, each Party shall, and shall cause its
Affiliates and Representatives to, treat all materials and information provided pursuant to this
Agreement as confidential. Notwithstanding the foregoing, the restrictions set forth in this
Section 4.4(b) shall not apply to the extent that any Person otherwise restricted hereunder can
demonstrate that the applicable information (1) was acquired on a non-confidential basis by such
Person, (2) is in the public domain through no fault of such Person or any of its Affiliates or
Representatives or (3) is required to be disclosed by applicable Law (whether by deposition,
interrogatory, request for documents, subpoena, civil investigative demand or similar process)
after providing prompt written notice of such request so that the other Party may seek an
appropriate protective order or other appropriate remedy.

          (c) No investigation by any Party or its Representatives will affect the representations and
warranties of such Party set forth in this Agreement.

     4.5 Advice of Changes. Parent and each Investor will promptly advise the other
Parties of any change or event (a) having, or that would be reasonably likely to have, individually
or in the aggregate, a Material Adverse Effect on Parent or materially adversely affect such
Investor’s ability to consummate the Investment Transactions, as the case may be or (b) that it
believes would, or would be reasonably likely to, cause or constitute a material breach of any of
its representations, warranties or covenants contained in this Agreement, except that (1) no such
notification will affect the representations, warranties or covenants of the Parties (or remedies
with respect thereto) or the conditions to the obligations of the Parties under this Agreement and
(2) a failure to comply with this Section 4.5 will not constitute the failure of any condition set
forth in Article VI to be satisfied unless the underlying effect or material breach would
independently result in the failure of a condition set forth in Article VI to be satisfied.

ARTICLE V

ADDITIONAL AGREEMENTS

     5.1 Cumulus Media Partners. Parent shall use commercially reasonable efforts to, on
or before the Investment Closing Date, consummate the transactions contemplated by that certain
Exchange Agreement, dated as of January 31, 2011, by and among Parent, The Blackstone Group and the
other parties signatory thereto

15

 

(the “Exchange Agreement”) and shall make all necessary
consents, approvals and filings contemplated therein. Parent will promptly advise the Investors
upon receiving any material communication from any Governmental Entity, the consent or approval of
which is required for consummation of the transactions contemplated by the Exchange Agreement.
Without the prior written consent of the Crestview Investor and the Macquarie Investor (in each
case, not to be unreasonably withheld), Parent will not effect any material amendment to the terms
of the Exchange Agreement.

     5.2 Certain Transactions. Parent shall not merge or consolidate into, or sell,
transfer or lease all or substantially all of its property or assets to, any other party unless the
successor, transferee or lessee party, as the case may be (if not Parent), expressly assumes the
due and punctual performance and observance of each and every covenant and condition of this
Agreement to be performed and observed by Parent.

     5.3 Nasdaq Stock Market Listing. Parent will use commercially reasonable efforts to
cause the shares of Parent Class A Common Stock to be issued pursuant to this Agreement and the
shares of Parent Class A Common Stock reserved for issuance pursuant to the exercise of the
Investor Warrants or reserved for conversion or exchange of Class B Warrant Shares or conversion of
Parent Series C Preferred, to be approved for listing on the Nasdaq Stock Market, subject to
official notice of issuance, prior to the Investment Closing.

     5.4 Monitoring Fee. At or prior to the Investment Closing, Parent and the Crestview
Investor shall enter into a customary monitoring agreement pursuant to which Parent will pay to an
Affiliate of the Crestview Investor designated by the Crestview Investor a monitoring fee in the
amount set forth on Exhibit F, payable quarterly in arrears, until the fifth
(5th) anniversary of the Investment Closing (the “Monitoring Agreement”).

     5.5 Registration Rights Agreement. Prior to the Investment Closing, each Party shall
negotiate in good faith with the other Parties to enter into, concurrently with the Investment
Closing, the Registration Rights Agreement.

     5.6 Stockholders Agreement. Prior to the Investment Closing, each Party shall
negotiate in good faith with the Parent Significant Stockholders and the other Parties to enter
into, concurrently with the Investment Closing, the Stockholders Agreement.

     5.7 Shareholder Rights Plan. On the Investment Closing Date, the Parent Board shall
adopt a shareholders rights plan substantially upon terms the terms set forth in Exhibit G.

     5.8 Employee Incentive Plan. Parent shall, prior to distribution of the Joint
Proxy/Information Statement to its stockholders, submit to its stockholders, whether at a meeting
or by majority action taken by written consent without a meeting, a proposal to approve a new
employee incentive equity plan substantially upon terms set forth in

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Exhibit H (the
“New Incentive Plan”), and, contemporaneously with the Investment Closing, shall make the
grant of initial awards thereunder that is described in Exhibit H.

     5.9 Debt Commitments.

          (a) Parent hereby affirms and agrees that it is bound by the provisions set forth in its Debt
Commitment Letter and that each Investor is in accordance with the terms of such Debt Commitment
Letter an express third-party beneficiary thereof, subject to the limitations set forth in such
Debt Commitment Letter, and that the Debt Commitment Letter provides that the Financing
Documentation (as defined in the Debt Commitment Letter) shall contain equivalent provisions upon
execution thereof in respect of periods prior to the Effective Time of the Merger. Parent shall
not, without the consent of an Investor, amend or waive such requirement that the Financing
Documentation contain such equivalent third-party beneficiary provisions with respect to such
Investor.

          (b) Parent will use its reasonable best efforts to take, or cause to be taken, all actions and
to do, or cause to be done, all things necessary, proper or advisable to arrange and obtain the
Debt Financing on the terms and conditions described in the Debt Commitment Letters and will not
permit any amendment or modification to be made to, or any waiver of any provision or remedy under,
the Debt Commitment Letters and, to the extent definitive agreements with respect to the Debt
Financing have been entered into, such agreements (but solely with respect to such actions to be
taken prior to the Effective Time of the Merger), without the prior written consent of each
Investor. Without limiting the foregoing, Parent shall use commercially reasonable efforts to
negotiate and enter into definitive agreements with respect to the Debt Commitment Letters on terms
and conditions contained in the Debt Commitment Letters or consistent in all material respects with
the Debt Commitment Letters as promptly as practicable after the date of this Agreement. In the
event that Parent is unable to enter into such definitive agreements, Parent shall cooperate and
consult with the Investors to arrange and obtain alternative debt financing if so elected by any
Party, which will be on terms acceptable to the Investors.

          (c) Parent shall use reasonable best efforts to (1) provide the Investors and their
Representatives with a reasonable opportunity to participate with Parent in all discussions
(including any meeting, conference or telephonic call) with any lender providing a commitment under
a Debt Commitment Letter and (2) consult with the Investors on all definitive agreements with
respect to any Debt Commitment Letter and (3) cooperate with the Investors with respect to
additions, deletions or changes suggested by the Investors in connection therewith.

          (d) The rights and obligations contained in Section 5.9(c)(3) shall not apply to the Macquarie
Investor to the extent (and only to the extent) that such rights or obligations involve actions to
be taken directly in respect of any Affiliate of the Macquarie Investor that is party to a Debt
Commitment Letter, acting in its capacity as a lender. For the avoidance of doubt, this Section
5.9(d) shall not apply to any actions to

17

 

be taken directly in respect of the lead arranger,
administrative agent or any other lender under the Debt Financing that is not an Affiliate of the
Macquarie Investor.

     5.10 Actions under this Agreement and the Merger Agreement. Neither Parent nor any of
its Subsidiaries shall (a) waive compliance with any covenants, agreements or conditions to closing
specified in Article VII of the Merger Agreement (the “Merger Closing Conditions”),
(b) amend or modify the Merger Agreement, (c) terminate the Merger Agreement, (d) agree to set the
Election Deadline on a date that is fewer than ten (10) Business Days preceding the anticipated
Closing Date under the Merger Agreement, or (e) take any other actions with respect to rights and
obligations under the Merger Agreement, unless in the case of (a) through (e) above, such action
has been approved by each Investor; provided, that Parent and its Subsidiaries may, without
the consent of either Investor, extend the End Date to a date that is not later than fifteen (15)
months after the date of this Agreement; and, provided further, that if the
Crestview Investor or the Macquarie Investor, as the case may be, is a Withdrawing Investor
pursuant to Section 5.11, then any action described in (a) through (e) above shall require only the
approval of the Crestview Investor (if it is the Continuing Investor) or the Macquarie Investor (if
it is the Continuing Investors), as the case may be. In the event that the Merger Closing
Conditions are satisfied or, with consent of each Investor (or the Continuing Investor(s), as the
case may be), validly waived, any Investor that has funded its Investment Amount or is willing to
fund its Investment Amount (each, a “Funding Investor”) may, with the consent of Parent,
terminate the participation in the transaction of any such other Investor (the “Failing
Investor”) if the Failing Investor does not fund its Investment Amount or asserts in writing
its unwillingness to fund its Investment Amount; provided that such termination shall not
affect Parent’s or the Funding Investor’s rights against such Failing Investor with respect to such
failure to fund, including those set forth in Sections 5.14 and 5.15. Notwithstanding any
provisions of this Agreement to the contrary, the Continuing Investor may replace the Failing
Investor’s Investment Amount with the consent of Parent (such consent not to be unreasonably
withheld). If an Investor becomes a Failing Investor, such Failing Investor shall no longer be
entitled to any approval or consent rights under this Agreement.

     5.11 Withdrawing Investor. If there is a right of an Investor to terminate this
Agreement with respect to itself, or a right of Parent to terminate the Merger Agreement, pursuant
to the terms hereof or thereof, and if such Investor desires to terminate this Agreement with
respect to itself, or an Investor desires that Parent terminate the Merger Agreement, as a result
thereof, such Investor (the “Withdrawing Investor”) shall notify Parent and the other
Investor of such desire. If Parent and the other Investor (the “Continuing Investor”)
desire to consummate the Investment Transactions without any involvement by the Withdrawing
Investor, then Parent, the Continuing Investor and the Withdrawing Investor shall cooperate in such
reasonable arrangements to permit Parent and the Continuing Investor to proceed with the Investment
Transactions and to terminate any liability or obligation of the Withdrawing Investor under this
Agreement (other than with respect to any breach by the Withdrawing Investor of this Agreement, the
Crestview Equity Commitment Letter (solely with respect

18

 

to the Crestview Investor) and its Sponsor
Guarantee prior to the date of the completion of such arrangements).

     5.12 Contribution With Respect to Sponsor Guarantees. In the event that the Merger
Agreement is terminated, Parent and each of the Investors shall cooperate in defending any claim
that Parent and the Investors are or any one of them is liable to pay the Parent Termination Fee
(or any portion thereof) and/or any amounts pursuant to Section 6.13(d) of the Merger Agreement
(such amounts, the “6.13(d) Expenses”). Subject to Section 5.13 (including, for the
avoidance of doubt, the Investor Liability Cap), in the event that the Merger Agreement is
terminated and Parent or any Investor has paid the Parent Termination Fee (or any portion thereof)
and/or any 6.13(d) Expenses in excess of such Party’s pro rata share thereof (based on such Party’s
Investment Percentage), Parent and each Investor hereby covenants and agrees to contribute to the
amount paid by Parent and/or the other Investor in respect of the Parent Termination Fee and/or the
6.13(d) Expenses so that Parent and each Investor will have paid an amount equal to such Party’s
pro rata share thereof (based on such Party’s Investment Percentage).

     5.13 Cross Indemnification.

          (a) In the event that (1) the Merger Agreement is terminated and the Parent Termination Fee
and/or the 6.13(d) Expenses are payable to the Company thereunder and (2) the Crestview Investor’s
breach of its obligations hereunder or under the Crestview Equity Commitment Letter caused the
termination giving rise to such obligation to pay the Parent Termination Fee and/or the 6.13(d)
Expenses, then the Crestview Investor shall indemnify and hold harmless each of Parent and the
Macquarie Investor from and against their respective pro rata shares (based on such Parties’
respective Investment Percentages) of the Parent Termination Fee and/or the 6.13(d) Expenses (the
“Crestview Indemnifiable Losses”). For purposes of this Section 5.13(a), the Crestview
Investor shall not be deemed to be in breach of its obligations hereunder or under the Crestview
Equity Commitment Letter if (A) the conditions set forth in Article VI have been satisfied and (B)
the Crestview Investor certifies in writing to Parent and the Macquarie Investor that it is
prepared and willing to contribute or cause to be contributed its Investment Amount but the
Crestview Investor has not contributed or caused to be contributed its Investment Amount because
the Macquarie Investor has refused to contribute or cause to be contributed its Investment Amount
in breach of this Agreement. Notwithstanding anything herein to the contrary, in no event shall
the liability of the Crestview Investor under this Section 5.13(a) exceed the sum of the pro rata
shares (based on Investment Percentages) of the Parent and the Macquarie Investor of the Parent
Termination Fee and Section 6.13(d) Expenses.

          (b) In the event that (1) the Merger Agreement is terminated and the Parent Termination Fee
and/or the 6.13(d) Expenses are payable to the Company thereunder and (2) the Macquarie Investor’s
breach of its obligations hereunder caused the termination giving rise to such obligation to pay
the Parent Termination Fee and/or the 6.13(d) Expenses, then the Macquarie Investor shall indemnify
and hold harmless each of Parent and the Crestview Investor from and against Parent’s and the
Crestview

19

 

Investor’s respective pro rata shares (based on such Parties’ respective Investment
Percentages) of the Parent Termination Fee and/or the 6.13(d) Expenses (the “Macquarie
Indemnifiable Losses”). For purposes of this Section 5.13(b), the Macquarie Investor shall not
be deemed to be in breach of its obligations hereunder if (A) the conditions set forth in Article
VI have been satisfied and (B) the Macquarie Investor certifies in writing to Parent and the
Crestview Investor that it is prepared and willing to contribute or cause to be contributed its
Investment Amount but the Macquarie Investor has not contributed or caused to be contributed its
Investment Amount because the Crestview Investor has refused to contribute or cause to be
contributed its Investment Amount in breach of this Agreement or the Crestview Equity Commitment
Letter. Notwithstanding anything herein to the contrary, in no event shall the liability of the
Macquarie Investor under this Section 5.13(b) exceed the sum of the pro rata shares (based on
Investment Percentages) of the Parent and the Crestview Investor of the Parent Termination Fee and
Section 6.13(d) Expenses.

          (c) In the event that (1) the Merger Agreement is terminated and the Parent Termination Fee
and/or the 6.13(d) Expenses are payable to the Company thereunder and (2) the termination giving
rise to such obligation to pay the Parent Termination Fee and/or the 6.13(d) Expenses was not
caused by (A) the breach of any Investor hereunder or under the Crestview Equity Commitment Letter
(solely with respect to the Crestview Investor) or (B) the failure of any lender to provide the
Debt Financing to Holdco at the Closing in breach of the Debt Commitment Letters or, to the extent
definitive agreements with respect to the Debt Commitment Letters have been entered into, such
agreements, then Parent shall indemnify and hold harmless each Investor from and against the Parent
Termination Fee and/or the 6.13(d) Expenses.

          (d) Parent agrees that if the Transactions are not consummated due to the failure of any
lender to provide the Debt Financing to Holdco at the Closing in breach of the Debt Commitment
Letters or, to the extent definitive agreements with respect to the Debt Commitment Letters have
been entered into, such agreements, then each Investor shall be entitled to bring or maintain any
claim, action or proceeding against any lender in connection with such Debt Financing, subject to
the terms and conditions of the Debt Commitment Letter, for any damages resulting from such breach
and shall be entitled to recover (on a pro rata basis with Parent based on such Investor’s
Investment Percentage) any proceeds received by Parent as a result of any recovery, judgment or
damages of any kind against any lender.

          (e) To the extent that the amount paid by any Investor, pursuant to the Merger Agreement or
its Sponsor Guarantee, in respect of the 6.13(d) Expenses, exceeds such Investor’s pro rata share
(based on Investment Percentages) of $600,000, Parent shall indemnify such Investor for the amount
of such excess.

     5.14 Notice of Closing. Parent will use its reasonable best efforts to provide each
Investor with at least fifteen (15) days’ prior notice of the Closing Date under the Merger
Agreement. Any notices or correspondence received by Parent under, in connection with, or related
to the Merger Agreement shall be promptly provided to each Investor in accordance with
Section 8.4(a).

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          5.15 Macquarie Investor Syndication. Prior to the Investment Closing, the Macquarie
Investor shall have the opportunity to sell or assign to third parties up to the full amount of the
Syndication Portion of the Macquarie Investor’s aggregate Investment Amount (the “Macquarie
Investor Syndication”); provided, that (a) no such assignment or purchase will relieve
the Macquarie Investor of its obligations hereunder; (b) any such purchaser or assignee will not be
entitled to purchase Parent Straight Preferred and instead will only be entitled to purchase shares
of Parent Class A Common Stock (if not a Non-U.S. Person), Parent Series C Preferred or, if a
Non-U.S. Person, Class B Warrants, and (c) the Macquarie Investor will not be permitted to so
syndicate to a single transferee (or one or more transferees with the same “ultimate parent entity”
for HSR Clearance purposes) an amount of Parent securities that would require such assignee to
obtain HSR Clearance in respect of such purchase of Parent securities, or that would require that
such transferee be named in the FCC Applications, or that would involve such purchaser, assignee or
its Affiliates acquiring more than 4.99% of the outstanding voting securities of Parent for
purposes of the Communications Act or FCC Regulations. The price per share of Parent Class A
Common Stock, Class B Warrants, or Parent Series C Preferred, syndicated by the Macquarie Investor,
and the other terms and conditions of such sale, shall be set by the Macquarie Investor in its
discretion and may vary from buyer to buyer, so long as Parent receives at the Investment Closing
$4.34 per share of Parent Class A Common Stock, or Class B Warrant Share, or share of Parent
Common Stock into which the Parent Series C Preferred is convertible (including Class B Warrants if
Parent Series C Preferred is exchanged for Class B Warrants), so syndicated by the Macquarie
Investor. Parent will use commercially reasonable efforts to provide to the Macquarie Investor, and
will cause its Subsidiaries to use commercially reasonable efforts to provide, at Parent’s cost and
expense as provided in Section 8.2, and will use commercially reasonable efforts to cause its
Representatives to provide, all cooperation reasonably requested by the Macquarie Investor that is
customary and reasonably necessary in connection with arrangement of the Macquarie Investor
Syndication and causing the conditions in this Agreement to be satisfied, including (1) assisting
with the preparation of offering and syndication documents and materials, including prospectuses,
private placement memoranda, information memoranda and packages, investor presentations, and
similar documents and materials, in connection with the Macquarie Investor Syndication, and
providing reasonable and customary authorization letters to the Macquarie Investor authorizing the
distribution of information to prospective investors and containing customary information (all such
documents and materials, collectively, the “Offering Documents”), (2) participating in a
reasonable number of meetings, due diligence sessions and drafting sessions in connection with the
Macquarie Investor Syndication, including direct contact between senior management and
Representatives of Parent and its Subsidiaries and the Macquarie Investor and potential investors
in the Macquarie Investor Syndication, (3) requesting Parent’s independent auditors to cooperate
with the Macquarie Investor’s commercially reasonable efforts to obtain accountant’s comfort
letters and consents from Parent’s independent auditors, (4) assisting in the preparation of
definitive Offering Documents, including underwriting or securities purchase documents and other
certificates and documents as may be requested by the Macquarie Investor and (5) facilitating the
evaluation by potential investors in the Macquarie Investor Syndication, including taking
commercially reasonable actions

21

 

necessary to permit such potential investors to evaluate Parent’s
and its Subsidiaries’ real property and current assets, cash management and accounting systems,
policies and procedures. In connection with the foregoing, Parent will file with the SEC all
Parent Reports for the annual and quarterly fiscal periods ending on and after December 31, 2010 as
soon as practicable but in any event not later than (A) ninety (90) days following the end of
Parent’s fiscal year, in the case of annual reports on Form 10-K and (B) forty-five (45) days
following the end of each fiscal quarter of the Parent, in the case of quarterly reports on Form
10-Q, all of which such Parent Reports will be Compliant. Parent hereby consents to the use of
Parent Subsidiaries’ logos in connection with the Macquarie Investor Syndication; provided,
however, that such logos are used solely in a manner that is not intended, or reasonably likely, to
harm or disparage Parent or any Parent Subsidiary or the reputation or goodwill of Parent or any
Parent Subsidiary. In addition, promptly following the date hereof, Parent shall engage Macquarie
Capital (USA) Inc. (“Macquarie Capital”), for no consideration or payment of any kind
(exclusive of any payment that might be made pursuant to the indemnification provisions thereof),
to act as exclusive placement agent in respect of the Parent Class A Common Stock, Class B Warrants
and Parent Series C Preferred to be placed out of the Syndication Portion. Such engagement shall
be on customary terms for such transactions at such time, including, as applicable,
representations, warranties, covenants, conditions and indemnities; provided, that no
consideration or payment of any kind (exclusive of any payment that might be made pursuant to the
indemnification provisions thereof) shall be paid in connection therewith.

     5.16 Termination Fee. Parent affirms and agrees that any Termination Fee under the
Merger Agreement and any amounts payable pursuant to Section 8.2(c) of the Merger Agreement
received by Parent, will, in accordance with the terms of the “Bank and Bridge Facilities
Commitment Letter” of even date herewith, first be shared ratably among Parent, the Crestview
Investor, the Macquarie Investor and the lenders under the Debt Commitment Letters to reimburse
their respective reasonable and documented expenses in connection with the transactions
contemplated by this Agreement and the Merger Agreement and, after payment of such expenses, will
be shared pro rata among Parent and the Investors based on each Party’s respective Investment
Percentage (but adjusted taking into account the foregoing expense reimbursement of the Parties so
that, in total, each Party receives its pro rata share based upon its respective Investment
Percentage of total amounts received by the Parties hereunder) (and Parent will direct the Company
to pay to each Investor directly such Investor’s pro rata portion of the Termination Fee and any
amounts payable pursuant to Section 8.2(c) of the Merger Agreement to be received by such Investor
in accordance with the foregoing), except that any Failing Investor or Withdrawn Investor shall not
share in any portion of the Termination Fee or any amounts payable pursuant to Section 8.2(c) of
the Merger Agreement, and any such Failing Investor’s or Withdrawn Investor’s share shall be
apportioned among Parent and the other Investors as provided in this sentence.

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ARTICLE VI

INVESTMENT CLOSING CONDITIONS

     6.1 Conditions of Each Party to Investment Closing. The obligations of each Party to
effect the Investment Closing will be subject to the satisfaction, or waiver by such Party, at or
prior to the Investment Closing of the following conditions:

          (a) Investment HSR Clearance. Investment HSR Clearance shall have been obtained.

          (b) FCC. The Initial Order shall have been obtained.

          (c) No Injunctions or Restraints; Illegality. No Injunction preventing the
consummation of the Investment Transactions shall be in effect. No statute, rule, regulation,
order, Injunction or decree shall have been enacted, entered, promulgated or enforced by any
Governmental Entity that prohibits or makes illegal consummation of the Investment Transactions.

          (d) Merger Transaction. All Merger Closing Conditions shall have been satisfied or
waived (subject to Section 5.10), and the Closing shall occur concurrently with the Investment
Closing. For the avoidance of doubt, a determination of the satisfaction of, or waiver by, any
Party of the Merger Closing Conditions in accordance with this Section 6.1(d) shall not be deemed
to constitute a determination of the satisfaction or waiver of such conditions by any other Party.

     6.2 Conditions of Parent to Investment Closing. The obligation of Parent to effect
the Investment Closing with respect to each Investor is also subject to the satisfaction, or waiver
by Parent, at or prior to the Investment Closing, of the following conditions:

          (a) Representations. The representations and warranties of such Investor set forth in
this Agreement shall be true and correct as of the date of this Agreement and as of the Investment
Closing Date as though made on and as of the Investment Closing Date (except that representations
and warranties that by their terms speak specifically as of the date of this Agreement or another
date will be true and correct as of such date); provided, that this condition shall be
deemed satisfied unless all inaccuracies in such representations and warranties in the aggregate
would have a material adverse effect on the ability of such Investor to consummate the Investment
Transactions at the Investment Closing Date (ignoring solely for purposes of this proviso any
reference to materiality qualifiers contained in such representations and warranties), and Parent
shall have received a certificate signed on behalf of such Investor by an authorized signatory of
such Investor to the foregoing effect.

          (b) Performance of Obligations of such Investor. Such Investor shall have performed
in all material respects all obligations required to be performed by it under this Agreement at or
prior to the Investment Closing Date, and

23

 

Parent shall have received a certificate signed on behalf
of such Investor by an authorized signatory of such Investor to such effect.

          (c) Investor Closing Deliverables. Such Investor shall have delivered, or caused to
be delivered, to Parent the items set forth in Section 2.5 applicable to it.

     6.3 Conditions of each Investor to the Investment Closing. The obligation of each
Investor to effect the Investment Closing is also subject to the satisfaction or waiver by such
Investor at or prior to the Investment Closing of the following conditions:

          (a) Representations. The representations and warranties of Parent set forth in
Section 3.1 (other than the representations and warranties set forth in Section 3.1(c)) shall be
true and correct in all material respects as of the date of this Agreement and as of the Investment
Closing Date as though made on and as of the Investment Closing Date (except that representations
and warranties that by their terms speak specifically as of the date of this Agreement or another
date will be true and correct in all material respects as of such date), and each Investor shall
have received a certificate signed on behalf of Parent by the Chief Executive Officer or the Chief
Financial Officer of Parent to the foregoing effect. For the avoidance of doubt, it shall not be a
condition to the Investors’ obligations under this Agreement that the representations and
warranties of Parent made in Section 3.1(c) be true and correct, either as of the date of this
Agreement or as of the Investment Closing Date, and the Investors’ sole remedy in respect thereof
shall be as provided in Section 8.1.

          (b) Performance of Obligations of Parent. Parent shall have performed in all material
respects all obligations required to be performed by it under this Agreement at or prior to the
Investment Closing Date, and each Investor shall have received a certificate signed on behalf of
Parent by the Chief Executive Officer or the Chief Financial Officer of Parent to such effect.

          (c) Parent Closing Deliverables. Parent shall have delivered, or caused to be
delivered, to each Investor the items set forth in Section 2.4.

          (d) Financing. Parent or Holdco shall have received (simultaneously with the
Investment Closing) the proceeds of (1) the Debt Financing and (2) the other Investors’ Investment
Amounts; provided, that if the only condition to funding the Debt Financing and/or the
other Investors’ Investment Amounts that is not satisfied at the Investment Closing is the
contribution of the Investment Amount to Parent by such Investor, then the conditions described in
clauses (1) and (2) in this Section 6.3(d) shall be deemed satisfied or waived.

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ARTICLE VII

TERMINATION

     7.1 Termination. This Agreement may be terminated prior to the Investment Closing
with respect to the applicable Parties as follows:

          (a) by mutual written agreement of Parent and one (1) or more Investors, which termination
shall be effective as between or among Parent and such Investor(s);

          (b) by any Party with respect to itself, upon written notice to the other Parties, if the
Investment Closing shall not have occurred on or prior to the End Date (as the End Date may be
extended in accordance with Section 8.1(b)(i) of the Merger Agreement and Section 5.10 of this
Agreement), which termination shall be effective with respect to such Party;

          (c) by any Party with respect to itself, upon written notice to the other Parties, if any
Governmental Entity of competent jurisdiction will have enacted or issued any final and
non-appealable Law or order or taken any other final and non-appealable action enjoining or
otherwise prohibiting consummation of the Investment Transactions, which termination shall be
effective with respect to such Party; provided that the Party seeking to terminate this
Agreement pursuant to this Section 7.1(c) has complied with its obligations under Section 4.3;

          (d) by any Party, upon written notice to the other Parties, if the Merger Agreement shall have
been terminated, which termination shall be effective as among all Parties;

          (e) by any Investor with respect to itself, upon a breach of any covenant or agreement on the
part of Parent, or any failure of any representation or warranty of Parent to be true and accurate,
in any case such that a condition set forth in Section 6.3(a) or (b) would not be satisfied and
such breach or failure is incapable of being cured, or if capable of being cured, will not have
been cured within thirty (30) days following receipt by Parent of written notice of such breach or
failure (or, if earlier, the End Date), which termination shall be effective as between such
Investor and Parent; or

          (f) by Parent, with respect to any Investor, upon a breach of any covenant or agreement on the
part of such Investor, or any failure of any representation or warranty of such Investor to be true
and accurate, in any case such that a condition set forth in Section 6.2(a) or (b) would not be
satisfied and such breach or failure is incapable of being cured, or if capable of being cured,
will not have been cured within thirty (30) days following receipt by such Investor of written
notice of such breach or failure (or, if earlier, the End Date), which termination shall be
effective as between Parent and such Investor; provided, however, that the right to
terminate this Agreement under this Section 7.1(f) will not be available to Parent if it is then in
breach of any

25

 

representation or warranty or covenant that would result in the closing condition set
forth in Section 6.3(a) or Section 6.3(b) not being satisfied.

     7.2 Effects of Termination. In the event of any termination of this Agreement as
provided in Section 7.1, this Agreement (other than Section 5.12, 5.13, 5.16, this Section 7.2 and
Article VIII, which shall remain in full force and effect) shall forthwith become wholly void and
of no further force and effect with respect to Parent and the applicable Investor(s);
provided, that nothing herein shall relieve any Party from liability for intentional breach
of this Agreement.

ARTICLE VIII

MISCELLANEOUS

     8.1 Survival of Representations, Warranties and Covenants; Indemnification.

          (a) None of the representations, warranties and covenants set forth in this Agreement or in
any instrument delivered pursuant to this Agreement will survive the Investment Closing Date,
except for those covenants and agreements contained in this Agreement that by their terms apply or
are to be performed in whole or in part after the Investment Closing Date. Notwithstanding the
foregoing, the representations and warranties of Parent set forth in Section 3.1(c) shall survive
the Investment Closing until the date that is nine (9) months after the Investment Closing and,
notwithstanding any provision of Law or this Agreement to the contrary, the Investors’ sole
recourse in respect of such representations and warranties shall be the right, but only if the
Investment Closing first occurs, to indemnification pursuant to Section 8.1(b).

          (b) Parent hereby covenants and agrees to indemnify each Investor and any Investor Party from,
and hold each of them harmless against, any and all losses, claims, liabilities, damages and
expenses of any kind or nature whatsoever (collectively, “Losses”), that may be incurred by
any of them or asserted against or involve any of them as a result of, arising out of, or in any
way related to any inaccuracy in or breach of Section 3.1(c). If any Investor shall deliver a
notice of a claim for indemnification under this Section 8.1(b) prior to the date which is nine (9)
months after the Investment Closing, then the obligation to indemnify in respect of such inaccuracy
or breach shall survive as to such claim, until such claim has been finally resolved.

     8.2 Expenses. Subject to Section 5.16, each of the Parties shall bear and pay all other
costs and expenses incurred by it or on its behalf in connection with the transactions contemplated
pursuant to this Agreement, except that the fees required for the filing of the Notification and
Report Form pursuant to the HSR Act by the Crestview Investor shall be borne one-half (1/2) by
Parent and one-half (1/2) by the Crestview Investor and the fees required for the filing of the
Notification and Report Form pursuant to the HSR Act by the Macquarie Investor shall be borne
one-half (1/2) by Parent, on the one hand, and one-half (1/2) by the Macquarie Investor, on the
other. Notwithstanding

26

 

the foregoing but without limiting Section 5.16, contemporaneously with the
Investment Closing, Parent shall reimburse each Investor for all reasonable out-of-pocket fees and
expenses, including reasonable fees and expenses of such Investor’s counsel and advisors, incurred
by such Investor in connection with the Investment Transactions.

     8.3 Post-Closing Third-Party Claims. If the Investment Closing occurs, Parent will
indemnify, defend and hold the Investors and the Investor Parties harmless from all Losses arising
out of or related to claims, litigation, proceedings or investigations (“Claims”)
(including derivative proceedings and third party Claims) arising out of or related to this
Agreement or the Merger Agreement or the transactions contemplated hereby or thereby (including the
Merger, the Debt Financing, or the transactions contemplated by this Agreement), excluding any
Losses resulting from the gross negligence or willful misconduct of an indemnified party.

     8.4 Notices. All notices and other communications in connection with this Agreement
will be in writing and will be deemed given if delivered personally, sent via facsimile (with
confirmation), mailed by registered or certified mail (return receipt requested) or delivered by an
express courier (with confirmation) to the Parties at the following addresses (or at such other
address for a Party as will be specified by like notice):

          (a) If to any Investor, to such address as is set forth on Annex B opposite such
Investor’s name.

          (b) If to Parent:

Cumulus Media Inc.

3280 Peachtree Road, N.W.

Suite 2300

Atlanta, Georgia 30305

Attention: Richard S. Denning

Fax: (404) 949-0740

with a copy to (which copy alone shall not constitute notice):

Jones Day

1420 Peachtree Street, N.E.

Suite 800

Atlanta, Georgia 30309-3053

Attention: John E. Zamer

               David Phillips

Fax: (404) 581-8330

     8.5 Counterparts. This Agreement may be executed in two or more counterparts, all of
which will be considered one and the same agreement and will become effective when counterparts
have been signed by each of the Parties and

27

 

delivered to the other Party, it being understood that
each Party need not sign the same counterpart.

     8.6 Entire Agreement. This Agreement (including the documents and the instruments
referred to in this Agreement, including the Merger Agreement), together with the Crestview Equity
Commitment Letter (solely with respect to the Crestview Investor) and the Sponsor Guarantees,
(a) constitutes the entire agreement and supersedes all prior agreements and understandings, both
written and oral, among the Parties with respect to the subject matter of this Agreement, and
(b) are not intended to confer on any Person other than the Parties and their respective successors
and permitted assigns any rights or remedies hereunder. Each Party affirms to the other Parties
that, except for this Agreement and the further agreements and instruments referred to in this
Agreement, except for that certain letter agreement, dated as of the date hereof, in the form
attached hereto as Exhibit J, there are no other agreements between or among any of the
other Parties relating to the subject matter hereof.

     8.7 Governing Law. This Agreement will be governed and construed in accordance with
the internal Laws of the State of Delaware applicable to Contracts made and wholly performed within
such state, without regard to any applicable conflict of laws principles.

     8.8 Jurisdiction.

          (a) Each of the Parties hereby irrevocably and unconditionally submits, for itself and its
property, to the exclusive jurisdiction of the Delaware Court of Chancery (and if jurisdiction in
the Delaware Court of Chancery is unavailable, the Federal courts of the United States of America
sitting in the State of Delaware), and any appellate court from any thereof, in any action or
proceeding, whether in contract or in tort or otherwise, arising out of or relating to this
Agreement or in respect of any oral representations made or alleged to be made in connection
herewith, or for recognition or enforcement of any judgment relating thereto, and each of the
Parties hereby irrevocably and unconditionally (1) agrees not to commence any such action or
proceeding except in the Delaware Court of Chancery (and if jurisdiction in the Delaware Court of
Chancery is unavailable, the Federal court of the United States of America sitting in the State of
Delaware), (2) agrees that any claim in respect of any such action or proceeding may be heard and
determined in the Delaware Court of Chancery (and if jurisdiction in the Delaware Court of Chancery
is unavailable, the Federal courts of the United States of America sitting in the State of
Delaware), and any appellate court from any thereof, (3) waives, to the fullest extent it may
legally and effectively do so, any objection which it may now or hereafter have to the laying of
venue of any such action or proceeding in the Delaware Court of Chancery (and if jurisdiction in
the Delaware Court of Chancery is unavailable, the Federal courts of the United States of America
sitting in the State of Delaware), and (4) waives, to the fullest extent it may legally and
effectively do so, the defense of an inconvenient forum to the maintenance of such action or
proceeding in the Delaware Court of Chancery (and if jurisdiction in the Delaware Court of Chancery
is unavailable, the Federal courts of the United States of America sitting in the State of
Delaware). Notwithstanding the foregoing, each of the Parties agrees that it will not

28

 

bring or
support any action, cause of action, claim, cross-claim or third-party claim of any kind or
description, whether in law or in equity, whether in contract or in tort or otherwise, against the
Financing Sources in any way relating to this Agreement, including but not limited to any dispute
arising out of or relating in any way to the Debt Commitment Letter or the performance thereof, in
any forum other than the Supreme Court of the State of New York, Borough of Manhattan, or, if under
applicable law exclusive jurisdiction is vested in the Federal courts of the State of New York (and
appellate courts thereof). Each of the Parties agrees that a final judgment in any such action or
proceeding will be conclusive and may be enforced in other jurisdictions by suit on the judgment or
in any other manner provided by Law. EACH PARTY ACKNOWLEDGES AND AGREES THAT ANY ACTION OR
PROCEEDING, WHETHER IN CONTRACT OR IN TORT OR OTHERWISE, ARISING OUT OF OR RELATING TO THIS
AGREEMENT OR IN RESPECT OF ANY ORAL REPRESENTATIONS MADE OR ALLEGED TO BE MADE IN CONNECTION
HEREWITH, OR FOR RECOGNITION OR ENFORCEMENT OF ANY JUDGMENT RELATING THERETO, IS LIKELY TO INVOLVE
COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE IT HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES
ANY RIGHT IT MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LITIGATION DIRECTLY OR INDIRECTLY
ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY, INCLUDING ANY
LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THE CRESTVIEW EQUITY COMMITMENT LETTER OR THE
PERFORMANCE THEREOF. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (1) NO REPRESENTATIVE, AGENT OR
ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD
NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE EITHER OF SUCH WAIVERS, (2) IT UNDERSTANDS AND HAS
CONSIDERED THE IMPLICATIONS OF SUCH WAIVERS, (3) IT MAKES SUCH WAIVERS VOLUNTARILY, AND (iv) IT HAS
BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND
CERTIFICATIONS IN THIS SECTION 8.8(b).

     8.9 Publicity. None of the Parties will, and none of the Parties will permit any of
its Subsidiaries to, issue or cause the publication of any press release or similar public
announcement with respect to, or otherwise make any public statement concerning, the Investment
Transactions without the prior consent (which consent will not be unreasonably withheld) of the
other Parties; provided, however, that any Party may, without the prior consent of
the other Parties (but after prior consultation with the other Parties to the extent practicable
under the circumstances) issue or cause the publication of any press release or other public
announcement to the extent required by Law or by the rules and regulations of the Nasdaq Stock
Market.

     8.10 Assignment. Except as provided in Section 5.15, neither this Agreement nor any
of the rights, interests or obligations hereunder shall be assigned by any of the Parties (whether
by operation of law or otherwise) without the prior written consent of the other Parties and any
attempt to do so will be null and void; provided that any Investor may assign its rights
and obligations under this Agreement to any Affiliate

29

 

(including any Affiliate of such Investor’s
ultimate parent entity or general partner of such Investor), but in each case only if the
transferee agrees in writing for the benefit of Parent to be bound by the terms of this Agreement
(any such transferee shall be included in the term “Investor”); provided, further,
that no such assignment shall relieve such Investor of its obligations hereunder. Without limiting
the foregoing, from and after the Investment Closing, none of the rights of any Investor hereunder
shall be assigned to, or enforceable by, and none of the obligations of any Investor hereunder
shall be applicable to, any Person to whom an Investor may Transfer Securities (including any
shares of Common Stock issued upon exercise of the Warrants). Subject to the preceding sentence,
this Agreement shall be binding upon, inure to the benefit of and be enforceable by the Parties
hereto and their respective permitted successors and assigns.

     8.11 Remedies.

          (a) The Parties agree that irreparable damage would occur in the event that any of the
provisions of this Agreement to which the right of specific performance is applicable were not
performed in accordance with their specific terms or were otherwise breached and that in any such
case any breach of this Agreement could not be adequately compensated by monetary damages alone.
Each Party accordingly agrees, to the extent specific performance is available to any of the other
Parties under this Section 8.11, not to raise any objections to the availability of the equitable
remedy of specific performance to prevent or restrain breaches or threatened breaches of, or to
enforce compliance with, the covenants and obligations of such Party under this Agreement all in
accordance with the terms of this Section 8.11. Any Party seeking an Injunction or Injunctions to
prevent breaches of this Agreement and to enforce specifically the terms and provisions of this
Agreement shall not be required to post a bond or undertaking in connection with such order or
Injunction sought in accordance with the terms of this Section 8.11. Notwithstanding anything
herein to the contrary, the Parties further agree that, except as set forth in this Section 8.11,
Parent shall not be entitled to an Injunction or Injunctions to prevent breaches of this Agreement
against any Investor or otherwise obtain any equitable relief or remedy against any Investor.

          (b) Prior to any valid termination of this Agreement pursuant to Article VII, in accordance
with and subject to this Section 8.11:

               (1) each Investor shall be entitled to seek and obtain an Injunction or Injunctions to prevent
breaches of this Agreement and to enforce specifically the terms and provisions of this Agreement;
and

               (2) Parent shall be entitled to seek and obtain an Injunction or Injunctions to prevent
breaches of this Agreement by any Investor and to enforce specifically the terms and provisions of
this Agreement; provided, however, that no such Injunction or Injunctions or
specific performance will be available to prevent breaches of this Agreement or enforce
specifically any term and provision hereof unless and until (A) the conditions set forth in Article
VI, including the Merger Closing Conditions, have been and continue to be satisfied, (B) the Debt
Financing has been funded or is available for funding subject only to a drawdown notice by Parent
or Holdco

30

 

and (C) Parent has irrevocably confirmed in a written notice delivered to each Investor
that, if the Equity Financing and Debt Financing are funded, the conditions set forth in Sections
6.1 and 6.2 are satisfied or waived (which waiver may be conditioned on the Investment Closing).

          (c) Notwithstanding anything herein to the contrary but subject in all cases to each
Investor’s rights to indemnification and contribution under Sections 5.12 and 5.13, the Parties (1)
agree that the maximum aggregate liability of each Investor, its Affiliates and any of its
Representatives for monetary damages under or relating to this Agreement, or any of the
Transactions, to any Person shall be limited to an amount equal to the product of (A) such
Investor’s Investment Percentage multiplied by (B) the sum of (i) the Parent Termination Fee, if
the Merger Agreement is terminated and the Parent Termination Fee is paid to the Company and (ii)
if the Merger Agreement is terminated and the 6.13(d) Expenses are paid to the Company, the lesser
of the actual amount of such 6.13(d) Expenses so paid and $600,000 (the “Investor Liability
Cap”) and (2) prior to any valid termination of this Agreement pursuant to Article VII, or if,
in connection with any such valid termination, no Parent Termination Fee or 6.13(d) Expense is
payable, then the sole and exclusive remedy and recourse of any Party against any Investor and any
Investor Party for damages, equitable relief or otherwise under or related to this Agreement shall
be the equitable relief as provided in Section 8.11(b)(2) and no other claim in law or equity of
any kind may be made against such Investor. Notwithstanding the preceding sentence, the Investor
Liability Cap shall not apply to the Crestview Investor under the circumstances described in
Section 5.13(a) and shall not apply to the Macquarie Investor under the circumstances described in
Section 5.13(b), and the Crestview Investor or the Macquarie Investor, as the case may be, shall be
liable for the Crestview Indemnifiable Losses or the Macquarie Indemnifiable Losses, as the case
may be, in accordance with Section 5.13(a) or Section 5.13(b), as applicable, under the
circumstances and subject to the limitations described therein.

          (d) Parent acknowledges and agrees that it has no right of recovery against, and no personal
liability shall attach to, in each case with respect to damages of Parent and its Affiliates, the
Investor or any of the Investor Parties, whether by or through attempted piercing of the corporate,
limited partnership or limited liability company veil, by or through a claim by or on behalf of the
Parent against any Investor Party, by the enforcement of any assessment or by any legal or
equitable proceeding, by virtue of any statute, regulation or applicable Law, or otherwise, except
for its rights to recover from such Investor (but not any other Investor Party) subject to the
Investor Liability Cap and the other limitations described herein. Recourse against any Investor
shall be the sole and exclusive remedy of Parent and its Affiliates against the Investor Parties in
respect of any liabilities arising under, or in connection with, this Agreement or the Investment
Transactions. Notwithstanding the foregoing, Parent shall be an intended third-party beneficiary
of, with the right to enforce, the Crestview Equity Commitment Letter in accordance with the terms
and conditions thereof.

     8.12 Amendment. This Agreement may be amended by the Parties hereto at any time prior
to the Investment Closing Date; provided, however, that no amendment may be made
that by Law requires further approval by Parent stockholders

31

 

unless such further approval is first
obtained. This Agreement may not be amended except by an instrument in writing signed by the
Parties.

     8.13 Waivers. The conditions to each Party’s obligation to consummate the Investment
Closing are for the sole benefit of such Party and may be waived by such Party in whole or in part
to the extent permitted by applicable Law. No waiver of any Party to this Agreement shall be
effective unless it is in a writing signed by a duly authorized officer of the waiving Party that
makes express reference to the provision or provisions subject to such waiver.

     8.14 No Duty to Other Investors. Each Investor acknowledges that it has not relied on
any other Investor, and that no other Investor (or any Affiliate or representative thereof) has
acted as a financial advisor or fiduciary of such Investor (or in any similar capacity) and has no
duty to such Investor with respect to this Agreement and the Investment Transactions. Each
Investor confirms to each other Investor that each Investor has conducted its own due diligence in
connection with its investment in the Issued Securities and the Investment Transactions and the
other Investors may therefore have information different from, or additional to, the information
possessed by such Investor. In addition, although certain of the other Investors may have shared
information received by them (including information contained in third party reports prepared for
such other Investors) with such Investor, no representation or warranty is being made with respect
to such information by any such Investor or any such third party. Nothing in this Section 8.14 is
meant to limit any duty, obligation or liability Parent may have to any Investor under this
Agreement or otherwise.

     8.15 Severability. If any provision of this Agreement or the application thereof to
any Person (including the officers and directors of the Investors and Parent) or circumstance is
determined by a court of competent jurisdiction to be invalid, void or unenforceable, the remaining
provisions hereof, or the application of such provision to Persons or circumstances other than
those as to which it has been held invalid or unenforceable, shall remain in full force and effect
and shall in no way be affected, impaired or invalidated thereby, so long as the economic or legal
substance of the Investment Transactions is not affected in any manner materially adverse to any
Party provided, that this Agreement shall not be enforced without giving effect to the
limitations of any amounts payable by any Investor hereunder to, as applicable, the Investor
Liability Cap or, under the circumstances and subject to the limitations described in Section
5.13(a) or Section 5.13(b), as applicable, the Crestview Indemnifiable Losses or the Macquarie
Indemnifiable Losses, as the case may be. Upon such determination, the Parties shall negotiate in
good faith in an effort to agree upon a suitable and equitable substitute provision to effect the
original intent of the Parties.

     8.16 Interpretation. Unless the express context otherwise requires:

          (a) the words “hereof,” “herein” and “hereunder” and words of similar import, when used in
this Agreement, shall refer to this Agreement as a whole and not to any particular provision of
this Agreement;

32

 

          (b) terms defined in the singular shall have a comparable meaning when used in the plural, and
vice versa;

          (c) the terms “Dollars” and “$” mean U.S. dollars;

          (d) references herein to a specific Section, Subsection, Recital, Schedule or Exhibit shall
refer, respectively, to Sections, Subsections, Recitals, Schedules or Exhibits of this Agreement;

          (e) wherever the word “include,” “includes” or “including” is used in this Agreement, it shall
be deemed to be followed by the words “without limitation”;

          (f) references herein to any gender shall include each other gender;

          (g) references herein to any Person shall include such Person’s heirs, executors, personal
representatives, administrators, successors and assigns; provided, however, that
nothing contained in this Section 8.16 is intended to authorize any assignment or transfer not
otherwise permitted by this Agreement;

          (h) references herein to a Person in a particular capacity or capacities shall exclude such
Person in any other capacity;

          (i) with respect to the determination of any period of time, (1) the word “from” means “from
and including” and the words “to” and “until” each means “to but excluding” and (2) time is of the
essence;

          (j) the word “or” shall be disjunctive but not exclusive;

          (k) references herein to any Law shall be deemed to refer to such Law as amended, modified,
codified, reenacted, supplemented or superseded in whole or in part and in effect from time to
time, and also to all rules and regulations promulgated thereunder;

          (l) the headings contained in this Agreement are intended solely for convenience and shall not
affect the rights of the Parties; and

          (m) if the last day for the giving of any notice or the performance of any act required or
permitted under this Agreement is a day that is not a Business Day, then the time for the giving of
such notice or the performance of such action shall be extended to the next succeeding Business
Day.

33

 

     8.17 Rules of Construction. The Parties have participated jointly in negotiating and
drafting this Agreement. In the event that an ambiguity or a question of intent or interpretation
arises, this Agreement will be construed as if drafted jointly by the Parties, and no presumption
or burden of proof will arise favoring or disfavoring any Party by virtue of the authorship of any
provision of this Agreement.

[Signatures appear on following page.]

34

 

     IN WITNESS WHEREOF, this Agreement has been duly executed and delivered by the duly authorized
officers of the parties hereto as of the date first herein above written.

	 	 	 	 	 
	 	CUMULUS MEDIA INC.

 	 
	 	By:  	/s/ Lewis W. Dickey, Jr.
 	 
	 	 	Name:  	Lewis W. Dickey, Jr. 	 
	 	 	Title:  	President, Chairman and
Chief Executive Officer 	 
	 
	 	CRESTVIEW RADIO INVESTORS, LLC

By: Crestview Partners II, L.P.,

        its managing member
 	 
	 
	 	By: Crestview Partners II GP, L.P.,

        its general partner

 	 
	 	By: Crestview, L.L.C., its general partner

 	 
	 	By:  	                                                  /s/ Thomas Murphy
 	 
	 	 	Name:  	Thomas Murphy 	 
	 	 	Title:  	Managing Director 	 
	 
	 	MIHI LLC:

 	 
	 	By:  	/s/ Tobias Bachteler
 	 
	 	 	Name:  	Tobias Bachteler 	 
	 	 	Title:  	Authorized Signatory 	 
	 	 	 
	 	By:  	                    /s/ Andrew Underwood
 	 
	 	 	Name:  	Andrew Underwood 	 
	 	 	Title:  	Authorized Signatory 	 
	 

[Signatures Page to Investment Agreement]

 

 

ANNEX A

Crestview Funds

Crestview Offshore Holdings II (892 Cayman), L.P.

Crestview Offshore Holdings II (Cayman), L.P.

Crestview Offshore Holdings II (FF Cayman), L.P.

Crestview Partners II (FF), L.P.

Crestview Partners II (PF), L.P.

Crestview Partners II (TE), L.P.

Crestview Partners II, L.P.

Annex A-1

 

ANNEX B

	 	 	 
	Investor	 	Investment Amount
	CRESTVIEW RADIO INVESTORS LLC
	 	$250,000,000
	 
	 	 
	Address for Notices:
	 	 
	 
	 	 
	Crestview Radio Investors LLC
	 	 
	c/o Crestview Partners II, L.P.
	 	 
	667 Madison Avenue, 10th Floor 

New York, NY 10065
	 	 
	Attention: Jeffrey Marcus
	 	 
	Tom Murphy 

Brian Cassidy
	 	 
	 
	 	 
	Fax: (212) 906-0793
	 	 
	 
	 	 
	with a copy to (which copy alone shall not constitute
notice):
	 	 
	 
	 	 
	Paul, Weiss, Rifkind, Wharton & Garrison LLP
	 	 
	1285 Avenue of the Americas
	 	 
	New York, NY 10019-6064
	 	 
	Attention: Kenneth M. Schneider
	 	 
	 Neil Goldman
	 	 
	Fax: (212) 757-3990
	 	 
	 
	 	 
	MIHI LLC
	 	$250,000,000
	 
	 	 
	Address for Notices:
	 	 
	 
	 	 
	MIHI LLC
	 	 
	125 West 55th St
	 	 
	New York NY 10019
	 	 
	Attention: Capital Advisors Legal Counsel
	 	 
	 
	 	 
	Fax: (212) 231 1718]
	 	 
	 
	 	 
	with a copy to (which copy alone shall not constitute
notice):
	 	 
	Gibson, Dunn & Crutcher LLP
	 	 
	2029 Century Park East
	 	 
	Los Angeles, CA 90067-3026
	 	 
	Attention: Jonathan K. Layne and Ruth Fisher
	 	 
	Fax: (310) 551-8741
	 	 

Annex B-1

 

Exhibits

The following exhibits have been omitted from this exhibit pursuant to Item 601(b)(2) of
Regulation S-K and are not filed herewith. The Registrant agrees to furnish supplementally a copy
of the omitted exhibits to the Securities and Exchange Commission upon request.

	 	 	 

	Exhibit A:

	 	Class B Warrant Term Sheet
	Exhibit B:

	 	Class A Warrant Term Sheet
	Exhibit C:

	 	Registration Rights Agreement Term Sheet
	Exhibit D:

	 	Stockholders Agreement Term Sheet
	Exhibit E:

	 	Terms of Parent Straight Preferred
	Exhibit F:

	 	Form of Monitoring Fee Agreement
	Exhibit G:

	 	Shareholder Rights Plan Term Sheet
	Exhibit H:

	 	Employee Incentive Plan Term Sheet
	Exhibit I:

	 	Parent Series C Convertible Preferred Stock Terms
	Exhibit J:

	 	Letter Agreement by and among the Crestview Investor, Parent and certain of the Parent
Significant Stockholders

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