Triple Crown Media (TCMI)

Introduction

The following analysis of our financial condition and results of operations should be read in conjunction with our audited combined financial statements and notes thereto included elsewhere in this Form 10-K. All references to Triple Crown Media, Inc., “TCM”, “we,” “us,” or “our” in this discussion refer to the consolidated Newspaper Publishing business. The Newspaper Publishing business has historically operated as a wholly-owned subsidiary or division of Gray and since June 30, 2005, has operated as Gray Publishing LLC, a wholly-owned limited liability company and subsidiary of Gray prior to the Spin-off and of TCM, subsequent to the Spin-off.

We do not anticipate meeting certain future debt compliance covenants (First Lien leverage and total leverage ratio) in the fiscal year ending June 30 2009. Without waiver of these violations, which could occur at any time between now and June 30, 2009, and/or restructuring of our debt, our bank could accelerate our payment provisions. Further, the sale of Host and Pinnacle resulted in $2.6 million of tax liabilities which began to come due on September 15, 2008. Assuming no acceleration of payments, material portions of our debt facilities become due in December 2009, June 2010 and December 2010. In order to meet these obligations, we will be required to restructure our current credit facilities and refinance with another lender. In the case of our income tax obligations, we are negotiating with the taxing authorities to arrange a payment plan which will allow us to spread our payments over an extended period of time. Should we be unsuccessful in these restructuring efforts, we will attempt to derive capital from alternate sources which may include any of the following; private placement, the issuance of additional shares of preferred stock or other means not yet identified. In the event that we are not able to arrange a payment plan for our tax obligations, or refinance our debt obligations, we may not have sufficient liquidity to operate.

These factors raise substantial doubt as to our ability to continue as a going concern. The accompanying financial statements have been prepared on a going concern basis which assumes continuity of operations and realization of assets and liabilities in the ordinary course of business. The financial statements do not include any adjustments that might result from the outcome of this uncertainty.

Introduction

FACE="ARIAL" SIZE="2">The following analysis of our financial condition and results of operations should be read in conjunction with our audited combined financial statements and notes thereto included elsewhere in this Form 10-K. All references to
Triple Crown Media, Inc., “TCM”, “we,” “us,” or “our” in this discussion refer to the consolidated Newspaper Publishing business. The Newspaper Publishing business has historically operated as a wholly-owned
subsidiary or division of Gray and since June 30, 2005, has operated as Gray Publishing LLC, a wholly-owned limited liability company and subsidiary of Gray prior to the Spin-off and of TCM, subsequent to the Spin-off.

Introduction

The following analysis of the financial condition and results of operations of Triple Crown Media, Inc., or the Company, should be read in conjunction with the Triple Crown Media, Inc. audited combined and consolidated financial statements and notes thereto included elsewhere in this Form 10-K. All references to Triple Crown Media, Inc., “TCM”, “we,” “us,” or “our” in this discussion refer to the consolidated Newspaper Publishing business, Collegiate Marketing business and Association Management business. The Newspaper Publishing business has historically operated as a wholly-owned subsidiary or division of Gray and since June 30, 2005, has operated as Gray Publishing LLC, a wholly-owned limited liability company and subsidiary of Gray prior to the Spin-off and of the Company, subsequent to the Spin-off. The Collegiate Marketing and Association Management businesses historically operated as divisions of Host Communications, Inc., a wholly owned subsidiary of Bull Run Corporation, or Bull Run, prior to the Merger and as a subsidiary of the Company, subsequent to the Merger.