Clear Channel Communications was one of the largest media outlets when it was purchased in 2006 by Thomas H. Lee Partners and Bain Capital Partners purchased the media giant in 2008 for a price of $17.9 billion dollars. The deal took nearly two years to complete as it was held up in negotiations for a lower purchase price and legal battles. Thomas H. Lee Partners and Bain Capital Partners purchased Clear Channel Communications by using a leveraged loan. A leveraged loan is when a company is purchased by a conglomerate of banks and private equity firms that then share a portion of the purchased companies debt with a risk that each is comfortable in taking on. Clear Channel Communications had about $8 billion in debt that was divided by Thomas H. Lee Partners, Bain Capital Partners and six banks that included, Citigroup, Morgan Stanley, Credit Suisse Group, Royal Bank of Scotland Group, Deutsche Bank and Wachovia Bank.

The six banks did not jump on board easily with the purchase and the large dollar figure of debt that Clear Channel Communications was holding. Thomas H. Lee Partners and Bain Capital Partners had to file lawsuits in New York and Texas against these banks to force them to agree to finance the deal. The banks and capital partners and private equity firms finally came to an agreement to complete the purchase once the share price was adjusted from $39.20 per share down to $36 per share. Once the purchase was finalized Clear Channel Communications went from a publicly traded company to a privately owned company.

In 2018 after accumulating the initial $8 billion in debt and adding an additional $12 billion more Iheart Media formerly Clear Channel Communications filed for bankruptcy. Even after company downsizing, restructuring, selling off of assets, corporate shrinkage the company continued to increase its debt. Shares of the company had been falling since the leveraged buy out in 2008 when they were $36 a share down to .52 cents a share in December of 2015.