Clear Channel Communications' (NYSE:CCU) buyout by private equity investors Bain & Co. and Thomas H. Lee Partners continues to sputter and may not get off the ground. The deal, which was struck in November, would have Clear Channel selling out for $37.60 per share, plus the assumption of $8 billion in debt. It therefore works out to about $26.7 billion for the world's largest operator of radio stations.

What's the impediment to getting the deal done? The company's two largest shareholders, Fidelity Investments and Highfields Capital Management, believe that Clear Channel is worth more than the agreed-to price. Highfields recently increased its stake in the company to about 5% of the total shares out, up from the 3% it previously owned. Fidelity owns slightly less than 10% of the company's shares.

Opposition to the deal -- whose passage would require the approval of two-thirds of the company's holders -- is also based on an analysis by advisory firm Glass Lewis, which believes that Clear Channel's real value lies between $39.71 and $41.40 per share. That opposition has resulted in the company's board moving the date of the shareholders vote to April 19, from the previous March 21. Shareholders of record on March 23 will be permitted to vote, itself a revision from the earlier January 22 date.

In the meantime, Clear Channel CEO Mark Mays and the company's president -- and his brother -- Randall Mays, two sons of the company's founder Lowry Mays, are attempting to generate institutional support for the buyout, with the aid of Goldman Sachs (NYSE:GS), which is representing the company in the transaction, reportedly with a $40 million fee interest in getting it consummated.

But those who would like to see the buyout scuttled point to the company's approximately 90% ownership of billboard company Clear Channel Outdoor (NYSE:CCO). Outdoor's shares have increased more than 20% in value since early 2006 but still trade at a discount to rival Lamar Advertising (NASDAQ:LAMR). The contention is that, absent a buyout, the value of Clear Channel Communications likely would benefit from a sale or spin-off of all or part of Outdoor. Were the buyout to progress, continues the argument, the subsidiary's increased value would result in insufficient value being accorded to the radio operation.

So we're a month away from a resolution of the planned private buyout. Given the distinct possibility that the deal does not get done, along with the subsequent incentives for management to push hard to increase shareholder value, I believe that the company warrants careful attention from Foolish investors.

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Fool contributor David Lee Smith does not own shares in any of the companies mentioned. He welcomes your questions or comments.

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