So here we are again, nearly 18 months after Clear Channel first took the plunge to go private. And once more, the word is that the deal is finally going to happen. The Wall Street Journal reports that the new price per share is $36 rather than the $39.60 agreed to by shareholders last September (which had been raised previously when the shareholders complained the offer was too low). The difference between now and last fall is substantial though not catastrophic, around $18 billion compared to the previous $19.4 billion. The deal is anticipated to close in the third quarter of '08, dependent on shareholder and regulatory approval. Meanwhile, the two lawsuits filed against the banks backing the deal, one by Clear Channel and one by the participating private equity firms, have been suspended.

Is it possible this previously doomed deal might be rescusitated in the final hour? It's hard to say. Just a week ago, the biggest news coming out of San Antonio was that of CEO Mark Mays's inflated pay package, which reached around $5.2 million in 2007, according to the Associated Press, thanks to a generous salary, bonus, incentives, perks, above-market returns on deferred compensation, and the estimated value of stock options and awards granted during the year.

The banks still stand to lose money on the loans they agreed to make. The shareholders may feel that they're getting the short end of the proverbial stick. At least Clear Channel's management has the action focused on its favorite realm: esoteric finance. However this pie is finally cut, you can bet the Mays family will serve themselves a generous slice.

When the largest concert promoter in the country was known as Clear Channel Entertainment, a division of Clear Channel Communications, it caused its corporate parent a whole lot of headaches, due to ill-timed notions of advertising "synergy," which instead sparked a public uproar. But as a free-standing public company since 2005, known as Live Nation, it has made a remarkable series of deals in a short period of time, all of which suggest the future of the music business may be far rosier than the scenario currently being presented by the imploding major recording labels. 

Live Nation's latest coup, an expected deal with Jay-Z valued at around $150 million, according to the New York Times, includes financial backing for Jay-Z's own entertainment company, as well as recordings and tours over the next ten years. Should the deal come to pass, it will eclipse the scope of two previous Live Nation headline-making maneuvers with Madonna and U2--and could provide sweet vindication for the Mays family, recently navigating extremely stormy waters in their attempt to bring the publicly owned radio giant Clear Channel Communications private.

While Live Nation's executive team does not include a Mays, its board of directors includes Clear Channel chairman Lowry Mays; his son, Randall, who is Clear Channel's CFO; and a daughter of Clear Channel cofounder B.J. "Red" McCombs.

Certainly it would be an astonishing coda to the Clear Channel story if the company blamed--rightly or wrongly--for the cultural decline of radio in some way seeded a company that became a key innovator and savior of the music business.

Something is happening over at Clear Channel these days, but it's hard to say what it is. Over the weekend the embattled radio giant finally closed a contentious deal with Providence Equity Partners, according to the Wall Street Journal. Providence had agreed back in April 2007 to buy the company's TV stations but later threatened to pull out of the agreement due to a softening market. Clear Channel ultimately made the deal happen by cutting the price from more than $1.2 billion to about $1.1 billion.

There was a certain urgency to make the sale. While it has little to do with Clear Channel's bid to go private--another deal that has been stuck in the hopper for a good while--there was a discernable note of schadenfreude in the stutter-stop tone of the closure. Some observers felt that if CCU had trouble closing the smaller deal, how would it fare in closing the other, larger deal, valued at $19.5 billion? CEO Mark Mays said on Saturday that the private equity deal is scheduled to close by the end of the first quarter 2008. But then today, Reuters quoted an inside source as saying the hotly anticipated deal, which has teetered on the brink more than once over the past year, was "not imminently about to close, though the source "believed the private equity buyers were still behind the deal." How's that for uncertainty?

Clear Channel's dilemma is rapidly becoming a good metaphor for today's maybe-it-will-happen, maybe-it-won't media atmosphere. What is the current value of big Old Media properties? It all depends on the week, on the day, and apparently even on the moment that the question is considered. Stay tuned.    

Could the tide be turning in mainstream media-land? If so, Clear Channel Communications is the new trend's bellwether. The Dow Jones newswire reported today that Richard Bressler, managing director of Thomas H. Lee Partners--one of the private equity firms involved in a deal to take Clear Channel private--told the House Telecommunications Subcommittee during a hearing that Clear Channel would be "best served" by owning fewer radio stations in fewer markets.

Guess "synergy" is officially dead.

Clear Channel, like many other big media concerns spent the late 1990's and early 2000's acquiring as many media properties as they legally could in pursuit of a "bigger is always better" strategy. Now these very same companies are tearing themselves apart. In Clear Channel's case, it spun off its entertainment division as Live Nation; it is also offloading its TV division and many stations in smaller markets.

Bressler said that "this streamlined approach" would "enable Clear Channel to more efficiently deploy and market its digital offerings in the face of competitive challenges from other digital platforms." Of course, Bressler was simply trying to defend the $22 billion deal his firm is involved in to a panel that was assembled to investigate the role private equity is playing in media consolidation. Then again, hearing such talk from Bressler, who also happens to be the former CFO of both AOL Time Warner and Viacom, carries much added weight, to say the very least.