"Great question, that's a really great question," Richard Bressler says after being asked a question that isn't actually all that great. But presiding over one of the most active and tenacious M&A teams in entertainment takes charm as well as dealmaking smarts - and Bressler, CFO of Viacom Inc., has plenty of both.

Last year alone, Viacom completed at least a half-dozen transactions, including the $1.23 billion acquisition from Time Warner Inc. of the 50% stake in cable channel Comedy Central it didn't already own. Viacom didn't use an investment bank for advice in these deals. "We know our asset base better than anyone," he says. "I'm not sure what an investment banker can bring to us that we can't duplicate ourselves."

Acquisition targets can originate anywhere within Viacom - from division heads to COO Mel Karmazin to CEO Sumner Redstone. But evaluating a potential purchase and executing the deal is the job of Bressler and his team of six, which includes senior vice president and treasurer Bob Freedline and vice president of corporate development Joe Ianniello. All potential acquisitions must be in a Viacom core competency, add to its growth rate and be accretive to earnings per share. If those three criteria are met, the team then delves into issues such as price, structure and payment method.

Now 45, Bressler joined Viacom in May 2001 after 13 years at rival Time Warner. The Long Island resident began his career with Ernst & Young LLP, rising to partner before joining Time Warner in 1988. By 1995 he was that company's CFO, a job he held until 1999.

Bressler was CEO of Time Warner Digital Media when the company announced its merger with America Online Inc. He was soon promoted to a four-person executive committee that oversaw integration of the companies' operations. Upon the deal's closing, AOL's Michael Kelly was named CFO of the combined AOL Time Warner Inc. Bressler became CEO of AOL Time Warner Investments, a nonoperating job. Unhappy with that role, Bressler freed himself from his noncompete and joined Viacom.

As CFO, Bressler's duties extend beyond high-stakes deal negotiations to the nuts and bolts of debt refinancing, budget planning and stock buybacks. The CEOs and CFOs of each of Viacom's six operating units - television, cable, radio, entertainment, outdoor advertising, video - report to and work with Bressler, who then reports to his only two superiors in the company: Karmazin and Redstone.

"I'm a pretty hands-on guy," he says, "so I'm in constant contact with senior management and heads of our divisions about how operations are doing, if we have appropriate budgets, whether we are exceeding those budgets or having any problems and if we are on track to meet our Wall Street guidance."

In 2003 Bressler opportunistically refinanced $1 billion of Viacom debt and renewed a $3 billion credit facility with J.P. Morgan Chase & Co. and Citibank. Buybacks are made at Redstone's direction - last year Viacom repurchased nearly $1 billion worth of its shares. From Jan. 1 through Feb. 9, Viacom acquired $133 million in stock, leaving $1.7 billion in its $3 billion repurchase program.

This year is already shaping up as a busy one for Bressler. Viacom recently announced record revenue of $26.6 billion in 2003 and free cash flow of $3 billion, and Karmazin has said he plans to use the latter for acquisitions. The company also confirmed Feb. 10 that it will divest its 81% stake in the Blockbuster video rental chain through a tax-free spinoff or other alternative (read: sale).

Remember when video rentals were a growth business? When AOL Time Warner seemed like a good idea? Time flies in entertainment. But Bressler clearly enjoys helping to keep Viacom a step ahead of the trends. - Peter Lauria

Join Corporate Dealmaker's LinkedIn forum