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Money Face-Off: Kirk Kerkorian vs. Carl Icahn

This post is part of our Money Face-Offs feature. Let us know who you think comes out ahead in this head-to-head match-up, and check out our other Money Face-Off posts.

In this corner, hailing from Beverly Hills and Las Vegas, is 91-year old billionaire investor Kirk Kerkorian, one-time amateur boxer know as "Rifle Right Kerkorian." And in the other corner, hailing from New York, is 71-year-old corporate raider and activist private equity investor, Carl Icahn, who is never afraid to go toe to toe with an opponent.

Let's get ready to rumble.

Round One begins: Kerkorian drops out of school and becomes a pilot. He gets his start in business buying surplus planes after World War II, as well as Las Vegas properties, becoming the landlord of Caesar's Palace. Icahn, meanwhile, establishes his reputation as a corporate raider during his hostile takeover of TWA in 1985, and becomes one of the inspirations for the character of Gordon "Greed Is Good" Gekko, the antagonist of the 1987 film Wall Street.

Along about Round Three, both contenders hit their stride. Icahn at one time or another holds controlling or significant stakes in such companies as RJR Nabisco, Texaco, Viacom (NYSE: VIA), USX, Revlon (NYSE: REV), Time Warner (NYSE: TWX), Motorola (NYSE: MOT), and even Marvel Comics. Kerkorian, however, purchases the MGM studios in 1973, downsizing and disassembling it, selling parts to Ted Turner and Sony (NYSE: SNE), so he can focus on his baby, the MGM Mirage resort. Kerkorian's holding company maintains a majority stake in it to this day. As well as being Director of Blockbuster (NYSE: BBI) and Chairman of Imclone (NASDAQ: IMCL), Icahn sneaks in a quick uppercut by acquiring casino interests in Las Vegas as well.

As the fight drags into the later rounds, both contenders stumble a bit. In 2006 Kerkorian acquires about 10% of General Motors (NYSE: GM), but is unable to effect a merger with Renault; Kerkorian dumps his stake in GM (and the stock price takes a hit). Meanwhile, Icahn has been pushing unsuccessfully for a breakup of Time Warner, and he also fails to get himself on the board of Motorola (though he doesn't sell off his stake). This past spring, Kerkorian also bids on Chrysler, but the automaker ultimately ends up in the hands of Cerberus Capital.

No doubt this fight will last until the end of the tenth and final round: It was recently announced that a Dubai holding company will invest $2.4 billion in Kerkorian's MGM Mirage (NYSE: MGM). And this past week, Icahn became chairman of struggling homebuilder WCI Communities (NYSE: WCI), and immediately took the company off the market. Clearly, he has plans.

With no clear knockout, we'll have to go to the judges for the final score. That would be you, dear reader. Who wins this smackdown?

Vote in our poll for Carl Icahn or Kirk Kerkorian, and let us know in the comments why your choice has the financial edge in this match-up. Also be sure to check out our other Money Face-Offs.

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Last updated: November 08, 2009: 09:42 PM

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