Antagonistic investor Carl Icahn became a billionaire by bullying already distressed companies, but his harassment of Yahoo Inc. could leave him with a black eye — and a hole in his wallet — if he’s wrong about Microsoft Corp.’s desire to buy the Internet pioneer.
Icahn, 72, has used a combination of guile, gall, grit and gamesmanship to get his way more often than not since he began tormenting vulnerable companies 30 years ago. The conquests helped Icahn build an estimated fortune of $14 billion after starting out on Wall Street with a $4,000 bankroll from his winnings playing poker.
His roll call of stock market successes include profitable showdowns with Marshall Field, Phillips Petroleum, Texaco, USX and, most recently, BEA Systems. There have been flops, too: the now-defunct airline TWA and video rental chain Blockbuster Inc., whose stock has lost nearly two-thirds of its value since Icahn bought a stake in the company in 2005 and muscled his way on to the board of directors.
Having spent more than $1 billion for a 4.3 percent stake in the company, Yahoo represents one of Icahn’s biggest bets yet.
The payoff — or possible loss — will hinge largely on the irascible financier’s matchmaking skills as he tries to patch up a tiff between two fellow billionaires, Microsoft Chief Executive Steve Ballmer and Yahoo CEO Jerry Yang.
If he can’t persuade Ballmer to change his mind and renew his pursuit of Yahoo, Icahn could find himself holding a losing hand as investors bail out of Yahoo’s stock.
“There may be some unintended consequences to Icahn’s actions that he hasn’t fully thought about,” said Dennis Carey, senior client partner for Korn/Ferry, which specializes in recruiting chief executives and board directors for corporate boards.
Icahn hasn’t returned repeated phone messages left by The Associated Press during the past three weeks.
But…