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Money winners of 2008: Bill Ackman knew Fannie and Freddie were in trouble

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This post is part of our feature on Money Winners of 2008. See all 20.

Bill Ackman, who manages the hedge fund Pershing Capital, was one of the first major investors to realize what poor shape Fannie Mae (NYSE: FNM) and Freddie Mac (NYSE: FRE) were in. He warned that the apparent back-up of the federal government wasn't going to do investors much good unless the company fell apart and had to be bailed out.

"It doesn't matter what the rating agencies say about their capitalization," Ackman told CNBC. "Implicit guarantees don't work in the market that we're in now." And he turned out to be right, of course. Ackman was shorting the debt of Fannie and Freddie.

While Ackman has had to take some heat from investors who blame him for profiting off Fannie and Freddie's collapse, some critics say he was a bloodsucker, others point to his keen analysis as the reason we should allow short selling: it's the only way to offer an incentive to investors not to believe the hype.

Ackman also did well with Wachovia (NYSE: WB). He figured Citigroup's (NYSE: C) deal was undervalued and he profited when Wells Fargo (NYSE: WFC) offered a better deal. But, even Ackman wasn't able to perfectly play the financial stocks meltdown. He lost money buying AIG (NYSE: AIG).

As of September he told investors that his main fund was up 1.9% for the year -- after fees. Which for this year makes him a big winner.

Be sure to check out more Money Winners of 2008.

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Last updated: July 06, 2009: 11:20 AM

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