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David Bonderman

Getty Images

David Bonderman

Loss this year, with partners: $7 billion

During a previous banking and real estate crunch, David Bonderman made a killing for investor Robert Bass. Bonderman, a former Washington lawyer, bought the troubled thrift American Savings with $1.7 billion in federal assistance in 1989. Seven years later the bank was sold to rapidly expanding Washington Mutual (WM) for $1.2 billion.

By then, Bonderman had already moved on to co-found TPG, a private equity firm that has since been behind some of the largest buyouts of all time, including utility TXU (TXU) and casino operator Harrah's Entertainment.

In early 2008, Bonderman saw an opportunity to profit again from a banking crisis. He put $1.35 billion into Washington Mutual. This time Bonderman didn't have the federal government backstopping his losses. He also didn't even have control of the company, just one seat on the board.

After frightened bank customers began withdrawing their deposits last fall, federal regulators stepped in, declaring Washington Mutual insolvent and selling it to JPMorgan Chase (JPM). Bonderman and his partners were wiped out. In distressed investing, they call a deal like Washington Mutual 'catching a falling knife.'