As chief dealmaker for oil billionaire Robert Bass, David Bonderman made a killing during the last real estate crash. In 1988 the ex-bankruptcy lawyer snagged a troubled California thrift, American Savings Bank, for a mere $400 million, thanks to the billions in federal assistance he received to complete the deal. Eight years later, Bonderman flipped ASB to Washington Mutual for a cool $1.2 billion.
By then he had left Bass to launch his own private equity firm, TPG Capital, which has been behind some of the largest buyouts ever, including casino operator Harrah's Entertainment and utility TXU (now Energy Future Holdings). So wealthy was Bonderman by 2002 that he booked the Rolling Stones for his 60th birthday.
In 2008, Bonderman saw a chance to profit from the latest real estate crisis by putting $1.35 billion into Washington Mutual, which was reeling from huge mortgage losses. This time, though, he didn't have the feds backstopping his losses, and with one board seat, he didn't have control, either.
After frightened bank customers began withdrawing their deposits last fall, regulators seized an insolvent WaMu and sold it to JPMorgan Chase. Bonderman and the rest of WaMu's shareholders saw their stakes wiped out.