#27 Kirk Kerkorian
$11.2 billionSource: investments, casinos
Last year's biggest gainer is one of this year's biggest losers. Slumping casino industry has pushed his 52% stake in gambling giant MGM Mirage (nyse: MGM - news - people )—worth $14 billion in October—to a mere $5 billion. Company's stock fell 65% between October and June, volatile since. Another poorly performing investment: Ford. After dabbling in GM for a few years, increased Ford ownership in June; has lost $160 million so far. Eighth-grade dropout trained fighter pilots during WWII. Flew surplus Air Force planes across Atlantic after war before building charter flights company Trans International Airlines; sold for $104 million profit 1966. Sold Flamingo, International hotels to Hilton 1970. Went Hollywood: bought, sold movie studio MGM 3 times between 1986 and 1996. Bought Steve Wynn's Mirage Resorts for $6.4 billion 2000, then Mandalay Bay Resorts for $7.9 billion 4 years later. Today MGM Mirage is Vegas' largest casino by hotel rooms.
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