Texas furniture kingpin Jim McIngvale better known as Mattress Mack won $75 million on Saturday after his bet that the Houston Astros would win the World Series paid off, taking home what is believed to be the largest payout in legal sports betting history. Ranking the Biggest Gambling Losses of All Time Harry Kakavas: AlmostR$1 Billion. ... Terrance Watanabe:R$204 Million. ... Archie Karas:R$40 Million. ... Charles Barkley:R$20 Million. ... Jim McIngvale: More ThanR$15 Million. ...
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