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Houston furniture magnate Jim "Mattress Mack" McIngvale made history Saturday night with the largest legal sports betting payout in history  $75 million thanks to the Houston Astros' triumph in the World Series.

Drake finally wins $2 million betting on the Kansas City Chiefs after losing millions on bad sports bets. Drake is known not just for hits like "Hotline Bling." He's also gained a reputation for bad luck when it comes to sports betting.