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Mattress Mack Wins $72.66 Million, Biggest Win in Sports Betting History.

Topline. 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.

A common sure bet is a two-way sure bet in which there's no draw outcome. An example of this would be a tennis match, a basketball game, an ice hockey game with overtime and penalties included and so on. It's easy to bet on a two-way sure bet, as you only have to bet on two outcomes between two sportsbooks.

A sure bet involves a customer betting on all the available selections for a specific betting market. In doing so, they make a profit no matter the outcome of that market, generally using a calculator. This type of betting must be done with more than one bookie and generally applies to 2-way or 3-way betting markets.