What is the Biggest Bet Ever Won?

Top 3 Biggest Ever Bets

Many of the biggest wins in sports betting have come from big-spending pro gamblers with budgets to burn. Here are three of the largest bets ever won. 

“Mattress Mack” Takes Down $75m World Series Score

• $10m placed on the World Series baseball finale
• Bedding businessman picks up when his bet comes in
• Mattress Mack had to travel to Las Vegas to collect his win

Many of the biggest bet wins come courtesy of millionaire entrepreneurs with the capital to back their hunches. And they don’t come much bigger than the $75m won by Jim “Mattess Mack” McIngvale in 2022. 

The furniture magnate won what is thought to be the biggest legal sports wager of all time when he bet $10m on the Houston Astros to beat the Philadelphia Phillies in baseball’s season-ending event. 

The $10m wager, at odds of +750, was too big for regulated online sportsbooks. Therefore, McIngvale journeyed several hundred miles to Las Vegas to collect his winnings. 

“The REAL Dave Oancea” Bags $2.5m on the World Series

• Twitter sensation and pro gambler wins on World Series
• “Vegas Dave” claims to have bet millions on sports
• Big wins include $2.3m on Super Bowl 50

Dave Oancea is a professional gambler and self-styled “#1 person on the planet” who’s also racked up some pretty big wins. He also famously sold a rare baseball card back in 2020 for a cool $3.9m, so “Vegas Dave” knows how to secure profits. 

Vegas Dave’s biggest recorded win came in 2015 when he won $2.5m on the Kansas City Royals. His futures bet came in when the Royals took down the World Series at the end of that season. Oancea followed that up a year later by winning $2.3m on Super Bowl 50. 

Archie Karas Spins up $50 into $40 Million

• Won and lost an alleged $40m in high-stakes cash games
• Arrived in Las Vegas with a $50 bankroll
• Secured $200,000+ in live tournament earnings

Archie Karas was one of the largest Las Vegas gamblers in the 1990s, allegedly racking up tens of millions in poker winnings. The legend goes that Karas arrived in Las Vegas with a few $10 bills in his pocket. Taking to the poker tables, Karas spun his bankroll up to win over $16m in the high-stakes cash tables. 

Like all the best pro gambler stories, Karas lost the lot, mostly in the high-roller Stud and Razz tables around Vegas. However, Karas also proved he was a dab hand at tournaments too. He came close to winning a World Series of Poker bracelet in 2009 when he came 5th in the $10,000 World Championship No-Limit 2-7 Draw event.