With Tiger Woods winning the Masters over the weekend and with sportsbooks online and in Vegas taking a beating with his victory – there are some feel-good stories out there when it comes to bettors winning big. One came from a man in Wisconsin who bet $85,000 on Tiger Woods to win the Masters, which paid out a whopping $1.275 million. It got us to thinking, what are some of the biggest and craziest sports betting wins of all time? Well, we compiled a list of our favorites.
5. Gambler Bets $85k And Wins $1.2Million On Tiger’s Masters Win
We may end up regretting not putting this one higher on the list, but to me, the story still seems, well, a little fake. Still, it’s quite the tale, if it’s all true and James Adducci was indeed on his own when it came to placing the wager with William Hill.
Well, he finally found a casino that accepted the bet at 14/1 odds (which was a horrible price since Tiger was 20/1 at offshore betting sites). Tiger ended up winning the 2019 Masters, and he got quite the payout of $1.275 million.
It’s a great story. I’m just not sure how accurate it is, but congrats to James, anyway.
4. Las Vegas Native Turns $5 Into $100,000 – NFL
We’re all about NFL betting here at Safest Betting Sites, and it’s always great to hear a feel-good story when it comes to wagering on the sport where the sportsbooks rake in the most money from the public. Notably, one that involves a Las Vegas native, who only made a single bet in her life before her big win and had no understanding of how points spreads work.
26-year-old Tayla Polia even thought her parlay was a loser after the Giants lost the game but ended up covering on the point spread. But, she ended up hitting every selection of a 15-team parlay in the 2015 NFL season, which included the Vikings -5, Falcons +3, Texans +1, Redskins +1, Chiefs -8, Cardinals -4, Patriots -14, Seahawks -14, Giants +5, Chargers -2, Packers -3, Steelers -6, Bengals -4, Lions +3 and, Steelers/Broncos Over 45 points.
Her $5 bet had payout odds of 20,000/1. She won a cool $100,000.
3. Anonymous Fan Bets Cardinals Win World Series At 999/1 – MLB
The Cardinals were five games out of the NL Wild Card spot on September 12, 2011. But one St. Louis fan wasn’t losing faith. With 15 games left to play, he placed a $250 bet on them to make the World Series at 500/1. He then put another $250 wager on them to WIN the World Series at 999/1.
Well, St. Louis went on quite the September run. They won game after game and managed to get themselves into the postseason in the NL Wild Card spot. Then, they beat one of the best on-paper teams in the Phillies.
The Cardinals went to the World Series and faced off against the Rangers. It wasn’t a comfortable victory for the anonymous gambler from St. Louis, but the Cardinals eventually defeated the Rangers in seven games to win 2011 World Series.
His payout? $375,000.
2. English Man Bets A Few Cents, Wins $784,000 – Soccer
As far as ROI goes, Mick Gibbs, a roofer from England, has just about everyone on this list beat. He placed a 30 pence bet on a 15-fold soccer accumulator (parlay). A 30 pence is equal to about 40 cents in USD. He needed to pick the winners in 15 different soccer matches. His potential payout, well, just 1,666,666/1. He picked 14 games correctly, with the final leg coming down to penalty kicks in a Champion’s League game between Bayern Munich and Valencia. And, well, he won that one too.
Gibbs won a whopping 500,000£ or $784,000 USD and risked less than 50 cents.
1. Billy Walters Bets $3.5 Million On Super Bowl XLIV
Though Billy Walters is currently behind bars for insider trading – he is still easily the most successful sports bettor of all time. Walters made a living beating Nevada sportsbooks and local sports bookies across the country.
Betting on the Super Bowl is always a massive time of the year for sportsbooks, and that means increased betting limits. Walters loved the New Orleans Saints against the Indianapolis Colts in Super Bowl XLIV, so much so that he thought the underdog, Saints, should be the favorite.
Walters began betting heavily on the Saints at sportsbooks in Vegas and with bookies across the country. By the time of kickoff, he had at least $3.5 million on the Saints. Even for him, that was more than he wanted or expected to get down on one side. But, the legendary sports bettor was right.
New Orleans beat the Colts by a score of 31-17 and Walters collected a massive payday.
About the Author
Joseph Falchetti
Editor-in-Chief, Pro Sports Bettor and Casino Expert
Joe is the author of the majority of sports betting pages on SBS and he serves as a gambling consultant to our content team. He's been mentioned on Forbes.com as a gaming analyst, and his articles have been linked by larger publications, such as the New York Times.
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