The Biggest Sports Betting Wins

Man happy with winnings. License acquired

The lure. The excitement. And most of all, the payoff.

Betting on sports is the exact opposite of sport fishing. Those who catch fish always lament about the one that got away. Sports bettors take the opposite tack. Their favorite way to pass the time is to tell the tale of their biggest score.

It could be a huge payday on a longshot in a horse race. Perhaps it’s a parlay of successful game forecasts that led to a magnificent payout from a relatively tiny investment.

Rest assured, if they hit it big, they’ll hit you up with the story and will tell the tale in intricate detail, right from the moment they connected with their favorite sportsbook and posted the wager

Any why not? As they say, it’s the winners who get to write history. And in the sports betting world, these are some of the biggest winners of all time.

Sir Charles And The GOAT

Charles Barkley never won a championship during his 14-season NBA playing career but that doesn’t mean Sir Charles doesn’t recognize a champion when he sees one. And he sure liked what he saw in the young Tom Brady.

Prior to Super Bowl XXXVI, Barkley put a $500,000 wager on the New England Patriots to beat the St. Louis Rams, who were 14-point favorites. The bet paid off when New England kicker Adam Vinatieri booted a game-winning field goal as time expired for a 20-17 victory.

Brady – AKA The Goat, as in Greatest of All-Time – had the first of his record six Super Bowl wins and Barkley cashed in a $800,000 profit on his bet.

Singing Hamilton’s Praises

When Richard Hopkins invested in Hamilton futures, it had nothing to do with Lin-Manuel Miranda’s hit Boadway musical.

Hopkins had taken his young son to an English go-kart track when he noticed the undeniable ability of another of the karters. It was a young Lewis Hamilton who caught Hopkins’ eye.

Hopkins placed a £200 wager at 300/1 odds that Hamilton would win a Formula One Grand Prix race before he celebrated his 23rd birthday. He wagered the same amount at odds of 500/1 that Hamilton would win a F1 world drivers championship before the age of 25. Then he parlayed both plays together for £50 at odds of 1,500/1.

All of those bets cashed and Hopkins pocketed a total of £165,000.

Vegas Dave Doubles Down

Dave Oancea, better known in the sports betting world as Vegas Dave, recorded a November to remember in 2015.

Oancea wagered $140,000 on the Kansas City Royals to win the 2015 World Series at odds of 30/1. The Royals did beat the New York Mets to win baseball’s Fall Classic and Oancea was awarded a $2.5 million stipend.

Within a couple of weeks, he’d make another big score. Vegas Dave backed underdog Holly Holm at 11/1 odds to topple unbeaten champion Ronda Rousey at UFC 193. His $20,000 wager cashed when Holm knocked out Rousey and Oancea walked away with over $200,000.

Lefty Gets His Fill

Just call him Baltimore Phil. Golfer Phil Mickelson is called Lefty on the PGA Tour but he was proven all right when he backed the Baltimore Ravens to win Super Bowl XXXV at the start of the 2000 NFL season at odds of 22/1.

When the Ravens beat the New York Giants in the big game, Mickelson pocketed $560,000.

Leicester Is More

An anonymous punter in England plopped down £100 on Leicester City to win the title prior to the 2015 English Premier League season.

When Leicester delivered the goods at odds of 5,000/1, this lucky bettor collected a £200,000 score.

More Legs Than A Centipede

Tayla Polia was making the second bet of her life when she opted for a wild 15-leg parlay in 2015 on that weekend’s NFL games in a $5 wager at William Hill.

Amazingly, she hit on all 15 games. At odds of 20,000/1, her $5 wager returned a $105,000 profit.

Tiger Masters Augusta

It had been 11 years since Tiger Woods won one of golf’s majors but that didn’t faze James Adducci. He wagered $85,000 that Woods would win the 2019 Masters.

When Tiger topped everyone at Augusta, the victory was worth $850,000 to Adducci.

These are just some of the biggest known betting winners, but who knows how many anonymous ones are out there. It will be interesting to see which great wins there will be in 2020!




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