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Walters ran into some trouble with the law in recent years due to insider trading, but prior to that, he was known as one of the best sports bettors in the business. He was sentenced to 5 years in prison in but due to the COVID pandemic, he was released to home confinement in It is unclear if he continues to bet on sports. Charles Barkley is a lot like Phil Mickelson, he is widely known for his success in his sport but they are popular amongst others for their gambling habits.

However, further down the line, Barkley placed a k wager on the Falcons to beat the Patriots in the Super Bowl and he had to watch them blow a lead and his k go by the wayside. Richard Hopkins discovered Lewis Hamilton when he took his own son to a go-kart track in These both ended up happening and Lewis Hamilton is now known as one of the greatest Formula 1 drivers of all time. Professional poker player Erick Lindgren has won millions of dollars at the poker table.

Lindgren walked more than 20 miles in the blistering heat, and he won the bet. Before the MLB season, an anonymous bettor went to the MGM sports book in Las Vegas and placed two bets that would come back to yield incredibly high rewards. Louis Cardinals would win the National League pennant.

Louis would win the World Series, the unnamed bettor was blessed with a Cardinals victory. Mickelson noted that Baltimore had finished off the previous season with a record and made some great off-season player acquisitions. He also reportedly won big later that same year, betting on the Arizona Diamondbacks to win the World Series. Two years after cashing in his winning ticket, Gibbs wagered 30 pence on a leg accumulator bet. His odds?

Incredibly, the first 14 games went exactly as Gibbs had predicted. In , a bettor named Darren Yates accomplished one of the greatest feats in the history of sports betting. In fact, the accomplishment is well-known in horse racing circles. In a life-changing wager, Yates placed 62 British pounds on a bet that jockey Frankie Dettorri would win all seven of his rides that day at Ascot.

UK bookmakers will forever remember November , a month in which the favorites seemed to win almost every match. Barkley has won some big bets throughout the years, but one sticks out above the rest. His biggest win came after he bet on one of the most unlikely Super Bowl champions in history: the New England Patriots. In , the Patriots were a point underdog against the St.

Atlanta took a lead after halftime, and the game appeared all but over. In , one big-time bettor in Las Vegas reportedly made a bet on the winning team of the World Series game—just one of five consecutive World Series games he had bet on. And after each win, he has bet the winnings on the next game. If reports of the bet are true, this would likely be the largest return in sports betting history. Now that sounds really insane. A widely recognized international gambler, Mike Futter owns bingo halls in Ireland and likes to bet on horse races.

So how much did Futter win? Craggs placed an eight-fold accumulator bet with selections from horse races around the world. Had Craggs made a no-limit bet, his ticket would have been worth about 1. One day in , Steve Whiteley took the bus to the races, used a free ticket to get in and placed a bet for two British pounds. Later that day, he left as a millionaire. Whiteley, a year-old heating engineer, accomplished a feat no other punter in the U. Gamblers filled the crowd at the race, trying to win the Jackpot: a Tote bet like a lottery which had been rolling over for more than a week.

Whiteley picked all six winners at the event, including a horse that had been beaten in each of its 28 previous races over hurdles. Billy Walters is widely considered one of the most successful sports gamblers in Las Vegas, with a winning streak that extended for more than 30 years.

Walters made a bold decision, putting a huge bet on New Orleans. But as Walters continued to win, trouble followed. Billy Walters became an accomplished gambler, but trouble loomed for the multimillionaire. Later on, the law finally caught up. Floyd Mayweather Jr. Mayweather has an outrageous personality. There are multiple reports of the boxer laying down bets of more than a million dollars on a single game.

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