Million Dollar Bets: The Biggest Sports Bets Ever Placed

Most people would recognise the name Drake. The Canadian is one of the most successful rappers in the world, amassing huge amounts of money from his musical abilities. He also likes to bet huge amounts of money though, and quite often he does so at very short odds too, taking a lot of risk for not much return.

Well known for losing big money, the 'curse of Drake' became something of an industry joke for a while, and even led to sports teams/people being forbidden from being seen with him before big events in case his curse impacted on the result.

Jim 'Mattress Mack' McIngvale is a furniture business owner in Texas, USA, who was initially known for whacky TV ads and catchphrases, but who is almost as well known these days as a high stakes sports bettor. His huge bets regularly make headlines, but he doesn't take the sort of risk you might think.

Mack ties his bets in with promotions at his store as a sort of hedge, so even if he loses, his store wins. He's famous for it. In 2022, he won a record $75 million payout on the World Series, which is a payout amount still yet to be beaten.

These days, Tony Bloom is most famous as the owner of Brighton and Hove Albion Football Club, but his life before that is all about the gambling industry. He started out in finance, but was always a keen bettor, and quickly moved into sports data analysis, supplying customers with rich statistical predictive information.

He still places his own bets, but most of them are kept under wraps via his high stakes syndicate Star Lizard, although info on one or two of them have leaked out, and he doesn't bet small let's just put it that way. Bloom was a very successful poker player in his earlier years too, and also owns racehorses.

A gambler for his whole life, Billy Walters was born very poor, earned a fortune selling cars, and lost a fortune in the casinos playing blackjack and roulette. Then he got his head around sports betting, and began wagering on an industrial scale.

The man has enough resources to move the line where he wants it with his own bets, and knows exactly how to take advantage of odds movements when they happen. So feared by the bookies is Billy Walters that he even has to place bets via other people in order to get them placed at all, and this explains why he is so secretive about the bets he makes.

Dave Oancea is not a popular man in the betting community, and many have even called him out for being a liar and a fraudster, but whatever you think of him, he has been proven to have placed some of the biggest sports wagers in history.

He doesn't bet himself anymore, but sells picks for hundreds and thousands of dollars to newbie punters who are all hooked on the idea of making their fortunes with Vegas Dave's help. Whether or not he is a genius sports bettor is up for debate, but the guy certainly has a lot of money, so his marketing skills ae unquestionably sound.

A man who divides opinion in betting circles, Harry Findlay is one of the most prolific punters in British sports betting. A Londoner with a big personality and an even bigger appetite for high stakes short odds wagers, Harry has won and lost millions in his lifetime, betting on horse racing, greyhound racing, rugby, football, tennis, and more.

He is a colourful character and no mistake, having lived a life worthy of a film script, including owning Denman, winner of the Gold Cup at Cheltenham, amongst other things. His biggest ever loss was £2.5 million, but Harry estimates he has spent more than £20 million in winnings during his lifetime.

Rumoured to be the most successful professional gambler in the world, Zeljko Ranogajec is certainly the most elusive. He is a man who does not like to be photographed or to appear in public in any way, yet everybody who knows about the gambling world knows who he is.

He is thought to wager billions every year, have a personal fortune worth several billion himself, and bets on every Australian horse race on the calendar not to mention those run elsewhere. His speciality is pool betting, otherwise known as pari-mutuel betting, where he waits until the pot is attractive enough, and then goes in all guns blazing to win it, usually with the benefit of a rebate from the bookmakers he uses too.

As the founder owner of arguably the biggest online sports blog in America, Dave Portnoy knows a thing or two about sports. Being a betting man as well, he uses that knowledge to make wagers on all sorts of sports from basketball, football, golf, and ice hockey. He hit the headlines in 2024 thanks to an insane winning streak where he was regularly winning over $1 million over the first few months of the year.

Portnoy likes to bet big on favourites, especially those he thinks are just too good to lose, and he tends to make those bets just before the competition in question begins, balancing the timing to get the best odds alongside but also having enough time to weigh up the odds himself.

His father was an unsuccessful betting man, but rather than putting Haralabos Voulgaris off from betting, it instead made him determined to find a way to beat the bookie.

Making his name in basketball, Haralabos 'Bob' Voulgaris studied the sport endlessly, beginning with small bets on points and then upping the stakes to exploit a weakness in the bookmakers' odds making process. It worked, for a while, and when it stopped working Voulgaris was smart enough to change his strategy, becoming an expert in predicting basketball outcomes along the way.

This would lead him to a later career actually working for a basketball team, but by that point, he had already made millions from his betting days.

A very private man and highly secretive about his betting activity, Matthew 'Moneyball' Benham is not an easy guy to write about. His background is in banking, but he was also one of the first to use hard data to make betting and business decisions, launching a data supply company before it was fashionable.

He made a lot of money by gambling using his own methods too, devised using analytical data and quantitative analysis, then used some of that money to buy a few football clubs which brought him wider attention that he probably wasn't keen on, but with the sort of success he has had, it's hard to stay invisible.

According to BoxRec, Floyd Mayweather Jnr is the 2nd greatest boxer in the history of the sport, and his achievements, unbeaten record of 50 professional fights, and over $1.1 billion in career earnings all back this up. As well as being one of the world's greatest ever boxers though, Mayweather is also one of the world's biggest betting fans.

He bets on American sports and combat sports for the most part, and although he is no longer throwing around 6 and 7 figure wagers like he used to, he still bets higher stakes than most of us could ever dream of. Keen to share his wins and very quiet about his losses, Mayweather isn't the most popular punter of all time, but he's certainly not afraid to put up.

Some high stakes gamblers made their money elsewhere and enjoy a 7 figure punt as part of their lavish lifestyle, others are maths wizards who take a calculated and methodical approach to their betting.

Alan Woods was both. A gambling man who started out as a loser, before making a fortune from card counting and then moving on to making millions betting on the horses in Hong Kong.

He was a very intelligent man who also had a taste for parties, girls, and other specific substances. Most notably though, he helped to develop one of the best predictive models for horse racing that has ever been created, and he would use it to place bets worth millions of dollars every day, sweeping up jackpots in betting pools as he went.

Although not a big name in the UK, Charles Barkley is one of the best known sports stars in America. He was a superstar during his time in the NBA, and he has been on television screens ever since, reporting on the sport and offering analysis on basketball games. He is also well know for his gambling though, be it sports betting or casino gaming, and has spoken about it openly.

He has calmed down as the years have gone on, but Charles Barkley loves to gamble, and would regularly wager hundreds of thousands of dollars at a time, winning and losing millions of dollars in a weekend. He is actually a bigger casino gambler than a sports bettor, but he has placed some might big sports wagers nonetheless.

Conor McGregor is a former UFC Champion, actor and latterly a high stakes bettor. The Irish fighter's stakes are almost as big as his personality, although many of his biggest bets came via a sponsorship deal with a crypto bookie called Duelbits.

Not one to for statistical analysis, McGregor bets using his gut, usually sticking to combat sports because that is what he knows best, but he does venture into other sports now and again too. You get the impression his enjoyment of high stakes betting is a short term phase rather than a life long hobby, but nevertheless, he is one of the few people in history to have placed a 7 figure sum on a bet.