Million Dollar Wagers: What Are the Largest Sports Bets Ever Placed?

For most of us, the idea of having a million dollars spare is hard to imagine, let alone betting that kind of money on a sporting event. There are however some very wealthy people out there with a passion for sports betting and such individuals have been willing to gamble seven-figure sums in one go. It may seem a crazy amount to bet but when you have so much money, you need to stand to win a huge amount to get that same gambling rush that most us might get from a £5 acca! Many of us might feel fantastic landing winnings of a few hundred pounds, but for a multi-millionaire – or even billionaire – this would feel like finding some spare change in their pocket.

You may be wondering how it is possible to bet in excess of a million dollars on a sporting event given the restrictions placed by bookmakers. Most bookmakers have limits on how much they are prepared to payout for any given bet. The more popular the sport, the higher the amount, but even for the most popular, the cap may well be less than £1m or so. This can effectively be bypassed though by placing several large bets at different bookmakers.

Due to this, it is possible for some extremely large bets to go unnoticed, because it has been split over so many different locations/websites. The more common scenario, though, is for the high-roller to make the bet with a specialist bookie or US casino, or via private arrangement. These punters do not just walk down to the local bookmakers with a suitcase (or two) of cash!

However these huge wagers are made, there are unlikely to be too many examples though, as few people are able, and willing, to spend millions of dollars on a single sporting bet. Even if a couple have been missed off though, the list below is still full of some absolutely massive bets, all of which are among the biggest and boldest sports wagers ever placed.

Mattress Mack — $17m

Exactly how much Jim ‘Mattress Mack’ McIngvale lost on the 2019 World Series varies depending on where you read it, but it was definitely a lot of money and the biggest bet to feature on this list. Some sources have it as $11.9m, others $13m, while the highly reputable Forbes claims a total of $17m was lost. The discrepancy partly stems from the fact that McIngvale placed various different bets at various different times, rather than it just being one single bet.

The outcome he had wagered so much money on was on his home-town club the Houston Astros to win the World Series. They came close but ended up losing 4-3 to the Washington Nationals in the 2019 edition of the championship. The blow of losing a gigantic bet and seeing his favourite side lose though did come with a major financial consolation.

Mattress Mack is not a pure gambler, rather he runs a chain of furniture stores in Texas and uses sports betting as a kind of exciting insurance policy. What he did here, and has done similar many times before, was offer customers a full refund of their purchase should the Astros win the World Series. Not every customer was eligible, as there were some qualifying rules attached, but this deal helped increase sales massively, to the tune of millions of dollars. So, really all McIngvale was doing with his huge Astros wager was hedging his bets, because had they lifted the World Series, he would have had an awful lot of customers to refund.

Mattress Mack — $10m

Mattress Mack loves to run a sporting promotion and given their popularity he often needs to bet big in order to ensure he can comfortably pay out all refunds without losing money. He was feeling especially generous this time too as he was not only offering to refund customers that made a qualifying purchase, but to give them double the money back. So, a customer spending $4,000 on a mattress would end up getting $8,000, as well as their new mattress.

For this to happen, hopeful customers were praying for an Astros win as McIngvale had once again selected his boyhood team as the focus of this deal. While they fell narrowly short in 2019, they made no mistake in 2022, winning the World Series for just the second time in their history as they beat the Philadelphia Phillies 4-1. Exactly how much Mack ended up paying back customers is not known exactly, but it is very likely to be less than the enormous $75m he won through several bets.

The largest single bet he placed from the $10m wagered in total was $3m at 10/1 (+1000) odds as it was earlier in the season. Later bets were placed when the odds had dropped to 5/1 (+500) with the average working out at 15/2 (+750).

Mattress Mack — $9.5m

We could continue to add Mattress Mack bets onto our list as he has been doing his money back if ‘x’ wins promotions for many years. We will end with this final one though, with this being the third most he has spent on a sporting event (to date). Earlier in 2022, months before his huge $75m Astros success, Mack ran a deal on the Super Bowl, in which customers would get their money back if the Cincinnati Bengals beat the Los Angeles Rams. It was a closely fought contest but one that saw the Rams prevail by a three-point margin.

McIngvale stood to win in a little over $16m on the game which ended up going right down to the wire but this was not to be his time. As normal though, he was not down by the value of his bet ($9.5m) because of the increase in sales he enjoyed as part of the promotion. Other examples of such promotions include in 2021 when he placed a $3.5m bet on the Super Bowl, backing the Tampa Bay Buccaneers with a +3.5 spread against the Kansas City Chiefs. With him putting on a spread bet here, had the Buccaneers lost by one to three points, his bet would have won but he would not have paid out any refunds. As it happened though, refunds were given as the Bucs crushed their opponents 31-9.

Anonymous — $8m

Not everyone likes to make themselves publicly known when making such a huge bet and one example of this was seen back in 2017. A mystery bettor, who was gambling in Las Vegas, went on an incredible run betting on the World Series, calling the first five matches correct. Having reinvested his winnings for each bet, by the time of the sixth game this anonymous figure was up $8m and not wishing to stop while his luck was hot.

For game six he used his $8m in winnings to back to the Dodgers, who had won games one and four earlier. His brave attitude earned him the nickname Sir Let it Ride but all we know about this fellow was that he was under 30 and Eastern European. Well, we also know he ended up with $14m in his pocket too as the Dodgers went on to win game six of the World Series.

We must admit we were a little sceptical reading about this story at first, as it is a huge amount to gamble especially for a non-celebrity but the source was reliable. The person reporting the Sir Let it Ride’s bet was RJ Bell who was (and still is) an odds provider for the Associated Press. He confirmed the rumour on his Twitter account, so we are more than happy to trust him on this one.

Anonymous — $5m

Now, this may not be a sporting bet as such but political markets are something you can increasingly see offered by bookmakers, so it felt worthy of a space on our list. This £3.9m/$5m wager placed on Donald Trump to retain his presidential seat was not placed by an American, but rather a British businessman. Why so much confidence in Trump given his relatively poor polling numbers? Well, reports indicated that this mystery gambler had contacts within the Trump campaign team who were bullish about their chances.

Seeming confident that Trump would be re-elected, the unknown Brit placed his bet at a private bookmaker on the island of Curacao. With the odds of 37/20, this meant securing a return of over $14m, of which over $9m would have been taken from the bookie’s coffers. With the world having seen Trump secure a shock victory four years earlier, it was far from outside the realms of possibility, especially given that incumbent presidents usually enjoy re-election. Things started well enough for the MAGA man too, who took an early lead, but as more states reported their results, Joe Biden chipped away and surpassed the all-important 270 electoral votes.

Drake — $2.3m

Canadian rapper, Drake, loves to gamble, whether it be at the casino or on sports, but even by his standards this was a particularly large bet. He must have been feeling rather confident ahead of this UFC event in London as he put $2.3m on the line to spice up the evening. Although the bet was a relatively safe one, with odds of just 1.62, it did cover two fights. Putting his full support behind the Liverpool representatives, he put on the ‘Scouse parlay’ which was a bet on Paddy Pimblett to win his bout and Moly “Meatballs” McCann to claim glory in hers.

The two Liverpudlian favourites did not disappoint in their respective bouts, resulting in Drake receiving a $3.7m payout. So chuffed was he, that the rapper vowed he would give the pair a brand new Rolex next time he met them and he ended up being true to his word.

Drake — $2m Stake

One of Drake’s favourite sports to bet on is UFC despite having something of a mixed record. After a couple of defeats back in earlier in 2022, by the time of UFC 276 he wanted to grab himself a win. A seemingly sure thing, Drake wagered $1m on strong favourite Israel Adesanya to defeat Jared Cannonier. Although there was a lot of money staked to win $250,000, Drake would not have been sweating too much as the Nigerian dominated the battle in yet another successful title defence.

Move forward slightly to the time of UFC 281 and Adesanya was back in the octagon and again found himself being backed by Drake. The Nigerian was the strong favourite with Drake set for a $2.9m payout if he was able to make it four victories in a row. There was to be an upset in New York though as the defending Middleweight champion lost to old kick-boxing rival Alex Pereira for the third time (the other two times coming in kickboxing). An expensive upset for the Canadian musician to say the least.

Billy Walters — $2m (Estimated)

This story gathered a lot of attention in the press at the time and, while most reports claim professional gambler, Billy Walters, won $3.5m, some believe this was the stake. From our research it definitely appears that the former is true and the stake of the bet was not made public. We have been able to produce something of a sensible guess as to the wagered amount though. The Colts were -5 favourites so in the moneyline market, and assuming that was what Walters went for, he would have gotten odds in the region of 9/5, or +180. So, to win a total of $3.5m this would mean betting around $1.95m.

This certainly not would be out of the question for Walters who was a big-money gambler. On at least two separate occasions he lost $1m at blackjack tables at Vegas and he won $2.2m betting on University of Southern California to beat Michigan in the Rose Bowl in 2007. In a good year, Walters claimed, he would make around $50 to $60m through his various business investments, gambling, real estate etc. so a $2m bet would not have represented a huge risk for him.

Vegas Dave — $1 million

Just sneaking onto our list is the man nicknamed Vegas Dave. That might sound like the dodgy character from your local pub with a bit of a gambling problem, but is actually a man who was well-known for winning large sums of money on UFC fights. Real name, Dave Oancea, he won six-figure sums betting on Holly Holm to beat Ronda Rousey and then again when Meisha Tate then toppled Holm. Having been so impressed with Tate, Vegas Dave put a $1m bet on her to defeat Amanda Nunes during a title defence, claiming Nunes was “not a champion like Miesha”.

Even though Dave was well aware of the recent underdog stories in the weight division, he opted for the favourite this time. There was not much of a wait to see how his $1m bet fared as the fight ended up lasting just a little over three minutes. Nunes dethroned Tate with a rear-naked choke, claiming the bantamweight belt in the process.

Vegas Dave did not seem too disheartened at the huge loss though, saying he actually felt more sorry for Tate who suffered a broken nose during the bout. Writing on Instagram, Oancea simply said “That’s part of the business. Win big or lose big. Wouldn’t want a different life. Again, I care more about Miesha’s health and well being than the money right now.”

Disputed Claim: Floyd Mayweather — $5.9 million

We put this bet at the end of our list because there have been some major doubts over its authenticity. Back in 2013, several news outlets reported that Floyd Mayweather had bet $5.9m on a Miami Heat game. This was never confirmed though and other sources claimed that this large bet was in fact a bogus rumour.

Overall, we are inclined to believe this did not happen for a couple of reasons. Apparently the entire bet was formed of 46 small (relatively speaking) bets but this is an awfully large number of bets to place between game 6 and game 7, which were played merely two days apart. He would also have real difficulty staking this much money before bookies started placing limits on him. Secondly, this would be a huge amount of money for Floyd Mayweather to bet on one event by his standards. There are numerous examples of him betting six-figure sums on sporting events, but not seven figures, let alone $5.9m. Whilst he could certainly afford it, it just seems too far out of line with his usual staking.