While most of us are happy tossing a cheeky fiver on the horses or throwing down a Saturday afternoon accumulator bet, there are some folks out there who are playing in a completely different league. Imagine having the guts—and the cash—to place a bet so large it could buy a mansion. That’s exactly what these high rollers are doing, betting sums that make the rest of us feel like we’re playing with Monopoly money.
These aren’t your typical wagers. These are the kind of bets that can make you a legend or leave you with a story of the one that got away. And yes, these bettors are usually loaded to the brim with cash, so they can afford to lose without breaking a sweat. But still, can you imagine the adrenaline rush?
I’ve pulled together some of the biggest sports bets ever placed, each one at least a cool million. Whether they won or lost, these bets are legendary. So, brace yourself and let’s take a ride through the world of eye-watering wagers.
Biggest Bets in Sports Betting History
Date | Bettor | Stake (€) | Odds | Result | Payout (€) |
| 30/10/2019 | Jim McIngvale | 12,305,000 | Lost |
| |
| 05/11/2022 | Jim McIngvale | 9,460,935 | 15/2 | Won | 70,957,012 |
| 13/02/2022 | Jim McIngvale | 8,569,007 | 17/10 | Lost |
|
| 04/04/2022 | Jim McIngvale | 8,395,000 | 15/8 | Won | 14,375,000 |
| 11/01/2022 | Jim McIngvale | 5,865,000 | Lost |
| |
| 03/11/2020 | Unknown | 4,535,260 | 37/20 | Lost | |
| 03/06/2013 | Floyd Mayweather | 4,453,340 | 11/10 | Won | 9,352,015 |
| 07/02/2010 | Billy Walters | 3,332,982 | 4/5 | Won | 5,994,295 |
| 06/10/2007 | Harry Findlay | 2,875,000 | 4/5 | Lost | |
| 13/11/2022 | Drake | 1,866,082 | 9/20 | Lost | |
| 15/01/2023 | Unknown | 1,333,788 | 0.01/1 | Lost | |
| 01/01/2007 | Billy Walters | 1,265,000 | 5/2 | Won | 4,427,500 |
| 02/05/2005 | Fred Done | 1,150,000 | 1/1 | Lost | |
| 20/01/2020 | Unknown | 1,150,000 | 8/15 | Won | 1,771,000 |
| 06/05/2023 | Jim McIngvale | 1,094,016 | 9/2 | Lost | |
| 27/01/2023 | Drake | 1,053,569 | 13/15 | Won | 1,970,175 |
| 18/12/2022 | Drake | 933,087 | 7/4 | Lost | |
| 22/04/2023 | Drake | 923,231 | 4/11 | Won | 1,274,059 |
| 29/09/2007 | Dana White | 923,139 | Lost | ||
| 01/01/2024 | Dave Portnoy | 918,263 | Evens | Won | 1,836,527 |
| 06/12/2008 | Charlie Sheen | 786,884 | 3/2 | Won | 1,967,211 |
| 18/10/2012 | Floyd Mayweather | 782,933 | 10/11 | Won | 1,494,692 |
| 05/02/2012 | 50 Cent | 727,225 | 1/1 | Won | 1,454,451 |
| 12/02/2023 | Drake | 667,000 | 11/10 | Won | 1,155,750 |
| 08/10/2014 | Floyd Mayweather | 583,326 | 10/13 | Won | 1,032,038 |
| 19/10/2014 | Floyd Mayweather | 570,740 | 18/19 | Won | 1,114,301 |
| 08/04/2024 | Dave Portnoy | 560,135 | 18/5 | Won | 2,576,621 |
| 21/11/2021 | Dave Portnoy | 460,281 | 11/5 | Lost | |
| 15/03/2023 | Tony Bloom | 460,000 | 7/5 | Won | 1,104,000 |
| 12/02/2024 | Dave Portnoy | 459,396 | 11/10 | Won | 964,913 |
Conclusion
High-stakes betting is a world of its own, far removed from the casual wagers most of us are familiar with. These legendary gamblers—Drake, Jim “Mattress Mack” McIngvale, Floyd Mayweather Jr., Billy Walters, Harry Findlay, and Dave Portnoy—have all placed bets that could buy mansions, cars, or even small islands. Their stories are filled with both astounding victories and crushing losses, each one adding to their mystique and reputation.
What sets these bettors apart isn’t just their willingness to risk vast sums of money, but their strategic approach and deep understanding of the sports they bet on.
Whether it’s Drake’s notorious “curse,” Mack’s clever promotional hedges, Mayweather’s fearless bets, Walters’ line-moving prowess, Findlay’s larger-than-life character, or Portnoy’s timing and analysis, each gambler brings a unique flair to the high-stakes game.
Their journeys remind us that betting at this level isn’t just about luck—it’s about strategy, knowledge, and sometimes, a bit of audacity. While their bets can lead to incredible payouts, they also come with the risk of significant losses.
But, in the end, it’s the thrill of the gamble and the stories they create that make high-stakes betting such a fascinating spectacle.
The Best Bitcoin Sports Betting Sites
Who are the most famous sports bettors?Some of the most famous sports bettors include Drake, Jim "Mattress Mack" McIngvale, Floyd Mayweather Jr., Billy Walters, Harry Findlay, and Dave Portnoy. These individuals are known for placing incredibly large bets and have made headlines with their high-stakes wagers. How do big sports bettors pick their bets?High-stakes bettors often use a combination of in-depth knowledge, statistical analysis, and personal intuition. They study team performance, player statistics, and other relevant data. Timing also plays a crucial role, as they aim to place bets when the odds are most favorable. What is the largest win in sports betting?One of the largest wins in sports betting history is Jim "Mattress Mack" McIngvale's $75 million payout in 2022, which he won by betting on the Houston Astros to win the World Series. This record-breaking win remains unbeaten. What is the biggest sports bet ever?The biggest sports bet ever placed is $13 million (€12,305,000) by Jim "Mattress Mack" McIngvale on the Houston Astros to win the World Series in 2019. Unfortunately, this bet was a loss. Where is the best place to bet on sports?One of the best places to bet on sports is Stake.com. Known for its wide range of sports betting options, competitive odds, and user-friendly interface, Stake.com is a popular choice among sports bettors. What is the easiest bet to make in sports betting?The easiest bet to make in sports betting is often considered to be a "moneyline" bet. This is a straightforward bet on which team or player will win a game or match. It's simple and doesn't require understanding point spreads or other complex betting terms.FAQ
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