7 Biggest Bets in Gambling History

By in Sports & Betting on
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Large Cash Pile and World Series

If you’re like me, then you consider a bet worth anything between $50 and $100 to be big. You may also dread the thought of losing this amount in a single wager.

But certain gamblers have no fear. They’re willing to bet massive fortunes on anything from roulette to sports.

Some of these same gamblers have recorded legendary wagers that are worth six or seven figures. That said, I’m going to cover seven of the biggest bets in history.

1 – “Mattress Mack” – Loses $13 Million on Astros World Series Bet

Jim “Mattress Mack” McIngvale is a huge Houston Astros fan. In fact, the Houston-area furniture mogul is such a big fan that he wagered millions of dollars on the ‘Stros.

The Astros were entering Game 7 of the 2019 World Series at the time. McIngvale pledged to fully refund customers who spent more than $3,000 on select mattresses if Houston won the game.

Mattress Mack also wagered $13 million on the Astros winning before and during the playoffs. He had to spread his wagers around sportsbooks from Mississippi to Vegas to get all of this action.

McIngvale isn’t a gambling fiend. Instead, he used the $13 million in bets to hedge his mattress refund promotion.

After all, he would’ve ended up giving away a tremendous amount of free bedroom sets had Houston won. McIngvale told CNN that thousands of customers could’ve walked away with $3k+ worth of mattresses.

The Washington Nationals won Game 7 by a score of 6-2 and were crowned the 2019 World Series champs. Mattress Mack seemed more upset about the World Series loss than his losing wagers.

“I didn’t break even [through the mattress promo],” he said. “My heart is broken, because I’m an Astros fan. I don’t bet with my wallet, I bet with my heart and the city’s heart is broken.”

McIngvale is famous in Houston for his TV commercials and philanthropy. He opened his bedding stores to those who were displaced by both Tropical Storm Imelda (2019) and Hurricane Harvey (2017).

Mattress Mack also gave $10 million worth of refunds to customers when the Astros won the 2017 World Series.

2 – Sir Ride A Lot – Wins $6 Million on Dodgers World Series Bet

During the 2017 World Series, a mysterious European visited Las Vegas and made several large moneyline bets on the L.A. Dodgers.

The anonymous gambler kept winning and letting their winnings ride on the next outcome. He earned the nickname “Sir Ride A Lot” as a result.


The European won a total of $6 million throughout the first five games. Sir Ride A Lot truly lived up to his name by putting the entire $6m on L.A. winning Game 6.

He earned $8 million after the Dodgers won. Sir Ride A Lot thought about betting $14 million on the Dodgers winning Game 7.

However, he finally decided to call it quits. This turned out to be a good decision. The Dodgers lost the final game by a score of 5-1.

3 – Floyd Mayweather – Wins $5.9 Million on an NBA Playoffs Game

Floyd Mayweather has made a number of giant sports bets throughout his boxing career. With career winnings worth over $1 billion, the undefeated legend can afford to take plenty of risks.

“Money” made one of his biggest gambles on a 2013 NBA Playoffs game between the Miami Heat and Indiana Pacers. He wagered $5.9 million that the LeBron-led Heat would triumph.

Miami dominated the contest en route to winning by 23 points. Mayweather hauled in a cool $5 million thanks to the Heat’s victory.

Money is tied to rumors involving other multimillion-dollar bets. However, this NBA wager is the largest one that’s been confirmed.

Another infamous Mayweather bet involved the time he tried wagering on his 2017 boxing match with Conor McGregor. He visited Las Vegas’ M Resort and tried splitting $400,000 between the under on 9.5 rounds and himself on a -200 moneyline.

M Resort officials spent a long time discussing if the bet was legal with the Nevada Gaming Commission. Mayweather got tired of waiting and left without betting.

4 – Billy Walters – Wins $3.5 Million Super Bowl Wager

Professional sports gambler Billy Walters built his career on solid bankroll management principles. However, he couldn’t resist going overboard on the New Orleans Saints in Super Bowl XLIV (2010).

The Saints were an underdog to the Indianapolis Colts. Walters was so confident in New Orleans’ chances of winning that he bet $3.5 million on them.

His risk paid off when the Saints pulled off a 31-17 victory. Walters has experienced many great wins in his gambling career. But this $3.5m payout is undoubtedly the largest payout.

Unfortunately for Walters, he was later convicted of an insider-trading scandal involving the former CEO of Dean Foods. He’s currently serving a five-year prison term and will be released in 2022.

5 – William “The Suitcase Man” Bergstrom – $1 Million Craps Bet in 1984

William Bergstrom was a real estate agent who turned high-stakes gambler in the early 1980s. He showed up to Binion’s Gambling Hall and began placing the largest wagers Vegas had ever seen at the time.


In 1980, he walked into the casino with two suitcases. One suitcase contained $777,000 while the other was empty (in case he won big).

Bergstrom chose Binion’s, because he’d heard that the casino would honor any first-time visitor’s first bet—no matter how large. He wagered the entire $777k amount on don’t pass line (1.36% house edge) in craps.

“The Suitcase Man” won the bet and walked out of the casino with $777,000 in profits. He left Binion’s and didn’t return until 1984, well over three years later.

Upon his return, Bergstrom brought $538,000 to the craps tables. He wagered all $538k on another successful bet.

Rather than leaving immediately, he stayed around and placed three more “smaller” bets. These wagers resulted in $117,000 in winnings ($655k altogether).

Bergstrom returned once more in late 1984. This time, he became the first Vegas gambler to place a $1 million bet.

The Suitcase Man wagered $550k in cash, $140k in gold coins, and $310k in checks on don’t pass line. He immediately lost when the shooter won on the come-out roll.

Just a few months later, Bergstrom committed suicide by overdosing on prescription pills. He’d been suffering from depression dating back to his first win in 1980.

Bergstrom had planned to commit suicide at any point when he lost everything. That point came shortly after his $1 million bet was a loser.

6 – Mike Ashley – Billionaire Wins £1.3 Million

Mike Ashley is the billionaire owner of the Newcastle United football club. He’s amassed a £2.5 billion fortune through his sporting goods business.

That said, Ashley didn’t exactly need to get lucky. Nevertheless, he proved just as successful in roulette as he is in business during a 2008 session.

Ashley visited London’s Mayfair Club and began making “complete bets.” A complete bet refers to placing chips on every inside bet surrounding a certain number, including single number, splits, streets, corners, and six lines.

In Ashley’s case, he surrounded the number 17 with these inside wagers. At one point, Ashley risked £480,000 total on a complete bet.

His strategy came through when he won a £1.3 million payout—£820,000 of which was profit. Following this win, Ashley quietly exited the casino with his giant payout.

7 – Ashley Revell – Bets Entire Net Worth on Roulette

Ashley Revell is another Englishman who bet big on roulette. But unlike Mike Ashley, Revell didn’t have a fortune to back up his huge wager.
Following a night of drinking, he decided to bet his entire net worth on a single spin. Revell followed up on his plan by selling everything he owned.

He also worked out a sponsorship deal with the bookmaker Blue Square. The sponsorship and fire sale netted him $135,000.

Roulette Table

Revell found a taker for his $135k bet in Las Vegas’ Plaza Hotel & Casino. He then travelled to Vegas to place his wager.

Both E! and Sky One Channel filmed the event for THS Investigates: Vegas Winners & Losers and Double or Nothing, respectively. With the cameras rolling, Revell stepped up to the table and placed all his chips on red.

The ball landed on red 7 and gave Revell a $135k payout. Afterward, he vowed never to make a crazy bet like this again.


The gambling world is sure to see more fortunes wagered in the future. But for now, the seven bets described above are among the biggest ever.

Jim “Mattress Mack” McIngvale’s $13 million worth of bets on the Houston Astros is the most ever gambled on a single outcome. Of course, Mattress Mack didn’t wager this amount for gambling purposes alone.

He was simply hedging a big mattress promotion based on the Astros winning. McIngvale lost the $13 million, but he made most of the money back through his bedding promo.

Sir Ride A Lot lays claim to the next-biggest wager. After a series of successful bets, he risked $6 million on the Dodgers winning Game 6 of the World Series.

His wager pulled through and gave him a total of $14 million in 2017 World Series profits. He briefly thought of making the biggest bet ever at $14m but chose not to.

Floyd Mayweather also made a legendary bet on the 2013 NBA Playoffs. He collected $5 million on a $5.9m wager when the Miami Heat beat the Indiana Pacers.

These three bets represent the biggest to date. But records are made to be broken, and these betting records will fall someday.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for GamblingSites.org since early 2016. ...

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