The Biggest Bets Ever Won

min read
A slot machine with the jackpot signs pointing towards 777
BetMGM Jun 19, 2023, 2:40 AM

In the world of high-stakes gambling, entire fortunes can be won or lost with a single roll of the dice or turn of a card. These exhilarating wagers have become the stuff of legends, renowned for the astonishing amounts of money involved and the shock of winning or losing it all in one fell swoop.

From the casino table games that have defined legends to gamblers who pushed beyond the boundaries of risk-taking, explore the big bets that have captivated both seasoned players and curious onlookers alike and uncover the true stories behind the biggest bets in history.

7. Amy Nishimura – $8.9 Million

Born and raised in Hawaii, Amy Nishimura found solace and excitement in her occasional visits to Las Vegas. The Fremont Hotel became her home away from home and she developed a unique connection with a particular slot machine — the legendary Megabucks slot by IGT.

It was the year 2003, just a couple of days before Amy’s birthday and the start of the holiday season. Within moments of starting her gameplay, the resounding chime of victory echoed through the casino as Amy found herself staring at the grand prize — an astonishing jackpot of $8,919,598.

6. Elmer Sherwin – $24.6 million

Prepare to be amazed at the incredible tale of Elmer Sherwin, a man whose fortune made him the embodiment of the phrase “lightning striking twice.” Sherwin etched his name in the annals of casino history by claiming not one but two life-altering jackpot slots.

Inside the opulent confines of The Mirage, the reels aligned and Sherwin hit the jackpot, claiming a substantial prize of $3.6 million. A single jackpot win would have satisfied most, but Sherwin was far from finished. In 2005 and against all odds, Sherwin struck gold once again, securing a staggering $21.1 million in prize money.

5. Anonymous – $27.5 Million

In 1998, an individual who preferred to remain anonymous managed to win a $27.5 million jackpot at the Palace Station Casino. The unknown player spent $100 and lost but decided to extend their budget by $200. This small decision proved to be a stroke of genius, granting them a jackpot of $27,582,539.48.

Unbelievably, this lucky individual had already experienced success at the same casino a few months prior, winning $680,000 on the Wheel of Fortune slot. Much like Elmer Sherwin, the second win led to the largest prize. Neither player would have hit the bigger jackpot if they had walked away after the first win.

4. Kerry Packer – $30 Million

As a billionaire tycoon with a penchant for big bets and live dealer casino games, Kerry Packer’s gambling escapades are usually a cause for excitement. One particularly fateful night in the MGM Grand Casino, Packer placed a series of shocking bets that left any and all spectators in awe.

With his substantial wealth to draw from, Packer unleashed bets of $250,000 on each hand. What made this move unforgettable? The fact that these bets were placed simultaneously and played across eight tables. In a matter of minutes, Kerry struck gold on all eight tables, stunning onlookers and side bettors as he pocketed just over $30 million.

3. Cynthia Jay-Brennan – $35 Million

Whilst the other stories on this list end with euphoric winners, Cynthia Jay-Brennan’s story is more a tale of tragedy than anything else. In 2000, at The Desert Inn Casino for her boyfriend’s birthday, Jay-Brennan noticed that the Megabucks machine nearby had a record-breaking jackpot of $35 million. She had only played seven $3 spins when she struck gold and won the pot.

Sadly, just a few months later, Jay-Brennan was left paralyzed after a tragic car accident — losing her sister in the process. Since then, she has donated a large portion of her winnings to charities aiding people with disabilities. The dichotomy of Jay-Brennan’s fortune is a perplexing example of the random nature of online casino games and their land-based counterparts.

2. Jim McIngvale – $75 Million

Jim “Mattress Mack” McIngvale is a Texas legend whose larger-than-life persona has made him a household name across the state. His fearless approach to gambling has caused him to lose millions betting on the Super Bowl, but his relentless pursuit of a single substantial payout finally bore fruit in 2022. 

Mack placed a series of bets totaling around $10 million on the Houston Astros to win the 2022 World Series, resulting in a monumental $75 million payday. Among these bets was an outright wager of $10 million on the Astros’ victory, boasting odds of 3-1. This particular bet is claimed to have resulted in the largest single payout in sports gambling history.

1. Edwin Castro – $2.04 Billion

Every now and again, the lottery in different countries will go without a winner for some time. As each week goes by, the jackpot rolls over and truly mind-boggling sums are up for grabs. This is exactly what happened in California’s Powerball lottery. The main prize hadn’t been won for more than three months, meaning the jackpot had swelled to a mammoth $2.04 billion. 

The prize went unclaimed until February of 2023, when Edwin Castro secured one of the biggest wins of all time. Thanks to the manner in which Powerball jackpots are distributed, Castro wasn’t the only big winner that day. The California public school system received $150 million, while the shop that sold the winning ticket netted a cool $1 million bonus.

Try Your Luck With BetMGM

If you’re inspired by these incredible tales, register with BetGM to play casino games such as online slots and roulette with call bets and explore sports betting platforms to your heart’s content. Join the ranks of those who have dared to dream big, embark on your own gambling adventures and experience the adrenaline rush of placing bets as you engage in thrilling, high-stakes gameplay.

Actress Vanessa Hudgens flipping casino chips next to the text "The King of Casinos"
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Our BetMGM editors and authors are casino experts with a wealth of knowledge of the online casino industry at all levels. Their coverage includes company news, game reviews, how-to instructional articles, strategy guides, and editorials showcasing BetMGM’s superior product and game library.

Our BetMGM editors and authors are casino experts with a wealth of knowledge of the online casino industry at all levels. Their coverage includes company news, game reviews, how-to instructional articles, strategy guides, and editorials showcasing BetMGM’s superior product and game library.