Ten of the Biggest Bets Ever Won

A vibrant graphic showcasing the word Jackpot, embellished in striking yellow and gold hues.

One of the most alluring aspects of a casino is the possibility for anyone to hit the jackpot and leave as a millionaire. Although such occurrences are rare, many gamblers enter the casino with aspirations of transforming a small amount of money into a life-altering fortune.

In this article, we explore some of the most substantial bets that have ever been won. For instance, one story recounts a billionaire making simultaneous $250,000 blackjack bets and walking away with millions, while in another tale, a fortunate Californian turned a modest $2 into a staggering $2 billion!

#10 Mike Ashley – £1 million

The number 17 is widely regarded as a lucky number on the roulette wheel, much of its fame attributed to the iconic character of James Bond, played by Sean Connery. In a memorable incident at the Casino de Vallee in Italy, Bond hit the number three times consecutively. The odds of repeating that occurrence are roughly 50,000 to 1, making it truly astonishing.

It’s hard to believe this extraordinary event, and many years later, it came to light that it had been staged to promote the launch of the Bond film Dr. No. Interestingly enough, Connery's character also struck it lucky with number 17 in the film itself!

Mike Ashley, a retail mogul, was blissfully unaware of the staged nature of this event, which ultimately worked to his advantage. Perhaps inspired by the suave demeanor of Bond, Ashley placed various bets, aggregating approximately £480,000, all centered around the number 17.

His betting tactic involved placing a 'complete bet' incorporating his lucky number, meaning he wagered on every possible outcome that included it. When the ball landed on 17, he reportedly remarked, “That’ll do me,” calmly collecting over £1 million in profit after a short 15-minute session—quite the return on investment!

#9 Beverley Whitten – $3.7 million

Beverley's experience is one that many fantasize about when visiting a casino. Having recently retired from her teaching job in Ohio, she decided to treat herself to a trip that would drastically alter her future.

She traveled to the Mountaineer Casino in West Virginia, where she enjoyed a lively afternoon of playing the slot machines. After dedicating two hours to the game 'Golden Chambers,' she was overjoyed to hit the jackpot, winning an astounding $3.7 million , which set the stage for a delightful retirement!

A vintage road sign proclaiming 'Las Vegas Fremont Street'

#8 Amy Nishimura – $8.9 million

Amy had frequented the Fremont Hotel in Las Vegas for two decades, but her fortunes changed dramatically with a life-altering win.

In 2003, just a couple of days before her birthday and three days prior to Christmas, Amy arrived at her hotel, grabbing a quick breakfast before hitting the casino floor. slots She was drawn to her favorite slot machine, the legendary Megabucks by IGT, where she deposited her initial $100. Almost instantly, the Hawaii native played a spin that would bring her unbelievable wealth.

With just a $3 wager on the one-armed bandit, she struck the jackpot and jubilantly held up a cheque for $8,919,598 !

#7 Charlie Wells – $13 million

Charlie Wells was notorious in the 19thThis tale involves a notorious cheat who seemed to have an unquenchable thirst for swindling. The con artist, originally from England, served multiple sentences in France for various scams. One of his more audacious schemes involved establishing a bank in Paris under a false name, accepting customer deposits, and subsequently squandering the money in Monte Carlo's casinos.

Remarkably, he is credited as one of only five individuals who successfully 'broke the bank' in Monte Carlo, a term that describes winning so much that the casino couldn't provide the necessary cash on hand to pay out. casino Wells achieved this remarkable feat not just once, but on two separate occasions, amassing over 500,000 francs—equivalent to around $13 million today. This achievement solidified Wells' position on our list of significant casino wins, potentially marking the largest bet ever won at a casino.

But can we genuinely believe that a lifelong con artist managed to strike it rich legitimately on two occasions? most famous gamblers in history The nighttime view of the MGM Grand, where Kerry Packer made one of the greatest bets in casino history. Martingale strategy Kerry Packer was a cricket enthusiast and media mogul who instilled fear in casino owners around the globe. As a billionaire, he had the luxury to wager massive amounts in his favorite game, often without worrying about the outcomes. This made his presence at casinos a double-edged sword, as his multi-million-dollar bets could significantly impact their revenue.

One fateful evening at the MGM Grand, Packer's legend was further solidified. In a rapid 20-minute span, the Australian tycoon juggled blackjack across eight tables, betting $250,000 per hand. As he accumulated a jaw-dropping payout of  <strong>$20 million</strong> , casino executives watched in horror, powerless to intervene.

#6 Kerry Packer – $20 million

The Megabucks slot machine has consistently been a prominent figure in our recounting of the greatest winning bets, but it’s certainly not the sole slot game capable of creating monumental jackpots. blackjack is considered one of the top online slots available today, attracting players with the irresistible promise of a progressive jackpot starting at a minimum of $1,000,000!

Yet these jackpots can increase significantly. This was the case for John Heywood in 2015, who had only signed up to play a mere 30 minutes earlier when luck smiled on him, leading to a staggering win of $21.2 million . This remains one of the largest payouts ever issued by an online casino.

#5 John Heywood – $21.2 million

They say lightning doesn't strike the same place twice, but Elmer Sherwin would beg to differ! He and his wife adored traveling, and during one of their adventures, they found themselves in Las Vegas. Like many visitors, Elmer decided to try his luck at the casino. Mega Moolah While at The Mirage, he quickly diminished his $100 bankroll to nothing. However, his wife stepped in with an additional $20, and that was the turning point; Elmer hit the jackpot, securing a remarkable $3.6 million prize.

Most people would be more than content with such a win. To achieve this once, Elmer faced odds of about 10 million to 1. Yet, he was determined to replicate his success, chasing the dream of becoming the first person to win the lavish Megabucks jackpot more than once.

#4 Elmer Sherwin – $24.6 million

In 2005, he made history once again, claiming yet another Megabucks jackpot totaling a staggering $21.1 million , making his cumulative winnings from the machine nearly $25 million .

The old Desert Inn casino's slots area.

While the other victories in this narrative end on a euphoric note, Cynthia’s story takes a tragic turn. Back in 2000, Cynthia was employed as a cocktail waitress in Las Vegas and seldom gambled. Her gambling was usually limited to the occasional pull on a slot machine.

Attending The Desert Inn for her boyfriend’s birthday, she became aware of the Megabucks machine, which had an eye-watering jackpot of $35 million . Remarkably, after just seven $3 spins, she hit it big and won the colossal amount.

Most people would likely quit their jobs on the spot, but Cynthia opted to work her final shift, formally announcing her two-week notice and taking the time to train her successor!

#3 Cynthia Jay-Brennan – $35 million

She ultimately married her boyfriend; however, just six weeks later, tragedy struck. While she was out with her sister, their car was hit by a drunk driver. Tragically, Cynthia’s sister lost her life, and Cynthia was left paralyzed from the chest down.

#2 Jim 'Mattress Mack' McIngvale – $75 million

'Mattress Mack' was already a renowned figure in Texas prior to winning the biggest payout in sports betting history.

He owned a chain of furniture stores, and his energetic TV commercials had made him a familiar face throughout the state. Mack placed bets with the same fervor he devoted to selling furniture and had already secured the largest mobile bet in sports history when he wagered $4.5 million on the Cincinnati Bengals to win the Superbowl in 2022 (they didn't win).

Later that same year, Mack made headlines again with an astounding $75 million win. This grand total was a combination of a series of bets amounting to nearly $10 million on the Houston Astros to clinch the World Series.

Among these wagers, there was an outright bet of $10 million on their victory, with odds set at 3-1, which is believed to have generated the largest single payout in the history of sports betting.

Ever the savvy businessman, Mack leveraged these bets to offset another gamble within his business. Throughout the baseball season, he had promised customers who spent over $3,000 that they would receive double their money back should the Astros triumph. Mack is committed to giving back to his community; quickly after his win, he was quoted saying, 'Whatever we can do to make people’s lives better, even if it’s through this magical game of baseball, we will.'

A Powerball lottery ticket that led to one of the greatest wins ever.

Occasionally, lotteries in various countries experience significant stretches without a winner. With each passing week, the jackpot accumulates to jaw-dropping amounts. In 2022, California's Powerball lottery witnessed exactly that.

The top prize had not been claimed for over three months, causing the jackpot to soar to an astonishing $2.04 BILLION. Understandably, the odds of winning such a massive jackpot are astronomical—Powerball officials estimate them at around 292.2 million to one!

The prize remained unclaimed until February 2023, when Edwin Castro was identified as the biggest lottery winner in history. The reasons behind Edwin's three-month delay in claiming his prize remain unclear—perhaps he couldn’t believe his $2 ticket had ballooned into billions!

#1 Edwin Castro – $2.04 billion

In a twist of fate, thanks to how Powerball distributes its jackpots, Edwin wasn't the only big winner that day. The California public school system received $150 million, while the store selling the winning ticket received a delightful $1 million bonus.

Tom Bogues has been immersed in the gambling sector since 2020, with a strong passion for every facet of the industry, from the casino floor to the intricate regulations that govern it.

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