The Biggest Payouts In Gambling History

Anyone who's gambled dreams of winning big, even having their name etched next to the biggest payouts in gambling history. However, when it comes to gambling, the house, as they say, always wins. Yet, every once in a while, a gambler beats the odds. The stray win here or there is what keeps a lot of us dreaming and at least casually sauntering around slot machines and casino tables (or downloading a sports app) to make a friendly wager.

The potential for big gambling wins is always calling out to bettors, even if the prizes can never compete with what the house takes home. As Bill Miller, president/CEO of the American Gaming Association, explained in a press release, "From the traditional casino experience to online options, American adults' demand for gaming is at an all-time high." (Read about what you can do if you know someone with a gambling problem.)

In fact, AGA reports that in 2023, U.S. commercial gaming revenue totaled $66.5 billion, marking the third consecutive year of record revenue for the industry. Keep that not-insignificant number in mind as you ante up, and read on to learn about some of the biggest payouts in gambling history.

It's not just the high rollers who win big — sometimes it's the normal-rolling grandmothers. The year was 2003. The season: Christmastime. Hawaii native (Molokai) Amy Nishimura was visiting Las Vegas for her annual birthday trip to the Fremont Hotel & Casino. This particular visit, the retired homemaker was celebrating her 71st Christmas Eve birthday, and she was in for the birthday gift of a lifetime and one of the biggest payouts in gambling history. Nishimura put $100 into a Megabucks slot machine, and won $8.9 million.

At the time, the shocked Nishimura told the Las Vegas Sun she'd been playing at the Fremont since the '80s, but on the morning she won her big payout, she had dreamed of winning big. She said, "On the way to breakfast, I saw the wall with the pictures of all the people who have won jackpots here at the Fremont, and I thought to myself, 'I want to be up there,' ... But I never thought it would be because of Megabucks."

Back in 2003, Nishimura's win was believed to be the biggest win by a Hawaii resident on Vegas slots in a long time. While few press photos of Nishimura's big win exist, her photo in the Honolulu Star-Bulletin features a tiny Nishimura holding a check from Megabucks almost as big as she is — and a smile to match.

Like an overnight success can be years in the making, so can a $10 million jackpot. Retired waitress Josephine Crawford won such a prize off of a modest $3 bet in 2006, playing a Megabucks machine at Harrah's Atlantic City. It was the casino's biggest-ever jackpot at the time, and a long time coming for the 84-year-old Crawford, who had been gambling in Atlantic City since 1978.

Crawford was visiting the Harrah's with her granddaughter, then-27-year-old Alicia Weeks. Weeks and Crawford were ready to head back to their hotel room for the night, when the blinking lights of the Megabucks machine's $10 million jackpot caught the duo's eye. Amazingly, Crawford initially turned down Weeks' suggestion they play, not wanting to play a nickel machine. Crawford eventually played about $40 worth of bets, winning her massive payout with about $5 in credits remaining.

It's wild how your life can change in just 10 minutes, and sometimes a little disappointing. Weeks recalled to The New York Times that her grandmother had wanted more time playing, but decided against returning to the casino floor, lest she seem greedy. Greed, however, doesn't seem to have been Crawford's speed anyway. When asked how she planned to spend her winnings, Crawford said she planned to give her family a big trip to Italy, but otherwise not change her lifestyle. "Somehow, I'll spend it," she told the Times, adding, "I'll spend it at the casino, and I might go to Vegas."

What are the odds? Never mind, never tell us the odds; it's too lovely a story to know that some of us have double the luck. Elmer Sherwin is one such lucky son of a gun, and proof it's never too late to win big. Twice. For his place among the biggest payouts in gambling history, Sherwin won two major Megabucks jackpots 16 years apart, totaling about $26 million in prize money.

Sherwin's first big win was in 1989. He was playing Megabucks slots at the Mirage, then so newly opened, it hadn't even seen its first full 10 hours of business. The then-76-year-old retiree spent $80 of his own cash, then $20 more borrowed from his ex-wife and longtime buddy, Florence Sherwin. Sherwin then won a $4.6 million jackpot, the biggest payout in Vegas history at the time.

In 2005, Sherwin won even bigger, at the still-vibrant age of 92. He won a $21.1 million jackpot on another Megabucks slot machine, this time at the Cannery Casino in Vegas. "I want to see the looks on their faces when they hear," Sherwin said about surprising his family with the win, per a statement from International Game Technology (via the Las Vegas Sun), adding that it had been his "life's dream" to strike another jackpot. He vowed to start working on his third.

Australian media mogul Kerry Packer was born wealthy, lived wealthy, and died wealthy. He was Australia's richest man when he died in 2005, at the age of 68, with $5 billion to his name. He was known for inheriting (and expanding) his family's media empire, and was a notorious gambler. Packer would regularly bet, win, (and lose) millions of dollars in a night of gambling.

Packer's gambling story is one shot through with legends, million-dollar tips to casino workers, as well as bullying the house to let him play by his own high-stakes rules. He allegedly used his endless bankroll to pay off a casino cocktail waitress's mortgage, bought a car for a valet, and secured a $20 million credit line in Vegas. The house might always win, but Packer sure made the house nervous — and for the MGM Grand, there was good reason.

The high-rolling Packer placed a $200,000 bet (not even the largest bet ever placed by him) while playing blackjack, on terms allowed by MGM. Then Packer reportedly won $26 million, with some legends placing the amount as high as $40 million. The executive in charge of MGM at the time — and the one who had recruited Packer as a gambler at the casino — resigned after Packer's big win. While Packer's payout might have caused MGM to reconsider its high-roller policy, the win was barely a bump in Packer's road to even more riches.

Sports betting impacts the economy, and in a delightful way when it comes to the biggest payout in legal sports betting history. Texas mattress magnate Jim "Mattress Mack" McIngvale must have slept like a baby the night the Houston Astros won the 2022 World Series. Why? Because the sports bettor (and already-made mattress millionaire) won $75 million for betting on his home team.

McIngvale's big wins came from a $10 million bet, broken up in a string of bets across the series, culminating in the Game 6 Astros win over the Philadelphia Phillies for a 4-to-1 victory, against 10-to-1 odds. McIngvale had an incredibly lucky night that night — he even got to throw out the first pitch of the game that won him millions. His $30 million win from Caesars Sportsbook alone is the biggest in sports betting history.

Mattress Mack paid those millions forward, too. McIngvale uses his betting wins to bankroll big promotions at his mattress stores, refunding customers up to double their money for purchases over $3,000 if the Astros win the World Series. "It's definitely a win-win," McIngvale told ESPN. "The customers love it [the promotion], so they're totally engaged and talk about it for years. Because it runs all season long, it probably ups the number of people following the Astros, too, because now they have a real vested interest in the team." To that, we say: Play ball, and sweet dreams!