Gambling has produced some of the most jaw-dropping stories in modern history — ordinary players walking away with tens of millions of dollars, and high-rollers betting fortunes on a single spin. Here are the 10 biggest gambling wins ever recorded, ranked roughly by payout size, with the place, year, and story behind each one.
A note on accuracy: Every figure below comes from official casino records, Guinness World Records, or verified media coverage. Where a figure is a widely repeated estimate rather than an officially documented record, that’s called out explicitly.
1. Archie Karas — roughly $40 million
Game: Poker, craps, pool · Location: Las Vegas · Years: 1992–1995
Greek immigrant Archie Karas arrived in Las Vegas with just $50 to his name. Over roughly two and a half years — now known in gambling lore as “The Run” — he turned that $50 into more than $40 million playing poker, pool, and craps, beating legends like Stu Ungar, Chip Reese, and Johnny Chan along the way. Guinness World Records recognizes “The Run” as the largest documented winning streak in gambling history. He lost the entire fortune within about three weeks at the craps and baccarat tables.
2. Kerry Packer — roughly $40 million (widely reported estimate, not an official record)
Game: Blackjack & baccarat · Location: MGM Grand, Las Vegas · Years: 1990s
The Australian media tycoon was one of the most legendary high-rollers ever known. In a single night at the MGM Grand, he’s said to have wagered a total of $250,000 and walked away with around $40 million. It’s worth flagging: this figure is an estimate repeated across media and gambling folklore, not an officially documented record like the other entries here — the casino never released exact numbers.
3. Anonymous winner (a Los Angeles software engineer) — $39,713,982
Game: Megabucks slot machine · Location: Excalibur Hotel-Casino, Las Vegas · Date: March 21, 2003
This is the largest slot machine payout ever recorded, officially confirmed by Guinness World Records. A 25-year-old software engineer from Los Angeles put about $100 into a Megabucks machine while visiting family in Vegas — and walked out an instant multi-millionaire. The record has stood for more than two decades and no slot machine win has topped it since.
4. Cynthia Jay-Brennan — $34.9 million
Game: Megabucks slot machine · Location: Desert Inn, Las Vegas · Date: January 26, 2000
A Las Vegas cocktail waitress changed her life with a few coins in a Megabucks machine, walking away with nearly $35 million. Her story remains one of the clearest proof points that progressive slot jackpots can turn absolutely anyone’s life around — including casino staff themselves.
5. Anonymous winner — €18,915,872 (≈ $21 million)
Game: Mega Moolah slot (online) · Location: Grand Mondial Casino · Date: September 28, 2018
This is the biggest online slot jackpot ever won, and the record still stands today. On a 75-cent bet, the mystery player hit the nearly €19 million Mega Moolah jackpot in under 50 spins from a mobile phone — proof that a win this size no longer has to happen on a casino floor.
6. Elmer Sherwin — $4.6 million (1989) + $21.1 million (2005)
Game: Megabucks slot machine · Location: The Mirage & Cannery Casino, Las Vegas · Years: 1989 & 2005
Elmer Sherwin, a World War II veteran, made history by winning a Megabucks jackpot twice. His first win, $4.6 million, came just 10 hours after The Mirage opened to the public. Sixteen years later, in his old age, he hit Megabucks again — this time for $21.1 million at Cannery Casino. He gave much of his winnings to family and charity.
7. Antonio Esfandiari — $18.3 million
Game: Live poker tournament (WSOP Big One for One Drop) · Location: Rio, Las Vegas · Year: 2012
With a $1 million buy-in per player, the “Big One for One Drop” was the most expensive poker tournament ever held at the time. Antonio Esfandiari won it, taking home $18.3 million — the largest single payout in live poker tournament history at the time — along with the WSOP bracelet.
8. Don Johnson — $15.8 million
Game: Blackjack · Location: Tropicana, Borgata, and Caesars, Atlantic City · Years: December 2010 – April 2011
Don Johnson wasn’t a lucky slots player — he was a businessman who negotiated player-favorable blackjack rules directly with casinos (hands up to $100,000 each, plus a loss discount). Over five months he took down three major Atlantic City casinos: about $4 million from Caesars, $5 million from Borgata, and $5.8 million from Tropicana — $15.8 million total.
9. Jon Heywood — £13.2 million (≈ $17–20 million)
Game: Mega Moolah slot (via mobile app) · Year: 2015
Jon Heywood set the record for the biggest online slot jackpot won on a mobile device at the time, a feat recognized by Guinness World Records. His win became a milestone proving that mobile gambling could mint instant millionaires just as easily as a desktop or casino floor.
10. Anonymous UK player — £11.5 million (≈ $15 million)
Game: Mega Moolah slot · Platform: Betfred.com · Date: June 5, 2025
One of the most recent big wins on this list. On a modest £1.50 bet, a UK player hit the Mega Moolah jackpot and walked away with £11.5 million — a reminder that this legendary jackpot is still minting new millionaires today.
Bonus: the boldest bet in gambling history
Not every legendary win is about the biggest number. In 2004, a British man named Ashley Revell sold everything he owned — his house, his car, even his clothes — to raise $135,300, then bet all of it on a single spin of red at the Plaza Hotel in Las Vegas. The ball landed on red, and his money instantly doubled to $270,600. The amount is far smaller than everything above, but the sheer nerve of it makes it one of the most-told stories in gambling history.
Sources
- Guinness World Records — largest winning streak & largest slot machine win
- Wikipedia — Archie Karas
- The Press of Atlantic City / ABC News — Don Johnson coverage
- Casino.org, PokerListings — Archie Karas profiles
- Galaxy of Slots, Casino Listings, Mega Moolah winner archives — Mega Moolah jackpot records
- CasinoLife Magazine, AskGamblers — Megabucks slot records