Biggest Wins and Losses in Casino History

Lady Luck can be fickle when it comes to casino gambling. While most players end up contributing to the house’s edge over time playing in online casinos like Stake, some incredible wins and losses have been recorded that beat the odds. These extreme cases combine skill, chance, and sheer audacity.

Massive Wins That Made History

One of the biggest slot machine wins in history came in 2003 when a software engineer named Elmer Sherwin hit the Megabucks jackpot at The Mirage casino in Las Vegas. His $21 million prize came just 16 hours after The Mirage opened. Sherwin played the same game at the same casino years later, winning another $4.6 million at the age of 92.

In 2004, Cynthia Jay-Brennan made what was then the largest single roulette payout ever when she won $35 million playing at the Desert Inn in Las Vegas. Sadly, she survived a tragic car accident just weeks later which took her sister’s life and left her paralyzed from the chest down. The casino offered to pay for her medical treatment following the accident.

An anonymous 25 year old software engineer who decided to try his luck after a talk at a tech conference walked into the Excalibur Casino in Las Vegas and put $100 into a Megabucks slot machine. 

Just moments later he won nearly $40 million and took home $15 million after taxes–more than he had expected to earn in his entire career. The man remained anonymous as the third largest jackpot winner in history at the time.

Incredible Skill and Bravado Behind Major Tournament Wins

Poker tournaments have created some of the gambling history’s biggest winners–and losers. Top poker professionals leverage skill, guts, and strategy to beat the odds against hundreds of players.

One incredible Cinderella story took place at the World Series of Poker Main Event in 2009. At just 21 years old, Joe Cada defeated over 6,000 players to take home the $8.5 million grand prize. He was the youngest player ever to win poker’s most prestigious title at the time.

Stu Ungar has the distinction of winning the Main Event three times, in 1980, 1981, and 1997. His aggressive style intimidated opponents, earning him the nickname “The Comeback Kid.” Sadly, he was plagued by a destructive drug and gambling addiction. He passed away in poverty in a Las Vegas motel room at the age of 45, shortly after his last big tournament win.

In 2006, Jamie Gold pulled off one of the greatest bluffs against 7,318 opponents to win the $12 million WSOP grand prize. The former Hollywood talent agent applied his skills in reading people to detect opponents’ “tells” at the table on his way to victory.

Notable Group Wins That Conquered the House

A group of students from MIT showed it was possible to turn blackjack into a profitable enterprise by legally counting cards. The team used strategies developed by professor Edward Thorp to beat casinos at their own game from 1979 to 1993. Their story inspired the popular book Bringing Down the House which was adapted into the movie 21. While counting techniques have largely been eliminated by continuous card shuffles, their mathematical approach leveraged skill and timing.

In 1992, a group of office workers from New Zealand calling themselves “The Four Horsemen” placed an auspicious NZ$1 million bet at the Casino de Monte Carlo and walked away with what was equivalent to NZ$30 million at the time. The bold bet was placed as part of a planned global backpacking trip made possible by one member’s inheritance. After converting to various currencies, they returned home to share NZ$7.5 million each.

The Largest Losses from Outsized Bets

Some massive bets have resulted in heartbreaking losses with dramatic consequences. These cautionary tales provide a sobering reality check for even the most daring gamblers.

One high roller named Archie Karas built an astonishing $40 million in winnings during a lucky streak across Vegas casinos from 1992 to 1995. When his luck turned sour after wagering almost everything he owned on high stakes baccarat, his huge profits turned into nearly $17 million in jetx game on 1win debt. His legendary run has been dubbed the largest documented winning and losing streak by one gambler ever recorded.

Terrance Watanabe reportedly lost a staggering $127 million gambling during an epic 2007 run at Caesars Palace and the Rio Las Vegas before the casinos cut him off from further losses. The Nebraska heir gambled away most of his fortune made from selling his family’s party goods company. His lack of restraint led to legal issues that ultimately resulted in probation and financial ruin.

Kerry Packer made what has been called “the biggest single gambling loss” ever as a media mogul who lost eight handheld throws in a craps game amounting to US $7.2 million dollars in less than an hour at Stratosphere Casino in 1995. While it was pocket change to Australian billionaire Packer, it illustrates how fortunes can change rapidly at the roll of a dice or turn of a card.


The house advantage means that over time, casinos will always come out ahead from the majority of bets placed by gamblers. However, these remarkable stories of wins and losses beating the odds provide powerful examples of audacity, skill, and remarkable timing. Lady Luck may yet have surprises in store for future bold fortune seekers willing to confront risk head on when opportunity comes knocking. Only time will tell if new massive wins or stinging losses are around the corner.

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