Rare Casino Win Stories

By Sarah Thomas
September 05, 2023

In the gambling realm, it is common for you to encounter several winners and unlucky participants. While some games, like poker, rely on strategy and skill, most are based on luck, meaning they are out of your control.

Winning is not an uncommon occurrence in the casino world. However, there have been some exceptional performances. This article will review some of the most unexpected casino-winning stories. Dig in to gain more insights.

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The MIT Blackjack Team

A common phrase you’ll encounter when dealing with casinos is the house always wins. The MIT Blackjack Team, however, tells a different story. This collection of students and alumni of the Massachusetts Institute of Technology employed their mathematical skills to beat the house at blackjack.

The team exploits enabled them to travel to several casinos from the city of lights, Las Vegas, to Atlantic City, racking millions of dollars due to proper bankroll management and their well-honed card counting technique.

Card counting involves tracking the ratio of high-value to low-value cards remaining in the deck during a game. This strategy effectively tipped the odds in their favour, allowing them to win severally.

Elmer Sherwin

Elmer Sherwin has to be considered the luckiest man in gambling history. He won two megabuck jackpots in Las Vegas within a decade. In 1989, at 76, Elmer won his first jackpot worth $4.6 million, instantly placing him on the radar in the gambling niche.

In 2005, he decided to make that trip to Las Vegas to try his luck again and at 92, he won again, amassing over $21 million. Most of his winnings were donated to charitable causes. Luckily, in the modern era, players can also take chances at casino games and win without physically visiting these establishments on online sites. Australian residents interested can begin by browsing  to find suitable avenues.

Archie Karas

Anargyros Karabourniotis, popularly known as Archie Karas, is a legend in the gambling realm. Born in Greece in 1950, this man came to the United States, where he started his wagering career as a pool shark.

He goes down in gambling history due to his massive streak of winnings. In the early 1990s, Karas had only $50 and managed to flip it into millions by playing poker, craps and baccarat. He was a high-stakes player and loved the thrill of the scene. One of his most iconic victories was defeating Johnny Chan, a two-time World Series of Poker (WSOP) Main Event champion.

Throughout his career, Karas earned a total of $40 million. This figure makes him one of the most prominent gamblers ever. However, he suffered several losses after his streak.

Cynthia Jay-Brennan

Cynthia Jay-Brennan is a respectable name in the gambling world due to her achievements. During the 2000s, she received massive attention for perfectly aligning the symbols on a slot machine in Las Vegas, winning the $35 million jackpot.

Being intelligent enough, she decided to receive her winnings in instalments over the next 25 years. However, after her big win, she and her sister were involved in a ghastly road accident. She faced several injuries, unlike her sister, who sadly lost her life.

She spent years in legal battles with the driver who caused the accident and in rehabilitation. Furthermore, she decided to issue some proceeds to charitable organizations.

Charlie Wells

Charlie Wells has to make the list when talking about notable figures in the casino industry. He came into the light after having a long winning streak at the Monte Carlo casino in the 19th century.

In the summer of 1981, the British gambler and trickster made a substantial fortune from his initial bankroll of 4,000 pounds. Initially, he fancied indulging in roulette, the even money bets. These include red or black and even or odd.

He employed the Martingale wagering strategy, which doubles your next wager in the event of a loss to give you a chance to recover. His most significant winnings were so massive that he “broke the bank”, a term commonly used in the gambling scene to site when a player makes a big win, the casino can’t pay immediately.

Ashley Revell

Casinos revolve around risk-taking and strategic thinking in some games. Regarding the risk factor, Ashley Revell didn’t miss any classes. He is famous for making one of the most outrageous single bets in wagering history.

In 2004, at 32, Revell sold all his possessions to raise his bankroll for a single roulette spin in Las Vegas. With around $135,300, he went to the Plaza Hotel & Casino with one goal: to place all the money on a roulette bet and let the wheel determine his fate.

With a group of spectators gathered round the table, television cameras broadcasting the occurrences live, Revell placed his whole bankroll on red. The wheel was spun, and the ball landed in a red slot. Everyone present was shocked at how he doubled his money to $270,600 in seconds.


The gambling niche is a rollercoaster driven by luck. Most of the stories here were based on chance. These participants took a risk and reaped big. Sometimes, however, like in the case of the MIT Blackjack Team, you have to tip the odds in your favour to win.



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Sarah Thomas poker author
Written By.

Sarah Thomas

Sarah Thomas is a content writer for entertainment websites. In her free time she enjoys playing all sorts of games, both live and online.

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