Unbelievable Casino Success Stories That Sound Almost Too Good to be True

Some casino success stories sound so unbelievable that they couldn’t possibly be true. But in a lot of cases, they are, with perhaps just a pinch of salt and pepper thrown on the story to spice it up. Many have heard about Chris Moneymaker's famous win at the 2003 World Series of Poker Main Event, or Australian media mogul billionaire Kerry Packer's famous jaunts at the blackjack tables. 

However, there are plenty more casino success stories out there. And we’re talking average, sometimes even shoeless individuals who have defied the odds and walked away a winner. It’s impossible to know for sure if all of these people were real, or just a tall tale spread by casino staff and patrons. Either way, some of these casino success stories seem too unbelievable to be true, but make for an exciting read nonetheless.

The Tale of Shoeless Joe 

If you can believe it, a man given the nickname Shoeless Joe walked into a Las Vegas casino barefoot in 1995 and walked out with around $1.6 million after striking it big at the blackjack tables. The story, which was even reported on by mainstream media such as the Washington Post, claimed poor old Joe was homeless after his wife kicked him out of their home for reasons unknown. All he had left was a $400 security cheque, which he decided to use on a game of blackjack. 

During his run, which lasted anywhere from one night to a week, depending on the source, Joe successfully implemented a reckless strategy to great effect. He split 10s, doubled down on hard 12s and indulged in other behaviors seasoned blackjack players would tear their hair out over. At his peak, Joe supposedly won a bankroll of $1.6 million.

As any regular casino player can tell you, eventually, variance catches up with everyone. Joe's strategy worked wonders, but it apparently ended up seeing him lose quite a bit of his winnings in the end. What happened next is just as vague as the rest of the tale and has a few different versions:

1. Joe was eventually kicked out of the casino because of his rudeness to staff. 
2. He left after he lost his whole bankroll. 
3. He walked away when he was on the winning streak or kept his streak going at other establishments. 

One rumor even suggests casino heavyweight Steve Wynn purchased the rights to Shoeless Joe's story for $10,000. While his true fate is unknown, this is a story that might be more fiction than fact, but as the old saying goes, never let the truth get in the way of a good yarn. 

COVID Years Yields Huge Prize 

COVID lockdowns were a crazy time for the world. For quite possibly the first time in history, most of the world was locked inside their homes at the same time. Luckily for one man in Belgium, online casinos can be played from anywhere with an internet connection. 

During a session in 2021, the lucky man found himself looking at a $23.6 million jackpot after playing the progressive slot Absolutely Mad: Mega Moolah at an online casino. Very little is known about him beyond his country of origin, the game, and the size of the prize, which still stands as the most significant single win from an online casino. 

The Run

Anargyros Nicholas Karabourniotis, or Archie Karas, as he was more commonly known around the tables, apparently had one of the longest winning streaks ever. According to urban legend, he went to Las Vegas with $50 in December 1992 and turned that initial bankroll into millions. As the story goes, by the start of 1995, Karas had won over $40 million in a winning streak colloquially known as The Run. 

A legendary high stakes travelling casino player along the same vein as Nick the Greek and Doyle Bruson, Karas always claimed to have won and lost many fortunes during his career. In this particular instance, he apparently won, a lot, for quite a while. 

If the story can be believed, Karas began The Run in December 1992 after losing his entire bankroll. He drove to Las Vegas with his last $50. After receiving a quick $10,000 loan from an acquaintance, he went straight to a razz poker table and won enough to pay his backer double and keep The Run going. 

Over the next few years, Karas apparently won at everything he played: pool, poker, and more. He knocked off poker players Chip Reese, Stu Ungar, Johnny Moss and even a pseudonymous person known as Mr X, who apparently lost millions to Karas. During this time, it’s also claimed he won all of a casino’s $5000 chips and had to start carrying a firearm because he had a few million dollars stashed in his car at all times. Not a bad problem to have. 

Karas was eventually a victim of his own success. After a time, nobody wanted to play games of chance with him anymore due to his ongoing winning streak. He soon resorted to playing craps and baccarat. His streak eventually ended, and by some accounts, he ended up losing his entire bankroll. Karas had more than a few streaks during his career, but the one known as The Run is easily the most famous and successful. Karas passed away in September 2024 at the age of 73. 

Luck Turns to Tragedy

Cynthia Jay-Brennan is quite possibly one of the luckiest casino players ever. Sadly, she is also one of the unluckiest. While celebrating her boyfriend's mother's birthday at the Desert Inn Hotel and Casino in 2000, Brennan played the Megabucks slot machine, hitting the jackpot on the third spin, netting her $34.9 million. 
Despite being a multi-millionaire, she returned to her job as a waitress the next day, gave two weeks' notice and even offered to help train a replacement. With her newfound wealth, Brennan quickly set out to help everyone she met. She gave financial support to old friends, family, and pretty much anyone who reached out with a story of woe. 

Sadly, only a few months after her win, Brennan and her sister were driving in a car that was struck by a drunk driver. Her sister died. Brennan was left in a coma for a time and permanently paralyzed from the waist down. To this day, she is still in a wheelchair and unlikely to ever walk again. Brennan still regularly makes charitable donations such as wheelchairs to patients in similar situations to hers.

Bingo Players Try to Break the Bank

Casino bingo isn't the first game that comes to mind when you think of big wins, but at least three instances have proven otherwise. In 2011, Granville Ritchie, a retired truck driver from Michigan, won $1.5 million playing bingo. He had been playing the game for over 30 years before scoring a big win for the first time. 

Two winners from the United Kingdom (UK) also managed to win over a million playing bingo. In 2008, Soraya Lowell, a mother of four from England, won $1.5 million on bingo. Lisa Potter, a single mother from Oxfordshire, also won $1.6 million playing bingo in 2015. 

Mega Moolah Progressive Slots Create Another Millionaire

Lance Corporal Jon Heywood, a soldier from the UK, is another player who became a millionaire thanks to progressive slots. In 2015 the then 26-year-old made history by winning the largest jackpot payout in an online slot machine game, which was then certified by the Guinness Book of World Records as a world record. 
According to media reports, Heywood had recently returned from a tour of Afghanistan and decided to try online slots to help pass the time. After depositing around $40 in his account, he played while watching a documentary about World War II tanks. However, his attention was quickly torn back to the game when lights began to flash. Heywood soon discovered he was $20 million richer. 

The Ultimate Double or Nothing 

In 2004, Ashley Revell entered casino folklore and made headlines after he raised roughly $135,000 by selling everything he owned to fund one spin of the roulette wheel. The ill-advised venture saw him take his bankroll straight to Las Vegas and put it all on red. Amazingly, it actually worked. The ball came down on seven, red, and Revell doubled his bankroll to over $270,000. 
Revell's action made him an instant casino legend, with his win filmed and used for an episode of a reality casino-based TV show called Double or Nothing. He was also featured in several documentaries detailing his life before and after his success at the roulette table. After his win, he set up a poker company which went bust in 2012. He was a senior account manager for an IT services and network company from 2014 to 2022 as well.

Elmer Sherwin's Dual Jackpot Defies the Odds

One jackpot win is rare. Two is almost unheard of unless you are Elmer Sherwin, a World War II veteran who liked to play slots. In 1989 the Mirage Casino in Las Vegas was newly opened and the then 76-year-old Elmer came to see what all the fuss was about. Known as an eternal optimist, the war veteran had a hunch that the Megabucks slot machine was going to pay out. His intuition soon proved right, with the machine giving him $4.6 million.

In media interviews after his big win, Emler said his goal was to hit the jackpot again. Not because he needed more prizes, but because he wanted to prove he could, and earn the prestige of being a dual jackpot winner. It would take another 16 years, but in 2005, the 92-year-old Elmer got his wish, winning $21.1 million at the Cannery Casino and Hotel in Las Vegas, once again on the Megabucks machine. 

Like other jackpot winners before him, Elmer spent his final years donating his vast fortune to charity and other philanthropic ventures, including aiding Hurricane Katrina relief efforts. He passed away a few years after his second win, leaving a legacy as a good man who beat the odds, won two jackpots and used his winnings to help others. 

Grandma’s Golden Arm 

Craps in is often portrayed as a fast, almost team-like sport where one player rolls winning numbers for hours on end to the joy of the crowd and other players. On at least one occasion in 2009, this actually happened. Patricia Demauro, a grandmother from Denville, New Jersey, made headlines after she smashed the record for the longest 'Golden Arm', which is a term used when craps players roll the dice for over an hour without losing.
However, Demauro didn't just play for an hour without losing; she played for four hours and 18 minutes without losing. She rolled 154 times total, including 25 passes, breaking the previous record held by Stanley Fujitake, who in 1989, rolled 118 times over three hours and six minutes. 

Demauro’s total winnings hasn't been made public knowledge. She apparently had $100 in her pocket when she first walked into the Borgata Hotel Casino in Atlantic City. Once the streak came to an end, Demauro had some champagne, took her grandkids to Disneyland and never went to a casino again. She set a world record and went out on top.