10 of the Craziest Gambling Wins

Even the professional gamblers can’t always hit it big. In fact, the most recent big—and controversial—win for pro gambler Phil Ivey of $9 million pales in comparison to massive wins from more or less regular people. These are some of their stories.

10. The Tragedy of the Big Megabucks Hit


The story of one Cynthia Jay is a sad one, and it includes a cash prize nearly four times that of Phil Ivey’s $9 million win. Jay won $34,959,458.56, to be exact, the largest win to date at the time. This was in January of 2000, and two weeks after her big win, Cynthia married her boyfriend Terry Brennan. Then, disaster struck.

Five months after her big win, a drunk driver slammed into Jay’s Camaro while she waited at a stoplight. The cost was high: Cynthia’s sister lost her life, and Cynthia herself was paralyzed from the chest down. Instead of enjoying her newfound wealth with her new husband, Cynthia was forced to mourn the loss of her sister while unable to feed herself let alone go on her honeymoon.

The drunk driver, Clark Morse, already had 16 prior arrests, and this most recent incident was the last straw. He received a minimum of 28 years in prison for his crime. Cynthia says she’d trade back all of her money just to take a walk in the park and see her sister again.

9. The Beginner’s Luck Craps Roll

Beginners luck is usually the higher power attributed when hustlers are in full swing. Craps, with its seemingly endless betting options, can be very intimidating to first-timers. Many people could blow entire fortunes at the craps table and walk away with their head down. Of course, instead you could win 154 consecutive throws your second time playing.

The latter was the case at the Borgata in Atlantic City in 2009. Patricia Demauro, a grandmother, bought in for just $10 and won over 50 times that amount. After her friend played briefly, Demauro stepped up to the plate. While she never disclosed her winnings, even if she was a conservative gambler, her $10 would have earned her a minimum of $500 on what would have seemed like an impossible number of winning throws.

8. The MIT Students Who Beat The System


You know you’ve made the big time when there’s a movie made about your exploits. If you have seen the movie 21, then you are already familiar with the plot of the next story in this big win saga. Through the use of a tactic known as card counting, a group of MIT gamblers beat the system.

The technique is designed to anticipate whether upcoming card will be high or low. High cards mean higher bets and if the players are right, then they win. The problem is, the house frowns on players that count cards, and if the dealer notices then he’ll ask you to take a hike.

The answer, as the MIT team found, was to work as a team. While some members counted, others would exclusively play the high roller tables. Meanwhile, the signal team members would blow lots of money with big bets to distract the dealers. After all was said and done they would end up ahead and over several years won millions. The team’s winnings were so significant that at one point they even formed an investment company simply to handle their excess cash and makes sure that the bankroll was there for future play.

7. The One-Man Blackjack Master


While a team of mathematicians from MIT crushed the house to bring home millions, a lone wolf had them beat in the end. Don Johnson, a single gambler who operated over several months during 2011, opted out of the card counting game.

Instead, Johnson negotiated favorable terms to gain better chances of winning—known as ‘edge’ in the gambling world. When selecting the casino he would play, Johnson sought out establishments that already had favorable rules. By sticking to tables that would let him double his bet on any hand, and dealers that would stop drawing when their hand totaled 17 he would have a serious advantage over other players.

If that wasn’t enough, Johnson negotiated an unprecedented guaranteed payback rate. Many casinos offer their biggest gamblers 10% of their money back as a buffer against big losses. Johnson enjoyed a 20% payback—he could reliably gamble much higher sums with less fear of going home broke. To top it all off, he negotiated the ability to bet higher than other players, up to $25,000 per hand.

The reason Don Johnson’s streak was so short lived: he won $15 million from three casinos in half a year. It’s no surprise then that his money isn’t welcome in Atlantic City, and I suspect that they called Vegas and California too.

6. Granddad Bets Big On Toddler

Life is funny isn’t it, in the way that it can turn out exactly the way we want against all odds. Peter Edwards should get a job as a talent scout for pro football teams, because he marked his three-year-old grandson as a football star. Edwards wagered £50 ($80), at 2500:1 odds, that his grandson Harry Wilson would play for the Welsh National Football team.

In October 2013, Harry Wilson was 16, and the Wales National team played Belgium in a World Cup Qualifier. Belgium wasn’t anticipating the 1-1 tie, and no one—except perhaps Edwards—expected to see the youngest person to date to represent Wales in national play. Late in the second half, Harry Wilson made his debut. No matter what his performance was on the field, simply stepping on as a player transformed his grandfather’s £50 investment into £125,000 ($200,000).

5. Betting On the Moon

If I had a time machine, I would use knowledge of the future to play the stock market. It almost seems as though a man named David Threlfall perhaps had access to a time machine. In 1964, he wrote to British Wagering company William Hill asking for odds that a man would walk on the Moon within seven years. William Hill responded with the offer of 1,000:1. Not wanting to tempt fate, Threlfall placed a £10 bet.

As time went by, more and more people were successfully launched into space. It seemed as though Threlfall’s wager was part of ‘the action’. Newcomers to William Hill didn’t get the same astronomical odds that Threlfall did, and he received many offers for his high-odds ticket. Threlfall held fast, and he received his £10,000 check on the spot.

4. Amarillo Slim’s Big Ping-Pong Bet


Mobsters and professional gamblers: two groups of people who reliably have nicknames. In the case of Amarillo Slim, or Thomas Austin Preston as his birth certificate said, was a pool hustler and a card shark. He is known as the winner of the 1974 World Series of Poker, but many people probably remember him for his crazy and somewhat unorthodox bets. The biggest and most memorable of which was his ping pong match with professional Bobby Riggs.

Riggs was a Wimbledon champion, and a gambler himself. He took a challenge from Slim, winner gets $10,000. There was only one string attached; that Slim select and provide the paddles. Riggs could pick whichever he wanted, but only from the two that Slim provided.

On the day of the match, held at the Bel Air Country Club, Amarillo Slim showed up with his chosen paddles: cooking skillets. Amarillo had practiced for months with skillets in preparation, and as a result he easily won the match (and the money) 21-8.

3. The Man Who Broke the Bank at Monte Carlo


When a player breaks the bank, it doesn’t mean that the casino is out of money. It does however mean that the ‘bank breaker’ won every chip at the table. A while back, in 1891, to be specific, a man named Charles Deville Wells managed to break the bank at Monte Carlo. This win netted him about a million francs which translates into about $500,000 today.

Wells wasn’t known for his honesty; many knew him as a cheater, and he bankrolled his entertainment by swindling investors out of their hard earned cash. That night, he tried his hand at roulette and (perhaps for the first time in his life) played a clean game over 11 hours where he won his massive payday.

Wells gained renown in his day for his gambling exploits, but his luck didn’t stay with him. He lost all of his newfound wealth in Monte Carlo, then he had the misfortune of arrest in England for his financial cons. After an eight year sentence he had two more arrests and ultimately died penniless. Luck can be a funny thing.

2. From $50 All The Way To $40 Million

Wells had a hell of winning streak with his eleven hour marathon, but other people have had similar luck, if not even more astonishingly so. Archi Karas had a streak so hot it must have left scorch marks on the tables. He showed up in Las Vegas with just $50 in his pocket. Once he started playing, he didn’t lose. The year was 1992.

Karas was not a novice player; he had just lost $2 million in a poker game in Los Angeles. His luck changed for the better when he ran into a friend at Binion’s Horseshoe casino, a friend that lent him $10,000 to bankroll as seat in a game of high stakes Razz. Razz is an inverted variant of traditional poker—here the lowest hand wins. His friend’s confidence was not misplaced, Karas needed only three hours to repay his debt with 50% interest and save enough to keep on playing.

Three hours turned into three years and at the end of his colossal streak he had amassed a fortune of over $40 million.

Of course, a streak is only a streak, and when his luck finally changed, he lost about $30 million in a little under a month. First he tapped out at craps. Then, in an effort to recoup his losses he lost another $17 million at the baccarat table. He decided to take a break but couldn’t stay away and when he returned he lost the remaining $10 million.

Instead of calling it quits, Karas went hot again by turning a $40,000 bankroll loan into $1 million. So it goes I suppose.

1. Sean Connery’s Roulette Run


Before he became the famous actor, and the rugged and refined James Bond, he was a child who was no stranger to the world of gambling. As a child he would accompany his father on gambling runs and even when he was making steady money as an actor he continued to gamble.

In 1963, Connery was staying at a casino in the Italian Alps. He was playing roulette and after a few unsuccessful spins for 17, his number finally came in. Connery left his winnings (at a 35-1 wager) and spun again on 17. It came in three times in a row, after which he collected and left 17 million lire richer (about £163,000 today).