There are many stories in the gambling world about huge wins and, conversely, huge losses. Most of these stories are great anecdotes but are far from incredible. They usually involve someone walking into a casino, walking up to a slot machine, and winning a huge payout. They could also involve someone who played the lottery for 20 years and finally hit the numbers to claim the jackpot.

But some stories are out of the ordinary. They’re actually incredible. Some of these stories date back a few hundred years and I’m sure have been exaggerated by the people who spread the stories.  No matter whether the entire story is true, or only parts are, they’re among some of the most fantastic stories of triumph and/or tragedy in the world of gambling.

Blackjack Tales

The MIT Blackjack Team

Among the most famous gambling stories is one that started almost 40 years ago. It revolves around students from the Massachusetts Institute of Technology and later students from Harvard University and Harvard Business School.

These students formed teams that would develop technique including counting cards and changing out players to avoid drawing suspicion at various casinos around the world. The team would eventually form a company called Strategic Investments. They solicited investments for their teams. Some years the investors would see as much as a 300% return.

Over the near 15 years of the company, there were at least 30 players on teams working in casinos around the world. Some would get identified and blackballed from casinos in certain cities and rotated out to other cities or countries. The goal was to win consistently without taking heavy losses. While big wins did not occur often, there were occasional windfalls. One weekend the team took in over $400,000.

The original company Strategic Investments was dissolved at the end of 1993. When this happened, members of the team split up and formed teams of their own which would last for the next 6 years. By 2000, the teams had broken up when players went on to pursue other interests. When it was all said and done, the combine teams made in the tens of millions of dollars.

Kerry Packer

Kerry Packer Gambler
Another famous tale involves Australian Billionaire Kerry Packer. In 1999, Packer was in London and dropped into Crockford’s Casino. He started playing blackjack. His luck that day would all bad. In the few hours that Packer played, he managed to lose $28 million. At the time, this was considered to be the biggest single casino gambling loss in the history of the United Kingdom. Interestingly enough, the loss didn’t stop Packer from gambling. He is said to have once one $33 million from the MGM Grand Casino in Las Vegas.

There’s another tale of Packer’s panache when it comes to gambling. Once a Texas oilman tried to goad him into a game of poker by saying “I’m worth $60 million.” Packer’s response was “head or tails” offering to flip a coin for the oil man’s net worth.

Spinning the Roulette Wheel

The game of roulette has several interesting stories of famous (or infamous) bets.

Charles Deville Wells

Charles Deville Wells BookThe first legend takes us back to the year 1891 and a con artist named Charles Deville Wells. Wells had recently scammed investors in a new invention of his (or so he claimed) called the musical jump rope. In reality, there was no jump rope. He took the £400 they invested and took a trip to Monte Carlo.

Wells headed over to the roulette table. In around 11 hours at the table, he parlayed the £400 into 1 million French Francs (just over US$500,000 in today’s currency). He wound up taking every chip on the table, a practice known as breaking the bank.

Due to this exploit and other gambling feats, Wells became famous all around the world. While he had amazing luck for those 11 hours, that luck would run out. He would wind up losing all of his winnings. Upon returning to England, he was arrested and spent the rest of his life in and out of prison for his con games. He died a debtor.

Sean Connery

Sean ConneryAre you a James Bond fan? I know I am. One of my favorite actors in the role is Sean Connery. Connery is an avid gambler. It started when he was a child. Connery’s father Joseph would take young Sean to watch him gamble. From there, Sean became enamored with the pastime.

Over the years, Sean would play at many casinos all over Europe and the US. One time in the Italian Alps, Connery walked into a casino and decided to play some roulette. As the legend goes, Connery bet on the number 17. He lost. So he tried again and lost again. But on the 3rd try, his luck would change.

He hit on the 3rd try and let it ride. Odds were 35 to 1 that he would hit, but hit he did. Defying logic, instead of walking away, Connery would let it ride for a 3rd time. He won again. He hit 17 three times in a row and won 17 million Italian lire. In today’s US dollars, that would amount to about $226,000. Incidentally, for years it 17 was the most common bet on a roulette table, due in part to Connery’s role in the Bond film Diamonds are Forever, where he bet on 17.

Gonzalo Garcia-Pelayo

Gonzalo Garcia-PelayoAnother incredible roulette story is that of Gonzalo Garcia-Pelayo. But this story isn’t one of luck or cheating like the previous stories. It’s a story of mathematics and science.

In the early 1990s, Garcia-Pelayo observed roulette wheels, and he noticed, by chance, that some numbers would come up more often than others. He decided that he was going to see if there was a way to determine which of the numbers would come up and how often.

Over the next few years, he would analyze the spins on the wheels. He and his family would eventually play these wheels to find the number that they would commonly land on. He found that each wheel had its own minor flaws and caused them to favor some spots over others.

Using his the data he accumulated, he and he family would beat the casinos at the game. Being the first to honestly do so at the roulette table. A movie was made about his exploits and released in 2012. The movie is called Winning Streak.

Incredible Craps

From the headline of this section, South Park fans may think I’m referring to the Randy Marsh character in the episode More Crap–a funny episode if you have the chance to check it out. But I’m referring to some crazy stories about the dice game.

William Lee Bergstrom

The first story is that of William Lee Bergstrom. Bergstrom is the best example of a risk taker that anyone can find.  In 1980, he borrowed $777,000 in cash and loaded it into a suitcase. He took that suitcase and another empty one into Ted Binion’s casino. The empty one was presumably for his winnings.

He would proceed to make the largest bet in Las Vegas history at the time of the full $777,000 on a single roll of the dice. He won. It was not known at the time, but Bergstrom was suicidal at the time. If he had lost the bet, he was going to end it all. However, this would not come to pass as he paid off the people he borrowed from and became a world traveler over the years that followed with his winnings.

Patricia Demauro

Patricia DemauroDid you know that the odds of rolling dice 154 times and not hitting a 7 is 1 in 1.56 trillion? New Jersey grandmother Patricia Demauro does because she did just that. In 2009, Demauro visited Atlantic City’s Borgata Hotel Casino and Spa to do a little gambling.

She sat and played the penny slots for an hour and got tired of them. She went to find the friend she had come with and he offered to show her how to shoot craps. They went to the first available table and waited until the 3 people in front of her finished shooting. At 8:13 pm, with $100, Demauro made her first roll. The point was set at 8.

According to Demauro, things heated up quickly. As she kept winning, more people would come over. They would use terms she didn’t know (after all, she was new to the game) and place their bets. As time went on, casino executives started standing at the table, watching the amazing run of luck that she was having.

Four hours and 18 minutes later, Demauro would make her last throw. She completed 154 consecutive rolls without hitting a 7. Demauro did not disclose how much she won. It’s estimated that she, at minimum won in the hundreds of thousands of dollars that day. More realistic estimates say that she could have taken home in the mid to high 7 figures.

Prior to that, a person in Las Vegas in 1989 managed 118 rolls in 3 hours and 6 minutes, and in 2005, another person made 147 rolls before hitting a 7. These are amazing feats especially when you consider that the average amount of consecutive rolls before a person loses is 8.

Slot Machine Tragedy

Cynthia Jay-Brennan

Winning isn’t everything. Some winners would give it all back if they could. That is the story of Cynthia Jay-Brennan. Brennan was a cocktail waitress at the Monte Carlo casino in Las Vegas. She had moved there from Sacramento, California in hopes of earning enough money to afford to go to college to pursue a degree in photography.

While there she met the man of her dreams, Terry Brennan. She and Terry fell in love and moved in together. Her idea of saving for college soon turned to saving for a wedding. To do this, she would work double shifts, often 20 hour days. Every extra bit of money she could earn went to pay for her wedding.

On January 26, 2000, Brennan met up with her fiancée’s family at the Desert Inn Hotel and Casino. They had gathered to celebrate her future mother-in-law’s birthday.  She wasn’t much of a gambler, but she likes to play the slots every once-in-a-while. Once the meal had finished, Brennan and her fiancée decided to play the slots–in particular, the progressive Megabucks slot machine.

The jackpot hadn’t been won in a while, and Brennan decided she would take a shot at it. Strictly budgeting herself $100, she originally blew through her first $21 at $3 per spin. She made another attempt and still won nothing.  Then came the third try. As the reels spun the first reel stopped on the Megabucks symbol. Then the second reel stopped again on the Megabucks symbol. Finally, the life-changing third reel would stop on the Megabucks symbol. The machine started making all sort of musical sounds along with siren and buzzers.

Brennan had won the progressive jackpot–$35 million. The next day, Brennan showed up to work and put in her 2-week notice to make sure they were not understaffed. She and Terry could now marry and about a month later, they married in a small ceremony with family and friends attending. They honeymooned in Fiji, all made possible with her incredible win.

When they returned, they had business affairs to take care of. They had to properly invest the money and make all the arrangements for contingencies such as wills and trusts. After all that was taken care of, Cynthia’s family came out to visit. They toured Las Vegas, took in a show, gambled a bit, and enjoyed what the city had to offer.

Because there were 8 people, they wound up having to use 2 cars to get around. Most of her family rode in the same car, but Cynthia and her sister Lela rode together in the second car. While stopped at a red light, a drunk driver who had 16 previous arrests crashed into Cynthia and Lela’s car. The crash instantly killed Lela and sent Cynthia into a coma. The driver, Clark Morse, was sentenced to a minimum of 28 years in prison.

Five days would pass before Cynthia would wake up. The doctors told her that her vertebrae were crushed and she was paralyzed from the chest down. Her sister was dead, her dream of having children was dead and she would never be able to walk again. The money she won was a blessing in that it paid for her extensive medical bills, although she would give it all back in a second to have her sister Lela back.

She decided that she could help others in her situation and has donated over 1,000 wheelchairs to charity. She also donates heavily to Mothers against Drunk Driving and speaks at schools about her experience. After she speaks, she donated money to the schools to establish Students against Drunk Driving Chapters. Cynthia’s story tells us that money doesn’t solve everything.

The Force Runs Hot or Cold with This One…No In-Between


Archie Karas

Archie Karas GamblerThe story of Archie Karas is nothing short of incredible. Karas arrived in Las Vegas with $50 to his name after losing $2 million in Los Angeles. While at Binion’s Horseshoe Casino, Kara ran into a friend that staked him $10,000 to play poker.

His luck changed that day, as he was able to pay back his creditor in a few hours plus interest. With the money Karas made, he kept playing. This would lead to one of the most incredible winning streaks in history as over the next 3 years, he would amass over $40 million.

When he hit $7 million, he changed from Razz to 7 Card Stud. He turned that $7 million into $17 million. He won over $1 million playing 9-ball. And he kept winning. Until he started playing craps.

Over a 3 week period, Karas lost over $11 million. He thought he could break the losing streak by jumping back to poker. It didn’t work. He lost another $2 million. After dropping $30 million of the $40 million, Karas took a vacation to his homeland of Greece. When he returned to Las Vegas, his losing streak continued, and the last of the $40 million was gone.

But that didn’t deter him. A few weeks after losing all his money, he found another person to stake him $40,000. He turned it into $1 million in a short time. Kara’s life as a gambler has no middle ground. He is either red hot or ice cold.

Other Incredible Bets

Fred Smith

Fred Smith FedexFred Smith started a small delivery business in 1971. It was tough at first, and at one point he was so low on cash, he couldn’t afford to fuel the planes to make the deliveries.  Fred took his last $5,000 and flew to Las Vegas. He was determined to get enough money to keep his company afloat.

While there, he turned his $5,000 into $27,000 and managed to keep the company going so he could afford to cover his fuel bills. Today that company isn’t so small anymore. It’s worth about $5 billion. You may have heard of it. It’s called FedEx.

Ladbrokes and the Biggest Novelty Bets in History

Another amazing bet involved a man predicting 4 different things that would happen in the year 2000. The man from Wales bet £30 that the TV shows EastEnders and Neighbors would still be on the BBC, that U2 would still be a band, and that musician Cliff Richard would be knighted.  Ladbrokes Casino took the bet and gave him 6,479 to 1 odds.

In 2000, Ladbrokes would wind up paying on what turned out to be the biggest novelty bet of all time when they gave the man £194,400. In 1964, David Threlfall contacted British wagering company William Hill and placed the following bet:

” . . . a man, woman, or child from any nation on Earth being on the Moon or any other planet, star, or heavenly body of comparable distance from the Earth before January 1971.”

He was taking the promise of President Kennedy to place a man on the moon by the end of the decade. William Hill gave him 1000 to 1 odds. He bet £10 and after Apollo 11 landed on the moon, they issued a check for £10,000.

Notorious for his strange bets, Thomas “Amarillo Slim” Preston, challenged 1939 Wimbledon champ and noted “Battle of the Sexes” participant Bobby Riggs to a game of ping pong. The bet was for $10,000, Slim would supply the paddles, and Riggs would get to choose which paddles to use. Slim chose 2 iron skillets as the paddles. He had been practicing with them for months. He won 21 to 8.


These are just a few of the most incredible bets ever placed. There are many more throughout history. For example, Terry Watanabe lost over $200 million on blackjack at Caesar’s Palace in Las Vegas. He was unable to pay the debt and wound up getting sued by the casino for a far lower amount of $15 million.

In another case of foreshadowing, a grandfather in Wales placed a bet on his 18-month-old grandson. The bet was that he would one day play soccer for the Welsh national team. 14 years later, Harry Wilson would become the youngest player ever to make the team and his grandfather would collect £125,000 on a £50 bet.

The common theme that we can see from all of these people is that they took a chance. Some took a huge financial risk. Others made a small amount into a huge sum with the use of some luck and educated guesses. Either way, they sure made for some great stories.

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