Great Gambling Stories

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• My life is full of gambling stories. Some are funny, some are sad, some other almost tragic. I enjoyed and was fascinated by many of your stories here and decided to share some of mine in a series of short stories. Here’s the first one:

  My gambling addiction goes back a couple of decades. I was 16 when I started playing slots (nobody bothered to check my age back then) and as soon as I turned 18 I started visiting casinos, playing roulette at first and then, later, black jack. I was completely addicted by my early twenties. Addicted to the point where I was late on my rent and had literally nothing to eat on many occasions. It was horrible and I sometimes resorted to actions that I never though I was capable of. Actions that I was often ashamed of. At one such occasion my rent was overdue and I asked a friend for a loan. There was no one else I could ask for help. I emigrated when I was 20 and was all on my own in a foreign country, with a bad, bad gambling addiction. He agreed to loan me money for my rent, but knowing of my gambling habit, he warned me not to gamble, but to pay my landlord immediately. I didn’t appreciate him telling me something that obvious. Of course I wasn’t going to gamble with that money! Why does he have to rub it in, I thought to myself. What an *******! Of course I was going to pay the rent. What was he thinking? That I would gamble away my rent money now that my rent is overdue? He just wants to rub it in, that’s all. Not the friendliest thing to do, but I have only myself to blame. Anyway, I was going to pay the landlord. Had somebody asked me what I thought the odds were of me stopping at the casino on my way home and losing all that money, I would have said less than 1 in 1000. And I really wasn’t gonna stop at the casino. No way was I going to do that. I knew I had to pay the rent and I knew that if didn’t the chances were I would end up on the street. Homeless. No, I wasn’t going to take that chance; I was going to go straight to the landlord and pay my rent.
  But then I realized something. My buddy loaned me 375 fl. (guilders, Dutch currency before introduction of the Euro) and my rent was only 360. He didn’t have change, so he gave me 3 hundred fl. bills, 1 fifty fl. bill and 1 twenty-five fl. bill.
  That extra 15 fl. opened a myriad of options for me, endless possibilities. Not only did I now have money to pay my rent, I also had 15 fl. above and beyond that. 15 fl. that I was going to parlay into something meaningful. I was loving life. Not only was I not getting evicted, but with some luck I was going to have 50 or maybe even 100 fl extra and treat myself to something nice. Something I was long due, something that I deserved. Maybe a steak, french fries and some snacks for later. I had been eating crap for months. Blood rushed to my head. I was excited, ecstatic even, thinking of what I could do with 50 fl. And parlaying 15 to 50, although not likely, is possible. 1 in 3 odds. I can do it. I was due a break.
  And if I lose the 15 fl? Too bad, but I didn’t count on that money anyway. I knew there was no way was I going to lose more than 15. Worse comes to worse I’ll lose the 15, go home and pay the rent.
  After some consideration I decided to play a single hand of Black Jack first. I liked Black Jack and had just learned the basic strategy. I bet 10 fl. and was dealt 11 against the dealer’s 7. For those of you not familiar with Black Jack, having 11 against the dealer’s 7 is a fairly big advantage. I was tempted to double down. Double down I did, adding another 10 fl. and I lost. Now I only had 355 fl left, meaning I was 5 fl short on my rent. Not the end of the world, I knew, the landlord would understand it and wait a couple of days for 5 fl. But, instead, I decided to chase the 5 fl. with 350 fl.
  Short story shorter, I lost it ALL.
  That was probably the worst night of my life. I knew I was going to get evicted. I walked home, a long, cold walk through rainy weather. I was happy it was cold and I was wishing it would rain harder. I wanted to be punished. I arrived home and I didn’t know what to do. I lied on my bed. I thought about my options and quickly realized I had none. I was so poor, I had no valuable belongings that I could sell, I couldn’t ask my friend for more money because he wouldn’t give it to me, I knew the landlord wouldn’t be too sympathetic and I had gotten fired from the restaurant I was working at, a week earlier.
  The near future looked grim. I was lying in my bed motionless, inspecting my surrounding. I was tired, but I was afraid to fall asleep. I was afraid to fall asleep for I knew it would be a night full of nightmares. I had been there before. But it was never this bad. I looked around me in desperation. My shabby belongings, my worn-out shoes, a few books, my walkman, a couple of t-shirts and underwear that I hung to dry. One object caught my attention though. A roll-on deodorant.
  Then, I don’t know how or why, an idea formed in my head. I don’t know where it came from or what led to it, but I suddenly found myself grabbing the deodorant (it was made of glass) and started banging my face. I hit myself hard, inspecting for bruises after every blow. No bruises appeared at first and I kept on banging my head with the deodorant bottle relentlessly. It hurt, but I deserved it. And besides, I wasn’t doing it to hurt or punish myself. I was doing it as a way out. A shameful and disgraceful way out, I knew; but still better than the alternative of becoming homeless.
  I stopped hitting myself after a few minutes and waited. My face turned first pink then blue. I overdid it. My entire face was swollen and looked terrible.
  I went to bed and fell asleep. I slept like a baby for I knew my problems would go away. At least for the time being they would.
  In the morning I saw the landlord and told him what happened. I was mugged by two guys in the park. And they robbed me. They robbed me of the rent money I was going to give him that day. He was very sympathetic and said he’d wait till I’m in a position to pay him. Told the same story to my friend and he loaned me another 375 fl a couple of days later. This time I made it home.
  It wasn’t until 20 years later that I told my friend what really happened that night. He and I have been through thick and thin together and he is the closes friend I have. Even so, I felt really uncomfortable coming clean about it. If you dine with the devil, bring a long spoon

  Boy to I feel that pain. Been there.. literally.. Thanks for posting. It reminded me of that horrible feeling in the pit of your stomach when you are desperate and know you have no way out and no one to blame but yourself. That horrible feeling of self loathing and desperation where ideas you never thought were possible pop into your head. I never want that feeling again. It cost me too much.
  Thanks again.
  I will make this work!

Given the nature of gambling, it can throw up a surprise or two. But sometimes, when the stakes are raised, the story becomes that bit more compelling. We’ve trawled the depths of the Internet to compile a comprehensive concoction of the crazy, the weird and the wonderful moments associated with gambling in collective human memory.

• Let’s end with a nice story involving mermaids “I was on a $2 table with three friends and a guy sat down and started betting 25k a hand. Bosses came over and asked if we wanted to change tables etc. So the table gets hot and we all start winning. I mean like 15 of.
• Gambling is more than just a pastime, it’s part of human nature, which is something that great authors understand and, sometimes, find a use for in their stories. Here are some great tales featuring card games. Take Roald Dahl, the master of the “twist in the tale” within a short story.
• Overview The Greatest Gambling Story Ever Told is an inspiring personal narrative about a filly who broke through the male-dominated world of horseracing and inspired crowds of men and women alike, along with a trio of gamblers who embark on an unforgettable adventure that’s as epic as the historic victory of Winning Colors.
• Will Ferrell chats with Jimmy Fallon about his comedy “The House,” his terrible real-life poker face and a gambling story that may or may not be too good to be true.

Great Gambling Stories Youtube

Many gambling addiction stories start out innocently enough—a trip to the casino here or there, a few good wins, then a loss or two. Then something happens. The same chemicals in the brain that cause a person to become addicted to alcohol or drugs soon start to react to the act of gambling in a similar way.

It’s likely that plenty of epic tales of gambling have passed without being recorded. After all, if you won £40 million playing baccarat before somehow getting trampled by an elephant while celebrating, you might not want people to know about it. If you had just robbed a bank, and then blown the lot in a casino the same night, you might not be very forthcoming when asked about it. Fortunately, some crazy gambling stories survived, including some truly legendary tales which have been immortalised in movies and books. Read on to find the best real gambling stories around.

All or Nothing – Players Who Went All In

Do you have to be crazy to risk everything? That’s probably a question you should ask Ashley Revell, who bet all he had on a roulette wheel landing on red. The Englishman sold everything he owns, including clothes and childhood football trophies, to fly to Las Vegas and gamble it all in one spin of a wheel. It was just under £80k, which included cash from an online bookmaker who sponsored him for changing his name to ”Ashley Blue Square Revell”. He won, and doubled his money.

The whole thing was filmed for a TV show entitled Double or Nothing, and has been a source of inspiration for nutcases the world over ever since. Possibly the craziest thing about the story is that he chose to risk it all on an American roulette wheel, which offers worse odds (47.3%) than on a European wheel (48.6%).

The Most Audacious Casino Cheats in History

There have been numerous cases of punters attempting to cheat a casino down the years. It’s likely that some of the best gambling stories slipped through the cracks because, well, they got away with it. Needless to say, these upcoming cheats didn’t get away with anything – eventually.

When a group of maths whizz kids from the famous MIT university in the US decided to play some blackjack in Las Vegas, they had a cunning plan up their sleeves. They found a way to predict when the cards being dealt would be favourable to them by using a technique called card counting. They won tonnes of money, including over $400,000 in one weekend. They were able to roughly predict how many cards are left, which ones have been spent and which ones remain in the shoe. To avoid detection, they rotated personnel regularly and employed a counter to sit in on games and secretly signal when the team’s designated high-roller should start playing. The tale was turned into a movie called 21, starring Kevin Spacey.

In the early 1990s, a Spaniard by the name Gonzalo Garcia-Pelayo realised a way to beat roulette. He noticed that some roulette wheels had very minor imperfections, which meant that some numbers came up more than others. He analysed data from thousands and thousands of spins to determine the statistical distribution and the hot spots. He, and members of his family, then bet on these numbers every spin. He is considered the first person to beat the roulette absolutely honestly, using mathematical precision. His story was told in the 2012 movie, Winning Streak.

The Luckiest Players Ever?

Sometimes the laws of nature, and probability seem to stand aside for a moment, letting some lucky punter slip through a loophole in the universe. Insanely good fortune can seem quite surreal when it occurs, and for the beneficiary, keeping a hold on reality might become a challenge.

In 2009, a Grandmother from New Jersey, USA, left the Borgata Hotel Casino in Atlantic City as the most fortunate player in a casino ever. The odds of rolling a pair of dice 154 times at a craps table, without throwing a seven are an astonishing 1 in 1.56 trillion. That’s a figure almost impossible to comprehend. The lucky lady was rolling the dice for four hours and 18 minutes, breaking the world records for the longest craps roll and the most successive dice rolls without hitting a seven. The amount she actually won from the casino was never revealed, but even if you wagered a paper clip, it’d probably be enough to buy a small country or perhaps 1.56 trillion paper clips.

On a slightly different tangent, the multinational delivery company, FedEx, would likely not exist today if it weren’t for blackjack. The owner, Fred Smith, realised the company was in trouble when it was down to its last $5k and it couldn’t afford to fuel the delivery planes.

He decided to head to Las Vegas and gamble with the last of the company money. The next week, he returned after turning the $5k into $26k – enough to keep the company in operation. The money wasn’t the solution to all his problems, but it was the catalyst to propel the company towards the huge success it has now become. Fred Smith is now worth an estimated $4.3 billion dollars.

What On Earth?!

The biggest wins are not always the best gambling stories. Money does add a bit of a ’wow’ factor, but some punters have won by some remarkably ridiculous and unconventional means.

• Five of the Strangest Bets in the History of Gambling
• A Welsh punter beat the odds of 6,479/1 with a strange novelty bet in 1989. He gambled £30 that in the year 2000, U2 would still be a band, EastEnders and Neighbours would still be on the BBC, and Cliff Richard would be knighted. Ladbrokes paid out £194,400 in one of the biggest novelty bet payouts ever.
• In 2014, a Norwegian gambling website offered odds of 175-1 that Uruguayan football star, Luis Suarez would bite someone in the World Cup. Given the striker’s penchant for such a thing, 167 punters took the bait. Suarez took the bite and made some very happy Scandinavians.
• Brian Zembic is a high-stakes gambler and magician, who developed a reputation for taking on any bet. In 1996, he agreed to have breast implants and keep them for one year in return for $100k. He grew accustomed to his new friends, and decided to keep them.
• In 1980, William Lee Bergstrom arrived at a Las Vegas casino with two suitcases. One contained $777k, the other was empty. He bet the $777k on a single roll of a dice – the largest bet in the history at the time, and he won. A friend, Ted Binion, said Bergstrom had intended to kill himself if he lost – after borrowing most of the money for the bet – but instead ended up travelling the world for several years.
• A grandfather saw his 18-month-old grandson kicking a football about and decided to put £50 on him one day playing for the Wales national team. Peter Edwards cashed in £125,000 when grandson Harry Wilson eventually became the youngest player to ever play for Wales, aged 16.

Winning Can Be a Curse

Life can often seem unfair. Sometimes, some people seem to have all the luck. And then there are moments where the universe seems to get its revenge, in order to restore an equilibrium; moments of extraordinary bad luck following on from the absolute opposite.

In 2000, cocktail waitress Cynthia Jay-Brennan became one of the biggest winners in casino history, winning an incredible $35 million on a Las Vegas slot machine jackpot. Just weeks later, Cynthia and her sister were in a car, stopped at a red light, when a drunk driver ploughed into their vehicle. Her sister died, and Cynthia was left paralysed and confined to a wheelchair. She had only just gotten married.

The culprit already had 16 charges of driving intoxicated and was sentenced to 28 years in jail by a Nevada jury. The extreme swings of fortune have turned many a person superstitious, and added fuel to the fabled ’gambler’s curse’. Cynthia told reports she’d give away all the money to have her sister back.

The self-styled ’King of Chavs’, Michael Carroll, lived an outrageous lifestyle after winning £9.7 million on the UK National Lottery. The former dustman turned up to collect his winnings wearing an electronic tag, and the money funded a lifestyle that left him with less than he had before. It took him 8 years to squander it all away on drugs, gambling and prostitutes. He ended up with a crack cocaine habit, and without his wife, who left him due to the strains his new lifestyle put on their relationship. Carroll now works in a biscuit factory.

The Unluckiest Player Ever?

There are plenty of tales of punters who have had a run of bad luck that defies belief. Most of the time, you won’t hear anything about it because big losers don’t want anyone to know about their exploits. However, some tales of misfortune slipped through the net, and made it into folklore; the punters’ names, into keywords for bad luck.

Gambling Addiction Stories Women

• Five Insanely Unlucky Punters
• Martyn and Kay Tott won over £3 million on the lottery. Unfortunately for them, they didn’t realise it. They discovered it six months later after seeing an appeal for the winner to come forward, by which time they had lost the ticket. The lottery organiser, Camelot, refused to pay up, even though computer records could prove they bought a ticket with the winning numbers. Martyn launched three unsuccessful legal battles, and the stress of not living the life he thought he should have cost him his marriage and his sanity.
• In 2012, bus driver Hazel Loveday pulled out of a work lottery syndicate just six months before the numbers came up. She experienced seeing her 12 colleagues win the £38 million EuroMillions jackpot without her. She says she pulled out of the syndicate because she couldn’t afford the weekly £2 contribution. Apparently, they didn’t even share any of the money with her. Harsh.
• In 2007, high-roller Terry Watanabe lost over $120 million at Caesar’s Palace in Las Vegas. Tourists crowded around the tables he played at so they could witness a man wagering staggering sums of money on blackjack. His play was notoriously bad, often hitting when on twenty, and his total losses reached over $200 million. He wasn’t able to pay the debt and the casino sued him for $15 million.
• Austrian casino enthusiast, Josef Reiner, lost thousands of dollars playing roulette, but he was more concerned about how his wife would react. He was willing to avoid telling her how he lost the money at all costs and fabricated a story about being mugged. To make the story seem authentic, Reiner broke his own nose, jaw and arm with an iron bar.
• Japanese high-roller Akio Kashiwagi was regarded as one of the biggest gamblers in the world in 1992. He holds the record for the biggest baccarat loss in history, waving goodbye to $10 million in one session at the Trump Taj Mahal Casino in Atlantic City. Soon after, he was stabbed 150 times with a samurai sword, in a murder still unsolved to this day.

High Roller No More?

For some punters, money is no object, and gambling with the GDP of a small country is their way of making that perfectly clear to everyone. To them, losing millions in one hand of blackjack is as life-changing as a mosquito bite. These are the people who draw crowds when they play; people who can bring a casino to its knees in one foul swoop; people who have spawned some truly crazy gambling stories.

Billionaire Kerry Packer goes down as arguably the highest high-roller in history. His exploits saw him win an enormous amount of money, but he also lost staggering sums on many occasions. As a consequence, casinos were by-and-large very happy to see him. In 1999, he lost close to $28 million in one session of blackjack at Crockford’s Casino in London. However, given his immense wealth, the loss wasn’t enough to stop him from continuing his gambling habit. Packer was renowned for paying off the mortgage of one dealer and tipping $1 million to dealers after clearing out one casino.

Archie Karas, on the other hand, achieved legendary status for turning $50 into $40 million in casinos, over the course of three years. He had an astounding run of success, largely playing poker, but also other casino games. Unfortunately for Karas, the laws of physics dictate that what comes up, must come down. His luck ran out, and he managed to lose $11 million dollars in three weeks playing craps. Then lost another $17 million trying to recoup his losses, before losing another $2 million playing poker. That’s $30 million, in just four weeks.

From Hero to Zero

Proving the dangers of gambling are well and truly real, these gamblers left with more than just a hole in their pockets.

A woman in Arizona won a $1,200 slots jackpot in a casino, but she failed to show her passport when trying to cash in. This prompted further questioning and the realisation that she was in the United States illegally. Consequently, she didn’t pick up her winnings, and she was deported back to Mexico.

In one of many sad gambling stories from the UK related to addiction, Justyn Larcombe squandered a massive £750,000 in online sports bets. Previously, he had a six-figure salary and he and his wife owned a £450,000 townhouse in an idyllic Derbyshire village. His addiction grew, and he was eventually forced to sell his possessions, including the house and his £30,000 Porsche. His wife left him and took their two children with her, and Justyn now lives alone in a rented cottage. The online gambling industry in the UK is worth over £2 billion, and there are many unfortunate punters with tales like that of Justyn showing just how important it is tomanage your bankroll and gamble responsibly.

Celebrities Who Gamble

Some people just want all the limelight for themselves. A whole host of famous faces have been spotted at high-roller casinos, and have lost their way, along with a fair chunk of their fortune. Needless to say, they tend not to be happy about being spotted, especially when they lose. But gambling is addictive, and it can lure even the most camera-shy celebrities towards the bright lights of Las Vegas or Atlantic City.

Golfing legend Tiger Woods is well known for his gambling exploits. He’s regularly seen in the exclusive high roller Mansion club at the MGM Grand in Las Vegas. The club set him a $1 million-dollar betting limit in the fear he’d win too much, and he frequently played blackjack at $25,000 a hand.

Spiderman star Tobey Maguire was sued for his involvement in a multi-million-dollar illegal gambling ring. Allegedly he won more than $300,000 dollars’ worth of illegal funds, stolen from a jailed hedge fund investor. He is a very skilled Texas Hold’em player, and poker legend Phil Hellmuth claims he has won as much as $10 million through playing the game.

Great Gambling Stories Podcast

Charlie Sheen is well-known for various extra-curricular activities, and his ex-wife, Denise Richards, said in divorce papers in 2006, that he was spending about $200,000 a week on gambling. She even claimed Sheen would have called his bookie to place a bet while en route to the hospital for the birth of their daughter, Lola.

Faulty Casinos or Crooked Punters?

Owning a casino is, by-and-large, an incredibly lucrative investment. Unfortunately, to hold onto your house edge, you need to ensure the casino equipment is up to scratch. There are always going to be eagle-eyed punters willing to meticulously check the equipment themselves, but they probably won’t be too keen on letting you know about it.

In 2012, poker legend Phil Ivey tried his hand at a high stakes baccarat table in Crockford’s casino in London. Being the prodigious gambler he is, he walked away with a whopping £9.1 million. However, the casino contends that Ivey cheated because they could find a faulty shoe (the mechanism that holds the decks of cards). If the cards were dispensed in a particular way from this shoe, Ivey would gain an advantage. The practice is known as edge counting, and experienced gamblers throughout history have sought to find such an advantage. The casino sued Ivey, while Ivey counter-sued for not paying his winnings out. It has got many people wondering whether the casino should deal with the consequences of having faulty equipment.

Way back in 1873, knowing that man-made inventions were imperfect, engineer Joseph Jagger managed to find a way to beat the roulette wheel at the Monte Carlo Beaux-Arts casino. He hired six helpers to study the outcomes on the wheels until they discovered one of them had a bias. Needless to say, Jagger went for broke and left the casino $300,000 richer. The story was immortalised in the 1935 movie, The Man Who Broke the Bank at Monte Carlo.

Fourteen baccarat punters took $1.5 million from the Golden Nugget casino in Atlantic City due to faulty cards and dealers. The players noticed that cards were not being dealt out randomly, and they began to spot patterns. The dealers didn’t notice, and the players all increased their bets until they’d won a huge sum of money. The casino decided to sue the card manufacturer for the error.

Great Gambling Stories Quotes

Conclusion

True Gambling Stories

Some of these real gambling stories have inspired books and movies. Some have inspired others to go out and create their own rags to riches story. Some have probably been the catalyst for epic tales of rags to riches and back to rags again. We just hope someone will be there to tell the tale. If you’re after your own incredible gambling tale, you don’t have to go far to get started. Our recommended online casinos are just as good a place as any to tempt fate and reach for that incredible win. Don’t get carried away, though – always operate within a manageable budget and find the best casino game that suits your style!