Real Gambling Stories

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.

Crazy capers in a casino

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

Some dice in a casinoDo 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?

Patricia Demauro after winning big 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.

Fred Smith, founder of FedExOn 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.

An image of a crazy gambler

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.

Cynthia Jay Brennan receiving a large chequeIn 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.

A cartoon image of an unlucky gambler

High Roller No More?

A luxury casino in all its gloryFor 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 fruit machine in a UK pubA 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

A picture of Charlie SheenSome 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.

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.


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!