Gambling Loss Stories

Horrific gambling stories have been around since the beginning of time. For as long as humanity has had language and access to stores of value such as livestock or currency, gambling has likely been a fixture of daily life. Sometimes these stories involve depths of depravity which reveal the darker side of human nature.

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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. Carolyn Crawford went to prison for stealing from her employer to support her pokies addiction, and now shares her story to encourage others to seek help for gambling harm. 1 The Gambler Who Blew $127 Million. Harry Watanabe founded a gift shop, the Oriental Trading.

Oftentimes gambling horror stories feature plot elements that are so unbelievable they seem made up. Nonetheless, the most gut-wrenching compulsive gambling loss stories all seem to feature corruption, loss, or lawsuits at some point along their ill-fated trajectories. Remember, whether you are playing at one of the best online slots casinos, or playing a casual game of poker with friends, you need to make sure that you gamble responsibly.

If you are worried about your gambling, or if there is someone in your life whose gambling is damaging their life and relationships, ask for help. You can get some advice on our responsible gambling page. Otherwise, head over to begambleaware.org/.

Gambling Horror Stories: The Worst of the Worst

3. Tommy Four Fingers Goes All in

Tommy Four Fingers dreamed of being a high roller. The only problem: he could barely count, struggled with basic math and didn’t really have the worldly sensibilities necessary to be able to understand the nuances of human emotions.

Nonetheless, he was determined to make it as a champion poker player, even if all the available evidence pointed to the futility of his desires. One day, while scheming and daydreaming, Tommy happened upon an idea which he believed would finally lead to the breakthrough he needed to make his dream of being a professional poker player come true.

To set his plan in motion and finally receive the backing he needed to enter into a high stakes poker tournament which he would surely lose, Tommy decided it was a smart idea to rob the bookmaker down the street from his Grandma’s house.

He had been scouting the bookmakers for some time and knew the perfect chance to strike was when Sergio the Stiff went outside to smoke a cigarette, leaving only Ronaldo the elderly bookmaker in the store.

As Tommy launched into his plan, he was struck with a moment of guilt and remorse, nonetheless, he went forward, bludgeoned Ronaldo and made off with about $20,000. His excitement would ultimately end up being short-lived but Tommy could barely hide his enthusiasm as he ran to the local casino to finally enter into a high stakes poker game

After playing a few hands and immediately going down $10,000, Tommy’s brow began to moisture with the sweat of remorse. Without warning, he decided to immediately go all-in on his next hand.

To his luck, Tommy had planned one thing right and actually won the hand, raising his winnings to a meaty and rather enjoyable $46,000. It was at that moment that the police stormed through the door and arrested Tommy before he could even pull the massive pot towards his side of the table.

Compulsive Gambling Stories

As the police brought Tommy out towards the squad car, he could be heard bellowing into the night: “But I finally won. I’m a winner. I went all-in and I won. I’m a winner. I’m a winner guys. You see, I finally won. I did it.”

2. The Baden-Baden Experience

Gambling Problem Stories

The stately and luxurious Baden-Baden Casino in Germany is the kind of place a James Bond villain would absolutely love. In its storied history, its hosted many horrific gambling stories over the years but nothing can compare to the time Prince Egor of Albania came to take part in what later became known as “The Baden-Baden Experience”.

The year was 1884 and Prince Egor of Albania had a score to settle with his rival, Prince Charles of Bavaria. To settle their score, the princes descended upon Baden-Baden Casino to lock themselves into a private room to play a head to head match of the legendary French game roulette. As both princes were known for outlandish boasting and gambling loss stories, it was not surprising that the game quickly escalated to a serious round of Russian roulette.

On the third round, both princes, full of alcohol, spite and malice, killed each other, leaving their trusted security staff to pick up the pieces. Each of the heads of security agreed to make a deal with each other in return for the other’s silence and loyalty: they decided to take all the prize money in the room, the carriages the princes rode in with and to flee to America to start new lives as wealthy paragons.

In their new lives, the former security guards became famous in their new home city of New York, whenever anyone asked how they had gotten together the funds to start their successful business as restauranteurs, the former guards would reply: “It all started during a high stakes tournament in Baden-Baden, we entered as enemies, but walked out as brothers.”

1. The Card Counters of Birmingham

Phillip, Rigby, and Charles were well known as some of the most successful professional gambling crew in all of Birmingham. Not a single unlicensed game, illegal casino, or reputable private gambling arena hadn’t seen their fury since the trio had moved to the city two short years ago.

Growing more and more brazen as time went on, Phillip eventually hatched the plan to bring the group’s proven strategy to a bigger stage, in pursuit of an even bigger prize. All was going to plan until Rigby was up by about $23,000 while the group hustled a high stakes blackjack table at the local casino.

Within no time at all, the trio found themselves on the wrong side of a beating and a warning never to ever return to a casino and attempt to pull another card counting trick again or else. Taking offense to this insult against their gaming integrity, Charles suggested the card counters take the casino to court.

In the end, the jury was split. When the tie-breaking vote came through it was a relief to all parties, except Phillip who somehow knew they would never get away with their brazen crime. He ended up being correct.

In the end, the court ruled that due to the brother’s obvious illegal malfeasance, not only did they have to pay the casino more than $100,000 in damages, they were ordered to report to a prison chain gang immediately.

Horrific Gambling Stories: Just Say No to Problem Gambling

Problem gambling is any gambling that causes issues in your daily life and functioning.

Consider the story of Tommy Four Fingers: despite the fact that he rarely had success gambling, he was compelled to go to any lengths to continue to try to support his habit. He ended up breaking the law to try to continue his dream of entering a gambling tournament.

Don’t forget the story of Prince Egor: he became so consumed with gambling it led to his untimely death and the loss of a vast amount of his kingdom’s fortunes.

Hi All
I have recently been looking and reading this forum since I made a huge loss on online roulette, and online blackjack.
It all started with watching some videos on You Tube, and a particular channel of this guy making and losing money. I thought wow this guy is using REAL money, and not fake play to show his gambling sessions.
This re-ignited a flame as I have gambled online, in bookies, and in casinos in the past.
The flame was now lit, and I initially started with depositing £20, and then the online casino doubled it.
In the past I had never done this deposit match, I just deposited my own money so I didn't have to meet the bull**** wagering requirements.
Basically I ended by gambling only on roulette, but then moved onto blackjack because the You Tube Channel I was watching daily made it look so easy to win at both roulette and blackjack.
I ended up losing £6000 in a matter of an hour initially chasing a loss of £100. I had to start moving money from my savings accounts, and felt physically sick when I made this loss.
I new that I could carry on, and either max out my overdraft, credit cards available to me etc, but it was at that point I knew I never wanted to GAMBLE AGAIN as I did not want to lose my money.
I think I am a BINGE gambler, the reason I say this is because did not gamble before stumbling upon this You Tube channel.

Worst Gambling Loss Stories

I also want to add I am extremely tight with my money. I have a wife of 8 years, and a 2 year old daughter, and try to save where ever I can always looking out for deals here and there.
How can I forget about the losses and see the loss as a positive?