Funniest, Craziest Gambling Stories – Tales from the Pit

A spin on the roulette wheel, 80 hours passing chips at the poker table, an incredible streak of luck at the races. Most of us know a funny, straight up crazy gambling story. Similar to a ‘rite of passage’ or ‘coming of age’, gamblers, and their friends, love to compare each other’s triumphs and even pitfalls. Here are our top 5 picks for funniest gambling stories.

Grandma Rolls, and Wins, 154 Times

The odds for this first story are 1 in 1.56 TRILLION. Grandmother Patricia Demauro walked to a craps table at Atlantic City's Borgata Hotel Casino and Spa with $100. She had only played craps one other time, but tired of the slots she had previously played, she picked up the orange dice and started off with a lucky “roll”, no pun intended. Four hours and 18 minutes later, Demauro had not only won all 154 rolls, but had also broken a world record for the longest craps roll and the most successive dice rolls without "sevening out." She never stated how much she won, but experts suggest it was likely to be in the hundreds of thousands, perhaps millions. Now that is luck.

A Lucky Win and then Deportation

You hear about gamblers undergoing serious despair and defeat after they’ve cashed in their winnings. But for a woman in Arizona, she had her moment of despair soon after she won the $1200 jackpot at a local casino. After heading to the cash booth to eagerly collect her winnings, she was asked to show her passport. Her failure to do so led to further questioning and the realization that she was illegally in the United States. Not only did she not get to collect her winnings, but she was deported back to Mexico. The key thing to take away here is have your legal I.D. ready to avoid problematic situations.

300,000 FedEx Employees (and Counting) Owe Their Jobs to Gambling

FedEx currently employs 300,000 people worldwide. The transportation company has a $33 billion dollar capital gain, with its founder and CEO Fred Smith having a personal net worth of $2.1 billion. Had it not been for a Blackjack table, the billion-dollar company may not have ever existed. In 1973, the company had $5,000 in the bank and a $24,000 fuel bill. Thinking they would have to liquidate, Fred Smith decided to take his last bit of money and head to Vegas. There, he turned the $5,000 into $27,000 at a Blackjack table. It was that night which put a man on the path to one of the wealthiest people in the world.

The 20-Second Win

Ashley Revell, an English gent, went for an all or nothing roulette spin. After emptying his savings account and selling every single thing he owned, Ashley had a whopping $136,000. He let the wheel work its magic and 20 seconds later, he turned his cash into $272,000. Not bad, but we don’t recommend spending every penny you own in one game.

Cheaters or Not?

In 2000, gamblers Michael Russo and James Grosjean were uncomfortably detained at a well-known casino. They’re suspected crime? Cheating. They’re names were etched into the Griffins’ Book, a database of undesirables. The casino considered this just another day at the office, but Russo and Grosjean sued. They claimed that they had not been found with any cheating devices, they didn’t steal chips and they didn’t cause uproar. They used their minds and their “style of play” to beat the casino, aka counting cards. They argued that the casino and Griffin Investigations illegally detained them and blacklisted them. The verdict? These two gamblers won the suit.

Citing the large financial awards, Griffin Investigations filed for Chapter 11 bankruptcy in 2005. Moreover, the casino and other strip casinos have changed their policies about counting cards. And, no, casinos are net letting players count cards; they just can’t take you into the backroom for an impromptu shakedown. Lesson here, lawsuits can indeed change behavior of not only people, but casinos too!

Fact or Fiction?

Our last funny gambling story is one which has not been officially confirmed, but it’s so good that we’ll include is as a bonus. In 2010, news about an 8-year-old boy from Chandigrah, India winning $500,000 spread like a wildfire on the internet. The story goes that this boy, dubbed a computer genius in the sense that he was building web pages at age 4, was using his uncle’s poker account when he hit the jackpot. Sources say the poker room refused to pay out because of the boy’s age, but the family insists that the website did indeed know the age of the boy and that they called him the “little poker wizard”. They claim he also won, and collected smaller amounts of money on the site and was paid via PayPal. Since, the anonymous poker site blocked his account. The family of the boy took the poker site to a New Delhi court. As of now, the outcome has not been released. If the story is true, this boy definitely has a solid future in online poker.