The Funniest Gambling Stories Ever Told

Gambling is a funny old thing. Not many activities can evoke such extreme emotions. Life is always far more enjoyable when you focus on the good times, so here’s a list of the funniest gambling anecdotes ever told.

funny gambling stories shared with friends

Student Loses £4,400 Betting on African Cup of Nations

One of the most infamous gambling stories of recent times came back in January, 2010. A British student was watching the African Cup of Nations match between Angola and Mali.

Angola were 4-0 up with just 11 minutes of the game remaining. So, the student chose to wager his entire student loan worth £4,400 on an Angola win in-play. In one of the greatest comebacks in modern football, Mali scored four goals without reply to secure a 4-4 draw.

The student lost their whole loan in an instant in extraordinary circumstances. To rub salt into the wound, the student had expected a potential return of £440 from the massive bet but in reality he would only have won £44 from the bet if it had been successful.

Grandma Wins 154 Rolls in A Row On Craps

Patricia Demauro, from the famous craps gambling story
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Atlantic City is often seen as the gambling destination for the older clientele that wish to stay clear of the intensity of Las Vegas and Macau.

This reputation has not been helped by the amusing story of a sweet little grandma that pulled off a feat that had odds of 1.56 trillion to 1.

Patricia Demauro had barely played a game of craps when she hit the tables at the Borgata Hotel Casino and Spa in Atlantic City. She laid down a $100 bet and proceeded to win 154 rolls on the bounce over a period of 4 hours and 18 minutes.

She achieved a Guinness World Record for the longest number of rolls on a game of craps and the most successive wins on a game of craps. Go on Patty!

Blame It on The Boozie

Terrence Watanabe leaving court
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Casinos are often finding ways of keeping the players at the tables. If a player is spending a high amount on the casino floor then the management will be happy to offer them complimentary offers on food, drinks, and entertainment.

That tactic was one that would come and bite one big roller in the rear after one trip to the casino. Nebraska businessman Terrence Watanabe claimed to have lost $127 million betting at the Caesars Palace and Rio All Suite in 2007.

Watanabe made the allegation that casino staff plied him with alcohol and pain killers, to make him lose awareness of where he was and what he was doing. The businessman took Caesars to court over the claims but the case was thrown out when it emerged that Watanabe had previously been banned from Wynn Casino for excessive drinking on the casino floor.

Nice try Watanabe.

The FedEx F*ck It!

FedEx CEO Frederick W.Smith speaking publicly
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Express courier company FedEx is one of the most renowned shipping firms around the world. The US-based company recorded revenues worth $50.365 billion during 2016.

Business is booming for the company now but it hasn’t always been smooth sailing since it was founded back in 1971. In fact, FedEx CEO, Frederick W. Smith, has shared a story about the time when the firm was experiencing tough times.

Within a few years of its inception, FedEx was losing $1 million every month and Smith decided to take desperate measures. Smith withdrew the last remaining $5,000 from the company account and did what any rational human being would do. He hit the casinos…

Smith spent a weekend playing on the blackjack tables in Las Vegas and quickly turned $5,000 into $32,000. It was enough money to rejuvenate the company finances and the rest is history.

Although, it should go without saying that sipping Muay Thai cocktails and enjoying a game of 21 with the last funds of your company is not a proven business strategy.

8 Year-Old Storms Online Poker Room

8 year-old Aashish Nanak, the gambling phenom
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The final inclusion on this list remains open to interpretation about its legitimacy. In 2010, a story about an 8 year old boy, Aashish Nanak, from Chandigrah in India who won 22,912,500 rupees ($500,000) playing online poker started to do the rounds across news websites and gambling forums.

Even to this day there are still question marks hanging over how much of this tale is true but it’s a fun one nonetheless.

The story goes that Aashish somehow gained access to his uncle’s online poker account. Instead of plundering all the funds in his uncle’s account, like all of our own children would probably do if they were in a similar situation, Aashish actually went on to earn half a million dollars.

The online poker room allegedly refused to pay out on the money stating they did not know Aashish was so young.

Further investigation showed that staff at the site referred to Aashish as “the little poker wizard”. The New Delhi court decision has remained unconfirmed but we all hope Aashish got to take home the money that he cheekily won at the poker tables.