It’s been said that there is “no money like won money.”  But playing Texas Hold ‘Em is so 2005. Fortunately for us, the sheer number of bizarre (and entertaining) ways that gamblers are upping the ante these days is truly hard to believe.

To that end, check out these 15 Most Outrageous Bets Ever Made and make sure to use “restraint” on your next trip to Las Vegas or Atlantic City. The life you save may be your own.

1. The Largest Novelty Bet in History

Nostradamus had nothing on one particular Welshman.  In 1989 he made a single novelty bet, for £30 ($47), with the following forecasts:

• Neighbours would still be airing (British TV)
• U2 would still be together
• Eastenders would still be airing (BBC)
• Home and Away would still be airing
• And, oh yea, Cliff Richards would be knighted
• All of this would be true by the  year 2000

11 years later, his winnings came to £194,400 ($307,793).  That makes it the largest winning novelty bet to date.

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2. Ashley Revell Bets Everything on One Spin

Ashley Revell took the advice “bet on black” to heart… selling all of his possessions and amassing his savings then putting all of it ($135,300) on a roll of roulette.  This video is the aftermath. Fortunately for Ashley…he choose “red.”

3. Fistfight Bet

Jonny Moss felt like pressing his odds, throwing a haymaker at a man who claimed he’d “never lost a fight”.  The odds his friends gave were 15 to 1, and apparently for good reason, because Moss ended up in the hospital with multiple broken bones and a few bucks poorer.

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4. Turning a Social Security Check into $1 Million

$400 bucks from social security and a dream is all one man had in 1995.  He’d been booted from his home, left by his wife, and hadn’t showered.  So he went over to Treasure Island Casino, won $1 million using a strange blackjack strategy, and then lost it all (plus the $400) back to the house. This “Million Dollar Bum” legend has made the rounds in Vegas for years. Is it true? You be the judge?

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5. William Lee Bergstrom Bets it All….and Loses!

Pigs get fat, hogs get slaughtered.  Berstrom bet $777,000 on the Don’t Pass Line (playing craps) and won.  Unfortunately, he kept playing…and lost everything. Three months later he wagered what remained of his saving on a game of Russian Roulette… and paid the wager in blood.

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6. Turn a Vegan into a Meat Eater.

Howard Lederer (2-time WSOP winner) was dangerously overweight and was advised by his doctor to get both a gastric bypass and become a vegan to literally save his life. He did both and lost over 75 pounds. Fellow gambler David Grey saw this as a golden (Arches) wagering opportunity and bet Lederer $10K he wouldn’t eat a cheeseburger. Bad bet…Grey lost every penny of the wager before Lederer had finished wiping the ketchup from his chin.

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7. Move to Des Moines, Win $100,000!

John Hennigan openly and vocally hates the “simple life” and the plight of normal people. A $100K wager by a group of friends said he couldn’t stay in Des Moines, Iowa for 6 weeks.  It proved to be a safe bet, as Hennigan sped back to Las Vegas after just 2 days.

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8. The $1 Million Weight Loss Bet”

The odds were 10 to 1 against Doyle Brunson bringing his weight below 300lb, with $100,000 in the pot from various other gamblers.  The Bet was made by a group of gamblers in 2003 who thought they could win big.  Brunson used the Atkins Diet and Weight Watchers and collected $1 Million in winnings.  Mike Matusow wasn’t as fortunate, losing a $20K wager to Erick Lindgren after losing 17lbs and then quitting.

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9. The Flight Attendant Bet

In 2009, Richard Branson owner of Virgin airlines and always the publicity whore, was so confident his Formula 1 team could beat Fernandes’ (LOTUS) team he put his masculinity where his mouth was. The loser dresses up like a flight attendant and works on the winner’s airline for a day.  Fernandes’ reply?  “Bring it on, the sexier the better.”

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10. Could you eat 450 Hot Dogs for $1500?

$1,500 on the table, a ‘friendly wager’ between two poker-playing university (McMaster University) students and a grocery store full of goodies always makes for a fun time. The bet? Who could eat the most hotdogs in a month?  450 hotdogs later, Jim Harrison was crowned the winner, eating an average of 15 hotdogs a day to snag the bet.

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11. Man Gets Breast Implants, Wins $100,000!

Some men pay money to get rid of man boobs, but one crazy Canadian gambler – Brian Zembic – got paid to put them in (1996).  This is the same guy that bet $15K he could stay in a bathroom for a month (and won).  Fourteen years later, and the man still has his man boobs (38C)… and an extra $100,000 he won from the bet.

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12.  I Bet I Out Live You!

When Evel Knievel, the famous stunt biker, got hepatitis C, in 1998 he bet $10,000 with the doctor treating him (who is 22 years his junior) that he would outlive him.  Sadly Evil Knievel died in 2007 but it’s not known if the doctor has cashed in on the bet.

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13. Cancer Man Gambles, Bets on Own Life and Nets $16,600

Jon Matthews bet against cancer, defying the doctors who gave him 5 months to live.  He was able to cash in over $8300 the first year and then another $8,300 the next year. In the third year – his odds to live went up to 100 – 1 and he could have netted another $16,000 but sadly he died in May this year.

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14. Man Loses Wife in a Game of Poker

In 2007, a Russian man, who was losing heavily in a game of poker, decided to use his wife as a bet. Andrei Karipov ran out of money so decided to use his wife as collateral to stay in the game. Sadly he lost the next hand and his opponent Sergey Brodov came to collect his winnings. Andrei’s wife was so upset at being used as a bet that she divorced him and started a relationship with Sergey!

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15.  The Lucky Number 23 Wins Man $1200″

This one has nothing to do with the terrible Jim Carrey movie, although it’s just as unbelievable. To commemorate his 23rd birthday, a man entered the Palace Casino on the Isle of Man and bet £23 on the number 23 at precisely 23 minutes past 11P (the 23rd hour).   The date was September 23rd, 1992 … and the man won to the tune of £800 ($1200).

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Tag(s): Gambling Industry, Uncategorized