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Whether for pride or money, gamblers do some pretty bizarre things.


History is replete with tales of man’s inability to back down from a challenge, especially if money is at stake.  From barroom brawls to swimming over Niagara Falls, crazy wagers are everywhere. Here are some of the world’s wildest.


Pedestrian Circumnavigation

Legend has it that notorious playboy Harry Bensley couldn’t help but overhear John Pierpont Morgan and Hugh Cecil Lowther, fifth Earl of Lonsdale’s conversation at the National Sporting Club in London in 1907. Morgan and Lonsdale were arguing whether a man could walk around the world without being identified. By the end of that evening, the two had placed a£21,000 wager—equivalent to £1.5 million today—on Bensley completing the journey. On January 1, 1908, Bensley began his journey from the Trafalgar Square, London, under 15 separate stipulations, among them that he was to walk through 169 specific British colonies in a particular order, push a baby carriage the entire way, wear an iron mask throughout, and find a wife along the way despite wearing said mask. The details of the trip have been muddled over the years, but some claim that he abandoned his journey after six years of walking with the onset of World War I.

Brawling into the Sunset

Toward the twilight of his rather wild and reckless life, poker legend Johnny Moss was once offered $15,000 to $1,000 odds that he couldn’t win a barfight. Moss, never one to back down from a challenge, ended up in the hospital with several broken bones. Legend has it that fellow gambling legend Puggy Pearson came to his bedside, pleading with Moss to stop his foolish bets. Moss told him, “Fifteen-to-one was too good to pass up. I had to take it.”

Deadly Swim

In 1875, Captain Matthew Webb became the first person to swim the English Channel. Webb must have assumed his reputation would hold up when he bet $10,000 that he could swim across the whirlpool below Niagara Falls. The boast proved costly, as Webb lost the wager and his life on the same day.

Millennium Bet

In 1989, a man in South Wales walked into a local sports book and put down a $75 bet on a series of events that he claimed would come to pass by the year 2000. They included singer Cliff Richard being knighted by the Queen, rock band U2 staying together, and soap opera Eastenders staying on the BBC. Sure enough, the man returned in 2000 with all these events having transpired. The cumulative 6,479-1 odds resulted in an estimated $486,000 payday.

A $100,000 Boob

Little did gambler Brian Zembic know that a discussion on the merits of breast implants would render him with a shapelier figure and a fatter bankroll. In 1997, Zembic’s friend, a high-stakes backgammon player, offered him a $100,000 wager.  All Brian had to do was get C-cup silicone implants and keep them in for a year. More than ten years later, he still has them.

The $10,000 Burger

Poker player and devout vegetarian Howard Lederer was once offered $10,000 by David Grey in exchange for consuming meat for the first time in years. He ate a cheeseburger practically on the spot.

Double or Nothing

Nobody ever heard of Ashley Revell before he entered the Plaza Hotel in Las Vegas in 2004. Revell sold all his possessions and raised a little extra, entering the hotel’s casino with $135,300 to his name. Without a hint of hesitation, the gambler walked up to a roulette wheel and bet it all on red. The ball landed on the red seven, doubling Revell’s net worth.  He tipped the croupier $600 and stopped playing immediately.  “He shouldn’t have done it,” his father later told reporters.  “He’s a naughty boy.”

Teed Off

Arguably one of the craziest golf wagers ever, Huck Seed accepted a six-figure challenge to play four rounds of golf in a single day, breaking 100 in each round,  using only a five-iron, a sand wedge, and a putter. He had to do it all without the aid of a golf cart on a day when temperatures soared up to 120 degrees. Seed won the bet.

You Bet Your Wife

In 2007 Andrei  Karpov from Murmansk, Russia, ran out of money during his poker game against Sergey Brodov. He made a quick run-through in his head of what belongings he had that he could bet and concluded betting his wife would be a good idea.  Karpov’s wife, Tatiana, was not at all pleased with his bet and divorced him. The kicker?  She later married Brodov.

Lost at Sea

During a day at the beach, Phil Hellmuth (r.) reportedly bet friend Huck Seed (l.) that he couldn’t stand in ocean water, up to his shoulders for 18 hours. The amount at stake was $50,000, and Huck figured he could do it. The former World Series Champ lasted…for three hours.

Marathon Man

When someone bet poker player Ted Forrest $7,000 that he couldn’t run a marathon in Las Vegas with temperatures soaring above 100 degrees, he obliged. He completed the run, severely injuring his feet in the process.  Forrest is also known for taking a $10,000 wager to drink 10 beers in 30 minutes.

Proud Papa

Steve Caldicott of Birmingham, England must have had high hopes for his young son when he walked into a William Hill sports book in 1997. Caldicott placed a wager at 50,000-1 that his young son would score a goal for England in the 2018 World Cup soccer final. At the time, Caldicott’s son was three and a half months old.

One Small Bet For Mankind

In 1964, enterprising punter David Threlfall believed in JFK’s promise that he would successfully land a man on the moon. When he approached famous bookmaker William Hill, with the bet and a deadline of January 1, 1970 the bookie gave him 1,000:1 odds on his ten pounds bet. In the subsequent years when it became obvious that either the USA or the USSR was going to get a man on the moon or bankrupt themselves trying, many people offered to buy Threlfall’s wager off of him at a discount in the hopes of cashing in. It was to no avail. In1969 astronaut Neil Armstrong’s “One small step for man” was one mighty big step for Threlfall’s wallet.


Alvin “Titanic”   Thompson

A legendary hustler throughout the early 20th century, the ambidextrous Thompson could beat golfers either right-handed or left-handed and won a bet that he could drive a ball 500 yards. He won the wager by driving the ball across a frozen lake.

Thomas “Amarillo Slim” Preston

The legendary poker player and self-proclaimed “greatest gambler who ever lived,” Slim has taken on all comers, doing everything from playing table tennis with a frying pan to playing pool with a broomstick, beating everyone from Larry Flynt to Evel Knievel.

Huck Seed

Carrying the mantle established by Titanic and Slim, the 1996 World Series of Poker champ has bet on just about everything over the years, including a $100,000 standing backflip, which he successfully completed.


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