12 of the Craziest Bets Ever Made

Humans love gambling and games of chance. From dice games in ancient Mesopotamia to newly legal sports betting across the United States, humankind has a long history of staking money on the outcome of events.

These days, most of us just buy a lottery ticket every now and then, or we enter the March Madness pool at the office. However, some people will pretty much bet on anything, even against the highest of odds. And they’ll do it in the oddest ways.

Here are some of the craziest bets people have made and the stories behind them.

The More Things Stay the Same

The band U2’s persistence is just one of the things that helped a publicity-shy man win an odd bet. Bono and his bandmates are shown here playing in 2018 in Washington, D.C. Brent N. Clarke / Invision / AP Photo

In 1989, a publicity-shy Welshman placed a £30 (about $50) bet that five things would remain the same by the year 2000: TV shows “Home and Away,” “Neighbours” and “EastEnders” would all still be on the air; singer Cliff Richard would receive a knighthood; and the band U2 would still be together and performing. The odds of it all happening, according to the bookmaker Ladbrokes: 6,479-1.

After waiting 11 years to see the outcome of his unusual bet, he was proven right. He walked away with £194,400 ($320,000) in winnings from a very unlucky bookmaker.

Betting Everything He Owned

A man wagered an incredible amount on a single bet on the roulette wheel. Getty Images

Ashley Revell has gone down in history as the man who quite literally bet everything he owned on one spin of a roulette wheel. Revell is an English gambler who, in 2004, sold everything he owned — including his clothes.

Revell was being filmed for a reality TV series called “Double or Nothing.” He took all the money he had raised selling his goods — $135,300 — and went to the Plaza Hotel and Casino in Las Vegas, where he placed the entire amount in a single bet on the roulette wheel.

He won, doubling up to $270,600. Revell later used his money to set up an online poker company. However, his good luck streak didn’t continue in business. His company closed down in 2012.

The Man With $100,000 Breasts

Brian Zembic agreed to have silicone breast implants put in and live with them for a year to win a $100,000 bet. Inside Edition / YouTube

Brian Zembic has a history of making crazy bets. He once lived in a friend’s bathroom for a month on a $7,000 bet. For another bet, he slept under a bridge with $20,000 strapped to his leg for a week. However, Zembic is best known for his stunt in 1997 in which he agreed to have silicone breast implants put in and live with them for a year to win a $100,000 bet.

Zembic found a plastic surgeon, who was also a gambler, and beat him at backgammon so the surgery was free. Zembic kept his implants in for a whole year and won his bet. He then decided that he liked having breasts and kept the implants for almost twenty years. He turned down another bet of $10,000 in 2014 to take them out.

He finally decided in 2017 to have his implants removed at the request of his teenage daughter. Zembic now says that becoming a father changed his outlook on life, and he doesn’t think money is very important after all.

A Swim Too Far

In 1883, a man took a bet of $2,000 to swim through the Whirlpool Rapids near Niagara Falls. Getty Images

Matthew Webb became internationally famous as the first person to swim across the English Channel in 1875, finishing in 21 hours and 40 minutes. He became a professional swimmer and went on to write a book, called “The Art of Swimming.”

In 1883, he took a bet of $2,000 to swim through the Whirlpool Rapids near Niagara Falls, on the U.S.-Canada border, a dangerous stretch of swirling water that no one had managed to safely swim before. Sadly, Webb lost his bet — and his life — and drowned in the attempt.

He was buried in Oakwood Cemetery in Niagara Falls, New York. In 1909, his family erected a memorial to him back in England, with the inscription: “Nothing great is easy.”

Federer Fever

Roger Federer holds the Wimbledon Men’s Singles trophy in 2003. His eight Wimbledon titles caused a man to win a long-shot bet. Dave Caulkin / AP Photo

In 2003, the tennis player Roger Federer won his first Wimbledon championship. That same year, a man named Nick Newlife placed a £1,500 ($1,900) bet that Federer would win the Wimbledon Grand Slam at least seven times by 2019. The odds against this happening were 66-1.

Federer went on to win the Wimbledon title seven times by 2012. Sadly, Newlife died in 2009 before he knew the outcome of his unusual wager. He left his estate, including the betting slip, to the charity Oxfam, which claimed the winning payout of more than £100,000 ($155,000) when Federer won his seventh Wimbledon title.

Beginner’s Luck

The odds of one woman’s lucky streak at craps were estimated to be about one in 56 trillion. Getty Images

In 2009, Patricia Demauro was at Atlantic City’s Borgata Hotel Casino with a friend, John Capra. Demauro first played penny slot machines but got bored after a few hours. She went to find Capra, who had been playing in the poker room. He was losing and decided to take a break to show Demauro how to play craps. She had never played the game before, but decided to try her luck.

Demauro proceeded to successfully bet 154 times in a row against rolling seven. Seven is the number that comes up the most often when throwing a pair of dice. Each of the 154 non-seven rolls of the dice meant she was winning. Big time.

According to Stanford University statistics professor Thomas Cover, the odds of Demauro’s lucky streak happening are about one in 56 trillion. Demauro finally rolled a seven after nearly four and a half hours, which ended her winning streak.

However, she walked away from the table with a sum that may have been as high as seven figures. The casino treated her to a champagne toast, a meal and a free room.

From Go-Kart to Grand Prix

British driver Lewis Hamilton celebrates wining his fourth Formula One championship after the Mexican Formula One Grand Prix auto race at the Hermanos Rodriguez racetrack in Mexico City, in 2017. Moises Castillo / AP Photo

When Richard Hopkins took his son Evan, 13, to race go-karts in 1998, he watched another youth race. He was so impressed by how the other boy was driving that he placed a £200 bet ($250) bet that the boy — Lewis Hamilton — would win a Formula One Race by the time he was 23 (at 200-1 odds).

Hopkins placed a second bet for £100 bet ($125) that Hamilton would be a Formula One world champion by the time he was 25 (at 500-1 odds) and a third for £50 ($62) that Hamilton would achieve both goals (at 1,500-1 odds). When Hamilton won his first race at 22, and then went on to become world champion at 23, Hopkins collected a total payout of more than £165,000 ($200,000).

The Luck of the Northern Irish

Golfer Rory McIlroy of Northern Ireland holds up the Claret Jug trophy after winning the British Open at the Royal Liverpool golf club, Hoylake, England, in 2014. Scott Heppell / AP Photo

Rory McIlroy is a Northern Irish pro golfer who won four majors before he turned 25. His Dad, Gerry McIlroy, was also a golfer. He could see early on that his son would be a champion.

When Rory was still 15, and had just won the Junior Ryder Cup, Gerry and three friends each made a £100 bet ($125) that Rory would win the British Open by the end of 2015. Rory won in 2014, a year before the bet was up, and Gerry and his friends each collected about £50,000 each ($85,000). The odds of their winning had been 250-1.

The Magnificent Seven Races

Jockey Frankie Dettori (right), shown with Britain’s Prince Harry and Meghan, Duchess of Sussex on the first day of the Royal Ascot horse race meeting in Ascot, England in 2018, won one bettor a fortune by winning seven races in a single day in 1996. Tim Ireland / AP Photo

In September 1996, jockey Frankie Dettori rode the winning horses in seven consecutive races to make history as the only jockey to do this in a single day. While most of the individual races carried decent odds of winning, ranging from 2-1 to 12-1, Dettori beat odds of 25,051-1 to win all seven.

Two lucky bettors had each placed a bet on Dettori winning all seven races and walked away with $630,000. One woman bet a total of $5.25 ($.75 on each race) and won a total of $210. If she had combined her bets in an accumulator, she would have won $18,500.

UK bookmakers, however, were spectacularly unlucky. On the day that has since come to be called Dettori’s “Magnificent Seven,” they lost over $37 million.

Eight Is Enough

Manchester United goalkeeper David de Gea

An unnamed person place a £100 ($125) bet on the combined results of eight football matches while all the teams were losing. And they all came back to win. Matt Dunham / AP Photo

Another bet in the UK saw an unnamed person place a £100 ($125) bet on the combined results (called an accumulator bet) of eight football matches. When the man placed the bet — 20 minutes before the games ended — all the teams were losing.

However, each team managed to overcome its deficit and win. The unknown man walked away with £650,000 ($820,000), having successfully beaten odds of 6,500-1.

The 50p Millionaire

Frankie Dettori reacts as he wins the Prince of Wales's Stakes

In 2008, a man in Yorkshire, England placed a bet on the combined outcome of eight horse races. The odds of his winning all eight races were 2,800,000-1. Alastair Grant / AP Photo

In 2008, to celebrate his 60th birthday, a man in Yorkshire, England, named Fred Craggs placed a 50p bet ($.63 cents) on the combined outcome of eight horse races. The odds of his winning all eight races were 2,800,000-1.

Amazingly, all his horses won and Craggs got a £1 million ($1.3 million) for his birthday. Two of the horses that he picked in his bet were called Isn’t That Lucky and A Dream Come True.

The Taser Wager

A recent NFL game between these two teams, the Chicago Bears and the Green Bay Packers, led to an unorthodox bet. Nam Y. Huh / AP Photo

While many couples have disagreements over sports, one couple took it pretty far. John and Nicole Grant made a wager on a Green Bay Packers and Chicago Bears game. The pair had been drinking and decided that the winner of the bet would get to use a stun-gun (taser) on the loser. It wasn’t a bet for money, but money eventually was involved.

Wife Nicole’s team — the Packers — lost and husband John proceeded to taser Nicole in her rear end. The couple maintains that the whole incident happened in fun and that Nicole wasn’t injured. However, local police didn’t agree and charged John with possession of an electronic weapon and disorderly conduct. He was later fined $250.

The following year, the couple again made a bet on a Bears-Packers game, which John lost this time. Luckily, he only had to wear a Packers jersey.