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10 Most Outrageous Bets Ever Made

by Steve Etherwood
fact checked by Rachel Jones

Gambling has been around in human society for thousands of years, and it is easy to see why. If you have ever been to a casino or even bought a lottery ticket, you know gambling can be a thrill. However, most of uswouldn’t take it to the level of the people on our list below (hopefully). The people on our list seem to have truly lost their common sense on what they are willing to bet on!Let’s explore the 10 most outrageous bets ever made.

Related: Top 10 High-Stakes Gamblers Who Managed to Break the Bank

10“The Suitcase Man”

The $5,000,000 Suitcase Man

William Bergstrom is the first gambler on our list. His exploits in gambling earned him two nicknames,”Suitcase Ma” and”The Phantom Gambler” Bergstrom is known for placing (at the time) the largest bet in casino gambling history.

Bergstrom’s claim to fame happened in September 1980. He entered the Binion’s Horseshoe Casino in Las Vegas, Nevada. With him, he brought two suitcases. One was empty, and the other contained $777,000 in cash. Benny Binion, the casino owner, had a policy where a player’s first bet would be honored, no matter the size. So, Bergstrom made a dice bet, then two subsequent bets. This resulted in Bergstrom winning $777,000. Binion helped him fill his empty suitcase, and Bergstrom hit the road. Reportedly, Bergstrom was planning to commit suicide if he lost this bet.

He was not seen at the casino again until March 1984. This time, Bergstrom bet $538,000 and won. Unfortunately, Bergstrom did not quit while he was ahead. He returned in November of the same year and bet $1,000,000. However, his luck was bound to run out! This time, he lost the bet. A year later, Bergstrom took his own life, though it is unclear if it was because of the million-dollar wager.

9 Losing to Win

Ted Forrest Weight

Ted Forrest is well known as a gambler; he has even won a World Series of Poker bracelet. However, the following bet was not about cards. Instead, he bet with another famous poker player, Mike “The Mouth” Matusow, that he could lose an enormous amount of weight.

Matusow challenged Forrest that he could not get below 140 pounds (from his weight of 188 pounds). These weren’t the only big numbers involved; Matusow put his money where his mouth was and bet $2 million. Forrest eventually did get below 140 pounds, reportedly as low as 138. So he won his crazy bet with Matusow! Seems like a double win to me.

As you might expect, professional gamblers tend to make more outrageous bets than most, even when it comes to weight loss.

8 A $10K Cheeseburger

Howard Lederer is known for several things; he is a professional poker player known for his thoughtful, pensive style. Therefore, he is nicknamed”The Professor.” Lederer has achieved a great deal of success in poker, winning two World Series of Poker bracelets and two World Poker Tour titles. However, he is also known for being a vegetarian. Or at least, he was.

Another professional poker player, David Grey, wanted to test Lederer’s commitment. The two had just cashed out of a game, both winning big. Grey asked Lederer if he would eat a cheeseburger for $10,000. Lederer, without batting an eye, said that he would. As you might imagine, both tried to get the other to back out. But, eventually, Lederer went “all in” and ate the cheeseburger, pocketing a cool $10,000 cash.

According to Lederer, if Grey wanted to win the money back, all he had to do was eat two olives. What a pair of whacky friends and outrageous bets!

7 Betting Big on FedEx

How The Founder Of FEDEX Saved The Company From Bankruptcy With His Blackjack Winnings

FedEx is a massive international freight company that is still thriving today. This was not always the case in the early days of the company. Frederick Smith, the founder and CEO of FedEx, was in a desperate situation. Just three years after it was founded, the company was hemorrhaging money, losing $1 million monthly, and facing a fuel bill of more than $20,000. To keep the company running, Smith tried everything, including acquiring more loans. Eventually, he decided to try his hand with lady luck.

Smith took all of the remaining money from the company’s accounts, equaling about $5,000. He then went to Las Vegas and gambled the money on blackjack. Smith must have hit some lucky cards because he left the casino with more than $30,000. This was enough to give FedEx some breathing room to grow, and we know how successful FedEx has grown to be!

Smith took an outrageous chance, betting his entire company on blackjack. At this point, he is happy that he did. FedEx is the largest freight company in the world.

6 Double or Nothing, Literally

Red or Black? – Betting your whole life on one roulette spin

As an English professional gambler, Ashley Revell is yet another high roller on our list. Revell sold all of his possessions, even his clothes, in 2004. All of his assets combined totaled $135,000. Revell then took his money to (where else?) Las Vegas. He placed all of his money on red for a single roulette spin. The spin was very lucky for him! The ball landed on 7 red, effectively doubling his money.

Revell’s gamble was featured in a reality mini-series filmed by Sky One. The series was appropriately named Double or Nothing. Revell was also featured on many other shows and series, including THS Investigates: Vegas Winners & Losers. Revell truly doubled down when it came to outrageous bets.

5 Blindly Confident and Deadly

Russian Pilot Caused Disaster After Bet He Could Land The Plane Blind

Our next outrageous bet is not located in a casino but on an airplane! While some of the others on our list are harmless and even funny, this particular incident was no laughing matter.

Russian pilot Alexander Kliuyev was piloting Aeroflight Flight 6502 in 1986. He was chatting with his co-pilot, and the two soon were arguing. Kliuyev believed that he could land the plane with no visual aid. In other words, he thought he could land the flight blind, with the curtains in the cockpit drawn.

The argument escalated into a bet, and Kliuyev decided to prove his point, putting the lives of his 90 passengers at risk. More than 60 of those passengers lost their lives to this stupidity. Kliuyev was overconfident and did not slow the plane down enough. Instead, the plane flipped over, causing a massive tragedy and many deaths.

Kliuyev survived and was sentenced to fifteen years in prison (which was later reduced to six years). His co-pilot was not charged.

4 A Shocking Team Rivalry

Husband and wife bet Taser shock on Bears-Packers

We all know sports fans can be crazy. Well, this betting couple took it to another level.

John Grant is a fan of the Chicago Bears, and his wife, Nicole, is a Green Bay Packers fan. The Chicago Bears and the Green Bay Packers have one of the biggest rivalries in the NFL. When the teams faced off in 2014, this couple had an idea for an interesting wager on the game. The loser does the dishes for a week? The loser rubs the winner’s feet? Not extreme enough for this couple!

Instead, John and Nicole Grant agreed that the winner would taser the loser. It is fair to say that drinking may have been involved. Surprisingly, the Chicago Bears won the game, and John was ready to cash in on his bet. However, Nicole was maybe not the greatest sport and called the police on her husband.

John was arrested and charged with felony possession of an electric weapon. The two learned their lesson because apparently, the loser of the next bet only had to wear the other team’s jersey (this time, the Bears and John lost).

3 Drinking and Flying

“Hold My Beer!” – The Story of Tommy Fitz and His Drunken Bet

Tommy Fitzpatrick served in the Marine Corps during WWII and the Army in the Korean War, even receiving a Purple Heart for his dedication and service. However, this is not what he is best known for! Instead, he is known for two separate, intoxicated flights that he took, the first in 1956 and the second in 1958.

In 1956, Fitzpatrick bet with some friends that he could travel from New Jersey to New York in only 15 minutes. He took a plane from the nearby Teterboro School of Aeronautics and landed it in front of a bar on St. Nicholas Avenue. Incredibly, he made this flight in the middle of the night and without the use of a radio or lights.

Two years later, in 1958, Fitzpatrick was rechallenged and continued his late-night flying escapades. This time, he landed the plane near Yeshiva University in New York. In the first incident, Fitzpatrick was never charged, but he was sentenced to six months in prison after doing it for a second time.

2 All Clothes Are Off!

Doria Tillier French Weathergirl Does Weather Forecast NAKED! Runs around Field

Doria Tillier is a French weather reporter, actor, and model. In 2013, she made an outrageous bet against the French national soccer team. The French national soccer team is consistently one of the best international teams globally, and maybe it was not the best call to bet against them.

Yet, Tillier bet that France would not qualify for the 2014 World Cup (following a 2-0 loss in the first-leg tie to Ukraine). What were the stakes? Tillier was so angry with her national team that she was willing to bet they would not qualify and put her body on the line. Literally!

Tillier told viewers that she would do her weather report naked if France made a comeback and qualified. Les Bleus came back against Ukraine, winning 3-0 and qualifying, and Tillier kept true to her word.

1 The Gambling Granny!

Greatest Craps Roll Ever? New Jersey Grandma Rolls 154 Times!

The last bet on our list is a doozy! It took place at the Borgata Hotel Casino in Atlantic City in 2009. Patricia DeMauro played slots, while her friend John Capra played poker. The two took a break from their losses, and Capra taught DeMauro how to play craps. Let’s just say she was a natural.

Demauro bet 154 times in a row against seven and won. That is over four hours of rolling. DeMauro literally set a record that has never been broken. DeMauro reportedly only started with $100 and made out like a bandit.

Apparently, the chances of her winning 154 times were lower than getting struck by lightning or even winning the lottery! DeMauro will forever be remembered as the gambling granny who set an unbreakable world record in craps. Talk about some beginner’s luck!

fact checked by Rachel Jones