Gambling Redefined: 10 Of The Most Famous Gambles/Bets Ever Placed

Gambling is putting money on an event with an uncertain outcome in hopes of wining money or material goods. For an event to qualify as a gamble, there must be chance, price and consideration. Some gamblers have the opportunity to make millions in just a few minutes.

People have  had mixed feeling about gambling all along. This is one of the main reasons why laws and societal standards relating to gambling will vary depending on the country. The U.S.  has had many gambling law amendments over the past 100 years, touching on the legalization and criminalisation of certain forms of gambling. Today, gambling in the U.S. is legal under U.S. Federal Law. There are however a number of restrictions on interstate and online gambling.

One of the most common forms of legal gambling is casino gambling. Modern day casino gambling originated from China and Europe. Popular casino games like baccarat, craps, blackjack and roulette originated from different parts of Europe. A modern day version of Keno, (a popular ancient Chinese lottery game) is played today in many casinos worldwide. This article will focus more on high rollers and risk takers who took gambling to the next level. Some gamblers in this list have even put their lives on the line. Although gambling has become more popular in recent years, some of the biggest gambles and bets in this list date back to over a century. Below is our list of the 10 greatest gambles/bets ever placed.

10 Captain Matthew Webb - Niagara swim: $10,000

Back in 1875, Captain Mathew Webb put his life on the line by placing a very brave bet. He bet he could swim across the whirlpool beneath Niagra falls. Desperate to strike it rich, he bet $10,000 on the basis that he could make it to the other side. Unfortunately, he didn't. Poor sea conditions and strong winds forced him to abandon his mission. He however made history as the first man to swim in the English Channel without using artificial aids. $10,000 bets were unheard of in the 1800’s.

9 Tottenham Spurs fan own goal - lost house

Back on September 29th 2001, a Tottenham fan placed one of the biggest bets of his life in an effort to impress his new girlfriend. Although the actual identity of the fan remains a mystery, the fan’s gamble remains in the minds of many Tottenham Spurs fans. The fan decided to put up his house in favour of his team wining. This was after he saw a very slim chance of a loss (Spurs was up 3-0 when he was making the bet). Unfortunately, luck wasn’t on his side. Manchester United thrashed Spurs 5-3 in the 2nd half leaving the Spurs super fan homeless and probably single.

8 Welsh Luck – Accumulative odds: $420,000

This bet is great because of the nature of odds. The bet proves that you don’t have to bet big or be a high roller to win big. Back in 1989, a 40 year old Welsh man walked into Ladbrokes South Wales to bet £30 on pop band U2 remaining together, Pop singer Cliff Richard being Knighted, Eastenders maintaining viewership on BBC (as a weekly soap) and Australian soaps Home & Away and Neighbours still showing on British TV by 2000. 11 years later, the same man showed up to collect his winnings. He was paid £194,400 ($420,000 today) on 6,479/1 accumulative odds.

7 Mike Futter - Grand National win: $2 million 

Two million may not be the biggest horse bet ever won however Mike Futter’s win deserves a spot in this list for a string of consistent wins on his own horse. Mike Futter won a monster Grand National gamble in 2003 on his own horse; Monty’s Pass.  He placed multiple bets of $10,200 each way at 33-1 and $20,400 each way at 20-1. A $2 million Grand National betting win is unheard off betting your own horse the Mike Futter way. This is precisely why his bet is considered one of the greatest.

6 The Hermits – Hackler’s Pride horse bet: $16.46 million (Inflation adjusted)

The Hermits from Salisbury Plain were a popular group of 5 professional gamblers known for pulling off some of the biggest gambles/bets in the beginning of the 20th century. Under the leadership of their financier Percy Cunliffe and assistance of Wilfred Purefoy (an Irish stud owner), the group won many bets involving horses which had been trained at Druid Lodge stables in Salisbury Plain. The group won their biggest bet when their horse (Hackler Pride) won Cambridgeshire in 1903. The Hermits made £250,000 which translates to £10 million today or $16.46 million.

5 Archie Karas – The Run: $17 million

Greek gambler Archie Karas also had to be featured in this list with his last chance poker game that earned him millions. Considering he was once a waiter, he clearly deserves a spot in his list. Archie didn’t think twice when he borrowed $10,000 from a friend in the 1990's to play a high stakes poker game in a legendary Las Vegas Binion's Horseshoe casino. Fortunately, he went ahead and defeated 15 great poker players in a head to head competition after which he headed to the craps tables to continue his 6 month winning streak. By the time Karas was done, he had won $17 million.  Pretty impressive for a guy who had gone to Las Vegas with only $50. His winning streak is popularly known as The Run.

4 Kerry Packer - Toss you for it: $100 million

Kerry Packer, (1937-2005) was a wealthy Australian media tycoon. In 2004, Business Review Weekly estimated his net worth to be $6.5 billion. Despite being wealthy, Packer had a very notorious gambling reputation. One which is believed to have cost him over $40 million once in a span of 10 months. He once recorded a $28 million 3 week losing streak in 1999 while gambling in London. However he makes it to this list for making one particular bet dubbed; Toss you for it.

This bet will be remembered for a very long time in gambling circles considering it is documented in his latest book; I'll Toss You for It. After noticing the attention a neighbouring punter was getting from a casino waitress, Kerry went ahead and asked the man why this was the case. He replied he was a Texas oilman worth $100 million. Packer decided to toss him for all of his worth. The Texan multimillionaire walked away.

3 Zhenli Ye Gon's – Meltdown: $125 million

Popularly known as Mr. Ye on the Las Vegas strip, Gon is a Chinese-Mexican businessman suspected of drug trafficking. Between 2004 and 2007, Gon had reportedly lost $125 million gambling in handful of casinos in Las Vegas. How Gon failed to find his gambling habit excessive is anyone’s guess. He was however arrested shortly after his gambling spree in possession of over $200 million dollars in cash cementing drug trafficking allegations against him. He had stashed the money in one of his houses in Mexico.

2 Terrance Watanabe – Losing streak: $127 million

Just recently (in 2007), businessman Terrance Watanabe decided to head to Las Vegas for a gambling spree that lasted one year. At the end of it all, Terrance lost $127 million. Although Terrance will soon be forgotten by the casinos and gamblers he enriched, he will never forget the year he blew his entire fortune considering he spent over two decades to get it.

1 Football match blackouts – Betting syndicate: Approximately $139 million

This bet happens to be the biggest of among all of them on this list. Back in the 1990’s a number of English football matches were rocked by blackouts. Many people suspected foul play. The suspicions turned out to be true when an Asian sports betting syndicate was convicted for remotely controlling floodlights during matches. The betting man was cashing in on Asian bookmakers paying out on scores as they stood even in cases where the game was abandoned. Although the exact amount the gang made away with is still unknown, the group is believed to have made over £60 million after disrupting two games in 1997. This is approximately $139 million today after making exchange rate and inflation adjustments.

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