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1. Kerry Packer’s “Toss you for it”
The late Australian media tycoon Kerry Packer was an inveterate gambler who is believed to have lost up to $40 million (£25 million) in just 10 months, including almost $28 million during a three-week losing streak in London in 1999.
However, there is one bet for which he will always be remembered in gambling circles. Having noticed the attention a neighbouring punter was receiving from a casino waitress, Packer asked the man why.
He replied that he was from Texas, in oil and worth $100 million, to which Packer replied: “Toss you for it.” The Texan millionaire walked away.

2. Captain Matthew Webb’s Niagara swim
On 24 August 1875, Captain Matthew Webb became the first man to swim the English Channel.
Desperate for money, he then attempted to swim across the whirlpool below Niagara Falls for $10,000 – effectively staking his life on making it to the other side. He failed.

3. The Hermits’ Pride 
The Hermits of Salisbury Plain were a group of five professional gamblers who pulled off some of the biggest bets of all time at the start of the twentieth century.
Led by City financier Percy Cunliffe and aided by Irish stud-owner Wilfred Purefoy, the group enjoyed a string of wins involving horses trained at Druid’s Lodge stables on Salisbury Plain.
And when the Hermits’ horse, Hackler’s Pride, won the 1903 Cambridgeshire, the group netted an estimated £250,000, or £10 million in today’s money.

3. Terrance Watanabe’s losing streak 
In 2007, businessman Terrance Watanabe went on a year-long gambling binge in Las Vegas that cost him close to $127 million.
Thought to be one of the biggest losing streaks by an individual in Las Vegas history, it consumed all the personal fortune that Watanabe had spent more than 20 years building up.

4. Zhenli Ye Gon’s meltdown 
Known on the Vegas strip simply as “Mr. Ye”, Gon has reportedly lost $125 million at a number of Vegas casinos over the years.
The wealth of the alleged drug trafficker, who is currently in prison, probably prevented him finding this excessive, though.
When police raided his house in Mexico City they found cash and assets worth $200 million.

5. Football match blackouts 
When a spate of English football matches were hit by blackouts in the 1990s, foul play was immediately suspected by some.
They turned out to be right after an Asian betting syndicate – cashing in on the fact that bookmakers in their part of the world pay out on the score as it stands if a game is abandoned – was convicted of using a remote control to cut the floodlights.
While the total amount made is debatable, the gang was thought to have netted up to £60 million from two games disrupted in 1997.

6. William Lee Bergstrom’s suitcase of cash 
Texan horse trader William Lee Bergstrom became known as the “Suitcase Man” after he turned up at Binion’s Gambling Hall and Hotel in Las Vegas in 1980 with two suitcases.
The casino had guaranteed to match any bet as long as it was a punter’s first, a pledge that Bergstrom planned to use to wager $1 million in a single craps bet at craps.
He could not as his suitcase (the second was for his winnings) contained only $777,000.
However, the casino still matched this amount – only to regret it when his bet came good. He later wagered $1 million, and lost.

7. Mike Futter’s Grand National win 
Blackpool-born Mike Futter, who owns three bingo halls in Dublin and seven in Northern Ireland, landed a monster gamble on his own horse Monty’s Pass in the 2003 Grand National.
Futter, together with his four co-owners, is reported to have netted well over £1 million from numerous individual bets of £5,000 each-way at 33-1 and £10,000 each-way at 20-1.

8. Spurs fan’s own goal 
On September 29, 2001, a Tottenham fan keen to impress his new girlfriend put his entire mortgage on his team – which was 3-0 up at the time – winning the match.
Unfortunately for him, however, Manchester United came back with five goals in the second half – leaving him homeless (and probably single).

9. Archie Karas’ last chance poker game 
Greek ex-waiter Archie Karas did not have two cents to rub together when he borrowed $10,000 from a friend to play poker at the legendary Binion’s Horseshoe casino in Las Vegas.
Fortunately for Karas and his friend, he went on to defeat 15 of the world’s greatest poker players in a head-to-head competition, before heading to the craps tables where he kept on winning. By the time he was done, he had about $17 million in his pocket.

10. The luck of the Welsh 
You don’t always have to be a high roller to win big.
In December 1989, a 40-year-old man walked into Ladbrokes in Newport, South Wales and put £30 on Cliff Richard being knighted, pop act U2 remaining as a group, Eastenders still being shown on the BBC as a weekly soap opera and Australian soaps Neighbours and Home and Away still appearing on British television by 2000.
Fast forward to January 2000 and the same man turned up to collect his winnings of £194,400 (paid out on accumulative odds of 6,479/1).

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