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The 11 most outrageous bets of all time, including three mind-blowing losses

There's gambling, then there's this...

The 11 most outrageous bets of all time, including three mind-blowing losses
Tom Victor
28 February 2018

Last week, poker player Jake Cody won more than £40,000 in a tournament and did what anyone would do in the situation.

Sorry, let’s try that again, he did what absolutely no one would do in their right mind – he took it all straight to the roulette table and put his winnings on black before he could even count the money properly.

Then this happened…

If you thought Cody’s bet was ridiculous… well, you’d be right. But we’ve seen bigger and wilder bets before.

Here’s just a small selection of some of the strangest ones we’ve come across. You’ll notice a lot of them involve poker players – they can be a weird bunch at times.

The proud father

England’s 4-0 win over Greece in a 2006 friendly isn’t a game likely to live long in the memory for many people, but at least a couple will remember it fondly.

With Steve McClaren’s team cruising at the break, the new manager brought Chris Kirkland off the bench for his debut. It was a great moment for Kirkland, but possibly even greater for his old man Eddie, who had bet just under £100 on Chris playing for England before his 30th birthday, getting odds of 100/1 at the time.

“Hopefully I can get it over and done with as soon as possible and then people can stop talking about it,” the younger Kirkland said before the game. Maybe you should be careful what you wish for, though – that ended up being his one and only England appearance.

The proud grandfather

You’d think that win might have deterred bookies from taking bets on future internationals, but you’d be wrong.

Harry Wilson is still waiting to make his Premier League debut for Liverpool, but Wales moved quickly to give him an international debut at the age of 16 back in 2013, in a World Cup qualifier against Belgium.

It’s unclear whether manager Chris Coleman knew about Wilson’s granddad’s bet at the time, but the £50 punt – made when Wilson was just a toddler – earned him a cool £125,000.

The former vegetarian

There are two types of vegetarian, just as there are two types of any other person: those who would never abandon their principles, and those who have a price. Howard Lederer is the latter.

The poker player (see!), who has won two World Series bracelets, has publicly been a vegetarian for much of his adult life. However, when another player bet him $10,000 he wouldn’t eat a cheeseburger, he was willing to put the meat-free diet on hold.

Was the vegetarianism all part of a long game to win that bet? We might never know for certain.

The student loan sacrifice

Not all of these bets are winners – that would be boring.

Back in 2008, at the Africa Cup of Nations in Angola, the host nation opened up a 4-0 lead over Mali in the first game of the tournament, former Manchester United striker Manucho scoring the fourth goal with just 15 minutes to go.

That was enough to convince one fan, back at university after a winter break, to chuck his entire student loan on the hosts at odds of 1/100. If successful, his £4,400 bet would have earned him a free night out at what he presumably thought was no risk. You can guess what happened next… Mali scored four, and the student said he’d have to drop out of uni altogether. Ouch.

The loss that felt like a win

Howard Lederer’s aforementioned bet wasn’t the only one from his generation of poker players, and it wasn’t even nearly the biggest.

That honour may go to Ted Forrest, another former World Series of Poker bracelet winner, who was bet $2 million by fellow poker pro Mike Matusow that he couldn’t drop his 188lb weight down to below 140lb by a set deadline.

He made the cut, of course, tipping the scales at 138lb, earning him more money than he made for his biggest ever poker tournament win.

The all-or-nothing bet

Many of us have said ‘I’d bet everything I own on that’ but few have actually done it. Ashley Revell has, though, and he has video proof.

Back in 2004, the English gambler sold everything he owned – bringing in more than £76,000 – and took it all with him to Vegas for a single spin on a roulette wheel.

Showing up at the Plaza Hotel and Casino with nothing more than his money, his ID and the clothes he was wearing at the time, the 32-year-old put it all on red. Here’s what happened.

What goes up must come down

Vegas Dave is something of a legend in UFC circles. The high-stakes bettor made bank backing Ronda Rousey to lose her unbeaten run before betting big against her conqueror Holly Holm next time out.

He won more than $200,000 on each of those fights, but his confidence in Miesha Tate (who beat Holm) might have gone too far.

The punter, whose full name is David Oancea, backed Tate to the tune of $1 million when the American launched a title defence against Amanda Nunes. Unfortunately for him, the Brazilian won by first-round submission and the million was gone.

The Leicester longshot

When bookmakers priced Leicester City at 5,000/1 to win the Premier League in the 2015/16 season, they will have felt as though they were buying money from anyone foolish enough to back the Foxes.

In the 20 years prior, only four teams had won the title, while Leicester had finished the previous season in 14th and had never finished higher than eighth in the Premier League era.

Of course we know what happened next, and those confident enough to back the unlikeliest of title runs were rewarded handsomely – one anonymous punter scooped £200,000, while Hollywood actor Tom Hanks claimed to be among those to have scooped a very tidy payout.

Bernard backs himself

If you’re a professional athlete, you’re probably pretty confident in your own abilities, so if the rules let you bet on yourself to win then why wouldn’t you go for it?

Bernard Hopkins is a former world champion boxer, ending his career with a 55-8-2 record, but here we’re focusing on his 2001 unification bout against Felix Trinidad.

The American was given $100,000 by sponsors Golden Palace, and may have felt he was freerolling when he chucked the whole lot on himself to win the fight, earning a reported $400,000 when he won by TKO in the 12th round.

The toughest round of golf ever

Any golfer worth his salt can go round a course in fewer than 100 strokes, but poker pro (of course it’s another poker pro) Erick Lindgren just had to make things that much tougher for himself.

Instead of one round under 100, he needed to complete four. While carrying his own bags. In the harsh Las Vegas heat. All in one day, between sunrise and sunset. Oh, and did we mention that, while a committed amateur, he isn’t actually a pro golfer.

By the time he teed off, there was $300,000 on the line. By the time he got onto the back nine for the final time, the bet was still live but he was visibly struggling from the heat. He got there, though, shooting a 94 and suffering dehydration and weight loss in the process.

The lose-lose

This one is, perhaps unsurprisingly, a little tougher to verify. However, we really want it to be true, and that’s the only thing that really matters here.

As referenced in Graham Sharpe’s book, Gambling’s Strangest Moments, a man named Matthew Dumbrell attempted to bet on the world ending in August 1999. He was offered odds of 1,000,000/1, took the bet and lost.

Having missed out on his windfall, he tried again, backing the same outcome before the turn of the millennium. He lost a second pound, of course, but one wonders how he would have collected on a win.

(Images: Rex)