Online Casino

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10. Howard Lederer

THE HISTORY

Along with sister Annie Duke, the poker bug seems to run in Howard Lederer's family. For those unfamiliar with the two-time WSOP bracelet winner's history, Lederer used to be a fairly burly bloke. Eventually requiring gastric bypass surgery to lose the majority of his weight, Lederer became a vegan and has remained at a healthy weight ever since.

But poker is all about taking advantage of your opponents, and David Grey seemed to think that Lederer's change in lifestyle was the perfect opportunity for him to make a buck or two.

WHAT HAPPENED?

With a giant smile on his face, Grey challenged Lederer with the task of breaking his vegan habits by eating a cheeseburger. The prize? A cool $10,000 from Grey's checkbook.

Not surprisingly (unless you're David Grey), Lederer gobbled up the burger without a second glance, collecting the $10k proposition bet while he was at it.

9. John Hennigan

THE HISTORY

John Hennigan (the poker player, not professional wrestler) has been involved in his fair share of bets over the years. Known for having a hatred for the simple life, there is nothing that the two-time WSOP bracelet winner despisers more than small town living.

WHAT HAPPENED?

As you have probably guessed, Hennigan was challenged to a lucrative bet that may seem simple to you or me: spend six weeks in quiet Des Moines, Iowa. If he succeeded, there was around $100,000 waiting for him back in Vegas.

Unfortunately for John, that unquenchable thirst for big city living got the better of him after just two days in Iowa. He may be happier in Las Vegas, but that's a pretty hefty offer to blow off after only a couple of days.

8. Chris Hertzog

THE HISTORY

This story isn't crazy in the sense of the size of the bet made, but rather the circumstances that led to it being one of the best ticket purchase/payout ratios in horse betting history.

A man by the name of Chris Hertzog was a fan of the odd bet or two on the races. However, one unfortunate Kentucky Derby morning, he had a problem. You see, prior to race day, Hertzog had purchased 100 superfecta tickets at $1 each. For those not too familiar with horse racing, a superfecta is achieved by picking the top four horses in order.

Chris Hertzog managed to do this.

Chris Hertzog also managed to lose the winning ticket.

WHAT HAPPENED?

As you can imagine, Hertzog went absolutely crazy trying to find the superfecta ticket. He and his friends waded through bags of garbage in the hopes of stumbling across that lucrative little slip of paper. They had no such luck.

Unbeknownst to Hertzog and his garbage cronies, however, the woman who had sold the winning ticket was informed of her accomplishment. Either by a stroke of luck or divine equine intervention, one of the few tickets that her machine had not shredded was Hertzog's winning superfecta.

Chris Hertzog was mighty pleased with the way things panned out, and managed to collect the $1 ticket, now worth $864,253.50.

7. Doyle Brunson

THE HISTORY

One of the men renowned for bringing Texas Hold'em to the forefront of Las Vegas casino gaming, Doyle Brunson has been in the poker spotlight for the past 50 years.

The 10-time World Series of Poker bracelet winner was renowned for his love of food, and that is exactly how the next crazy bet came to be.

WHAT HAPPENED?

In 2003, Brunson had a weight loss challenge handed to him. Offered a $100,000 bet at 10:1 odds, the poker legend had to lose enough weight to see him under 300 pounds. Using all the resources at his fingertips, including Weight Watchers and Atkins, Brunson cleaned up the wager and managed to pick up a cool $1 million for his efforts.

Now, if only we could all be offered those sorts of odds to get back on the treadmill.

6. Richard Branson

THE HISTORY

There's not much you can say about Richard Branson that hasn't already been said by himself or the tabloids. The Virgin boss thrives off massive marketing ploys, beautiful woman, and ludicrous stunts – and he knows how to get your attention.

While one could infer that Branson's entire life has been full of gambles, his most recent bet has been highly publicized throughout the world.

Think Richard Branson. Think stewardesses. Now get that filthy thought out of your head because you're dead wrong.

WHAT HAPPENED?

In true Richard Branson fashion (is there any other kind?), he let his ego do all the talking at a recent press conference. Declaring that his new Formula 1 team would doubtless beat Air Asia boss Tony Fernandes's own F1 team in the upcoming season, Branson said that the Malaysian could "come and work on our airline as a Virgin stewardess."

Not one to dole out punishment just to his rivals, Branson quickly asserted that he would be more than willing to do exactly the same thing if the Air Asia team finished above his at the end of the season.

I think Fernandes said it best when he countered, "The real challenge will be to prevent him [Richard Branson] from asking our guests, 'coffee, tea or me?'"

5. Phil Ivey

THE HISTORY
Phil Ivey is known around the world for his brilliant poker playing abilities and regular appearances at the high stakes tables. But after the most recent Super Bowl, perhaps that's where he should stay.

If you don't know already, Ivey is a big player on any sort of gambling event. He'll wager tens of thousands of dollars at the craps table just as quickly as he'll take on Isildur1 in a multimillion-dollar poker match. Unfortunately for Phil, sports betting hasn't been treating him too well recently.

WHAT HAPPENED?

Leading up to the 2010 Super Bowl between the Colts and the Saints, Phil Ivey must have had a pretty good feeling that the Colts were going to take out the title. Why do I say that? Well, Ivey went out and slapped a $2 million money line bet on the Colts to win after collaborating with Billy Walters.

Just because Billy Walters is a Vegas sports gambling legend, doesn't mean he is exempt from making mistakes. Fortunately for Ivey, that cool $2 mil will probably be doubled on his next win at the tables.

4. George Harrison

THE HISTORY

Known around the world as the moustachioed Beatle, this is one story that you may not have heard about George Harrison.

Over his lifetime, Harrison collaborated with a number of unique talents, ranging from musicians to authors to film stars. One such partnership was forged with Monty Python's Eric Idle. The two quickly became friends, and went on to work together on a number of different projects.

WHAT HAPPENED?

During the late 1970s, the Monty Python troupe was keen to make another film after the success of The Holy Grail. With a premise that stirred up the religious folk as much as the conservatives, Monty Python needed steady financial backing for their Life of Brian movie.

Thankfully for Python, George Harrison's ties to Eric Idle allowed him to hear of the need for cash, and he duly obliged. With plenty of speculation leading us to believe that he mortgaged his house (or at least one of them) in the process, Harrison gambled £3 million on the project, in what Idle described as the "world's most expensive cinema ticket".

As we all know, the bet certainly paid off.

3. Calvin Ayre

THE HISTORY

The founder of Bodog wasn't always in the money. In fact, this Canadian from a Saskatchewan pig farm was once closer to being bankrupt than you might imagine.

Calvin Ayre may have been on the cover of Forbes 2006 Billionaires Edition, and he may have even been named one of the Most Eligible Bachelors in 2007 by Star Magazine, but the man behind Bodog didn't always have such cash-lined pockets.

WHAT HAPPENED?

In 1994, Ayre packed up the essentials, sold everything else, and decided that with $10,000 to his name he was going to launch a software development company. That idea soon evolved into the online gambling firm we are familiar with today, and since then, Ayre has dabbled in records labels, MMA, and even charity foundations.

With a multibillion-dollar price tag to his name, I think it's safe to say that Calvin Ayre's rags-to-riches life has been one of the craziest bets (that has actually paid off) in recent history.

2. Isildur1

THE HISTORY

Anyone even remotely familiar with online poker has heard of Isildur1. No, not that bloke from The Lord of the Rings. Isildur1 is the alias of one of the most popular high stakes poker players of all time.

His popularity didn't spawn from wins at major tournaments like the World Series of Poker or WTP; rather, he rose to notoriety after a string of ridiculously expense poker matches against other online pros.

While he could win or lose several million dollars in any one day, his identity remains hidden to this day. All we know is that he's a Swede who enjoys taking down the big boys of online poker.

WHAT HAPPENED?

In November of 2009, Isildur1 burst onto the Full Tilt Poker scene. He had been hanging around for a few months beforehand, but mainly kept to himself until he could start taking on the pros. He eventually competed against the highest calibre poker players, including Phil Ivey, Patrik Antonius, Brian Townsend, and Tom Dwan. By the middle of November, Isildur1 was up an incredible $6.4 million.

Unfortunately for the Swede, that's when his run finally came to an end. On December 8, he copped a heavy beating at the hands of Hastings, eventually costing him $4.2 million (a world record), and sending him $2 million into the red.

After disappearing for a couple of months, it was something of a shock to see Isildur1 return to the tables, especially high stakes, but he hasn't changed a bit since his that incredible November. Whether he's winning or losing, you'll always see Isildur1 taking on the best poker players around for the most insane amounts of money.

1. Ashley Revell

THE HISTORY

Ashley Revell's wager may not be the most lucrative in the history of crazy bets, but it is certainly one of the gutsiest. It's hard enough for some to part with that $10 on a "sure bet", let alone every cent to your name on a 50/50 outcome.

If you haven't already guessed by now, Revell is a roulette man. Words fail to adequately describe what the London man did with all his possessions (including his clothes), so just watch the video below.

WHAT HAPPENED?

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