7 of the Craziest Bets Ever | Poker & Sports Bets | Grosvenor

Whether it’s a night out at the casino or a friendly bet between friends, the prospect of making money rarely loses appeal. But can you imagine throwing down millions of your own cash on a poker game or a sports match? This is the life of the high roller: a faction of gutsy gamblers who have etched their bravery into betting folklore.

Here is our pick of some of their crazy bets.

Golden Boy


Floyd “Money” Mayweather Jr. has never been shy of dipping into his $400 million net worth. Like a modern-day Scrooge McDuck, he quite literally carries bags of cash around with him – as much as one million dollars at any one time. He’s also thought to spend in the region of $6,000 a year, just on underwear!

In 2013, however, he redefined the word “frivolous”. Known for betting six-figure sums on everything from football to basketball, the boxing champ wagered a whopping $5.9 million on Miami Heat to beat the Indiana Pacers by seven points or more. Of course, in true Mayweather fashion, he came out victorious.

The eye-watering punt earned him a knockout $6.49 million in cash. No wonder they call him ‘Golden Boy’.

Biggest poker pot


Televised poker is known for bringing high-stakes heavyweights to the big stage. But when Tom Dwan and Phil Ivey butted heads at the Full Tilt Million Dollar Cash Game, poker fans saw an incredible amount of cash hit the felt.

In what seemed like a near impossible situation, Tom Dwan hit a straight with a 6 & 7, while Phil Ivey made a straight with an A & 2. As the pair went back and forth, exchanging raises, the pot swelled to a blistering $1,108,500: the biggest pot in televised history. To say Phil Ivey was a little shell shocked is an understatement.

Red or black


In an attempt to win big, an Englishmen named Ashley Revell sold off all his worldly possessions and flew to Las Vegas. Once there, he made the bold – and very risky – decision to put his entire life savings on the spin of a wheel.

At the roulette table, the barmy Brit placed $135,000 on red in an attempt to double his stake. Lo and behold, his lunacy paid off and he walked away with a cool $270,000. Let’s hope he took a suitcase to carry all that cash away in!

Sensational Swiss


In 2003, an eagle-eyed gambler named Nick Newlife backed Roger Federer to win Wimbledon not once, not twice, but seven times, and all before the year 2019!

Although the Swiss tennis player is now considered one of the greatest ever, back in 2003 he was greatly overlooked, despite ranking world No.6 at the end of 2002.

The man from Oxford took his chance and wagered a whopping £1,520 at odds of 66/1! Unfortunately, Newlife passed away in 2009, three years before Federer won his seventh Wimbledon title. However, he left his ticket to Oxfam, and the charity claimed £101,840 in winnings.

Faith in Formula 1 champion


Sometimes you just have to be in the right place at the right time for a big bet to pay off.

That’s what happened when Richard Hopkins spotted a 13-year-old go-karter named Lewis Hamilton zip around the track. Hopkins, from Folsworth, was so taken aback by Hamilton’s skills that he bet £350 on the rising star to win the F1 World Championship before he reached the age of 25. When Hamilton won the race a decade later, Hopkins pocketed a whopping £165,000.

Magic McIlroy


In a similar vein to the previous story, Rory Mcllroy’s dad spotted his son’s talent early on in his career. When Rory was just 15 years old, his dad, Gerry, bet £200 at odds of 500-1 that his son would win the British Open by the age of 25.

Gerry was so confident, that he tipped his friends to do the same thing. As we now know, Rory won the British Open in spectacular fashion, and has gone on to dominate the world of golf. In turn, Rory’s dad bagged £180,000 without having to break a sweat.

Good things come to those who wait


If you have ever perused Grosvenor Sport, you will know that you can gamble on more than just sports. In fact, in 1989, a Welshman claimed one of the biggest pay-outs in history by solely betting on popular culture.

The anonymous punter bet on an accumulator which included the following predictions:

  • Cliff Richard to be knighted before the turn of the millennium.
  • Both Eastenders and Neighbours continuing to be part of the BBC schedule until after the year 2000.
  • U2 staying together and making music until after the millennium.


While some of these predictions may seem obvious with hindsight, one bookie at the time was so cocksure of the bet failing that they gave odds of 6,479/1 – longer odds than Dean Gaffney winning a best actor Oscar (1000/1). The man stuck £30 on his bet and, eleven years later, walked away with £194,000.

Fancy trying your luck? We’ve got some great odds for this year’s Nobel Peace Prize; the ultra-optimistic can back Donald Trump to win at odds of 50/1!

What’s the most mind-blowing bet you’ve ever won? We’d love to hear from you! Leave us a comment, below.





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