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Celebrity Sports Betting: Big Wagers On & By Star-Studded Celebs

Celebrity Sports Betting: Big Wagers On & By Star-Studded Celebs

Betting on sports can be intoxicating. Putting your hard-earned cash on a match or game adds another dimension to what are typically thrilling encounters. The trick is to find outlandish odds, wager the proverbial ‘shirt’… and win!

We’ve all heard the stories about ordinary folk cashing in on a lucky bet. Canadian, Gino DiFelice hit the headlines when he banked $725 000 from a $5 wager on the Sea Hawks beating the Packers! But some of the biggest sports wagers in terms of bet size and payouts have involved start studded celebrities.

But before we make it sound too easy, bear in mind the majority of punters blow their bankrolls without ever generating big dollar returns. Even if you do hit a five or six figure payday in crisp Canadian bank notes, there’s a strong probability you’ll end up broke, as many of the biggest lottery winners in history can attest.

If you want to learn how to bank it or blow it when betting on sports, here are a few celebrity-infused sports betting stories that reveal big bets, cool payouts and chose shaves:

Floyd Mayweather – Multi-Million Dollar Pac-Man Put Down

Floyd Mayweather - Multi-Million Dollar Pac-Man Put Down Image Source:

In 2012, American rapper 50 Cent ignored the media hype around the Fight of the Century and stuck to his ‘man’.  He wagered $1.6 million on Floyd Mayweather beating Manny Pacquiao in what was billed the second edition of The Rumble in the Jungle, the legendary bout between George Foreman and Muhammad Ali.  Although there was no dazzling KO in the 8th round, Mayweather won on points, dishing up a $2.3 million payout to the hip hop star.

Rory Mcllroy – The Dad, The Wager & The Claret Jug

Rory Mcllroy – The Dad, The Wager & The Claret JugImage Source:

Four-time grand slam winner, Rory McIlroy is a talented golfer with a large and active fan base.   But one fan towers above the rest and that’s his dad, Gerry.  The affable Irishman was so convinced his son was made of the right stuff, he bet £200 at odds of 500 – 1 on Rory lifting the Claret Jug by the time he was 25.  Rory was a shy and awkward teenager of 15 at the time.  In 2014, the youngster happily obliged, winning the Open Championship by two strokes.  Dad promptly pocketed $171k and Rory added the ‘home’ title to his US Open and PGA Championship wins.

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Roger Federer – 7 Times Wimbledon Champ

Roger Federer - 7 Times Wimbledon Champ Image Source:

Recognising talent early can pay off, but one tennis fan sadly missed out on an astounding return on his investment.  After watching the great Roger Federer win his first Wimbledon title in 2003, an Oxfordshire resident wagered £1 520 on Federer bagging seven more men’s singles titles at the All England Club by 2019.  As the history books now tell us, Federer has indeed accomplished this astonishing feat.  The fan did not live to cash in on his wager but British charity, Oxfam was bequeathed the bet ticket and paid out the equivalent of $160 245!

Alan Denkenson - The NHL Tie Shakedown

Alan Denkenson was one of the biggest illegal bookies in America but even he got it wrong at times.  The notorious punter placed $25k on a plus-1/2 goal on a 1987 NHL match between the Toronto Maple Leafs and Quebec Nordiques.  Needless to say in the final 60 seconds the score was leveled and the Canadian teams tied.  Denekenson, who was chasing a winning streak at the time, lost the biggest bet of his life by the slimmest of margins.  It just shows how easy it is to win and lose!