Every gambler has their day, and none more taxing than high flying sporting celebrities who obviously have boatloads of cash to throw away on a whim. This is just one of the reasons why famous celebrities often make the headlines with outlandish wins or as we shall see in this article, mind blowing losses of small fortunes, that rarely cause the victim to even bat an eye. There is an ever-growing list of famous faces that could be in this article, but unfortunately we don’t have nearly enough space to cover them all. Let’s just focus on a few standouts that everyone should know.

Phil Mickelson

Let’s begin with arguably the best golfer of our time, if not in the history of golf. Phil Mickelson has long been known to never shy away from a bet and there are numerous stories of him indulging in wagers on and off the course.

One of the funniest, must surely be a $1 bet with a noisy onlooker during a practice round at Augusta,
which he actually lost. Having no money on his person at the time, it is reported that he had to borrow
the money from a fellow competitors caddy to pay his debt, which definitely drew a smile from
everyone who witnessed it.

There is still some mystery shrouded around the alleged debt payment of close to $2 million to a questionable bookie Billy Walters. Even though this seems like a large amount, its mere petty cash for the man who grossed close to $48 million that year.

Pete Rose

“Charlie Hustle” as he was affectionately known by his fans, played in major league baseball and ‘still
holds the record for number of hits’, before starting his career as the manager of the Cincinnati Reds
baseball team. This is when the story gets good. He was accused of betting against his own team, a
tactic unheard of prior and caused a sensational stir in the media.

In 1987, over a three month period, it is reported that Pete Rose managed to rack up a ludicrous debt of around $400.000, which at that time was a substantial amount of money, even for those with deep pockets. Since this revelation Mr. Rose has still retained his penchant for the odd wager and sources have revealed that he currently loses approximately $1 million dollars annually, a fact that surely does not sit well with his wife.

Floyd Mayweather

The undisputed, undefeated, superstar boxing champion is no stranger to the betting world. Proficient in making money yet currently sitting with debt in excess of $50 million, you wouldn’t be surprised with a nickname like “Money” that he has seen his fair share of losses. This eccentric sportsman would walk around with a briefcase holding the apparent sum of $1 million, which he often proclaimed was a bet he was willing to make should anybody want to test his prowess with the gloves. As of today, there are still no takers as yet.

Michael Jordan

Michael Jordan is probably the greatest basketballer to ever have graced the court. Michael Jordan has
seen his fair share of big-time losses; some so grand it’s hard to believe. No stranger to the delicate art
of gambling, he has been lured in by various forms of the past time. Whether it be making $100 on the
spot bets with team mates over trivial things, such as whose baggage comes out first to dropping
$100.000 on a single blackjack hand at one of the many spots on the Vegas strip.

Without a doubt his biggest loss being handed to him at a craps table in Las Vegas, where he reportedly
racked up a hefty loss of close to $5 million at one of the casinos he frequented, jaw dropping to say the
least. That’s not it for the big spender. Once on a 10 day golf trip he managed to incur a majestic debt to
the sum of $1.3 million, apparently betting $100.000 per hole, which he obviously lost dismally.

If you thought that was the last betting shenanigans of the “GOAT” you’re mistaken, a former team mate declared that Michael would often make wagers of $100.000 on the well-known game of “rock, paper, scissors” with friends.

These losses may seem big but there are far larger losers in the history of Vegas. Take Terrance
Watanabe, for example, who managed to blow more than $100 million in 2007. These are some of the
most outrageous losses in sporting’s history, so be sure to learn from the pro’s on what not to do.