The 15 Biggest Degenerate Celebrity Gamblers

by 10 years ago

Imagine for a second that you are an extremely wealthy individual, like Bill Gates or Scrooge McDuck. Would you spend hours of your spare time gambling all your fortunes away, potentially jeopardizing the livelihood of your three nephews and your trusty pilot, or would you do something better with your time, like the backstroke in a vault full of money or nail every chick who crosses your path? Personally, I can't say what I would do. On the one hand, I love to gamble — although, I'd like to think I am not stupid enough to lose millions; but on the other hand, sex addiction is still trending up right now, so I might want to ride that train… see where it takes me.

Being famous and disgustingly rich is probably not as easy as it seems. For some athletes and celebrities, pissing money away at casinos or on sporting events may offer them something the layman cannot understand; to them it may be an outlet for stress, an exciting rush, or maybe just a massive tax write-off (and they don't care for charity). Whatever their reason — competition, pride, boredom, etc. — some famous people just don't give a shit when it comes to gambling money and lots of it. Here then, are 15 of the most degenerate celebrity and athlete gamblers, including my childhood hero, who allegedly lost $1 million playing golf with friends and whose son is following in Dad's footsteps. And you thought trusting a fart was high-stakes gambling.

Phil Mickelson
Although this has never been confirmed as fact or truth, it is rumored that Phil turned his back on Titleist — the brand that won him his first two majors — and became a member of the Callaway family because he needed the money to pay off gambling debts. What makes this decision even more questionable is that Phil's unexplained switch came just days before the 2004 Ryder Cup.

Michael Jordan
His Airness can hit a casino with the best of 'em, but what's even more impressive is that he is said to have lost over a cool million playing golf. If he was trying to play to his alleged sub-5 handicap, his loss doesn't surprise me since he seems to never break 90 in any celebrity pro-am he enters. He must calculate that handicap using his scores and the slope rating from his local pitch and putt.

Charles Barkley
He is both highly entertaining and incredibly honest and when he said he was not a good role model, he meant that shit. Chuck has fired men through windows, fought a losing battle against obesity and his golf swing, and he proudly admits to having lost over $10 million at casinos throughout his adult life.

Tiger Woods
When you hang with the likes of Jordan and Barkley, you're bound to get involved in some unsavory shit. Shit that you will someday regret. I don't know what ill-fated actions he can or cannot pin on MJ and CB's influences but his gambles in adultery will probably cost him more than the $25,000 per hand he reportedly bets on the Black Jack table. Tiger seems to take everything he does to an elevated level so it's probably a good thing he never became friendly with Ben Roethlisberger.

Joe Francis
Wynn Hotels recently sued Francis for $2 million in unpaid gambling debts. The reason why Francis — a normally upstanding and classy gentleman — hasn't paid said debts is because he claims the casino offered him a discount (somewhere between 10% and 30%) for his losses. Apparently, if you are a big shot who videotapes tits for a living, you can get up to 30% of your gambling debt forgiven. Who knew? Anyway, the casino admits to giving Joe the discount but they also state that he didn't pay his debts on time so they Indian-gave that mother f*cker.


Gladys Knight
The former queen of the Pips once had a $40,000-a-night addiction to baccarat that she has since kicked. In other, completely irrelevant news, I just learned that Knight owns a restaurant chain in Atlanta called Gladys Knight and Ron Winan's Chicken & Waffles. She must eat there often.

Allen Iverson
The NBA seems to be the league to go to if you want to make, and then subsequently squander, millions of dollars. Iverson earned over $200 million throughout his NBA career and it is reported that he managed to gamble and drink away most of it.

John McCain
If choosing Sarah Palin as his running mate wasn't enough evidence that McCain has a gambling problem, the senator's friends claim that he has been known to go on 14-hour benders at the craps table. That seems like torture, even to a former POW.

Click here for the rest of the 15 biggest celebrity degenrate gamblers, including Ben Affleck, Pete Rose, and everyone's favorite mullet-wearing golfer…

TAGScharles barkelyGamblingMichael JordanPhil Mickelson