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The Most Infamous Athlete Gamblers of All Time

by: @dickiesalvatori - posted on: 04-Feb-2014

When it comes to gambling, there are a variety of people involved in the equation. As far as gamblers go, if you’re involved in it, you probably already have an idea as to how this works. From a sharp to a true degenerate, everyone is different and tends to use a variety of approaches. 

Sports “stars” and athletes in general are not supposed to be involved. They teach kids at the collegiate level not to get involved in even so much as a Super Bowl box pool.

But once these guys hit the pro ranks, everything is thrown out the window. As anyone who has been to Vegas knows, money can take you a long way. Athletes and celebrities alike get “comped” like no one else.

To add fuel to the fire, many athletes have arrived where they in their profession based on a competitive spirit and drive. That sort of mentality is difficult to check at the door no matter the occasion, and gambling is no different.

More than a few athletes have gotten themselves into a bit of trouble thanks to their gambling prowess. We’ll try to touch upon some of the biggest whales out there and give some insight into their tendencies and the stories that make them such legends within this world.

Jaromir Jagr

Growing up in Pittsburgh, as in any sports-centric town, you hear a ton of gossip regarding pro athletes. During my teen years, I once heard that the famous hockey legend was contemplating buying property in the next town over. Many in my neck of the woods said it was a done deal.

Jagr never showed up at the property he was rumored to be interested in buying, and rumors started swirling. Some speculated that money he owed to bookies prevented him from having the necessary capital to put a down payment on the home at that time.

Just a few short years later, Sports Illustrated came out with a story on Jagr indicating that he had lost hundreds of thousands to an online gambling website operated out of Belize. Jagr at one point publicly admitted to paying off close to a million in gambling debts, but that wasn’t the end of it.

Jagr floated around to several teams after leaving Pittsburgh. He spent time in Washington, D.C. and New York between 2001 and 2008 before joining the Kontinental Hockey League. The rumor this time was that at least one of his trade requests had come in lieu of his owing certain people in certain regions money.

The federal government also came after Jagr in the middle part of that decade thanks to a $3.27M debt he apparently owed to the IRS. Jagr hasn’t had many flare ups in the last 8-10 years, but the stories surrounding both he and his gambling tendencies early on appear well documented.

Floyd Mayweather, Jr.

Mayweather, Jr. could be viewed as the inspiration for our article in many ways. Twitter has been rife with news of him placing a $10.4M wager on this year’s Super Bowl. Anyone who knows anything about the gambling industry knows that is unlikely, but Floyd’s love for this hobby is definitely something fans have known about and been aware of for some time.

TerezOwens, the infamous sports/dirt blog, has previously posted photos of Floyd possessing gambling tickets representing $100K wagers on the Orlando Magic 1H point spread. Mayweather has also released documentation via social media of other large, and relatively believable bets, most notably on NFL games.

When you hang out with 50 Cent, refer to $25K black jack chips sitting on your dashboard as “spare change,” and take home $20M+ per fight, you are definitely living large. Floyd has the defensive mechanics and foot speed to avoid big hits in the ring. But his fans better hope his pockets don’t take major hits once he retires, because the way he bets, his bankroll might not last forever.

Antoine Walker

The former Celtic great probably has the saddest story of anyone on this list. Walker claimed he was broke back in 2010, a shocking revelation given the fact he earned well over $100M in his playing career and that it had ended only a few short years prior to that.

But those around him claimed to have seen it coming for quite some time. Friends say he began betting big after training with one of the NBA’s all-time greats (who also just happened to make our list) back in the summer of 2001.

Walker was also well known for spending on virtually anyone and everyone in his crew, often buying people vehicles for their birthday celebrations. Clearly, not all of his monetary losses were due to gambling, but his tendencies didn’t help. He was reported to have lost a large sum in some real estate ventures that amounted to little more than gambling, and the Boston Globe once reported that Walker was being tailed for up to $4M in gambling debts by various creditors. 

Michael Jordan

The “GOAT” as he is referred to by many in both the basketball and sports world in general is the only guy on this list to amass a fortune that prevented his losses from being too tragic.

In addition to an illustrious playing career, Jordan has made quite a lucrative fortune from his shoe brand, and he has thus been able to sustain a gambling habit that only helps to add to his already outrageous legend.

From blackjack to poker to wagering hundreds of thousands on merely a hole of golf, Jordan has been known to not only be larger than life, but to also have influenced many athletes around him. His gambling ventures in practice and workouts with fellow pros Walker and Rip Hamilton are quite notable, and Jordan was willing to wager with anyone who had the coin to match him.

Jordan’s competitive fire was his best asset on the basketball court. The “alpha dog,” personality which made him such a great end of game performer also extended into his social life, and it has helped elevate him to quite the celebrity status within the gambling world as well.

John Daly

Daly has always been larger than life thanks to his absurd story-lines regarding his career in pro golf. From trips to AA to bashing hotels the night before a final round, Daly has been mixed up in a variety of activity that has made him the subject of more than one message board conversation.

But when it comes to gambling, few can surpass Daly in terms of outrageousness. His tell-all book revealed he had lost between $50-60M in casinos over time. It was also stated that Daly squandered away roughly $1.5M in 2005 at slot machines. For a pro athlete to be gambling is one thing, but to have it be connected to something as mundane as the slots is seemingly unbelievable.

Daly has done a certain amount of good with his wealth as well, however. He has a clothing line called “Loud Mouth,” which at one point had deals with both the Dallas Cowboys and the University of Arkansas. He also once gave $30K in winnings to the family of a man who had died in a lightning strike. This came in 1991 and was long before Daly was famous or wealthy.

“Wild Thing,” as he has been dubbed by many on the tour, is the definition of “larger than life.” His coach once claimed that “the most important thing in his life is getting drunk.” He also made a song with Kid Rock and once stated that many on the PGA Tour were cocaine users, implying that while he did have a drinking problem, he was “one of the cleanest guys out there.”

Daly transferred that carefree attitude into the world of gambling, but it didn’t pay off in the manner illustrated on the golf course. He is widely viewed as perhaps the most ridiculous athlete gambler of all time and, regardless of who you talk to, warrants legitimate inclusion in the top portion of our list.

Charles Barkley

Barkley is likely atop the leader-board when it comes to off color statements and a media driven attitude which makes him one of the more popular former athletes out there. Among his many gambling claims to fame, he alleges to have lost $2.5M in six hours while playing blackjack and was once sued by the Wynn in Vegas over $400K in casino related gambling losses.

He is one of the only individuals to publicly admit that he needs to stop gambling, and he also hasn’t been shy about estimating his overall losses through various media outlets.

Barkley spends part of his time in the Philadelphia and Arizona regions when not working in the broadcasting booth. It is cleverly convenient that both cities are within a few hours of major gambling hubs Atlantic City and Las Vegas.

Barkley is a revered family man and often the center of the party. He is a wildly popular figure whose mouth has earned him respect for his honestly. His friendship with fellow NBA legend Michael Jordan has also enhanced his legend both on and off the court.

Barkley has been rumored to be one of MJ’s biggest gambling buddies on the golf course, and the two are A-listers when it comes to the casino world. Like many others, Barkley has been influenced by Jordan and he appears to get at least some of his wagering prowess from the man so closely linked to his own legacy.