Sports Stars Crazy Gambling Stories

From the field to the felt, check out these sports stars who lost (and won) millions placing bets.

What’s the most you’ve lost on a bet? 10 bucks? Maybe $100? Imagine losing $1.65 million in five hours. While that’s something you can probably only dream of, these pro athletes crazy gambling stories will show you it’s a reality for some high rollers. In fact, that’s exactly what happened to Pro-golfer John Daly while playing slot machines with a $5,000 max bet. In fact, he wrote in his autobiography that he lost an overall $50-$60 million from playing casino games.

“Aaand there goes $60 mil!”

Sure, someone losing anywhere close to $60 million on a casino game seems insane. But with their exorbitant salaries, what else could sports stars possibly do with all of that money? Not only that, but these guys are both competitive and adrenaline junkies by nature. The excitement of risking large sums of money falls right in line with their competitive, thrill-seeking personalities.

You won’t believe the incredible salaries of The World’s Highest-Paid Athletes.

Known best for his eight year run with the Celtics, retired NBA basketball player, Antoine Walker, also had a notorious gambling habit. He managed to rack up $822,500 in debt between three Las Vegas casinos. He was later arrested when he tried paying the debt using an account with insufficient funds – at a casino.

“Shh… don’t tell my wife! I just lost over 800 grand at the casino.”

Then again, Charles Barkley takes the cake when it comes to basketball players and their crazy gambling habits. Over time, he lost close to $10 million from gambling. When word got out about his debts, he responded:

"Do I have a gambling problem? Yeah, I do have a gambling problem but I don't consider it a problem because I can afford to gamble. It's just a stupid habit that I've got to get under control, because it's just not a good thing to be broke after all of these years. I gamble too much, I gamble for too much money, and it's something I have to address. I am addressing it. That would be the best way to explain it. I'm not going to quit gambling because it's my life and it's my money.”

“I’m down by $10 million?! Oh sh#t…”

Michael Jordan may have been one of the best men to dribble a basketball, but his skills on the court definitely didn’t translate into gambling. He accumulated something around $1 to $3 million in gambling debt mostly betting on golf games and his soon became a name synonymous with gambling scandals in sports. Jordan famously bet $1 million on a single hole in golf and rumor has it that he frequently bets 6 figures on game. Unfortunately for him, when news got around about his bad betting habits, he lost many sponsorships.

After losing $1 million betting on a single hole of golf, we suggest you keep your day job, Michael.

So why do star athletes wager such insanely high amounts when they gamble? According to David Schwartz, the director for the Center for Gaming Research at the University of Nevada at Las Vegas, “All their lives, these guys have been the best at what they do, so they’re used to beating the house.” While their competitive nature and strong sense of self confidence pays off on the field, stories about athletes with gambling problems are not uncommon. Their confidence and competitive nature leads them to throw around copious amounts at the casino. Naturally, risking thousands on one bet will eventually rack up some pretty substantial gambling debt.

“Is the potential there for a little to become a lot? By mortal standards, you bet. And that's the problem with stuff like this: Trying to figure out what makes Jordan or Barkley hurt financially is like trying to gauge a lineman's pain threshold. Generally, you don't know until you know.” – Mark Kreidler, ESPN from Athletes and Gambling: A Longtime Love Affair.

However, plenty of sports stars know how to play their cards right when it comes to gambling. Take, for example, pro-golfer Tiger Woods’ gambling wins. He frequently plays Blackjack at $25,000 per hand with a $1 million limit at the MGM Grand in Las Vegas. He does pretty well for himself, and no news has surfaced over major losses.

The 11-time PGA Player of the Year also devotes his gambling interest to a good cause. In 2013, Woods hosted a charity poker event, “Tiger’s Poker Night” at the Mandalay Resort and Casino in Las Vegas. Celebrity players like Phil Ivey, Kid Rock, Mark Cuban, Mekhi Phifer, Doyle Brunson, Chris Paul, Daniel Negreanu, and Mike Sexton showed up for the charity event which had a $10,000 buy in.

Tiger Woods tries his luck with professional poker player, Phil Ivey, at the Tiger’s Poker Night charity event.

Floyd “Money” Mayweather has a perfect boxing record and consistently ranks as a top paid professional athlete. The undefeated boxer often tweets pictures of himself winning sports bets well over $100,000. Hands down, Mayweather’s biggest payoff came back in 2012 when he won $1.1 million betting on a college football game between Oregon and Arizona. They didn’t nickname him “Money” for nothing!

“I make it rain!”

Mayweather also got paid big bucks to host a Halloween party with Lindsay Lohan at Foxwoods Casino in Connecticut. Read more about how the casino asked Lohan to return $50,000 when she showed up late to the party.

American swimmer Michael Phelps holds the record for the most decorated Olympian of all time, with 28 medals (23 gold). Phelps is worth $55 million, and apparently enjoys throwing thousands of dollars around at the poker tables. In May 2013, Michael Phelps participated in his first World Series of poker festival where he joined in a $5,000 tournament. During another game, he tweeted a photo of his $100,000 dollar chips while playing high stakes poker:

Stacks of $100,000 poker chips? NBD.

Alex “A-Rod” Rodriguez’s off-the-wall antics make him famous not only for playing third baseman and shortstop for the New York Yankees. A-rod also made himself famous for gambling in sports issues when he made headlines for participating in an illegal poker ring with some of Hollywood’s most well-known actors. According to reports, Rodriguez played underground high stakes poker with movie stars like Leonardo DiCaprio, Matt Damon, Ben Affleck, and Tobey Maguire. These games allegedly took place in a Beverly Hills mansion and would usually have a $40,000 buy in. But that’s hardly a dent in the wallet for a guy who makes close to $20 million a year.

A-Rod has been known for his over the top antics, but who wouldn’t want to play poker with guys like Leonardo Dicaprio and Matt Damon?

Despite the millions wagered each year on sporting events like the Super Bowl or March Madness, most professional sports leagues frown on players or staff participating in even recreational gambling. They worry about the players associating with people who might have an interest in influencing game results would damage the reputation of league.

Read more about March Madness when Americans wager millions each year betting on the NCAA Men’s Division I Basketball Championship.

Say It Ain’t So, Joe! – Baseball, above all other sports, is particularly sensitive to gambling controversies. Flashback to the 1919 Chicago World Series, which still stands as the most notorious sports gambling moment of all time. The scandal involved eight White Sox players including superstars Shoeless Joe Jackson and Eddie Cicotte, who received a total of $100,000 to intentionally lose the Fall Class. Although a grand jury found all players innocent, they were all banned from baseball – a ban still in effect to this day.

As Jackson departed from the Grand Jury room, a small boy clutched at his sleeve and tagged along after him.
"Say it ain't so, Joe," he pleaded. "Say it ain't so."
"Yes kid, I'm afraid it is," Jackson replied.
"Well, I never would've thought it," the boy said.
- from the Chicago Herald and Examiner, September 30, 1920

Flash forward to 1989 and there’s no doubt that the name Pete Rose should ring a bell. Like Joe Jackson and Eddie Cicotte, Pete Rose also remains banned from baseball for life. He has a one-up on our previous baseball stars though, being the only living person to date who is ineligible for the Hall of Fame. Why? Pete had a bit of a betting problem, and in 1989 it was rumored that he actually bet against his own team, the Reds, winning a heap of dough but losing his title as manager forever.

Despite the over the top and sometimes controversial gambling habits in sports, one thing remains: gambling is big business amongst star athletes, and they have plenty of dough to throw around on it. With their larger than life personalities and lavish lifestyles, it’s no wonder that these adrenaline junkies need another way to get their competitive fix.

About The Author

I made my entrance to online gambling in 2004 in an attempt to understand the psyche of the casino goer. I've spent prolonged periods delving into the industry and its inner functions and continue to do so at VegasMaster every day. My research and experience has given me insights into gambling that I hope you'll benefit from.

1 Comment

  1. __LEON__

    It doesn’t shock me that sports stars are such heavy gamblers nor does it shock me that they lose far more than they win. I guess when you make big money like that it’s tempting to hit the higher stakes tables!

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