Top 10 Worst Gambling Celebrities

The border between harmless thrills and life-altering addictions is narrow, and it takes a powerful person to walk it for long. 

There's undoubtedly something exciting, or, dare we say, even sexy, about the low-lit, dazzling luxury casinos. Indeed, the looming dangers make wins a lot sweeter. But one should stay weary of them, or they risk losing a lot more than plastic chips. 

The celebrities below know how exhilarating a hobby of gambling can be. However, they had to learn the hard way that it will quickly turn on you unless you have a firm grip on the steering wheel. 

10. Leonardo DiCaprio

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Recent years had us gambling on who's going to be Leo Dicaprio's next girlfriend, but few people know the Wolf on Wall Street has a bit of a gambling habit himself. If we were to believe the high-stakes poker player Houston Curtis, Leo would love everything about poker except one thing. Gambling with his own money that is.

Irish singer Ronan Keating reported that he lent Leo hundreds of dollars over the poker table, money which he never saw back. In all fairness, at the time, Leo's finances were better spent on PR efforts. The man really wanted his Oscar.

In any case, it's obvious that the actor thoroughly enjoyed his card games, as it is rumored he was one of the high-profile celebrities to participate in the illegal gambling ring that inspired Molly's Game. 

9. Drake

[ Source: ihearts143quotes.com ]

Shawties had gambled with Drake's heart ever since 2006 when he started his music career. It really seems like the musician can't properly manage the risks of his love life. But who would have known that he's equally as bad at managing bets? 
Some celebs stick to a tried and true game, but Drake seems to be testing the waters by chasing an Instagrammable win. Luckily for us, he doesn't shy away from posting his losses, either, which is how we came to learn how terrible of a gambler he is. Sorry, Champagne Papi!

According to Fight Sports, the singer placed some questionable UFC bets, for which he had to leave behind $275,000 and $550,000, respectively. Jorge Masvidal is unquestionably better-looking than Colby Covington, but Drake shouldn't have let that inform his bets. 

Fast-forward a few months, and Drake wagered again a whopping $230,000. This time, the money was supposed to inspire F1 driver Charles Leclerc to win the Spanish Grand Prix. 

Unfortunately, the pressure could have been too much for Leclerc's car, which suffered a power unit failure, preventing Leclerc from finishing the race. 

After this long streak of bad luck, some might say they were jinxed and call it a day. Not Drake, though! Through sheer determination, the rapper recently managed to lose a mind-boggling $20 million on online roulette, according to Gambling News. 

Let's hope this is a lesson learned for our Certified Loser Boy. 

8. Ben Affleck

[ Source: telegraph.co.uk ]

Everyone who watched 21 tried to count cards at some point, so let's not try to fool ourselves. Casinos have caught wind of this since 2008, and the practice is frowned upon, if not downright prohibited. Apparently, the news never made it to Ben Affleck, who was banned by the Hard Rock Casino for trying to count cards. Some might try to brush it off as an honest mistake, but Ben already had an extensive history with gambling by then. 

The addiction ran in the family, as his father, Tim Affleck, would frequently jeopardize the family finances to support his gambling. Over decades, Ben Affleck lost and won millions of dollars and sparked a raging addiction. 

In 2001, he sought help and was admitted into rehab for both gambling and alcoholism. He claims that rehab worked wonders and allowed him to kick both habits, but rumor has it that's not entirely true. 

He was allegedly kicked out of other casinos post-rehab, so we're inclined to believe that the actor is still battling his addiction. 

7. Charlie Sheen

[ Source: denverpost.com ]

I bet no one is surprised to see Charlie Sheen on this list. Gambling seems to be the cherry on top of a timeline of questionable behaviors.

During his 2006 divorce from Denise Richards, some of the details regarding Sheen's gambling came to the surface. The actor was betting close to $200,000 every week, mostly on sporting events. That shouldn't be too bad, considering he could afford it. But reports state that Sheen experienced extreme mood swings when losing, while wins failed to raise his spirits. 

In an interview with the New York Times, Sheen recounted betting $1 million on Manny Pacquiao before his match with Oscar De La Hoya. He said that winning the enormous bet made him feel nothing, which is why he finally decided to call it quits. 

Nowadays, Sheen proclaims himself a "retired gambler" rather than recovering addict, although he admits he will check the lines from time to time. 

6. Tiger Woods

[ Source: golfdigest.com ]

By our understanding, golf should be quite a pleasurable pastime, but it seems that's not the case in highly competitive environments. A solid proof of that is the uncontested emperor of golf, himself. 

Tiger Woods is known to leave the high tensions on the golf course and look for relaxing ventures elsewhere whenever he's got the chance. We wouldn't need to mention his famous adulteries if these didn't go hand in hand with his gambling habits, though. 

The athlete was known to waltz through Vegas casinos, accompanied by his mistresses. Woods was said to bet up to $25,000 per hand in blackjack during these sessions. 

It is unclear whether his gambling practices really threaten his mental health.

One thing we can say for sure, though, is that the athlete has a $1 million upper betting limit at The Mansion, an MGM Grand Casino club for high-rollers. And we can only suppose that your gambling needs to get a bit out of hand for a casino to stop you from wagering more money. 

5. Allen Iverson

[ Source: exnba.com ]

At the height of his basketball career, Allen Iverson was worth close to $200 million. However, a burning passion for slots and card games saw this All-Star player gamble it all away. 

His journey wasn't exactly smooth. As you can imagine, gambling with $200 million gives you a copious amount of time to ruin your life in various other ways. In 2004, Iverson was banned from Bally's Atlantic City casino for disorderly conduct. 

A mere year later, Iverson made a scene by refusing to return $10,000 in chips that were mistakenly paid to him. Many bans followed, and Iverson quickly turned from a beloved athlete to a bad role model. 

Following two other bans in 2011, Detroit News blamed Iverson's boorish behaviors. Apparently, the player was a sore loser, frequently throwing chips or cards at the dealers, being loud, and being exceptionally rude to the staff. It's true when they say that money can't buy everything, as it couldn't buy Allen Iverson some manners. 

4. Tobey Maguire

 

[ Source: thedailybeast.com ]

You need to be a special kind of evil not to like Spider-Man. However, Tobey Maguire's fans might be unpleasantly surprised to hear about his gambling exploits. 

The actor has been a defendant in a series of civil lawsuits related to an illegal poker ring. Maguire participated in these poker nights along with celebrities like Gabe Kaplan, Dan Bilzerian, and Nick Cassavetes. 

It is alleged that bigger names, such as Leo DiCaprio, Ben Affleck, and Matt Damon, had places at these underground meetings. Bradley Ruderman, a successful hedge fund manager, held the poker nights. 
Now, I know what you're thinking. A private game of poker between friends isn't grounds for a lawsuit. However, it seems the copious amounts of money Maguire won during these meetings were stolen from investors who were previously lured into a Ponzi scheme. 

The lawsuit against Maguire stated that he had won $311,000 in this fashion between 2007 and 2008. The games were allegedly held at luxury hotels such as The Four Seasons and Beverly Hills Hotel and, sometimes, at the private residences of those involved. 

This entire story was filtered through the lens of Hollywood and released as a fairly successful movie - Molly's Game. Molly Bloom, who is said to have organized these games, mentioned Tobey Maguire played a pivotal role in the entire scheme. 

Ruderman is currently serving a 10-year federal prison sentence after embezzling $44.3 million from his investors. In court, Maguire agreed to pay $80,000 of his winnings to the estate of Ruderman, so the victims could recover some of their money. 

It is still being determined if the judge will approve the settlement, considering that Maguire allegedly knew the origin of the funds and willingly participated in these games. If only Uncle Ben was still among us. 

3. Antoine Walker

[ Source: thehoopdoctors.com ]

How many gambling addicts does it take to replace a broken lightbulb? 
Hm? 
None! The lightbulb is fine. There's no problem with the lightbulb. 

This seems to be Antoine Walker's overview of his gambling problem. After racking up to $4 million in losses and approaching an arrest for failing to pay his gambling debts, Walker denied having a gambling addiction. 

In an appearance at Rex Chapman's podcast in 2021, the former NBA All-Star said he wasn't one of those people who played for hours, describing himself as more of a hit-and-run guy. No problem there. 

Antoine Walker's memory might sometimes slip, but the Internet does not forget. We still remember the athlete opening up about a high-stakes game of spades he played with Michael Jordan. Far from being a hit-and-run leisure activity, the game lasted 36 hours. 

Thirty-six. 

So, Walker denies having a gambling problem. But he was down millions chasing losses, hunted down by various casinos for outstanding debts, and transcended time over cards with Michael Jordan. 

I am not saying Walker is battling any addiction, but if it walks like a duck and quacks like a duck… 

2. David Milch

[ Source: Variety.com ]

Four-time Emmy-winner David Milch might have one of the saddest gambling stories out there. The extremely talented writer-producer of classics like NYPD Blue and Deadwood has struggled with a severe gambling addiction for most of his life. 

Horse races were his poison of choice, a habit that cost Milch more than $100 million. Although Milch still enjoys a place among HBO staff, where he is reportedly very loved and cherished, the producer suffers from massive financial distress. 

As a result of his gambling issues, which remained hidden from his wife for an extended period, he is currently $17 million in debt to the IRS. 

Milch and his wife have agreed to a payment plan with the IRS, due to which the couple had to sell one of their two homes for $4.8 million. The second estate is listed for $8.95 million but is still looking for a buyer. 

David's friends and family report that the producer struggled on and off with his addiction and appeared completely sober and in control of his behavior several times throughout his career. However, each subsequent relapse damaged his self-esteem and the trust of his loved ones. 

Currently, Milch lives off a $40 weekly allowance he receives from his wife, as the two of them are fighting to clear off the massive debt. 

1. Pete Rose

 

[ Source: NBCSports.com ]

Pete Rose and his gambling behavior must be among the most debated topics in professional sports history. 

Following the 1986 season, Pete Rose ended his career as an outfielder for the Cincinnati Reds. With 4,256 hits and 3,562 games played, he was set to live his retirement in constant acclaim as one of baseball's all-time greats. 

Two years prior, he accepted the role of a manager for the Big Red Machine, a position he held for six more seasons. 

Rose was a known gambler, but no one batted an eye at his habits until 1989 when suspicions that he was betting on baseball matches rose to the surface. Pun intended. 

Judging by slips seized by the IRS, Rose was betting $8,000-$10,000 per day on baseball. A full investigation ensued, at which Rose was found to have wagered on 52 different Reds games. 

Although this resulted in a lifetime ban, Rose did not admit to any accusations. He served five months in prison for tax fraud, and he was unanimously voted out of the Baseball Hall of Fame's ballot. 

It took another 14 years for him to admit the truth in his autobiography. Rumors regarding the possibility of lifting the ban regularly surface, but that seems unlikely. 

The now 83-year-old, extraordinarily talented athlete still pleads for his reinstatement, but even the most optimistic of you can probably understand how low those odds are.