High-Profile Celebrities Who Racked Up Huge Gambling Losses

  • Michael Jordan claims that he has an addiction to competition
  • Charlie Sheen quit gambling after winning a $1m boxing match bet
  • Tiger Woods would bet as much as $100,000 on one hand of blackjack
  • Rapper Drake has a track record of losing seven-figure sports bets
  • Pamela Anderson provided sexual favors to clear a $250,000 poker debt
Dice and cards on cash
Bruno Mars is not the only high-profile celebrity to rack up significant gambling losses – our list showcases other notable cases. [Image: Shutterstock.com]

Getting out of hand

While celebrities often have the resources to place big bets when gambling, this doesn’t mean that the losses don’t hurt. A long list of well-known people from the entertainment and sports worlds have lost significant sums over the years.

popstar Bruno Mars has a $50m gambling debt with MGM

Rumors in recent days suggested that popstar Bruno Mars has a $50m gambling debt with MGM Resorts. We decided to look at other occasions when celebrities lost staggering sums of money as a result of their poor wagering:

Michael Jordan

Regarded by many as the best basketball player to ever grace the court, Jordan has a reputation for being a big gambler. The popular documentary “The Last Dance” highlighted the prevalence of Jordan’s betting, even showing footage of him wagering on who could toss a coin closest to the wall:

He would go as far as betting teammates $1,000 to see who could get their airport luggage the fastest and $100,000 on a round of rock, paper, scissors.

This didn’t stop before big games – Jordan had a long night of drinking and gambling before the historic Team USA gold medal victory in the 1992 Olympics. He was also seen in an Atlantic City casino before Game 2 of the Eastern Conference Finals in 1993 against the New York Knicks.

Many people speculated when he retired from basketball for the first time in 1993 and started playing minor league baseball that this was due to a betting-related NBA suspension. Rumors even did the rounds that his father’s murder had links to gambling debts.

biggest reported loss was $5m in Las Vegas during a single craps session

Betting on golf is a particular favorite of the six-time NBA champion, who once lost as much as $1m on 18 holes and had up to $300,000 riding on a single putt. His biggest reported loss was $5m in Las Vegas during a single craps session. Jordan has always denied having a gambling addiction, saying instead that he has a “competitive problem.”

Charlie Sheen

The wild man of Hollywood was never shy about courting controversy. Charlie Sheen was the highest-paid US television star for a time when he was the lead on the sitcom “Two and a Half Men,” reportedly earning about $1.8m per episode.

This money fueled his gambling, with Sheen reportedly racking up losses of $2.5m over a three-month period at one point. Sheen’s ex-wife Denise Richards alleged in divorce filings that her husband typically spent about $200,000 weekly on sports betting.

Ironically, Sheen is now part of a new HBO sitcom called “Bookie” in which he plays a gambling addict.

Richards even outlined how Sheen rang his bookie when they were driving to the hospital for her to give birth to their child and said he would have major mood swings when he lost.

Sheen’s biggest-ever wager was $1m on Manny Pacquiao to defeat Oscar De La Hoya. Despite this bet winning, he said that he felt nothing, leading to him quitting gambling.

Tiger Woods

As the most dominant golfer in modern history, Tiger Woods built up a huge mystique around himself. His fellow players often crumbled when competing down the stretch of a tournament against him.

This ice-cold mentality didn’t appear to translate over to the gaming tables, with Woods racking up significant losses in the early stage of his career, according to Las Vegas insiders. He rubbed shoulders with other big gamblers like Michael Jordan and Charles Barkley.  

sometimes stake as much as $100,000 on a single hand of blackjack

Woods was a regular in Sin City, often playing at the MGM Grand’s Mansion high roller club where he had a $1m betting limit. He would sometimes stake as much as $100,000 on a single hand of blackjack and he once picked up $5m worth of markers at the cashier’s cage.


The superstar rapper loves placing big sports bets and posting screenshots of them on social media. He places wagers on a wide range of sports, including basketball, UFC, NFL, boxing, and soccer.

A losing streak led to people talking about the “Drake Curse” as the people or teams he backed seemed to constantly come out on the wrong side of his bets. He has lost seven-figure sums on multiple occasions, including a $1m bet for Argentina to beat France in the 2022 FIFA World Cup final in 90 minutes. The Lionel Messi-inspired Argentina did go on to win the game, but only after extra-time and penalties.

Phil Mickelson

Mickelson was one of the most dominant golfers of his era, capturing six Major Championships during his career. His gambling results weren’t as good, reportedly racking up $100m in debt over three decades and betting over $1bn in total, which led to Mickelson opening up about his addiction and seeking help.

was close to the renowned professional sports bettor Billy Walters

He was close to the renowned professional sports bettor Billy Walters before their relationship eventually went sour following an insider trading investigation.

Walters even alleged in his book that Mickelson tried to place a $400,000 bet on Team USA to win the 2012 Ryder Cup in which he was competing.

Other notable mentions

Many other celebrities have gambled away big sums, just maybe not as much as those on the above list. Ben Affleck was a regular poker player and lost $400,000 in a single hand when playing in a high-stakes game in Los Angeles. He was also an avid blackjack player, with the former Hard Rock Casino in Las Vegas banning him from playing the game due to his success.

self-proclaimed degenerative gambler

Many Las Vegas casinos have UFC President Dana White on their ban list due to his proficiency at blackjack. He reportedly lost a $1m bet on a boxing match and is a self-proclaimed degenerative gambler.

Pamela Anderson is an avid poker player and she reportedly lost $250,000 in one night in a Las Vegas casino. Appearing on the Ellen DeGeneres Show, she explained that she “paid off a poker debt with sexual favors” before falling in love. She married poker professional Rick Salomon in 2007 before divorcing a few months later.

Athletes feature heavily on our list, as many of them seek the thrill that playing their sports at the highest level gave them. 11-time NBA All-Star Allen Iverson made and lost about $200m during his career and is banned by casinos in Detroit and Atlantic City, while Charles Barkley estimated his gambling losses to be about $10m before quitting for good.

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