Shocking Stories by  Celebrities with Gambling Addiction

Gambling addiction is a behavioral condition involving an uncontrollable urge to gamble, causing severe consequences on an individual’s personal and financial well-being. Genetic, environmental, as well as psychological factors cause it. There are a lot of famous gambling addicts including Hollywood stars, who often engage in high-stakes poker games called “invitation-only” or “underground” games. 

Ben Affleck, Tobey Maguire, Matt Damon, Leonardo DiCaprio and many more are featured in this article below with history, details and shocking facts. Everyone must have heard the name of many of the famous celebrities with gambling addiction  at least once, but never guessed about such problems.

Key Symptoms: Celebrity Gambling Addicts

Such famous celebrity gamblers with gambling addictions problems have severe conditions causing financial losses, strained Relationships, along with mental health issues. They often experience similar symptoms to the general population, but their high-profile lifestyles amplify their addiction’s impact, attracting media attention and intensifying its consequences. 

Florens Phunsi, Australian casino expert and chief content editor on the page here, reviewed the analysis of gambling addiction information and research. She highlighted key common symptoms to be aware of in order to prevent the problem:

  • Preoccupation: Individuals constantly think about gambling, even when not planning sessions and losses, leading to constant obsession.
  • Increase gambling amount for excitement: They may gamble excessively, leading to reckless spending of large sums of money, causing them to lose their excitement.
  • Unsuccessful attempts to control or reduce: Involves individuals making promises to stop, but they cannot keep them for a specific duration or maintain them.
  • Feeling restless when trying to stop: Symptoms such as anxiety, irritability, along with sleep issues.
  • As a method of relieving negative emotions: Playing to cope with stress, anxiety, or depression, believing it helps them forget problems.
  • Risking meaningful relationships: Negatively impacts relationships, work, and education, leading to missed responsibilities or job loss.
  • Lying: Deceive others about playing or financial loss (one of the main facts described here in review).

20 Famous Gambling Addicts: Celebrities Gamblers

Some famous celebrities with gambling problems or addicts are known for their lavish spending habits with an occasional lack of caution. They can easily drop millions on luxurious homes, fancy cars, and even gambling for excitement. For some, nothing beats the rush of placing a bet on a single spin of the roulette wheel or poker.

1) Ray Romano

  • Date of birth: December 21, 1957
  • Nationality: American
  • Age: 65

Ray Romano, an comedian, actor, and writer, has been open about his gambling addiction problems since the early 1990s. He lost significant money, including his stand-up comedy earnings. Romano sought help from Gamblers Anonymous and has been sober since 1998. He admitted to losing hundreds of thousands of dollars, including $10,000 in a single night. It profoundly impacted his life, causing lies to his wife, feelings of shame, along with depression.

2) Ben Affleck

  • Date of birth: August 15, 1972
  • Nationality: American
  • Age: 50

Ben Affleck, born in 1972, is an actor, director, and screenwriter. He won awards for “Good Will Hunting” (1997) and for “Argo” (2012). Affleck has been open about it, which started in his early 20s. He estimated losing over $100,000. In 2001, he sought treatment for his gambling addiction problems and alcoholism. Affleck made headlines after the Hard Rock Casino in Las Vegas banned him from playing blackjack due to card counting. Despite personal challenges, he overcame his addiction, having a successful Hollywood career.

3) Tiger Woods

  • Date of birth: December 30, 1975
  • Nationality: American
  • Shocking fact: celebrity gambling addicts 
  • Age: 47

Tiger Woods, a professional golfer from the United States, gained international fame for his exceptional skills and achievements. As one of the most popular famous gamblers with gambling addictions began in the early 2000s, leading to financial, marital, plus legal issues. After he hit a fire hydrant with his car in 2017, he was taken into custody for DUI. Woods has since entered rehab, but some believe he may still be gambling. He admitted that he was losing $1 million every week

4) Charlie Sheen

  • Date of birth: September 3, 1965
  • Nationality: American
  • Age: 57

Charlie Sheen, an actor, is also known among famous celebrities with gambling addiction problems. Sheen’s ex-wife, Denise Richards, filed for divorce in 2006 due to his ludomania. In 2011, he was prohibited from entering Las Vegas casinos due to a debt of over $1 million. In 2015, he was arrested for criminal possession of cocaine as well as threatening a casino employee. Sheen was released on bail but ordered to enter rehab.

5) Matt Damon

  • Date of birth: October 8, 1970
  • Nationality: American
  • Age: 53

Matt Damon, a renowned actor, producer, screenwriter, and one of the oldest american celebrities with gambling addiction problems. He gambled on sports and poker games, often losing more than he could afford. It has led to financial, marital, along with legal issues. Damon was arrested for public intoxication in 1998 after being found dead in a casino parking lot. 

6) Charles Barkley

  • Date of birth: February 20, 1963
  • Nationality: American
  • Age: 60

Charles Barkley is a retired American famous gambling addict and professional basketball player. He has been open about his problem, which started as a teenager. Charles has estimated that he has lost over $10 million in gambling-related money. In 2000 he entered a rehabilitation program. He lost millions of dollars and faced lawsuits from casinos. He once lost $2.5 million in two hours

7) Shannon Elizabeth

Shannon Elizabeth, an American actress and model known in the list of gambling celebrities with addictions. She has lost over $1 million over the years. She lost over $1 million in gambling. Elizabeth started playing poker with her family and later discovered Texas Hold’em. From 2006 to 2010, she won 12 major poker tournaments, including a charity event in 2010.

8) Michael Jordan

  • Date of birth: February 16, 1963
  • Nationality: American
  • Age: 60

Michael Jordan, a basketball star and entrepreneur, has publicly admitted to his gambling addiction since he was a teenager. He admits to having a “competition problem” and using gambling to “take the edge off” his competitive drive. Like other famous celebrities with gambling problems and addictics, Jordan has lost more than $100 million, causing significant financial damage and potentially putting him at risk of a lawsuit from the casino. One of his worst experiences was losing $1.2 million in one blackjack session and $5 million every week

9) George Clooney

  • Date of birth: May 6, 1961
  • Nationality: American
  • Age: 62

George Clooney, a popular actor among famous celebrity gamblers with gambling addicts, a director, producer, and screenwriter. He lost millions and won significant amounts, including $250,000 in one sitting. In 2005, he was sued for involvement in an illegal poker ring. He became obsessed with poker after winning a considerable sum. Clooney has been in recovery since 2005 and has spoken out about his addiction to help others. He lost over $10 million and won $250,000 in one sitting, causing financial problems in the early 2000s.

10) Tobey Maguire

  • Date of birth: June 27, 1975
  • Nationality: American
  • Age: 47

Tobey Maguire, an American actor known for his role as Peter Parker in the Sam Raimi film trilogy, has a gambling addiction that began in the early 2000s. He won millions of dollars in poker. Maguire was sued in 2011 for his involvement in an illegal poker ring. He has been in recovery since 2011 and has spoken out about his addiction to help others. News reports say about the Tobey Maguire gambling problem, he won more than $10 million playing high-stakes poker with celebrities and Wall Street executives. Maguire’s addiction forced him to file for bankruptcy in 2009.

11) Michael Phelps

  • Date of birth: June 30, 1985
  • Nationality: American
  • Age: 37

Michael Phelps, the most decorated Olympian and three-time world record holder among celebrities with gambling problems. He became obsessed with poker in his early 20s, losing millions of dollars and causing depression with suicidal thoughts. Phelps has been in recovery since 2014 and has spoken out to help others. He lost millions of dollars and was arrested in 2014 for DUI.

12) Floyd Mayweather Jr.

  • Date of birth: February 24, 1977
  • Nationality: American
  • Age: 46

Floyd Mayweather Jr., a renowned boxer began gambling with friends in his early teens and quickly developed a taste for high stakes. He has continued to bet large sums of money on sporting events and has even engaged in questionable activities, such as betting on fights. He has lost over $100 million and won $50 million gambling. Mayweather’s passion for gambling has led to embarrassing situations, such as his ban from the Bellagio casino in 2012.

13) John Daly

  • Date of birth: April 28, 1966
  • Nationality: American
  • Age: 57

John Daly is an American professional golfer known for his flamboyant personality and long drives. Like other popular gambling celebrities with addicts began as a teenager. He lost $50 – $60 million gambling, primarily on sports and casinos. Daly has been in treatment for his addiction and is committed to staying sober. He lost $1.65 million in five hours while gambling in Las Vegas and $500,000 in one sitting. 

14) Gladys Knight

  • Date of birth: May 28, 1944
  • Nationality: American
  • Age: 78

Gladys Knight, the lead singer of the R&B group Gladys Knight & the Pips, has won numerous awards.  Knight’s obsession began with blackjack after winning a large sum of money in a casino. She has been in recovery since the early 2000s and has spoken out about her addiction to help others. Knight lost up to $60,000 in one-night playing baccarat and borrowed money from friends and family to cover her debts. Her addiction caused her to miss important events, including her daughter’s wedding.

15) 50 Cent

  • Date of birth: July 6, 1975
  • Nationality: American
  • Age: 47

Curtis Jackson, better known by his stage name 50 Cent, an American rapper, entrepreneur, and actor. He lost millions of dollars and has been in recovery for several years. He has also bet $1 million on the New York Giants to champion the Super Bowl and has been known to gamble on high-stakes poker games with celebrity gamblers with gambling problems.

16) Allen Iverson

  • Date of birth: June 7, 1975
  • Nationality: American
  • Shock fact: gambling celebrities addiction
  • Age: 48

Allen Iverson, a retired basketball player, is considered one of the greatest point guards ever. He lost millions of dollars gambling, being banned from some casinos. Although Iverson has admitted to no longer gambling, he still struggles with the craving. He lost up to $100 million and bet on his games while playing in the NBA. A passion for gambling forced Iverson to declare bankruptcy in 2012.

17) Denise Richards

  • Date of birth: February 17, 1971
  • Nationality: American
  • Age: 52

Denise Richards, an American actress known for her roles in films like “Wild Things,” “The World Is Not Enough,” and “The Bold and the Beautiful”. She often gambled large sums of money to relieve stress, becoming dependent on the thrill of winning. Richards has been in recovery for several years. She lost over $1 million plus bet her engagement ring on a blackjack game. As one of the most popular celebrity gamblers with gambling addictions, she led to her filing for bankruptcy in 2006.

18) Sean Connery

  • Date of birth: August 25, 1930
  • Nationality: Scottish
  • Age: 91 (died in 2020)

Sean Connery, one of the Scottish celebrities with gambling addiction problems, actor known for playing James Bond,. He lost over $100 million in gambling debts and filed for bankruptcy in 1993. It significantly impacted his life, causing him to lose millions of dollars as well as even sell his house in the Bahamas to pay debts. Despite financial struggles, Connery persevered and had a successful Hollywood career. 

19) Leonardo DiCaprio

  • Date of birth: November 11, 1974
  • Nationality: American
  • Age: 48

Leonardo DiCaprio is an actor, producer, and environmental activist. His appearances in movies like Titanic, The Departed, and The Wolf of Wall Street have made him well renowned. Leonardo DiCaprio was one of the famous people named in the Tobey Maguire poker game lawsuit. Some stories say he may have started gambling heavily in the 1990s. 

20) David Gest

  • Date of birth: November 11, 1953
  • Nationality: American-British
  • Shock fact: one of the celebrity gamblers 
  • Age: 62 (died in 2016)

David Gest, a singer, producer, and television personality, was known for his flamboyant personality and gambling addiction. He began in his early twenties after winning a large sum of money in a casino. Gest’s obsession continued until he died in 2016. He tried to get help but was unable to overcome it. As other gambling celebrities with addictions get lost over $10 million as well as £100,000 in a single day. His gambling problem led him to file for bankruptcy in 2004. Gest was caught on camera feeding two slot machines simultaneously, stopping to take selfies with fans.

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