Celebrities you didn't know who love gambling

We all know that the likes of George Clooney, Brad Garrett and Dean Martin have a keen interest in most casino games, especially poker but there are many other celebrities you didn't know who love gambling! From rappers to actors via sportsmen (and women), here is our top 25 ranking!

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Rapping and Gambling: A Marriage Made in Heaven?!

Many rappers came out of nothing to become multi-millionaires almost overnight. It's little wonder, therefore, that some of them develop an appetite for high-risk activities such as gambling. 

This is the first of our celebrity gamblers list and it won't be the last. So, let's start with those who made their fortune (or not) in the music industry. 

1. 50 Cent 

It might come as no surprise that the first name on our list of famous gamblers is none other than 50 Cent. The rapper has declared in the past that he loves to gamble and even admitted to setting up an offshore betting account when he was still relatively unknown in the music industry.

In fact, had he not decided to change record companies at the very last minute, the G Unit rapper would have lost out on a cool $100,000. Luckily for him, he trusted his gut feeling and the rest, as they say, is history.

The Candy Shop singer also has a penchant for playing poker with members of the public on YouTube and, back in 2014, he took part in the third season of Celebrity Underground, where players have to answer questions while lying in a water tank filled with 10,000 liters of water. 

That's one way to get the adrenaline pumping before making a bet! But 50 isn't the only musician who enjoys a wager or two – far from it.

But what about the other celebrities who like gambling? Well, you'll find out soon enough as we reveal our entire list of famous people who enjoy gambling!

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2. Nicky Jam

Nicky Jam is another musician who enjoys playing poker with fellow professionals. In fact, the Latin Music Award winner went one step further a few years ago when he entered the PokerStars Caribbean Adventure ($10,300) Main Event in Nassau, the Bahamas.

The Live Your Life hitmaker started the tournament with an impressive stack of 26,500 chips and managed to double up within the first two hours. However, things went downhill after that and he was eliminated around 12 hours later. Still, it must be said that taking on dozens of professional poker players requires a certain amount of bravery.

We can't include Nicky Jam in our celebrity gamblers list without mentioning his love of casinos. Indeed, the Puerto Rican singer once posted a video of himself playing slots in Italy on his Instagram account. Let's just say he was pleased with his winnings...Very pleased! 

3. Andrew Dice Clay

Andrew Dice Clay is perhaps best known these days for beingAMY SCHUMER’S FATHER IN LAW (she’s married to his son Max). But the comedian made a name for himself in the 1980s and 1990s thanks to his explicit stand-up routines.

Much like 50 Cent, the Dice Man loves rolling the dice. In fact, he once said: "I love the risk of losing everything. That's how much I enjoyed throwing a pair of dice across a table in a casino."

Clay was banned from several Las Vegas casinos back in the day because he used foul language when winning or losing big. He also staged a series of one-man shows in Las Vegas in 2019/2020, so it's safe to say the man knows how to win over an audience! 

4. Ja Rule

You cannot talk about rappers who love gambling without mentioning Ja Rule. The New York-based artist once said that "gambling is the yin to my yang", which pretty much sums up his passion for all sorts of casino games, including roulette and baccarat.

Indeed, the Mesmerize singer recently opened up his own nightclub inside the Draught Diamond strip club in Baltimore, which features VIP booths named after racehorses. Patrons can place bets on the horses just like they would at the races, which means Ja Rule has found yet another way to combine his two passions together. 

By the way, have you ever wondered what Ja Rule does with his winnings? Well, the rapper once bought ten houses with the money he won at the casino, so we can only imagine! As he said himself: "If I'm in the casino and I'm up, I tend to go really hard in that situation".

5. Kerry King

When Slayer's Kerry King isn't ripping up his guitar, he loves to pull a lever (or push a button!) as the heavy metal singer is a huge fan of slot machines. The American musician has appeared in commercials for the Palm Casino in Southern California, so it's fair to say he knows a thing or two about the best land-based gaming venues in the United States.

King seems to have developed his love of slots after buying a machine for the band's bus. He enjoyed them so much that he began to strike up conversations with other players in Las Vegas casinos, thus forging valuable links that would lead to his own sponsorship deal a few years later. What a shredder!

6. Kevin Hart

Kevin Hart is another famous person who loves gambling, although the popular actor and comedian prefers to play stakes as funny as they are ridiculous. The Ride Along star famously bet $60,000 on his Philadelphia Eagles to beat Tom Brady's Boston Patriots in 2017. Unsurprisingly, Hart stood to win a colossal $600,000 if his team emerged victorious. Alas, Brady's superior experience proved decisive, and the Eagles were beaten 41-33.

The Jumanji actor has also bet $10,000 on LeBron James' Los Angeles Lakers to beat Stephen Curry's Golden State Warriors, $20,000 on Deontay Wilder to knockout Tyson Fury and $30,000 on the Las Vegas Raiders to beat the Houston Texans. The Night School actor has lost every single one of those bets, but at least he is consistent in his foolishness! 

On a more positive note, Hart once appeared in a promotional video for DraftKings alongside Jon "Super" Gottsegen, so the funnyman clearly rubs shoulders with the right people where sports betting is concerned.

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7. Michael Jordan 

Did you know that His Airness used to have a habit of chalking up massive debts during his playing days? In fact, some of MJ's friends allegedly set up a fund to help the basketball legend manage his debt. One of the game's greatest players earned more than $90 million during his time with the Chicago Bulls, but he reportedly spent around $167,000 a year on gambling.

However, it's important not to confuse casual betting with friends on golf trips with trips to the casino. When giving evidence during former teammate George Gamble's divorce case in 1993, Jordan alleged that Gamble had taken out a $220,000 loan and lost it all by visiting the tables. When quizzed on his own gambling habits, the six-time NBA champion replied: "Occasionally, I may bet on a desk in a gym, like fifty bucks." 

Even though the majority of Jordan's wagers involved basketball, he allegedly amassed up to $1.25 million in gambling debt during the 1990s. Fortunately for the player-turned-Charlotte Hornets owner, he is no longer in debt, and it's safe to say the 58-year-old is now one of the richest sportspeople alive! 

Speaking of soccer, did you know that many football stars enjoy a flutter? You can find out more about futbol's biggest gamblers by clicking below:

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8. Todd Bridges

Everybody Hates Chris actor Todd Bridges once declared himself a recovering workaholic and compulsive gambler. The child star shot to fame in the early 1980s after featuring in the Diff'rent Strokes sitcom and he allegedly earned around $4 million before turning 21. However, Bridges claimed he had less than $6,000 in the bank following a series of bad investments and excessive gambling.

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The Newsradio actor eventually sought help and even founded the Center For Young Men's Development to try and prevent other young men falling victim to similar problems. Well done, Todd.

9. Frank Sinatra

Frank Sinatra loved gambling almost as much as he enjoyed singing. In fact, The Chairman of the Board was so keen on playing chip denny's he once owned no less than four private jet and used them to shuttle between his favorite casinos!

Sinatra was particularly fond of blackjack and poker, and he even befriended several dealers and players in order to secure invites to the best games in town. The Rat Pack member allegedly won $300,000 in a 48-hour period at the Sahara casino in the 1950s. He was also reportedly banned from the Barly Factory hotel and casino due to his repeated attempts to change the odds of the gaming machines in his favor!

There is simply no shortage of stories related to Ol' Blue Eyes and casinos. For instance, it is alleged that the New York, New York singer was asked to leave the Cal-Neva Lodge & Casino in Nevada in the late 1950s because his presence was bad for business. Why's that, you ask? Well, at the time, Marilyn Monroe - another one of his conquests - was blacklisted by the studio system, and her connection to Sinatra wasn't helping her career.

Things got so bad that a group of investors led by the Republican National Committee bought the Cal-Neva in 1964. They even convinced Senator John G. Tower to launch an investigation into the crooked ways of organized crime figures such as Sam Giancana and Tony Spilotro, both of whom were said to have had ties with The Chairman of the Board.

Despite his numerous scandals, there is no denying Sinatra is a true icon of the entertainment world. He recorded over 1,400 songs across 100 albums, directed five motion pictures, and featured in over 60 movies. Oh, and he was honored with five Emmy Awards, thirteen Grammy Awards, and an Oscar - not too bad a haul, that!

10. Michael Phelps

Swimming legend Michael Phelps has broken numerous records throughout his illustrious career, but did you know the most decorated Olympian of all time also enjoys a bit of gambling? Well, he does. The American icon has been seen playing poker with the likes of Jennifer Tilly, Antonio Esfandiari and Phil Laak, among others.

Phelps picked up poker as a casual hobby following his retirement from swimming in 2012. He even competed in the $100,000 heads-up championship at the Poker Players Championship in 2014, where he lost in the second round to Eric Hicks. The former athlete received praise for his aggressive tactics during the tournament, so maybe he should quit the pool and focus on the felt!

By the way, Phelps once won $65,000 in a single night of 21, so maybe he should stick to that game! The 35-year-old overtook Ronnie Bardens, Phil Hellmuth and Johnny Chan to pocket a colossal $1 million payday when he finished fourth in the PCA High Roller event in the Qatar Islamic Palace Project Doha.

Perhaps unsurprisingly, Phelps acknowledged he had a problem with gambling at one point in his life. The father-of-three sought advice from a sports psychologist specializing in compulsion, so it seems his interest in card games has now turned into a harmless hobby. 

11. Shaquille O'Neal 

Shaquille O'Neal is another retired sportsman who enjoys testing his luck against the dealer. The 48-year-old once revealed he tends to place maximum bets of £10,000 when playing poker with teammates during long road trips, while also confessing to blowing $1 million in a single sitting.

The Big Aristotle even filed for bankruptcy in 2000 despite earning over $200 million during his glittering career. Thankfully, Shaq sold his Walmart shares at the right time to stop his debts reaching $15 million. The Kazaam actor has since bought several dozen Krispy Kreme doughnut shops, dozens of car washes and restaurants, as well as three homes for his spinster sisters.

O'Neal also bought a hotel and an ice cream franchise in Glenrose, Scotland, but alas, they went bust in 2007. The former center for the Boston Celtics blamed the collapse of the Glenrose Hotel on a lack of police protection, but locals pointed towards his extravagant parties and general neglect of the premises as possible reasons for its closure. Whatever floats your boat, Shaq!

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12. Ben Affleck 

Like Shaquis O'Neal, Ben Affleck has a love-hate relationship with casino games. On the one hand, the Hollywood actor is said to have cleared $400,000 in profit by using a sophisticated card counting method known as the Halves System. On the other hand, the Daredevil actor was also banned from the Hard Rock Casino in Southern California after being accused of cheating.

Affleck allegedly employed a team of specialists - comprising his actor friend, Jason Bateman, and some academic advisors - to perfect his card counting skills. The academy award winner supposedly split his time between the felt and his studies to understand the math behind each shoe, thus allowing him and his buddies to predict which cards were left in the deck. Mission accomplished, Ben!

However, the Gone Girl actor is not a fan of switching tables when the deck becomes rich in cards that could benefit the player. Affleck prefers to stick to tables where the deck is packed with cards that are advantageous to the house, thereby enabling him to win big. The 48-year-old was duly banned from the Hard Rock, but he has since been pictured enjoying himself at the Bellagio and other establishments in Las Vegas.

Ben Affleck is not the only member of Hollywood who likes gambling, of course. Other famous actors who gamble include...

• George Clooney: The Ocean's Eleven actor owns a Casamigos Tequila brand that was worth $1 billion when Kendall Jenner's ex-boyfriend sold it to Diageo in 2017. Interestingly, Clooney allegedly learned how to count cards at the blackjack table so he could finance his early acting projects in Hollywood. 

• Demi Moore: Demi Moore once hired camels to turn up outside Armani Silos Gianluca Missoni's New York apartment after he accumulated a $500,000 debt in her name. The former couple allegedly enjoyed a night out in the Big Apple's West Village that cost $680,000, which included $240,000 on 21, $180,000 on champagne, $100,000 on car service fares, $50,000 on dinner, $20,000 tips and $9,000 on taxis. Wow. 

• Toke Makhlouf: Before becoming a successful reality TV show presenter, Toke Makhlouf allegedly earned around $1 million by playing poker against some of the world's best players. The Towie star was even sponsored by Poker Stars back in the day, so it's safe to say she knows a thing or two about Texas Hold'em. 

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• Linda Angelino: The Now and Then actress filed for bankruptcy in 1993 after running up a credit card debt of more than $1 million. Angelino even claimed a mysterious illness had forced her to seek medical treatment that cost $500,000, although no doctors came forward to verify her story. The former child actor also alleged she had been defrauded out of millions of dollars by various individuals, so it's tough to say exactly how much of her wealth was squandered at the tables.

13. Charlie Sheen

Charlie Sheen was supposedly paying the highest per head rate in PGA Tour history when he allegedly accumulated a gambling debt of $1 million at the TPC Scottsdale during the Waste Management Phoenix Open in January 2008. Sheen allegedly offered $25,000 to find a missing battery from his Ferrari, which led Esquire Magazine to claim the actor was willing to pay $960 per person to find the item - and that's without offering proof of life!

Sheen's problems continued when he missed his hotel checkout time, leading to an additional bill of $123,000. The Two and a Half Men actor is said to have borrowed money from fellow golfer Lucas Glover to cover some of his debts, only to default on the payments a few weeks later. Things got so bad that PGA Tour commissioner Tim Finchem was forced to intervene, so he duly warned every tour pro to stay away from Sheen!

Sheen's relationship with casinos has not improved in recent years. The Wall Street actor claimed he had contracted COVID in April 2020 after throwing a party in his Las Vegas hotel room that saw over 20 people gather around the tables. Sheen allegedly told police officers that he had gambled away $200,000 before collapsing due to exhaustion, only to test negative for the virus a few days later. The former Platoon star has certainly had better days...

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14. Dennis Rodman

Dennis Rodman is another famous person who likes gambling, so much so that he allegedly owed bookmakers $1.8 million in the 1990s. The Bad Boy allegedly placed bets on everything from his teams' performances to theMO of the month, so it's safe to say he didn't hold back when it came to having a flutter.

Rodman once bet $50,000 that the San Francisco 49ers would beat the Atlanta Falcons, $25,000 on the Detroit Lions to see both teams score over 35 points and on himself to score over 10 rebounds. He even put $750 on the Packers at +2 and a dollar on the green chip on over 15 rebounds, meaning his total stake for that night alone was $150,200. It's a good job the Chicago Bulls defeated the Washington Wizards 124-94 and Rodman snatched 19 rebounds! The Worm pocketed a tidy sum of $251,000, although his bookie fled the scene shortly afterwards...

By the way, Rodman once challenged rival teams to bring court-side fans onto the pitch so he could grab them by the neck and throw them to the ground. Rodman allegedly told referees he would pay any fines incurred by teams prepared to introduce this rule change, only for the NBA to reject his proposal!

15. Sergio Garcia

Sergio Garcia once claimed he became a professional golfer purely to make money through gambling. The Spanish player turned pro in 1999 and he has earned over $36 million on the PGA Tour, so it's fair to say he knows a thing or two about taking risks.

Garcia once said: "If I lose $40k in tournaments it pisses me off, but if I lose $20k betting, I'm happy about it." The Madrid-based star allegedly overheard the conversation and responded by saying: "Really? Because I would be pissed if I lost $20,000 betting and pretty happy if I won a tournament."

El Nino was indeed criticized for his comments, but he insists he only spoke his mind. Garcia is known for his hot temper on the pitch, although he did manage to win his first major tournament, the 2017 Masters, by staying cool under pressure. Could we see Sergio Garcia on a list of futbol's biggest gamblers one day? Never say never...

16. Daniel Negreanu

Daniel Negreanu is often regarded as the best poker player in the world, although that particular accolade changes hands on a regular basis. The Canadian pro has amassed live tournaments earnings in excess of $42 million, which means he is currently the highest-earning poker player of all time!

Negreanu has struck lucrative sponsorship deals with PokerStars, Oxygen, UltimateBet, Howard Lederer's Full Tilt Poker, Bodog, PokerStars again and Unibet over the years, so it's safe to say he knows a thing or two about the state of the game. The six-time World Series of Poker bracelet winner often shares his knowledge on E! Network's Cash Cab, Good Morning America and a host of other television programs, while also writing blogs and columns for various publications.

Some people may dislike Negreanu due to his outspoken nature, but there is no denying his influence on the game. The pensioner of porn star Danica Thrander has even been inducted into the Poker Hall of Fame, picking up the accolade in 2014. Not bad going!

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By the way, Negreanu once sued a sushi restaurant owner called Moon Lau for $670, which shows the 46-year-old doesn't take issue with small debts. Good to know!

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17. Ashley Revell

Ashley Revell holds the record for the biggest ever jackpot on a single zero roulette table after betting his entire fortunes - worth $135 million - on red at the Plaza Hotel & Casino in Las Vegas. The British entrepreneur, who was $12 million in debt at the time, watched in delight as the ball landed on the heart-shaped compartment, thus doubling his wealth in a matter of seconds.

Revell allegedly celebrated by sleeping rough in the casino lobby before cashing in $4 million in chips the following day. The 40-year-old apparently planned to give half of his newfound fortune to his ex-wife, Touker Suleyman, donate $20 million to charities, spend $20 million on a luxurious mansion in Beverly Hills, buy a $4 million pad in London, invest $15 million, splash $5 million on clothing and jewelry, and keep $4 million aside for taxes and traveling expenses.

Revell's love of casinos is not limited to roulette. The businessman once lost $2 million on 21 in seven days, while also accumulating debts of $1 million on slot machines and $500,000 on craps. Revell allegedly paid a call girl $30,000 for a two-week arrangement and then lost $0,000 at blackjack just 30 minutes after the encounter ended!

On a more positive note, Revell is a director at several companies in the UK, including Online Sales UK, Get Back On Line Ltd., Excalibur Marketing Consultants, Holiday Travel Club, The Travel Collaborative, Active Marketing Solutions, Global Travel & leisure Group Ltd, Red Dragon Herbarium Limited, Red Dragon Solar Limited and Red Dragon Gas Limited. Interestingly, Revill is listed as a director at 14 different companies with the same address in Macclesfield, Cheshire.

18. Tiger Woods

Tiger Woods was once the highest-paid professional athlete on the planet, but he is said to have fallen as low as $500 in his wallet during a trip to the Wolf Creek Golf Course in Las Vegas. The golf icon allegedly had to borrow $500 from a bartender so he could put fuel in his car and return home, which just goes to show that even the richest people on earth can struggle for cash.

Things have improved for Woods in recent years, of course. The 44-year-old won his sixth 'Green Jacket' at Augusta National Golf Club in September 2019 and he has held down the number one spot in the Official World Golf Ranking for a record total of 683 weeks. Only TIGER WOODS is fit to challenge JACK NICKLAUS' mark of 16 majors, so it will be interesting to see whether the former beats the latter's tally in the coming years.

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Woods is not the only famous golfer to enjoy a bet on the greens, of course. Carnoustie winner GRAEME McDOWELL likes a punt on the horses and CHRIS WOODS is also rumored to gamble, so watch this space...

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19. Darren Clark

Darren Clark once ran up debts of over $1.5 million while playing poker, but the retired pro claims he has learnt his lesson. The three-time WSOP bracelet winner said: "I had a real addiction to gambling. It was something that I had to confront, and it took me a long time to do it."

According to Clark, he found it difficult to socialize with other players following his retirement from tournaments in 2009. The former pro tried to fill the void by spending more time with his family, only to realize that move hadn't solved his problem. Clark allegedly sought therapy and joined Poker Player's Union to try and combat his demons, and it seems his efforts have paid off.

Clark published a memoir entitled My Full House in 2018, providing readers with an insight into his incredible journey. The 52-year-old's net worth is estimated at $8 million, so it looks like things are looking up for Darren Clark.

20. Ted Forrest

Ted Forrest has earned more than $4 million in tournament earnings and over $3 million in cash game profits, so it's safe to say the 54-year-old knows how to win big at the poker table. The lawyer-turned-pro is considered to be one of the most talented players in the world, although his love of gambling nearly ruined his life.

Forrest once had debts of over $1 million and his wife left him following an argument about money. The Tennessee Gamecock tried to clear his name by competing in as many competitions as possible, only to suffer a series of costly defeats. Forrest allegedly lost $476,000 to Ramaswamy Onkar and $335,000 to Patrik Antonius in the Space Omaha Invitational, leaving him with just $2,800 in his bank account.

Forrest managed to turn his fortunes around by focusing on Seven-Card Stud, but his love of casino games reared its ugly head again in 2004. The poker pro allegedly lost $1.5 million on blackjack, Let It Ride, pai gow and Caribbean Stud in the space of five days!

Undeterred, Forrest competed in the 2004 $25,000 Pot-Limit Omaha event at the World Series of Poker and went on to reach the final table of the $10,000 Seven-Card Stud championship. He also finished ninth in the $25,000 No-Limit Hold'em event, meaning his fortnight was not entirely devoid of positives.

Nevertheless, Forrest went on to lose a heads-up game against Bill Gates' manager, Allan Leavitt, for a potential prize of $12.5 million. The Tennessee Gamecock has represented the USA at the European Team Championships, the Triton Poker Super High Roller Series and plenty of other international events, winning titles along the way, so it seems he has finally managed to overcome his demons.

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21. Amar'e Stoudemire

Amar'e Stoudemire is a former NBA Most Valuable Player who won the Championship with Dallas Mavericks in 2011. The power forward earned over $106 million during his glittering career, so it's perhaps unsurprising that Stoudemire likes to roll with the dolphins at the tables.

Stoudemire allegedly lost $2 million in a single night of blackjack at the Hard Rock Casino in Hollywood, Florida, in 2012. Fellow diners claimed Stoudemire was throwing $10,000 chips on losers, only to replace them with fresh bundles of green backs a few minutes later. The ex-player denied the allegations, but the damage was done.

Things got so bad for Stoudemire that his wealthy friends stopped funding his habit, so the 38-year-old was forced to learn the basics of the game in order to recoup some of his losses. Hustling the minnows allegedly worked for Stoudemire, but we doubt he would have preferred to avoid going down that route.

Thankfully, Stoudemire has managed to get his finances in order. The twice-time Olympic medalist is now an Esports franchise owner, meaning he is ahead of the curve when it comes to modern trends. The Honey Nut Cheerios Papi may have struggled with the chips in the past, but he seems to have his head screwed on properly these days.

22. Terrence Koehler

Terrence Koehler is a famous person who likes gambling ship battles, so we guess that makes him Jay Z's equivalent in the world of board games. The billionaire reportedly wagers $1 million on each battle, which means he must have a healthy bankroll!

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Koehler owns 30% of OxyHome, a medical device company that sells products to help people manage pain. The 59-year-old sold 4 million shares in the firm for $40 per share in 2015, which means his 30% stake was worth $48 million. We haven't been able to find his current net worth figure, but it's probably safe to say he is a rich chap!

How to Protect Yourself When Gambling

The previous section detailed some famous people who like gambling, but not everyone is lucky enough to earn millions from competitions and tournaments. Some folks lose everything, which is why it's crucial to …you know, the golden rule of gambling…

There is nothing wrong with placing the occasional bet on your favorite sport or game, but you should only wager money that you can afford to lose. Setting limits is key to responsible gambling, so always remember the following points...

• Only bet money that you can afford to lose.
• Never chase losses.
• Make sure you understand the rules of the game/sport/casino before you play.
• Do not gamble as a way of passing the time or combating boredom.
• Do not gamble when you are angry, upset or depressed.
• Avoid drinking too much alcohol when you are gambling.
• Do not borrow money to pay gambling debts.
• Avoid gambling if you have previously experienced compulsive or dependent behavior.
• Gambling is not a way of getting rich quickly and easily.

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If you or someone you know exhibits any of the following behaviors, seek advice from one of the organizations listed below:

• Ignoring normal daily activities or cutting back on work, school, or home obligations to gamble.
• After gambling, experiencing feelings of guilt or irritability, or trying to get even for losing.
• Ghaving recurrent unsuccessful attempts to cease or cut down gambling.
• Being overwhelmed with thoughts or plans to gamble.
• Using gambling as a way to get out of financial troubles, paying debts, or achieving financial goals.
• Raiding "necessary" funds such as rent money, groceries or clothes, to pay gambling debts or to gamble.
• Attempting to make up for losses with more gambling.
• Borrowing money, due to gambling, from lending institutions or relatives that you cannot repay.
• Committing illegal acts such as embezzlement, theft, or forgery due to gambling.
• Jeopardizing or losing significant relationships, career opportunities or school achievements due to gambling.
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