Our Top 5 Picks for Celebrity Gamblers

Celebrity Gamblers

Let’s face it, for whatever reason, people are drawn into celebrities. For some it’s Hollywood A-listers, others its sports players, but for the gambling enthusiast, a famous poker player may be fascinating. We’ve listed our top 5 picks for famous gamblers, and shared their story below. Be sure you let us know who your own favorite gambler is, especially if they’re not listed.

Here’s a taster of what you’ll read about:

  • How Nick the Greek would play five-month poker marathons, inspiring the WSOP
  • The man with the longest winning streak, turning $50 in $4M
  • The math-wiz who gave birth to computer betting
  • The fraudster who won big, got busted and now works as a top security consultant

Nick Dandolos

Celebrity Gamblers

Nick Dandolos or more famously known as ‘Nick the Greek’ was a fast paced, high stakes gambler that lived for the action of the game. He was known to play the odds and the superstitions of his opponents and openly spoke about beating the man not the cards.

Born in Crete in 1883, Nick Dandolos came from wealthy parents and had a privileged upbringing. After he attained a degree in Philosophy he moved to Chicago with an allowance of $150 a week from his grandfather. Shortly after, he soon moved to Montreal where he began betting on horse races eventually cashing in $500,000 bet. He took the money and moved back to Chicago where he lost it all playing cards. This is the legacy Nick the Greek is known for, winning big and losing big.

In January 1949 he would play a two-person heads up poker marathon for five months against Johnny Moss. Unfortunately, he ended up being down between 2 and 4 million dollars. Many believe this poker marathon was set up by Benny Binion as a tourist attraction and became the real inspiration behind the World Series of Poker.

It is widely known that Nick won and lost millions over his life, but no one knows exactly how much. What we do know is that at the end of his life he was gambling small stakes poker in California where he died on Christmas Day 1966. Thirteen years later he was inducted into the Poker Hall of Fame. It is rumored near the end of his life another player asked him how could he go from betting millions to betting single dollars and he supposedly answered, “It’s action, isn’t it?”.

Anargyros Karabourniotis

Celebrity Gamblers

Anargyros Karabourniotis better known as Archie Karas has to be one of the world’s most famous gamblers. Archie, a Greek American, became a legend due to having the longest and largest winning streak in casino gambling history, turning $50 into $40 million. This event would become known as ‘The Run’.

Archie was born in Greece to a poverty stricken family in 1951. His home was anything but stable, and at 15 he left his home. He eventually got a job on a ship making $60 a month and finally disembarked in Portland. From there he moved to Los Angeles and began working at a restaurant next to a pool hall. This is where he made began his life of gambling. Eventually, he was making more from pool hustling than working, and so playing pool became a full time career. Quickly, the competition dried up and he turned to poker.

Poker is where Archie Karas would leave his mark. He had a bankroll of over $2 million and lost all but $50 playing high stakes poker. In 1992, he started a three year winning streak that made use of the last $50 and turned it into $40 million (including $2 million from beating Chip Rees). Within three weeks of that streak, he lost $11 million gambling with dice, $2 million to Chip Reese, and another $17 million playing baccarat. He made his way to Vegas and began putting down $300,000 per bet in more dice games. He lost all but his last million which he entered into a freeze out event with Johnny Chan and doubled his money. He lost it all within a few days.

Archie's story was far from over. He went on a few more winning streaks including one in which he turned $40 thousand into $1 million at the Desert Inn. During another winning streak, he turned $200 into a little short of $1 million.

Just when everyone thought the headlines about Archie were over, he was arrested for suspicion of cheating at blackjack in a San Diego casino. This 2013 event was the fourth occasion in which he had been suspected of cheating. This time he was caught and pleaded guilty in 2014 after 73 days in jail. He was sentenced to three years of probation.

“Archie became a legend due to having the longest and largest winning streak in casino gambling history, turning $50 into $40 million. ”

Brian Molony

Although one of the most famous gamblers in history, gambling is only half of his story. Books and movies have been made about his exploits in the early 80’s. Sometimes the line between fact and fiction gets blurred when it comes to his life.

Brian Molony was a gambler from an early age. It is said he got his first taste of gambling at a race track at the age of ten and soon became a bookie for his classmates. Eventually he would graduate with a degree in journalism, but before graduating he took a placement test for the Canadian Imperial Bank of Commerce (CIBM) and placed high enough where he was offered a management position. He earned $10,000 a year and, by an outward appearance, lived a simple modest life.  Little did many know that he was embezzling millions from CIBM and gambling it away between Atlantic City and Las Vegas.

Because he worked in various branches for CIBM, he understood their vulnerabilities and weaknesses and took advantage of them by creating loans for real and fake companies. For example, he transferred over $10 million into a third party company which then transferred the money into the casinos of his choice. He spent around 18 months doing this. Sometimes winning big and other times losing. He eventually lost $1 million in one night at Caesars.

The day after he was arrested by Canadian authorities and pled guilty to embezzlement, which he served two and half years in prison. CIBM filed a federal lawsuit in 1982 against Caesars for encouraging Brian Molony to gamble and enticing him with free hotel rooms and private jet rides between Las Vegas and Atlantic City while being aware he was using money he obtained fraudulently. The two parties settled the sum out of court, but Caesars was forced to shut down for an entire day by the Division of Gambling Enforcement. Brian Molony is now a business consultant and says he no longer gambles.

Patrik Antonius

Celebrity Gamblers

The Finnish heads-up sensation, also known as Patrik Antonius, became famous for winning the largest pot in online poker history; a whopping $1,356,946 against Viktor Blom in November 2009.

Patrik was born in Finland in a town outside of Helsinki. At the early age of 12, he started playing poker with his friends and by 18, he entered his first No Limit Texas Hold’ em tournament. He won.

Poker quickly became his bread and butter. He was playing in some of the biggest poker tournaments around the world and placing high in the rankings. He continues to play in tournaments around the world, coaches and mentors while also being a frequent face at various online high stakes poker matches. Patrik is estimated to be worth between six to seven million dollars and is considered to be one of the top players in the poker community.

Alan Woods

Celebrity Gamblers

At the time of his death in 2008 Alan Woods was said to be one of the top three gamblers in the world. Alan is most famous for using mathematics to gamble, eventually writing programs which allowed computers to analyze track data, weather conditions, riders, horses’ previous wins and losses as well as, many other things he kept secret.

Some consider Alan Woods to be the father of computer betting because he helped to develop various programs to predict outcomes. These were so accurate that over a given period of time, it made him the most successful gambler in horse racing history. In the 1980’s he met Bill Benter. Both men had been using mathematics to win at blackjack in the local casino. Together, they started a gambling syndicate that would become notorious worldwide.

It is estimated at the time of his death he was worth over 650 million Australian Dollars. One of the most interesting things about Alan was he did it all from his computer. Rarely did he attend an actual race. Ultimately, play big and play smart is the legacy he left behind.