The Biggest Gamblers In History

Nick “the Greek” Dandolos – The Gentleman Gambler

Born in Crete in 1883, Nick Dandolos, better known as Nick the Greek, became one of the most famous gamblers of the 20th century.

His Legacy

·     He claimed to have won and lost over $500 million in his lifetime (in today’s money).

·     Dandolos was renowned for his generosity, often giving away winnings to strangers or charities.

·     He was involved in one of history's most famous poker marathons, a five-month-long heads-up game against Johnny Moss in Las Vegas, organised by casino mogul Benny Binion.

His Style

Dandolos wasn’t just about money; he embodied the idea of a gentleman gambler. Well-dressed, charming, and philosophical, he once remarked after losing millions: “Mr. Moss, I have to let you go.”

Verdict: Nick the Greek set the template for the modern gambling legend, rich in stories and winnings.

‍

Archie Karas – The Man Who Won (and Lost) It All

Few stories are as dramatic as that of Archie Karas, a Greek-American gambler who turned up in Las Vegas in 1992 with just $50 in hispocket.

The Run

·     Karas went on a legendary streak over the next three years, turning $50 into $40 million.

·     He beat some of the best poker players in the world, dominated pool hustlers, and crushed casino games.

The Fall

·     Just as spectacularly, Karas lost it all. Within a few years, his fortune had evaporated.

·     Arrests for casino cheating later in life further tarnished his reputation.

Verdict: Archie Karas epitomises “easy come, easy go.” His run remains the most famous hot streak in gambling history.

‍

Kerry Packer – Australia’s Billionaire High-Roller

Australian media tycoon Kerry Packer wasn’t just wealthy; he was fearless at the tables. Casinos loved and feared him in equal measure.

The Wins

·     In 1990, Packer reportedly won £7 million in one night at a London casino.

·     He once walked away from Las Vegas with $20–40 million in winnings.

The Losses

·     He could also lose just as spectacularly, sometimes dropping $20 million in a single session.

·     He once famously tipped a group of dealers $1 million after a winning streak.

The Legend

·     Packer was notorious for his wit. When a Texan oilman bragged about being worth $60 million, Packer replied: “I’ll flip you for it.”

Verdict: Kerry Packer takes the crown as the ultimate high-roller, a man who treated millions like pocket change.

‍

Stu Ungar – The Tragic Genius

Stu Ungar is widely regarded as one of the most talented card players who ever lived.

Achievements

·     Won the World Series of Poker Main Event three times (1980, 1981, 1997).

·     Also a gin rummy prodigy, he was feared across the country for his brilliance.

The Downfall

·     Despite winning an estimated $30 million in his lifetime, Ungar’s demons, drugs and reckless gambling left him broke.

·     He died in 1998 in a cheap Vegas motel with just $800 to his name.

Verdict: Ungar remains a tragic legend, proof that genius at the tables doesn’t guarantee a happy ending.