Three Of A Kind: A Trio Of The Highest High Rollers

Posted on September 9, 2016

[toc]When you’re having a casual $5 bet on roulette at Bet365 Casino, have you ever played at a communal table and marveled at the high rollers betting $500 or more each spin?

There’s always a bigger fish, and we’re all a bit jealous that we don’t have that kind of money to splash around.

Well, try these guys out for size: there’s gambling, and then there’s gambling.

3. Nick “Nick The Greek” Dandolos

The story of Nick The Greek isn’t a typical rags to riches one, but rather a riches to rags to riches to rags tale.

Nick Dandolos was born in Crete to wealthy parents and moved to the USA at the age of 18 after attending school. His grandfather gave him an allowance of $150 per week – mind you, this was 1901, so that’s somewhere in the region of $4,000 today.

Dandolos quickly became known for gambling, winning and losing vast sums of money. He won over $500,000 on horse racing before losing it all on card and dice games.

He soon became a master of these games, however; he claimed the secret was not playing the tables, but knowing the table odds and betting against others who have superstitious beliefs about the outcome.

Famously, he played a marathon heads-up poker match against Johnny Moss in a game that would inspire the World Series of Poker. The game was set up by Benny Binion, lasted for five months and covered essentially every poker variant that existed.

It ended with Dandolos, down somewhere around $3 million ($30 million today), uttering the infamous sentence, “Mr Moss, I have to let you go.”

Dandolos claimed to have gone from rags to riches and back over 73 times and donated over $20 million ($159 million adjusted for inflation) to education and charity. Near the end of his life, he was broke and playing $5 draw poker games in California.

2. Andy Beal

Andy Beal was a self-made billionaire when he became infamous in the gambling world, particularly the world of poker. A real estate mogul and founder of Beal Bank, he is currently worth around $7.6 billion (as of Q1 2016).

As well as being a savvy investor and entrepreneur, Beal is a number theorist and in mathematics is known for the Beal Conjecture. It was this interest in mathematics that led him to the world of Limit Hold’em, at the time the most popular poker variant in the world, in the early 2000s.

Between 2001 and 2004, Beal participated in high-stakes poker games against the world’s best professional players. Beal wanted to beat the best in the world, and one of his tactics was to raise the stakes beyond anything the pros had played before.

While “The Big Game” at the Bellagio would play with betting limits of $4,000/$8,000, Beal insisted on playing stakes as high as $100,000/$200,000. This forced the pros to pool their bankrolls in a team known as “The Corporation” to take on Beal.

With the stakes and the mathematics on his side, Beal wanted to negate his opponents’ reading abilities and practiced betting in the same fashion each time, using the same mannerisms. He even had a buzzer installed in his shoe that would vibrate every six seconds, only acting on a decision he had made when it buzzed, so as to randomise the timing of his bets.

Beal won approximately $13.6 million from the pros in a three-day heads-up marathon, before losing $16.6 million to Phil Ivey later that month. Beal has occasionally played high stakes poker since, and there’s little arguing that he’s one of the world’s best Limit Hold’em players.

He now is advising Donald Trump’s presidential campagain.

1. Archie Karas

Anargyros Karabourniotis went by Archie Karas in the US, much to the relief of every non-Greek who had to say his name. He has often been compared to Nick The Greek, and Karas himself claims to have gambled with more money than anyone else in history. It’s a claim that’s tough to argue with.

You’ve got to understand something. Money means nothing to me. I don’t value it. I’ve had all the material things I could ever want. Everything. The things I want, money can’t buy: health, freedom, love, happiness. I don’t care about money, so I have no fear.
– Archie Karas

Karas is best-known for the largest and longest documented winning streak in the history of gambling, known in the industry as simply “The Run” – Karas turned $50 into $40 million within the span of three years, only to lose it all again.

He began by driving to Vegas with $50 in his wallet. After making $10,000 he began playing pool with a fellow gambler for $10,000 a game, winning several hundred thousand before raising the stakes and winning $1.2 million. He then played the same man in poker to win another $3 million.

Three months in, he had turned his $50 into $7 million and sat down at the poker tables with $5 million of that in front of him. He bested Stu Ungar and Chip Reese, two of the world’s best players, for over $3 million. He then turned to dice, betting $100,000 per roll.

By the end of his streak, he was up over $40 million – at one point, he held every single $5,000 chip in Binion’s Casino.  However, in just three weeks, he had lost it all: $11 million to dice, $2 million to Chip Reece and $17 million in baccarat.

Karas currently resides in Las Vegas and continues to gamble today, though he has been added to Nevada’s infamous “Black Book.”

Image credit: Kobby Dagan /

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Matt Perry

A veteran of the online gambling industry, Matt Perry has worn a number of hats since he first began working in online poker and iGaming in 2007. He currently writes for a variety of publications focused on legal online gambling, and in the past has served as an editor, copywriter, content manager and reporter.

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