A Journey Through History’s Most Famous Gamblers

Gambling has been around for thousands of years, with the earliest six-sided dice dating to about 3000 BCE in Mesopotamia. Over time, this activity has become even more popular, and today, it is a favored hobby or, in some cases, even a profession for many people, including many famous gamblers.

The allure of gambling comes from the fact that this one single activity combines various elements, including risk, skill, luck, psychology, and more. This article will explore the most famous gamblers in the history of the world, so stay tuned to learn about them and what qualities and achievements made them stand out.

Article contents:

• A Journey Through History’s Most Famous Gamblers
  • The Early Icons of Gambling
    • “Wild Bill” Hickok – The Dead Man Hand OG
    • Nick “The Greek” Dandolos – A Tale of Fortune and Philosophy
    • Titanic Thompson – The Man Who Bet on Everything
  • Modern Masters of the Casino
    • Edward Thorp – The Father of Card Counting
    • Doyle Brunson – The Godfather of Poker
    • Phil Ivey – The Tiger Woods of Poker
  • Women Who Shaped Gambling
    • Lottie Deno – The Poker Queen of the Wild West
    • Vanessa Selbst – Breaking Barriers in Professional Poker
    • Judy Bayley – The First Lady of Gambling
  • Conclusion: The Timeless Fascination with Gambling Legends
  • References

The Early Icons of Gambling

If I should start anywhere, let’s do it from the very beginning with the early icons of gambling. In this section, I’ll discuss famous gamblers from the 19th century. Following in-depth research, our experts have highlighted three particular names – “Wild Bill” Hickok, Nick “The Greek” Dandolos, and Titanic Thompson.

“Wild Bill” Hickok – The Dead Man Hand OG

James Butler Hickok, better known as “Wild Bill” Hickok, was born on May 27, 1837, in Deadwood, Dakota Territory. He was many things, including an avid gambler. More particularly, Hickok liked to play poker, and one early August night in 1876, he was enjoying a game or two at Nuttal & Mann’s saloon (later renamed “No. 10 Saloon”).

Another man playing there at the same time was Jack McCall – heavily drunk and enduring loss after loss. When confronted by Hickok to cover his losses and quit playing for the night, McCall agreed and even accepted some money for breakfast, but that was not the end for the two gamblers.

The following day, “Wild Bill” Hickok was playing poker again when McCall appeared out of nowhere, drew his revolver, and shot and killed Hickok. At the time of his death, Hickok was holding two pairs – black aces and black eights – a combination that became known as the “dead man’s hand”^[1].

Nick “The Greek” Dandolos – A Tale of Fortune and Philosophy

Nick “The Greek” was born in Rethymno, Crete, on April 27, 1883, as Nikolaos Andreas Dandolos. Although he earned a degree in philosophy from the Greek Evangelical College, his career path took quite a turn, and he became one of the famous professional gamblers. Famously, Dandolos played a heads-up poker match against one of the all-time best poker players, Johnny Moss, from January 1949 to May 1949.

Dandolos may have ended up losing between $2-4 million, but the 5-month game arranged by Benny Binion is believed to have been responsible for the inspiration behind the World Series of Poker^[2]. It is estimated that Nick “The Greek” has won and lost over $500 million over the years. He is also known to have continued to play right until the end of his life in 1966.

Titanic Thompson – The Man Who Bet on Everything

Alvin Clarence Thomas was born on November 30, 1893, in Monett, Missouri. He was a hustler and gambler who has also allegedly killed 5 men throughout his life and has been married to 5 different women. He was willing to bet on anything, including weird and nearly impossible things like throwing a large room key into its lock.

You might be wondering why he was called Titanic. Well, according to the story^[3], he was playing pool and won $500 against a man called Snow Clark. He then proceeded to bet $200 that he could jump across the pool table without touching it and actually managed to do that. When someone in the room asked about his name, Clark said “It must be Titanic, he sinks everybody.”, and so the name stuck.

Modern Masters of the Casino

Now that I’ve covered some of the early gambling legends, let’s move on to a few famous gamblers from more recent history. First, there is Edward Thorp, the mathematician behind blackjack card counting. Then there’s Doyle Brunson, who was called the Godfather of poker, and Phil Ivey – the Tiger Woods of Poker.

Edward Thorp – The Father of Card Counting

Edward Thorp is the American mathematician behind the card counting strategy^[4], which proved that the house edge in blackjack could be overcome. He tested his theory in practice at casinos in Las Vegas, Reno, and Lake Tahoe, and it ended up with him winning $11,000 in one weekend.

In 1964, he released his book Beat the Dealer: A Winning Strategy for the Game of Twenty-One, and in 1990, Villa Crespo Software published Thorp’s Real Blackjack video game, in which the mathematics professor guides you into becoming a better blackjack player.

Doyle Brunson – The Godfather of Poker

Doyle Brunson was a professional poker player for 50 years. Known as the Godfather of poker, he was the first to win $1 million in poker tournaments. Over the years, Brunson has won ten World Series of Poker bracelets and was inducted into the Poker Hall of Fame. He is also among the very few players to have won the Main Event at the World Series of Poker more than once – in 1976 and 1977.

Phil Ivey – The Tiger Woods of Poker

Phillip Dennis Ivey Jr. is among the most famous professional gamblers in the world. In 2017, he was elected to the Poker Hall of Fame, having won ten World Series of Poker bracelets and one World Poker Tour title at the tender age of 40. Phil Ivey is also known as “No Home Jerome”, “The Phenom”, and the “Tiger Wood of Poker”. As per the data from different sources, Ivey’s net worth amounts to $100 million^[5].

Women Who Shaped Gambling

Our article about the most famous gamblers in history won’t be complete without the following three women who have helped define and shape the industry as we know it. These are Lottie Deno, Vanessa Selbst, and Judy Bayley, and they deserve to be in a category of themselves. Every one of them has left a lasting mark in the minds and hearts of true gambling aficionados.

Lottie Deno – The Poker Queen of the Wild West

Carlotta J. Thompkins, more commonly known as Lottie Deno, was born on April 21, 1844, in Kentucky, US. Her father was a well-known gambler, and it is believed that it was actually he who taught her about the tricks of poker. According to different sources, Lottie Deno was the best poker player in the Southwest in the 1800s, and she went down in history as one of the most famous female gamblers.

Vanessa Selbst – Breaking Barriers in Professional Poker

Vanessa Selbst was born on July 9, 1984, in New York and graduated from Yale University with a degree in political science. Selbst made history by becoming the first woman to win three World Series of Poker bracelets in open-field events. She retired in 2018 with her total live poker tournament winnings at the time amounting to over $11 million.

Judy Bayley – The First Lady of Gambling

Following the death of her late husband and owner of the Hacienda Hotel and Casino on the Las Vegas Strip, Warren “Doc” Bayley, Judy Bayley became the first woman to own a gambling establishment of such magnitude. She may not have been a famous gambler, but she went down in history as the “First Lady of Gambling”. She was so popular that they named a theatre in her name shortly after her death of cancer in 1956.

Conclusion: The Timeless Fascination with Gambling Legends

The famous gamblers discussed so far are only a small fraction of the dozens of players who’ve made history one way or another. I haven’t even begun to mention names like Archie Karas, Stu Ungar, or the notorious MIT Blackjack Team. If the topic interests you and you want to learn more, I recommend you stay tuned and follow the articles on our website.

References

1. Dead man’s hand, Wikipedia, Retrieved January 30, 2024
2. Duckworth, Tim, (December 15, 2023), 2024 WSOP Dates Announced for May 28 to July 17, PokerGO Tour Official Website, Retrieved January 30, 2024
3. Kindred, Dave, (June 19, 2020), Golf’s killer gambler: The legend of Titanic Thompson, Golf Digest, Retrieved January 30, 2024
4. Davies, Rob, and Lock, Simon, (November 15, 2023), How To Count Cards in Blackjack and Bring Down the House, Blackjack Apprenticeship, Retrieved January 30, 2024
5. Phil Ivey Net Worth, Celebrity Net Worth, Retrieved January 30, 2024