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Famous Gamblers in US History

Who are the Greatest of Them All? 

If you’re a history buff who would like to know who the most famous gamblers in US history are, stay with us in this blog post to find out who these interesting and amazing characters were. We start off with Archie Karas, the Greek gambler who ran away from home at the age of 15 and move on to Nick the Greek. We cover John ‘Doc’ Holiday and Wild Bill from the 1800s. This post isn’t only about famous men, however, and we’ve found some interesting female figures such as the American Pie actress, Shannon Elizabeth, singer Gladys Knight, and of course the most infamous casino cheat, Ida Summers. It was not easy to find reliable source of information about famous US gamblers, luckily we took our cue from that has dedicated section on this topic

Archie Karas

Archie Karas, or Anagyros Karabournitoris was just 15 when he came to America from Greece on a ship working as a waiter. He then found work at a restaurant in Los Angeles. He is known as a legend in gambling circles, both winning and losing huge fortunes several times. He is considered to be the greatest gambler of all time.  “He is most famous for his incredible winning streak between 1992 and 1995, when he turned $50 into more than $40 million. This is the both the longest and the largest winning streak ever to be documented. Karas went on to lose the lot throughout 1995. Even before that run he had won and lost millions. ” As a teenager moving to the US, he worked at a restaurant that was near a pool hall and after improving his skills, he started to make money by winning games. He then started to play poker, building a bankroll of $2 million over time. He lost this amount by December 1992, leaving him with just $50. At this point, he moved to Las Vegas where he sought a “change in fortunes.” This is where his incredible luck started. He began gambling as soon as he arrived in Las Vegas and this is where he built his initial payroll. Poker was his game of choice.

It was in Vegas where he won fortunes playing pool and poker. Although he beat some of the best players at the time, “soon his action dried up” leading him to move on to the dice tables where he won even more. By 1995, his fortune had built up to $40 million although he lost it all in the space of several weeks by playing dice, baccarat, and poker. Thus far, he has had a series of winning and losing streaks, although none as large as his $40 million loss. He once said:

“I’ve gambled more money than anyone in the history of the planet.
What most gamblers make in their whole life, I gamble in one roll of the dice. Unless the casinos decide to raise their limits after I’m gone, I don’t think anyone will ever gamble more than I have. I’m the biggest ever.”

In September 2013, he was arrested on suspicion of cheating at blackjack at Barona Casino in eastern San Diego where he had won $6000. He had allegedly marked his cards with dye from a hollowed-out chip. The police found the chips in his home confirming their allegations. He pleaded guilty to the charges and was sentenced to three years of probation. In addition, he had to pay $6800 in fines. At present, he lives in Las Vegas where he still plays high stakes poker games and competes in the World Series of Poker (WSOP), where he has had some success. In total, he has cashed in at the WSOP for a total of seven times with his biggest accomplishment being coming into fifth place with $53,783.

Nick Dandolus

An immigrant to America from Greece, Nick Dandolos also earned himself a reputation for gambling, with sources saying that he went from rags to riches several dozen times. Nicknamed ‘Nick the Greek’. he was also known as the ‘King of Gamblers’. Born in 1883, Nick had wealthy parents who sent him to the US as a young man where he first settled in Chicago. He lived off a generous allowance from his family. Soon after moving to Chicago, he decided to move to Montreal where he began gambling on horse racing, forming a partnership with a jockey although they later parted ways after suspicions were raised about their professional relationship and the cash they won together. Although he saw some success at horse racing, on his return to Chicago, he lost everything playing card and dice games. Soon thereafter, he found out what made the games tick and he continued to play poker and gamble. A well-rounded gambler, Dandolus “excelled at betting on horses and playing poker throughout the early to mid-1900s.” For his many accomplishments, he was inducted into the Poker Hall of Fame in 1979, nearly 13 years after he passed away. He was also known for his generous contributions to charitable organisations. Regarding gambling, he was quoted as saying:

“I play for the risk, not for the money. A trout fisherman fishes for sport, not for meat. This attitude creates mystery in the mind of the opposition. Nobody wants to put a mystery out of action. They want to see how it comes out.”

Dandolos travelled all over America, visiting every casino along the way. He played in cities in Illinois, New Orleans, New York, and, Nevada. “The first time Nick experienced Las Vegas, he was overwhelmed by all the choices he had when it came to gambling facilities. Everywhere he gambled, he made sure he first studied the odds and probabilities of winning in that casino according to their house edge and other contributing factors.” Although he was successful at the tables, luck wasn’t always on his side. He had some runnings-in with the mafia where he called on a mafia friend of his to settle a score where he thought he was being cheated and wanted his money back. He also allegedly gave Albert Einstein a tour of Vegas and also gave tips on how to play poker to the famous scientist and Nobel Prize-winner, Richard Feynman. Several books have been published about Nick the Greek. He is well-known for his charitable donations and financial assistance to people in need.

Brian Molony

Some gamblers become famous for the wrong reasons and Brian Molony is one of them. He was known as a compulsive gambler who had poor gambling habits. “He misappropriated company funds of over $10 million to fund his frequent casino trips to Atlantic City, losing the majority of the money very quickly. His theft was exposed in April 1982 and he was placed under arrest. Molony had lost close to $1 million at Caesars just a day before the arrest which landed him a sentence of two and a half years’ prison time.” The book by the name of Stung was written about him and his gambling exploits. A movie, ‘
Owning Mahowny’ was also developed about his story. Some sources described him as follows:

“Molony wasn’t really interested in money and what it can buy. He was interested in accumulating infinite amounts of money, so that he could keep playing. That was his sustenance. The more money he made, the more he could lose,”

“During his prime, he was betting up to $75,000 a hand and winning millions of dollars almost every weekend through playing anything from craps to poker. He even dabbled in sports betting, waging $500,000 on the winning team of the Superbowl, and successfully doubling his money overnight. He spent his money almost as quickly as he had earned it, by taking expensive trips to Las Vegas in less than two years.” Soon thereafter, his gambling addiction grew, and he started to exploit his position at work and the company’s weaknesses, embezzling thousands and eventually millions from it. However, he continued to gamble despite some serious losses. For instance, in 1982 he lost $1 million at a craps table in Ceasar’s Casino & Resort in Atlantic City. It was around this time that the Canadian Imperial Bank of Commerce discovered what he had been doing and soon thereafter had him arrested. Moloney pleaded guilty to the embezzlement charges and he was sentenced to six years in jail. It was also compulsory for him to attend gambling addiction counselling sessions. He was released early from prison based on good behaviour. Today, he is a motivational speaker for those struggling to address gambling addiction. He is married with three children and lives in Pickering, Ontario.  His story has inspired books and a movie, where Philip Seymor Hoffman played the lead representing Molony in 2003.

Titanic Thompson

Alvin Clarence Thomas, more popularly known as Titanic Thompson, “could easily be considered the best hustler in the 20th century.” He was known for striking bets that he was expected to win and became famous for winning various kinds of “proposition bets that he devised himself.” In addition to this, he was very skilled at playing cards and “was not averse to cheating to win money.” He was great at hustling people out of all their money by placing bets on the outcomes of card games, golf tournaments, and horse races. He was famous for betting on absolutely anything, “often fixing bets to ensure himself a win.” He became famous for winning millions of dollars in his lifetime by travelling throughout the country and betting against anyone who crossed his path.

He was born in 1892 in Missouri but as his father was a compulsive gambler, his mother soon divorced him to later marry a hog farmer. With his new family of several step-siblings, Thomson dropped out of school and would be considered illiterate by today’s standards. He was known for developing hustling strategies from a young age. He was good with checkers and dominoes until he “found a strong natural ability when it came to poker.” He later moved out of his family’s home as he found he could no longer live under their strict, Christian rules. “He hustled people at each town he stopped at, slowly but surely building up a bankroll to be proud of. He fished and hunted for his meals while on the road until he had enough money to eat solely at restaurants.”

As for how he earned his name, it was in 1912 when the Titanic sunk killing over 1500 people. At that time, Thompson decided to stop at Snow Clark’s pool hall in Joplin, Missouri. Here, he won the huge amount for that time period of $500 and jumped over a pool table where he won an additional $200. The owner of the pool hall said that his name should be Titanic because he “sinks everybody.” He was later drafted to go to the military whereafter, upon his discharge, he had made $50,000 over a period of eight years. As a free man leaving the army, he decided to travel across the country where he would make bets with absolutely anyone who crossed his path and designing the bets in such a way that he would win. “Titanic generally won every bet he placed, but he did have a weakness when it came to betting on horses, where he generally lost millions of dollars in just one night. He also lost over one million dollars to Minnesota Fats after a long night of playing pool for high wagers.” He was also known for killing five people during his lifetime. In his late 30s, he became an avid golf player who would hustle rich country club members out of their money. On average, he hustled over $30,000 from players in a week, sometimes making $15,000 bets at a time. A book has been dedicated to his life. He died aged 82 in 1974 penniless and allegedly, without any friends.

Wild Bill Hickok

Born in 1837 in Ilinois,
James Butler Hickok or Wild Bill, is known as a hero of the American Old West. He had several careers including that of a lawman, a gunfighter, and a gambler. He was one of the most famous gamblers from this era and his game of choice was poker. In fact, it was about 100 years after his death that his name was inducted into the Poker Hall of Fame. He was only 39 when he was killed by a shot from behind in the back of the head in a saloon. It is believed that the many who show Wild Bill, Jack McCall, had a grudge against him for having lost money to him previously. At the time that he was shot, he was holding a pair – aces and eights – and to this day, this hand is known by poker players as “the dead man’s hand.” During his lifetime, he was a jack of all trades taking on responsibilities of a farmer, a train conductor, a spy in the military, and the Marshal of Abilene. He would often play poker for fun at saloons and he would often win enough money to make that his main means of support. In one instance, he used his winnings to create a show called “The Darling Buffalo Chase of the Plains.” Although the show went to Niagra Falls, his luck didn’t follow him as some of the buffaloes caused serious injuries to some members of the audience.

John ‘Doc’ Holliday

Born in 1851 in Griffin, Georgia,, John ‘Doc’ Holliday was a famous gambler from the American Old West. Professionally, he was a dentist and a gunfighter. “While his gambling exploits are a big part of his legend, he is probably best known for his friendship with Wyatt Earp and the fact that he took part in the famed Gunfight at the OK Corral. Holliday’s life has remained of great interest and he is considered a hero of the time.” “John ‘Doc’ Holliday is a Western cowboy who was a successful poker player that not only had beaten the odds in cards games but in the myriad of gunfights he participated in as well. John was an excellent poker player, as he had learned how to play at a very young age and had developed his skills over the years through hours of practice at nearby saloons. He accomplished many things during his short life, passing away from Tuberculosis at age thirty-six. He was a fearless man with many interesting qualities and some would even say he changed the way the West dealt with gamblers and gunfighters.”

The Denver Republican Newspaper wrote the following after his death:

“Few men have been better known to a certain class of sporting people, and few men of his character had more friends or stronger companions. He represented a class of men who are disappearing in the new West. He had the reputation of being a bunco man, desperado, and bad-man generally, yet he was a very mild-mannered man, was genial and companionable, and had many excellent qualities.”

As a teenager, he dealt with the death of his mother as a result of tuberculosis and grew up riding horses and learning how to shoot guns. He was also very well educated, learning to read, write, and speak French, Greek, and Latin apart from his other classes. One of the family’s slaves taught John how to play various card games including poker, creating the foundation he needed to become an excellent gambler later on life.  When he was 19, he moved to Philadelphia in Pennsylvania to attend dental school, graduating within the shortest period of time for any graduate recorded. Once he graduated, he returned back to Georgia to start his own private practice. However, after a year he was diagnosed with tuberculosis just like his mother and he decided to head West hoping that the better climate would help him overcome his disease. He opened up a dentist’s practice in southern Texas, where he first developed an interest in gambling. He would visit various saloons to play poker and allegedly, drink heavily. His disease soon started to take over his body, however, getting in the way of his work. He worked as a dentist for four years before he retired. Thereafter, he travelled throughout America, visiting saloons and playing poker. His behaviour started becoming erratic as his disease affected his emotions, making him angry and leading him to take out his anger on those who hustled him. He passed away in November 1887 at only 36 years of age.

Shannon Elizabeth

Men aren’t the only gamblers famous in US history, There are some prominent female names, too, and we’ll start off with Shannon Elizabeth, who played a starring role in the American Pie series. Apart from acting, she has started to make a name for herself in poker circles.  The actress has established her table presence in a number of celebrity tournaments. Born in 1973 in Texas, she now has around 35 movie titles under her belt. But where did her gambling hobby kick in? Initially, she started playing poker at a young age with her family but was later introduced to Texas Hold’em, which she didn’t like. She didn’t “warm up” to this game until she befriended some poker professionals who included Antonio Esfandiari and Phil Laak, together with actress Jennifer Tilly. With the first two as her guides, she started participating in poker tournaments with a more serious intent. For instance, she appeared in Celebrity Poker Showdown and in Calvin Klein’s 2nd Annual Celebrity Poker Tournament, where she notched a sixth-place finish. “In 2005, Elizabeth entered the Main Event at the World Series of Poker, where, under the guidance of Daniel Negreanu, she survived the first day of competition and barely missed landing in the money.”

“Following a number of successful finishes in early 2006, including a sixth-place finish at the W Las Vegas Poker Invitational, and her win at the Nicky Hilton New Year’s Eve Poker Tournament, Elizabeth publically admitted she was addicted to poker …. Shortly after her admission, Elizabeth scored her first cash in a World Series of Poker event, finishing 201st in a $1,000 No-Limit Hold’em event, and followed up with two more cashes during the final days of the WSOP.” During the 2006 WSOP, Elizabeth competed as the newest representative of Full Tilt Poker.

According to sources, “Elizabeth has also found a way to bring her dual careers together. In 2006 she starred in the Burt Reynolds movie Deal, about an ex-gambler who returns to the World Series, where he must face his hot-shot protégé at the final table; and, in 2007, The Grand, an improvisational poker-themed comedy featuring Jason Alexander, Woody Harrelson and Doyle Brunson.”

Gladys Knight

Gladys Knight is famous for her lovely voice and this American singer has also been affected by the luring temptation that is gambling. However, her situation was not a happy story like some of the other individuals we have discussed above. Instead, hers was a sad tale of addiction. As the
story is told, a friend of hers invited her to play blackjack at a casino and this is where she became hooked. She enjoyed the experience so much that she forgot to send her son to school one day. This was her wake-up call and she immediately called Gamblers Anonymous who sent someone over to help her right away. Her losses amounted to $45.000 A slightly tragic story with a happy ending.

Ida Summers

Operating in casinos in Las Vegas in the late 1960s and early 70s, Ida Summers is possibly the most famous US female casino cheat in history.  
Sources indicate that she was placed in Casino Placard’s Casino Cheats Hall of Fame and was rated six on ListVerse’s Top 10 Casino Cheats. It is surprising to hear that a woman was able to beat the system, but she did so nonetheless. Let’s talk about some of her cheating strategies. First, she used her looks to flirt with dealers to get her decks of cards she wanted to take home to “practice with”. However, what she did was pull off very risky hustling techniques. One of these was called hand-mucking, which involves bringing one or two of your own cards into play at the table. Obviously, these cards have to match the dealer’s cards exactly and she used flirtation to get decks of cards from the dealers. She would then discreetly bring these cards into play whenever they would be useful. Sometimes, she would hide these cards in her sleeves and then secretly swap them with another card in her hand in order to reach 21 in blackjack. She earned thousands of dollars this way, moving on from one casino in Vegas to the next. Her next and much bolder technique entailed using ‘coolers’ as a method of cheating. Coolers also known as ‘cold decks’ were blackjack shoes filled with prearranged cards that “were equipped to flawlessly beat the house.” This was a risky move as she had to find a shoe that matched the casino shoe perfectly and then physically switch the original shoe with her own within seconds without being seen by anyone. She recruited several men to help her bring in and switch the coolers and it is assumed that one of these men gave her up to the authorities as she was later arrested. Although she should have spent several years in prison for her crimes, she received probation instead, while some of her male accomplices received several years’ worth of jail time. ‘Breaking Vegas’ was a show that aired in 2004 and 2005 on The History Channel and it centred on the criminals who managed to cheat the casinos of Las Vegas out of millions of dollars. One of the last episodes they featured was called Vegas Vixen, which was based on Ida Summers.

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