Famous Gamblers From History & Today

Throughout time there have been many gamblers who have become famous. For one reason or another, they have captured the attention of the masses and written their places in history. Some have been big winners, while some have been big losers. Some have gained fame through their cheating exploits, while others are known hustlers. Several professional gamblers, especially poker players, have made it into the public eye.

The stories surrounding such individuals are often fascinating. Indeed, many of them have had books written about them or even films made about them. Some of these books and movies glamorize the life of a gambler, while others show the depths of despair that gambling can lead to. Some do both.

Either way, they’re typically very entertaining for anyone with an interest in gambling. You can find information on some of the best gambling books and movies on this site, on the following pages.

In this part of our site, we look at the most famous gamblers ever to have walked the planet. Below you will find details of some of the greatest gambling legends of all time. We’ve not provided an exhaustive list by any means, we have just picked out a few of our favorites and the ones that we find the most interesting.

We’ve then provided information on more famous gamblers in a range of different categories.

Gambling Legends

Archie Karas

Archie Karas, a Greek-American is quite simply a legend in gambling circles. He has won and lost huge fortunes several times over and is considered by many to be the greatest gambler of all time. It could of course be argued that a truly great gambler would have held on to his fortunes, but there is little doubt that Karas has earned his reputation.

He is most famous for his incredible winning streak between 1992 and 1995 when he turned $50 into more than $40 million. This is 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.

Born in Greece, Karas ran away from home aged just 15. He came to America after working on as a waiter on a ship and found work at a restaurant in Los Angeles. The restaurant was next to a pool hall and after working on his skills he started to make money through winning money games. As the number of opponents willing to play him dwindled, he started playing poker.

Archie Karas picked up the game of poker easily, and soon became a skilled player.

Karas built his bankroll up to above $2 million over time. However, by December 1992 he had lost it all bar $50. At this point, he headed for Las Vegas seeking a change in fortunes, and it was there that his amazing run started. He started gambling as soon as got to Vegas and built an initial bankroll playing poker.

He then won fortunes playing pool and even more poker. He beat some of the very best players of the time and soon his action dried up. Karas turned to the dice tables and won even more. By early 1995 he had built up a fortune of $40 million. In the space of just a few weeks, he lost it all by playing dice, baccarat, and poker.

Since then Karas has had a number of other winning and losing streaks. Although these streaks would be considered amazing to most gamblers, he has never quite done anything on the scale of his biggest run. He still lives in Las Vegas today.

Nick Dandolos

Like Archie Karas, Nick Dandolos was born in Greece. This led to his nickname, Nick the Greek, although he was also known as the King of Gamblers. He was born in 1883 to wealthy parents and he was sent to the USA as a young man by his grandfather. Dandolos first settled in Chicago, where he lived off a generous allowance from his family.

He later moved to Montreal, which is where he began gambling on horse racing. He was successful at horse racing betting and won significant sums, but he then went back to Chicago and lost everything playing card and dice games. He soon got the hang of them though and continued to gamble and play poker. Throughout his life, Dandalos continually won and then lost and he said that he went from rags to riches and back again dozens of times.

John Montagu

British statesman John Montagu was the 4th Earl of Sandwich and lived during the 18th century. He had roles in the military and in politics, and he was also a keen gambler. He deserves a mention in this list not specifically for his gambling exploits but rather because he was the man who invented the sandwich. That is certainly the legend anyway.

The story is that, during his lengthy gambling sessions, Montagu often asked to be brought slices of meat between two slices of bread. This habit of his was noticed by his gambling buddies and others began to order “the same as Sandwich”. Eventually, the snack became known as the sandwich and the name has stuck since.

Kerry Packer

Kerry Packer was a media mogul from Australia and a legendary gambler. He died in 2005, aged 68, and will be remembered for many reasons. He was a successful and wealthy businessman and also founded World Series Cricket. For many, though, it is his gambling exploits that will live long in the memory.

Kerry Packer High Roller

Packer often made large horse racing bets in addition to his casino gambling exploits in Vegas and other parts of the world. He would typically gamble for the highest stakes available and multi-million dollar losing sessions were not uncommon. He had his fair share of big wins too though. Unlike many other high-rollers, Packer had an excellent reputation for settling his markers in a timely fashion.

Brian Molony

Infamous rather than famous, Brian Molony is a compulsive gambler whose gambling habits hit the headlines. Molony embezzled over $10 million from his employers (Canadian Imperial Bank of Commerce) in order to fund his regular trips to the casinos in Atlantic City. His theft was uncovered and he was arrested in April 1982. Just the day before his arrest he had lost around $1 million at Caesars Casino.

Molony spent around two and a half years in prison for his crimes. A book, Stung, was written about his exploits and his story was also the basis for the movie Owning Mahowny.

Titanic Thompson

Titanic Thompson, real name Alvin Clarence Thomas, could perhaps be better described as a hustler than a gambler as he generally struck bets that he expected to win. He was famous for winning all kinds of different proposition bets that he devised himself. He was also a very skilled card player and not averse to cheating to win money. He died in 1974 aged 81 and will definitely go down in history as one of the most famous gamblers of all time.

Wild Bill Hickok

James Butler Hickok, better known as Wild Bill, was something of a hero of the American Old West. He was a lawman, a gunfighter, and a gambler. He is one of a number of famous gamblers from that era, arguably the most famous of all. Poker was his game of choice and he has been inducted into the Poker Hall of Fame.

In 1876, aged 39, Hickok was playing poker at a saloon bar with his back to the door. It turned out to be the wrong seat as he was shot in the back of the head by a man named Jack McCall. It is not known for sure why McCall killed Hickok although it is believed that he may have held a grudge having lost money to him previously.

At the time that Hickok was shot, he was holding two pairs – aces and eights. To this day that hand is known by poker players as the dead man’s hand.

John “Doc” Holliday

John “Doc” Holliday was another famous gambler from the American Old West. He was also 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.

King Henry VIII

Henry VIII is remembered as one of the most famous English kings and a significant historical figure. He has a legendary reputation for lavish gambling and betting too. He was known to enjoy betting on all kinds of things, particularly dice and card games. It is rumored that he even once lost the bells to St. Paul’s Church in a bet.

More Famous Gamblers

Famous Big Winners

Ever wondered about the lucky few who win life-changing amounts of money when gambling? You can find out their stories in our section on famous big winners. Here’s a selection of some of the people covered.

  • Gloria McKenzie
  • Elmer Sherwin
  • Charlie Wells
  • Colin & Chris Weir
  • Cynthia Jay-Brennan
  • Don Johnson

Famous Casino Cheats

Experienced casino players will know that the house edge is impossible to overcome without the ability to count cards (and even with that ability it’s very challenging). Some gamblers refuse to accept the house advantage though, and resort to cheating. You read about some of the most famous cheats, including those listed here, in the section linked below.

  • Tommy Glenn Carmichael
  • Richard Marcus
  • Ida Summers
  • Monique Laurent
  • Dennis Nikrasch
  • Louis Colavecchio

Famous Card Counters

Card counting is not easy, as we alluded to above. It’s possible though, and there have been many players that have managed to beat the casino at blackjack. Our section on famous card counters features some of the most successful and well-known counters, including the following.

  • Standford Wong
  • Keith Taft
  • Ken Uston
  • Edward Thorp
  • Tommy Hyland
  • Four Horsemen

Famous Poker Players

With so much televised poker these days, and plenty of glamor to the game, this is perhaps the best of form of gambling for anyone wanting to make a name for themselves. They’ll need to be good though, as the top players are very skilled and make it to the top for good reason. We’ve covered some of the very best, past and present, in our section on famous poker players. It includes the following players and many more too.

  • Chip Reese
  • Doyle Brunson
  • Tom Dwan
  • Phil Ivey
  • Daniel Negreanu
  • Chris Moneymaker

Annette Obrestad: Female Poker Player from Norway

Not many people can claim their life-long career started when they were only fifteen years old, but that’s exactly how it happened for Annette Obrestad. Having no way to transfer funds to an online poker account, Annette took advantage of freeroll tournaments in order to build up her bankroll to nearly $500,000.

Her career may have started in cyberspace, but it’s certainly not limited in that way anymore. Ever since she was old enough to start entering live tournaments, she took every opportunity she could get her hands on. She has accomplished so much in her young career from being the youngest person to win the WSOPE main event to being deemed number two on Norway’s All Time Money List, having earned nearly $4 million from live tournaments alone.

“I love waking up every day and playing poker. It’s something I really enjoy. It’s not like a job, it doesn’t feel like something I have to do.”~Annette Obrestad

How a Career in Poker Started

On September 18th, 1988 Annette was born in the small fishing town of Sandes, Norway to a middle-class family. When she was quite young, her father taught her how to play a couple different versions of poker: five card draw and seven card stud. It was because of this reason that her parents weren’t overly shocked when she asked to use their credit card so that she could start playing poker over the Internet.

Annette’s mother became very concerned for her daughter. Not only was she afraid Annette would end up spending too much money, but she was worried that Annette would become addicted to gambling as well. Those concerns on top of her mother’s realization that it was illegal for her daughter to play online at such a young age, led her to refuse her daughter’s request.

Annette wanted to respect her mother’s wishes, but she still was passionate about playing poker. So, she continued to play online for free, oftentimes competing in free roll tournaments. It was possible to win a little cash here and there from these tournaments, so she was hoping to build up her bankroll using this method, and that’s exactly what she was able to do. Her username then and her username now remain the same: Annette_15. She chose this username because it was simple, she wanted her name to be known, and because she was only fifteen when her online poker career started.

Her Career Highlights

It took Annette a few years to get on her feet, but once the money started rolling in, she felt like it would never stop. Of course, the kicker was she had to wait until she was eighteen to actually withdraw any of the money from her account. For a while, she watched her bankroll grow and grow, and never told anyone how much she was making. In just a matter of three years, Annette managed to win almost half a million dollars across three of the major online poker sites in the business at that time: Full Tilt Poker, Poker Stars, and UltimateBet.

When she turned eighteen, she dropped out of high school and was ready to start playing poker professionally. Early on, she went down in history as the only poker player who was able to win a $4, 180 contestant sit and go tournament while only peaking at her cards once the entire time. How was she able to do this? She covered the part of her computer screen that displayed the hole cards with a post-it note, and used her skills to read the other players as best she could.

The first live tournament she qualified for was UltimateBet’s Aruba Poker Classic where she earned 37th place and brought home over $12,000. She was discouraged by her early live tournament performances, but we realize now she just needed time to adjust to the differences in competing online versus competing in real life. In an interview with Bluff Magazine, Annette gave advice to those who were in that same transition period.

“If you’re making the move from online to live, it’s important to continue playing your own game, just like you do on the internet. Don’t worry too much about looking for “live tells”; they’re not that much a part of the live game. If you try too hard you’ll just confuse yourself. Sometimes I think I have a tell on a guy and I go with it and I’m totally wrong. It turns out he was actually drinking water because he was thirsty!”

In September 2007, Annette entered the World Series of Poker Europe main event. Not many people had even heard of her before this event, but afterward, her name would never be forgotten. After the first day of this three-day long competition, Annette was already a lead chip holder. This was quite an accomplishment, considering she was up against top performers like Patrik Antonius, Annie Duke, and Gus Hansen.

The last day of the competition, it came down to Annette and a man named John Tabatabai. Although the final round was intense, it was Annette that would land the 1st place finish, bringing home over $2 million dollars. She managed to set two records that day! Not only was she the first female to win the WSOPE, but she was also the youngest person in the event’s history to win as well. In fact, it was only a few days before her nineteenth birthday when she won.

A little over a month later she found herself at the European Poker Tour main event that took place in Dublin, Ireland. Annette performed very well in this competition, placing second right behind Reuben Peters. Second place came with a $400,000 cash prize and the bittersweet taste of defeat. She has competed in the EPT several times since then, but has yet to come as close to winning as she did that first time.

Annette wasn’t allowed to start competing in the World Series of Poker in Las Vegas until her twenty-first birthday. By the time she was of age, people knew who she was and had high expectations of how she would perform. Although she did cash out at four different events that first year, her fans were disappointed that she had failed to win a WSOP gold bracelet. Winning a bracelet won’t be easy, but Annette is far from ready to give up on her dream of bringing one home.

Viktor Blom — Professional Poker Player from Sweden

If the name Viktor Blom doesn’t ring a bell, then maybe you would know him better by his screen name: Isildur1. Viktor spent years playing poker at a variety of different online poker sites, competing against some of the top players in the world without them knowing who he was. Everything changed when he signed a one-year contract with PokerStars; not only did everyone now know who he was, but he started competing in live tournaments for the first time as well. He has made millions of dollars over the course of his career, and we don’t see that changing anytime soon.

“I have never read a book or watched a training video before, ever. I learnt by playing and taking shots at playing the best, and by playing the best you learn to do the things they do, mix it with your own play, and get great more quickly.”~Viktor Blom

Early Exposure to Poker

Viktor was born on September 26th, 1990 in Gothenburg, Sweden. He was the youngest of four children, having two older sisters and an older brother named Sebastian. Viktor and Sebastian started playing poker together when he was only fourteen years old; their game of choice was No Limit Texas Hold’em. Viktor longed for more competition, so he taught his friends how to play. Soon, his love of poker spread throughout his school; many of his classmates were eager to play on school grounds in order to get their hands on a little extra cash.

One lunch period, in particular, twenty-five students gathered around to play. Although some of the students were older than Viktor, he was easily able to defeat all of them before the period ended. Viktor decided to deposit some of the money he had won over the past year into an online poker site. Since he was only fifteen years old at the time, Sebastian had to help him open the account. He first played under the screen name, Blom90.

Viktor’s career would have a series of high and low moments. In the beginning, he only played low limit games for up to fifteen hours a day. Over time he moved on to $500 sit-n-go tournaments that allowed him to build his bankroll up to $275,000. After making too many risky moves, however, he would find himself completely broke. He was greatly discouraged, but he still managed to press on and build his bankroll back up to $50,000, which he would again proceed to lose. Viktor decided that it would be in his best interest to take a break from playing poker for a while so that he could re-evaluate his strategies and see what areas he needed to improve.

When asked in an interview with Bluff Magazine, Viktor admits that he was concerned with how he dealt with bankroll management

“I am always struggling with bankroll management because I take too many shots, but at the same time, these shots are how I end up getting better. I am better than I was in the past, and I am still always trying to improve with managing the roll.”

Back in the Game

When Viktor came back, he was more determined than ever to make a living from playing poker. He moved from Sweden to London, to avoid the high Swedish taxes that were associated with gambling. He opened new accounts at all the major online poker sites, now playing exclusively under the username Isildur1. He later admits that his username is based off of a character in J.R.R. Tolkien’s book, Lord of the Rings.

Viktor wasn’t there to mess around this time but instead started taking on some of the best players in the world including Patrik Antonius, Tom Dwan, Phil Ivey, and Brian Townsend to name a few. His encounter with Tom Dwan was especially eventful as he went up against him for a series of $500/$1000 No Limit Hold’em games at the Full Tilt Poker website which resulted in Viktor being able to add $5 million to his bankroll. He also was able to win $500,000 after defeating Isaac Haxton in a $200/$400 No Limit Hold’em heads up challenge.

Viktor wasn’t always on the winning side of things, however, as he once lost over $4 million dollars in less than five hours after playing against Brian Hastings. Shortly after his defeat, it was released that Brian had acquired private hand history information that illegitimately gave him an upper hand against Viktor. The person who gave him this information, Brian Townsend, was given a one-month suspension from his Red Pro status as punishment for breaching his contract.

Finding Out Who Isildur1 Really Is (Thanks to PokerStars)

Ever since the report came out that Isildur1 had been cheated, players were more eager than ever to find out who this player was. Some people thought it was Robert Flink, while others thought it may be the very talented Phil Hellmuth. Clearly, these people were wrong. Viktor wasn’t planning on revealing his identity until PokerStars called him up and offered him a spot on their team.

“I decided to join Team PokerStars because I felt I needed a new challenge. I wanted to improve my live game. Things had changed and people weren’t willing to play NLHU on the Internet as much as before. I just felt right doing this, and it has always been a dream for me signing with Team PokerStars. They are the best site by far.”

On January 8th, 2011, PokerStars announced that they would be adding a new member to their team: Viktor Blom, also known as Isildur1. Viktor was certainly not the person everyone was expecting him to be. For someone that plays over-aggressively, they didn’t think he would look so harmless. He was skinny, he had no facial hair, and his un-washed blonde hair swooped gently over his eyes. On top of that, he was hardly twenty-one at the time of the big reveal.

Despite his looks, he was still able to earn the respect of his fellow teammates; they enjoyed playing against him and watching his aggressive moves in person. His partnership with Team PokerStars only lasted about a year, but he’s thankful for the time he got to spend with them. It forced him to come out from behind his computer screen and enter some live tournament events that he otherwise wouldn’t have tried.

Coming to the realization that everyone would know who he was at these tournaments was certainly an adjustment for him. He wasn’t in this for the fame, and talking to strangers was never something he was very fond of. Still, he continues to compete in tournaments across Europe and the United States even to this day.

Live Tournament Accomplishments

Viktor Blom has landed three World Series of Poker cash finishes over the course of his career. He took 16th place at the 2010 World Series of Poker Championship event, 151st place in the 2012 No Limit Hold’em Six-Hand event, and 14th place in the 2012 Poker Players Championship. Viktor Blom has also dedicated a good amount of his time to compete at the European Poker Tour. He placed second in two No Limit Texas Hold’em events and is hoping to acquire an EPT title soon.

Although his performances at the WSOP and the European Poker Tour were decent, his greatest live tournament accomplishment occurred at PokerStars’ 2012 Caribbean Adventure that took place in Paradise Island that year. During this competition, he was able to play face to face against other well-known professionals such as Jonathan Duhamel and Daniel Negreanu. Despite the odds being against him, Viktor managed to walk away from the competition with the 1st place prize of over $1.25 million.

Kevin Roberts
Kevin Roberts Administrator

Kevin Roberts, previously published under the pseudonym Noah Davis, is one of the more diverse writers at GamblingSites.com. Like many of his colleagues, he's a huge fan of both football and basketball. But he also writes about box office records, TV show prop bets, DFS, and all kinds of other subjects.

When it comes to the NFL, Kevin's favorite team is the Green Bay Packers. He enjoys cheering them on with his wife and daughter.

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