The biggest gamblers in history

Legendary high rollers like Archie Karas and Edward Thorp didn’t just bet big—they challenged the system and changed the game. Their stories inspire awe, but they also remind us of the fine line between passion and obsession. Today, with gambling more accessible than ever, it’s crucial to strike a balance. Modern players can learn from the past while maintaining their health and well-being. Whether it’s knowing when to walk away or integrating mindful habits, find your balance between online casinos and a healthy lifestyle.

Many gamblers who got involved in gambling became famous for many different reasons. Some of the names you will see us presenting to you managed to make huge profits, while in the case of others, the opposite happened. Movies have been made and books have been written about these individuals, while surely thousands of others involved in gambling have studied their techniques in an attempt to achieve similar success. It is important to mention that there are two people of Greek descent on this list. Let's take a closer look at some things from their lives and the particular case of each of them:

John Montagu

John Montagu. In his spare time he was very much involved in gambling. He had the title of the fourth Earl of Sandwich. It is said that after hours of gambling, Montagu often asked for a meat snack between two pieces of bread. Montagu's acquaintances noticed that this happened quite often and began to make the "same order as the sandwich". Eventually the snack became known as a "sandwich" and the name has stuck to this day. 

Brian Molony

Brian Molony became known for all the wrong reasons. His name often appeared in the headlines for embezzlement and misappropriation of money he made in order to play his favorite gambling games. He managed to embezzle over $10 million from companies he worked for to make his trips to Atlantic City, losing most of that money in record time. He was arrested in April 1982, the day after he had lost a million dollars at the casino. A movie (Owning Mahowny) has been made about Molony and a book has been written about his life story.

Wild Bill Hickok

Known to most as Wild Bill he was a lawman and a big gambler. He was a famous figure of the American Wild West with a favorite game being poker, at which he was a very good player. In 1876 Wild Bill was in his favorite saloon playing poker with his back to the door. Jack McCall shot him in the head and this was probably because he had lost a lot of money to Wild Bill. At the time of his death, he was holding two pairs of eights and aces. Today this particular "hand" in poker terminology, which you will find in the best online casinos, is called the "dead man's hand".

Kerry Packer

This is an Australian tycoon who loves gambling. He died in 2005 at the age of 68 and his gambling activity was mainly related to horse racing. We are talking about the man who has placed the biggest bets on horse racing in the world. He always bet at the highest possible limits, which led to him losing millions. There are so many stories and legends about Packer. One of them states that at one point he showed up in Las Vegas to gamble. When he arrived at the hotel some staff member had lost the key to his room and to avoid disappointing the good customer, he used a crystal ashtray to break the lock. The story is indicative of the level of respect and power he had in the casinos. It is said that he would slowly call the casinos and ask how much money they had in their safe so he could bet accordingly.

Archie Karas

Greek-born Archie Karas is one of the most famous gamblers of all time. Over the course of his career he won and lost huge amounts of money many times. The son of immigrants from Greece to America, he left home at the age of 15 and worked as a waiter in restaurants etc. From an early age he started gambling by playing poker. Within a short time he managed to accumulate two million dollars, while in December 1992 he had only 50 dollars in his pocket. He went to Las Vegas to chase his fortune and became known for his huge winning streak from 1992 to 1995, when with $50 he managed to win a total of $40 million. This is the longest winning streak ever officially recorded. He then lost all his money playing baccarat, poker and craps. Although he had some winning streaks afterwards, they were never as successful. Today he lives in Las Vegas.

From daring high rollers to legendary risk-takers, the world’s most famous gamblers have shaped how we view casino culture today. Their stories, filled with fortune and risk, highlight the excitement of betting big. But while personalities make headlines, the games themselves are what bring the action to life. Curious which ones draw the most attention? Find out which casino games are most popular and why they’ve stood the test of time among casual players and pros alike.

Nikos Dandolos

Nikos Dandolos was born in Greece and acquired the nickname Nick the Greek. He is considered the king of gambling. He was born in 1883 and came from a wealthy family. He travelled to America and settled in Chicago, where he lived on his parents' allowance. He then settled in Montreal and began to play in horse racing. He won very large sums of money, but when he returned to Chicago he lost all his money playing dice and card games. He managed to recover his lost money and won even more money. Nick, who among other things was very superstitious, one day he was filthy rich and the next day he didn't have a dollar in his pocket. This happened many, many times.