The most interesting high rollers in gambling history

The most interesting high rollers in gambling history

In the long run, it’s the players that make a profit for the casinos. However, every once in a while there comes a big player that wipes the slate clean and wins big. These are known in the industry as whales or big fish players.

Players like this become legends in the gambling world and stories are told about their success. They are often professional gamblers that make their living by getting into tournaments and gambling for large sums of money. Here are a few stories about these types of players, that those who are new to the gambling world can aspire to.

Akiro Kashiwagi

Akiro Kashiwagi is a mysterious figure outside of his gambling success. He’s a Japanese high roller, and a  tycoon, and the rumor goes that he has ties to the Yakuza, the Japanese mafia.  Kashiwagi also served as an inspiration for the character of K.K. Ichikawa in De Niro’s film Casino.

Kashiwagi is known for playing baccarat and blackjack. Baccarat is one of the most popular games amongst high rollers both in Japan and in the West. Kashiwagi usually plays for about $200.000 per hand. Games such as these had led him to owe about $12.000.000 to different casinos.

One of such epic games took place in a casino owned by former president Trump. Kashiwagi won $2.000.000 in two days, but end up losing far more because he kept playing at the instance of Trump himself. Kashiwagi was brutally murdered in 1992 and the killer was never caught.

Phil Ivey

Phil Ivey is known as one of the best poker players in history and some would argue that he was the best player ever. Ivey did a lot on fostering his own legend and was known for flying in his private jet, visiting one casino after another, and playing $100.000 a hand in every one.

One of the strange things about Ivey’s strategy is the ease with which he gives up on a game. He was known for giving up and leaving the table after a few lost hands. Ivey would return a day or two later once he was sure his luck would change.

Ivey was involved in a scandal after winning $12.000.000 at a London game of baccarat.  He was caught cheating with a help of his girlfriend and ended up in court about it. They were refused their winnings but claimed they haven’t counted cards or cheated.

Terence Watanabe

Watanabe was born a millionaire since he inherited a multi-million-dollar family business in Nebraska. At first, he was known in the gambling world, not for his winning but for the amounts he’s able to lose. Watanabe wasn’t very good but he kept playing and losing millions in the process.

Some assess that Watanabe lost between 200 and 300 million in about five years. In 2007 he lived in Vegas and lost as much as 120 million in that year alone. This strange approach to the game became widely known and casinos were very happy to accommodate Watanabe with suits in which he lived while gambling.

It was said that Watanabe played drunk, that he took great risks and played in an amateurish way. After a while, he took on debt and casinos started to refuse him since he wasn’t able to repay them.

Don Johnson

John earned his claim to fame when he won $15.000.000 by beating three casinos in Atlantic City in three days’ time. What was especially interesting about these winnigs was that they were clean and simple and that the casinos did all they could to attract high rollers such as Johnson.

This lead to giving Don Johnson a celebrity status and allowed him to negotiate with the casinos about the rules of the games he played in. Johnson changed the difference between the minimal and maximal bet and thus made the game more advantageous for him, and other players. He also set up a 10 percent cashback agreement with the casinos.

After these wins, the casinos closed their doors to Johnson since the odds now started to change slightly in his favor. However, he’s still remembered as a man who beat Atlantic City.

Archie Karas


Karas is probably the most well-known professional gambler of all time. He’s known as a man who started playing with $50 and end up with $40.000.000 at the end of the longest winning streak in history. Karas was an immigrant from Greece. He worked on a cruise ship and learned to play poker on his own.

He become known in LA for winning and losing as much as $2.000.000 in a matter of few days. With this kind of reputation, Karas moved to Vegas and started making a name for himself there as well. There he played poker, blackjack, craps, and many other games, usually winning in most of them.

After just three years in Vegas, Karas won $40.000.000 and tend to bet about $100.000 per hand. However, he lost just as quickly as he won and in just a few years, he hit rock bottom and played poker for $2 per hand.

The world of gambling is exciting and it attracts great personalities. It’s often a story about winning big and losing everything in a short period of time since high-end gamblers are attracted to risk and games with high stakes in which luck can turn on you just like that.






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