Greatest High Rollers In Gambling History

Greatest High Rollers In Gambling History

Whales, high-rollers, and big-spenders – there is something that grabs your attention about someone throwing millions at a casino. Casinos have depended on people with high net worth to keep the lights on and entertain all who visit them. 

You might be surprised to learn that the stories of the well-dressed man who doubles his net worth by playing blackjack are real. This article will highlight the most iconic and famous casino whales.

1 – Phil Ivey

Phil Ivey is one of the most renowned poker players of all time. It is not uncommon for Phil to be seen at a table at a casino. Lvey can be seen in the poker room and elsewhere, playing for a large fortune. Ivey often places wagers of up to $200k at the Roulette table.

Phil was later accused of cheating and faced a legal battle. Phil ultimately lost his small fortune. It’s impossible to determine the exact amount Ivey has won and lost at casinos around the globe. Phil is treated like royalty in every casino that he visits.

2 – Amarillo Slim

Amarillo Slim was a man with a larger-than-life persona. Amarillo Slim was a man of extraordinary strength. Amarillo Slim was a frequent guest on The Tonight Show, Starring Johnny Carson. He used the platform for bragging. He was a big high roller.

Slim was proud to boast about defeating champions and presidents. Amarillo Slim, however, seemed to get the most pleasure from taking down other high rollers with cleverly designed prop bets.

Amarillo often reported these wagers as being in the six-figures range. Amarillo Slim is still a well-known poker legend. Amarillo Slim’s cowboy style and ability to self-promote ensured that his legend would continue in gambling lore.

3 – The Sultan Of Brunei

It is not surprising to see one of the world’s most famous high rollers among the wealthiest men — especially when that man loves gambling as much as the Sultan. The Sultan is well-known for his crazy car collection.

He is well-known for his habit of gambling up to $1,000,000 per day. Luxurious Las Vegas casinos in gambling circles. It takes the pain out of losing money if your net worth exceeds $30 billion. This would be similar to having $30,000 but losing $1.

It’s unlikely that you are losing sleep over it. The Sultan isn’t worse for the wear, we are sure. However, we cannot help but wonder if the $1 million in casino would have been better spent on someone with significantly less.

Greatest High Rollers In Gambling History

4 – Sir Charles

Charles Barkley is one of the most important names in America today. Charles Barkley, a former NBA All-Star who was also a member of the original Dream Team, is the gift that keeps giving. He is one of the biggest high rollers of all time.

On the NBA on TNT, he is currently seated opposite Shaq, who we consider to be one of the funniest men on TV. Barkley’s hilarious antics, wild predictions, and outlandish jokes are unmatched.

Sir Charles has a 30:1 odds of a large payday if the wager pays. It’s not difficult to see why he is one of the most famous high rollers.

5 – Archie Karas

Many Vegas insiders immediately think of famous gamblers when they think about Vegas. Karas owned one of the most powerful heaters ever made. He started with just $50 and turned it into more than $40 million. 

He was able to knock the top poker players around the world off their feet like school children. He eased them all of their chips, one after the other. Johnny Chan, the master himself, was his only loss. Karas’ long streak came to an abrupt halt, as many others have done. Lady Luck was blind, and Karas lost it all.

Karas was last seen as he was being added to the Nevada Black Book. This prohibited him from gambling in the state. Karas was also on probation for cheating for several years. He was the greatest high roller of all time.

6 – Kerry Packer

An Australian billionaire has been known to bet almost $500k on one hand of blackjack. Packer is a wealthy gambler who loves action, he is one of the biggest high rollers. 

Even if it’s small, it’s still action. He once bet over $25 million at multiple roulette tables simultaneously. Packer isn’t afraid to take care of the casino staff. After a casino visit, Packer is known for leaving waitresses with million-dollar tips.

7 – Fouad al-Zayat

A gambler’s reputation will be built by adding drama or danger to the mix. Fouad Al-Zayat spent the majority of his career and his gambling career away from the spotlight. The businessman isn’t looking for a huge welcome package during his gambling sessions. He is one of the greatest high rollers of all time.

Fouad was required to pay $3 million to a London gambling house. Fouad had lost over $35 million in ten years of gambling. Al-Zayat could pay off the debt and made a vow never to gamble again in a London casino. Being a billionaire allows you to choose from a wide range of locations.

8- Terrance Watanabe

However, not all whales go to the casino. Sometimes it’s the exact opposite. Terrance Watanabe is an example of such a man. Watanabe, a wealthy American businessman, is well-known as one of the biggest whalers in Las Vegas.

Watanabe’s net worth of $150 million was only half, and he lost the majority of his fortune at Las Vegas casinos. He was involved in a long-running legal battle with Harrah’s Casino for nearly $15 million in losses. Watanabe refused payment.

Watanabe claimed the casino deliberately kept him drunk while gambling and even gave him pain pills to prolong his session. Both sides settled, and Watanabe seems to have greatly reduced his gambling habits. Watanabe is one of the most famous high rollers in history, despite his long losing streak.


It’s fascinating to learn about the lives of super-rich people. This is made all the more fascinating when you consider that these wealthy people have wagered incredible fortunes at felt tables worldwide.

While most people won’t reach these heights, it is proof that even a small amount of money can make you a millionaire if you are lucky enough.

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Name: Greatest High Rollers In Gambling History

Posted On: 16/09/2021

Author: Tony Willets

Greatest High Rollers In Gambling History
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