10 of the Most Notorious High Rollers on Record

Casinos value every dollar, I mean, customer that walks through their doors. They lavish patrons with everything from free meals to free stays and even trips.

However, another level of service and attention is reserved for the rare and highly sought-after whale. These high rollers are greeted with luxury from the moment they board their private jet (many times provided by the casino) until they check out of their luxurious VIP suite.

Let’s get to know 10 of the most notorious high rollers on record.

1 – Phil Ivey

Phil Ivey is one of the greatest poker players of all time. So, not many people would be surprised to see Phil at a casino table.

Still, the poker room isn’t the only place you’ll see Ivey playing for a sizable fortune. Ivey regularly makes wagers as large as $200k at the roulette table.

Ivey once won nearly $10 million in an Atlantic City casino playing baccarat. He followed that massive payday with another when he won $11 million at a London casino.

Unfortunately, Phil was accused of cheating, and a legal battle ensued. Ultimately, Phil lost out on his small fortune.

However, it’s impossible to know the exact figure that Ivey has won or lost in casinos around the world. One thing is for sure, Phil gets the VIP treatment in almost any casino he steps foot into.

2 – Amarillo Slim

Amarillo Slim had an almost larger-than-life persona. And that’s mostly because Amarillo himself went to great lengths, making sure the world knew of his antics.

Amarillo Slim was a regular on the Tonight Show Starring Johnny Carson. He used the platform to boast about his outrageous winning ways.

Slim would brag about beating presidents and champions alike. However, Amarillo Slim seemed to take the most joy from destroying other high rollers in cleverly constructed prop bets.

Amarillo himself regularly reported these wagers to be in the six-figure range. Still, Amarillo Slim is most notorious for being one of the early poker greats.

Amarillo Slim’s cowboy style and a knack for self-promotion ensured that his legend would live on in gambling lore for the ages.

3 – The Sultan of Brunei

It’s probably no surprise to find one of the richest men on the planet among the most notorious high rollers on record — especially if that man loves to gamble as much as the Sultan of Brunei, the Sultan is notorious for his insane car collection in automobile circles.

He is notorious for dropping up to $1 million a day gambling in luxurious Las Vegas casinos in gambling circles.

Of course, when your net worth is over $30 billion, it takes some of the sting away. That would be like having $30,000 and losing $1.

You’re probably not losing any sleep over it. I’m sure the Sultan isn’t any worse for the wear. Still, I can’t help but wonder if maybe that $1 million would be better off in the hands of those with significantly less money than the casinos.

4 – “Sir Charles”

Charles Barkley is one of the most significant characters we have in America today. The former NBA All-Star and member of the original Dream Team is the gift that keeps on giving.

He currently sits opposite Shaq, whom I consider one of the funniest men on television, on the NBA on TNT. Barkley is continuously going over the top with his hilarious antics and wild predictions.

Barkley recently signed a multi-year endorsement deal with Fan Duel. On the NBA’s opening night, Barkley placed a very public, yet highly unofficial, wager.

During the live broadcast, Barkley yelled through the TV for Fan Duel to place a $100k bet on a team to make the NBA Finals.

At 30:1, Sir Charles is set for a hefty payday if the bet pays. 


Barkley has had a very public battle with problem gambling, but he seems to be winning the fight for now. There’s no disputing that he’s one of the most notorious high rollers out there.

5 – Archie Karas

When many Vegas insiders think of notorious gamblers, they instantly go to Archie Karas. Karas had one of the giant heaters of all time.

The crafty poker player started his run with only $50 and turned that into over $40 million. He was knocking the best poker players in the world off like they were school children.

He smoothly relieved them of their chips one after another. His only loss came from the master himself, Johnny Chan.


Karas’ long streak ended as so many have before. Lady Luck turned a blind eye, and Karas lost it all.

The last we saw of Karas, he was being added to the Nevada Black Book, which barred him from any gambling activities in the state. Karas also served several years probation for cheating.

6 – Kerry Packer

Kerry Packer is a whale’s whale. The Australian billionaire is known to regularly bet nearly $500k on a single hand of blackjack.

The wealthy gambler loves action, and if it’s not huge, it’s not action for Packer. He once laid over $25 million on several roulette tables simultaneously.

He lost every bet and the entire $25 million. That’s only enough money for any of us to live out the rest of our lives exceptionally comfortably and have enough left that the kids fight about it for years.

Packer doesn’t forget to take care of the casino staff. He’s known for leaving million-dollar tips for waitresses after a casino stay.

7 – Fouad al-Zayat

An element of danger or drama goes a long way into building a gambler’s notoriety.

Fouad al-Zayat has spent most of his professional and gambling career staying out of the media spotlight. The wealthy businessman doesn’t want any massive welcome wagon during his gambling sessions.

Fouad was ordered to pay over $3 million to a London casino. He had reportedly lost north of $35 million over a decade of gambling.

Fortunately, for al-Zayat, he could slip the debt, and he made a firm resolution to never gamble in a London casino again. 

I suppose being a billionaire gives you basically unlimited choices on where you do your casino gambling. 

8 – Mo Chan

Mo Chan is almost mythical in the way he magically appeared, seemingly out of nowhere. He then disappeared just as quickly, but much heavier in the wallet.

Chan burst onto the gambling radar after fleecing an Australian casino for over $10 million. That’s a tremendous amount, but it’s much easier to get to if you’re betting $500k per hand on baccarat.

Eventually the casinos caught onto Mo’s winning ways and limited his wagers. After all, they can’t regularly have millions walking out the door.

Chan vanished when he was no longer able to play for his incredibly high stakes.

I like to think that Chan is still out there, raking up massive wins in the online casinos. Hopefully, the story doesn’t end with merely disappearing, but it’s pretty cool either way.

9 – Adnan Khashoggi

Adnan Khashoggi could easily be a character in a blockbuster action film. The Saudi businessman made his fortune as an international arms dealer.

In the early 1980s, his net worth had topped $4 billion. This was great for Adnan but not so great for the casinos.

Khashoggi was as apt to casino gambling as he was dealing weapons to heads of state. He was also equally motivated to make a profit on the casino floor.

Khashoggi would wager millions in the high roller lounge, and he reportedly won quite a bit. One particular hot streak by Khashoggi was so monumental that the casino stock he preferred dropped by 20% over the same period.

Adnan seemed to beat the casino at their own game. In the end, he solidified himself as one of the most notorious high rollers on record.

10 – Terrance Watanabe

Of course, not all whales take the casino to the cleaners; sometimes, it’s quite the opposite.

Such is the case of Terrance Watanabe. Watanabe is a wealthy American businessman that was well known as one of the largest whales in Las Vegas.

Watanabe is most famous for having one of the most substantial losing streaks of all-time. Watanabe lost over $125 million at the tables in 2009.

Despite his $150 million net worth, Watanabe lost most of his fortune in Las Vegas casinos.

He spent years embroiled in a nasty legal battle with Harrah’s Casino over nearly $15 million in losses that Watanabe refused to pay. 

Watanabe claimed that the casino purposefully kept him intoxicated while gambling and went so far as to provide pain pills to prolong his session.

The two sides eventually settled, and it seems Watanabe has largely curbed his casino gambling. Either way, the massive losing streak Watanabe went on makes him one of the most notorious high rollers in history.

Conclusion

From the promising to the outrageous, high rollers come in as many different varieties as jelly beans. Some can’t seem to lose, and others appear to win at everything they do.

It is surprising to learn so many of the 10 most notorious high rollers on record have had trouble paying their bills. You know what they say, “More money, more problems.”