How The Biggest Gamblers Became Rich

By Dumb Little Man

January 10, 2024

Casino culture has a term for non-professional big-time gamblers who spend shocking amounts of money at the tables. These are known as high rollers or whales. These fabulously wealthy players are some of the biggest gamblers in the world but whose fortunes were made with different kinds of wagers.

For these kinds of gamblers, casinos will bend over backward to welcome them in, offering them VIP exclusivity and instant, million-dollar credit lines. You’ll usually find whales around a blackjack, baccarat, or poker table, a roulette wheel, or even a craps table. These games tend to offer a lower house edge, which is why you’ll hardly ever see one near a slot machine.

But these high rollers didn’t make their millions (or billions) inside of a casino or even gambling online. Let’s look at a few of the biggest (and most fearless) gamblers out there that brought their fortunes to the gaming tables.

Akio Kashiwagi

With a reported income of a hundred million dollars a year and a billion dollars in assets, Akio Kashiwagi was a Japanese real estate investor who made a name for himself both in the global real estate market and with his astronomical bets in Atlantic City and Las Vegas.

Akio Kashiwagi was one of the biggest gamblers of the last few decades, even having a character based on him in the movie Casino (K.K. Ichikawa played by Nobu Matsuhisa). His favorite game was baccarat, sometimes betting more than $100,000 on a single hand.

Terrance Watanabe

terrance watanabe

Some high-rolling gamblers didn’t make their money at all. Some of them inherited it. Let’s take a look at Terrance Watanabe, an American businessman who acquired his father’s company, the Oriental Trading Company, in 1977.

In 2000, Watanabe sold his entire share of the company to a private firm and resigned as president and CEO. He had made millions in his family business and planned to enjoy it. He was known for living a lavish lifestyle and wagering millions on bets at the casino.

On one of his most notorious gambling excursions, Watanabe reportedly lost $127 million in 2009 alone, securing him the record for the biggest losing streak in Las Vegas history. Currently entangled in a lawsuit with Harrah’s over $14 million, Watanabe claims the casino kept him overly intoxicated with booze and pills to keep him gambling (and losing millions).

Fouad al-Zayat

A super-secretive, Syrian businessman, Fouad al-Zayat was the founder of many companies, including Mortimer Off-Shore Services Ltd. His wealth sprang from the oil industry in the Middle East and he used it to diversify into many organizations.

Fouad al-Zayat was a high-roller in London’s Mayfair club, Aspinall’s, wagering £91.5 million and losing £23.2 million ($37.5 million) over a 12 year period. He was ordered to pay £2 million to the casino but somehow won his appeal and escaped prosecution, claiming the credit line he received was unlawful under the Gaming Act.

Kerry Packer

kerry packer

Perhaps the biggest whale of them all, Kerry Packer was an Australian media tycoon, considered by many to be one of Australia’s most powerful media proprietors of the last century.

Packer’s father’s media company (the Packer Empire) owned a controlling interest in both the Australian Consolidated Press and the Nine Network, both of which were later consolidated into Publishing and Broadcasting Limited (PBL). Also known outside Australia for founding World Series Cricket, at the time of his death in 2005, Kerry Packer had a net worth of roughly $6.5 billion.

Playing big and losing big were part of Packer’s business life and personal life. In his free time, he routinely gambled in both Vegas and the UK, placing astronomical bets of hundreds of thousands of dollars on one hand of blackjack. He would also reportedly leave casino waitresses 7-figure tips when his luck was good.

In 1999, his luck turned bad and Packer went on a 3-week losing streak, losing approximately $27 million in bets spread across four roulette tables. Packer still holds the record for the biggest reported gambling loss in British history.

Play big, lose bigger

Yes, people have won some very large jackpots playing at an online casino, but those winnings pale in comparison to the wealth of the biggest gamblers. These are very rare people, usually only making the news when they lose big. These prominent gamblers are both a blessing and a curse for casinos, bringing in massive amounts of money, but usually dogged by lawsuits and scandals.

The biggest whales are also the highest risk-takers, not afraid to lose millions on a roll of the dice or a hand of cards. With a keen intuition that brought them massive success in the business world, it’s not hard to see how that savvy would translate to the gaming table too.

Dumb Little Man

At Dumb Little Man, we strive to provide quality content with accuracy for our readers. We bring you the most up-to-date news and our articles are fact-checked before publishing.

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