5 Gamblers Who Blew An Incredible Fortune

People who staked everything on their parents' wealth

What would you do if somebody handed you a fortune on a plate? You might spend it on life experiences, such as traveling the world, or maybe you would invest it for the future – but that's not what these people did.

From a professional gambler who squandered his life savings to a former mayor who gambled as a way of coping with tragedy, read on for the sad stories of five people who inherited unbelievable sums but gambled them all away. All dollar amounts in US dollars unless stated.

Clarissa Dickson Wright: $31.7 million in today's money

One half of the duo who fronted British cookery show Two Fat Ladies, Clarissa Dickson Wright became a household name in the 1990s.

Before embarking on her TV career, however, she managed to burn through a £2.8 million inheritance (equivalent to $31.7m today) in just eight years.  

Clarissa Dickson Wright: $31.7 million in today's money

Dickson Wright inherited the money from her mother, an Australian heiress who died of a heart attack in 1975. When her father Arthur (pictured) also died the following year, she fell into a deep depression and started drinking heavily.

By her own admission, Dickson Wright drank two bottles of gin and four pints of tonic every day for 12 years. And she didn't just battle alcoholism – she was reportedly also a compulsive gambler and spent huge sums on chartering yachts and private jets.  

Clarissa Dickson Wright: $31.7 million in today's money

Dickson Wright originally trained as a barrister and was reportedly the youngest woman ever to qualify, at 21 years old.

But as her lifestyle became increasingly out of control, she was disbarred. By the early 1980s, she was homeless and penniless, her once-impressive fortune just a memory.  

Clarissa Dickson Wright: $31.7 million in today's money

Unlike some of the other people in this round-up though, Dickson Wright managed to turn her fortunes around. 

After going sober, she worked as a cook and was eventually scouted by the BBC to star in Two Fat Ladies, which ran from 1996 to 1999. Famous for her calorific recipes and fiery temper, she died aged 66 in 2014, leaving behind a modest but solvent estate of $43,600.  

Maureen O'Connor: $93 million

Maureen O’Connor served as the first female mayor of San Diego from 1986 to 1992. In 1994, she inherited around $50 million (the equivalent of $93m today) from her husband Robert O. Peterson, who founded the Jack in the Box fast food chain.

Although Peterson was a Republican, he supported O’Connor’s career as a Democrat, and when he died O’Connor struggled to cope emotionally.  

Maureen O'Connor: $93 million

To make matters worse, the death of her husband was followed by the deaths of some close friends. As a coping mechanism, the former mayor turned to “grief gambling” and quickly burned through her inheritance by playing video poker.

Between 2000 and 2008, O’Connor won a whopping $1 billion – but she lost even more. 

Maureen O'Connor: $93 million

O’Connor’s gambling debts were so large that her substantial inheritance couldn’t foot the bill. To make up the shortfall, she began to raid a $2 million charity foundation.

Meanwhile, casinos in San Diego and Las Vegas kept sending her extravagant gifts to keep her coming back. And she did. Speaking to CBS in 2013, O’Connor compared video poker to “electronic heroin”, and described how the habit lost her more than $100,000 in a single day.  

Maureen O'Connor: $93 million

O’Connor has described her life as being split in to two halves. She says it was ‘Maureen 1’ who became mayor of San Diego, while ‘Maureen 2’ was the uncontrollable gambling addict. She now believes a slow-growing brain tumor, diagnosed in 2011, could have contributed to the switch.

O’Connor was charged with money laundering in 2013 and ordered to repay the money she took from the charity foundation. The judgment apparently left her “destitute."

Terrance Watanabe: $272 million

Known as one of the biggest whales (high-spend gamblers) in Las Vegas history, Terrance Watanabe's fortune came via Oriental Trading Company, the party-and-craft-supply business that had been founded by his father Harry.

In 1977, Terrance became the company president. He eventually decided to sell his stake in the business in 2000, resigned as CEO and president, and began to live off the proceeds of the sale. His original plan was to become a philanthropist. However, the major beneficiaries of his multimillion-dollar fortune weren’t foundations and charities... 

Terrance Watanabe: $272 million

Young and filthy rich in Las Vegas, Watanabe soon started frequenting casinos, including Caesar’s Palace, The Rio, Harrah’s, and Wynn Las Vegas.

The ex-CEO was a prolific gambler, staking a total of $825 million in 2007. That same year he lost an estimated $204 million, the equivalent of $272 million today.  

Terrance Watanabe: $272 million

At first, the casinos offered Watanabe expensive gifts and impressive perks to keep him coming back. These included everything from Rolling Stones tickets to $500,000 credit at the gift shop.

The incentives worked: according to the Wall Street Journal, Watanabe was responsible for a staggering 5.6% of Harrah’s Casino gambling revenue in 2007. But the relationship soon went spectacularly downhill.  

Terrance Watanabe: $272 million

In July 2010, Harrah’s took Watanabe to court for failing to pay an outstanding $14.75 million bill (the equivalent of $18.7m today). Two years later, Harrah's parent company, Caesar’s Entertainment, was fined $225,000 by a regulator in New Jersey for allowing Watanabe to gamble while drunk.

In 2017, Watanabe started a GoFundMe page to cover a $100,000 medical bill for the treatment of prostate cancer. The page, which is no longer accepting donations, shows he raised just $28,610.  

Clint Murchison Jr: $1.5 billion

The son of a Texas oil magnate, Clint Murchison Jr inherited $200 million when his father died in 1969. Today, Murchison Jr’s fortune would be worth an incredible $1.5 billion.

But failed investments, excessive spending, and a penchant for gambling drained his bank balance, forcing him to file for bankruptcy less than 20 years later.  

Clint Murchison Jr: $1.5 billion

At first, Murchison Jr began to follow in the footsteps of his father, Clint Sr, who had made his fortune by founding the Southern Union Gas Company.

In the 1950s, Murchison Jr and his brother John were both part of a syndicate that wanted to obtain oil drilling rights in Spain. However, Murchison Jr evidently preferred to follow his passions – namely sport, music, and married women.  

Clint Murchison Jr: $1.5 billion

In 1960, Murchison Jr founded the Dallas Cowboys NFL team. Between 1966 and 1985, the Cowboys enjoyed a record 20 consecutive winning seasons. 

But behind the scenes, Murchison Jr’s career and chaotic personal life weren't quite as successful. A failed pirate radio station and failed marriage both cost him dearly. And although the NFL was funding his lifestyle, it was also his downfall. An article in D Magazine claims Murchison Jr bet “tens of thousands of dollars” on sport, including the NFL, every single week. 

Clint Murchison Jr: $1.5 billion

By the early 1980s, Murchison Jr was in serious debt and his health was failing. To fund treatment for a rare degenerative nerve condition, he was forced to sell the Dallas Cowboys for $60 million, the equivalent of $154 million today. 

Even this wasn’t enough to settle his debts. He owed almost $200 million ($514m in 2021 money) to creditors, including banks in Arkansas, California, and Illinois. Despite selling off all his assets, a significant portion remained unpaid upon his death in 1987. 

Nick Dandolos: $4.3 billion

Known in gambling circles as ‘Nick the Greek,’ Nick Dandolos (pictured second from left) was born in Crete in 1883.

His wealthy family made a fortune selling rugs and when Dandolos was 18, his grandfather sent him to America with an allowance of $150 a week. In 2021, that’s the equivalent of almost $4,500 a week or $234,000 a year – plenty to kickstart a lifelong addiction to gambling.  

Nick Dandolos: $4.3 billion

Dandolos started out in Chicago before moving to Montreal. There, he met a Canadian jockey called Phil Musgrave who introduced him to the world of horse racing.

After winning around $500,000 (the equivalent of over $13m today), Dandolos moved back to Chicago and blew the lot on card and dice games at a casino.  

Nick Dandolos: $4.3 billion

Unperturbed, Dandolos, who was well-educated and had a degree in philosophy, began to study the psychology behind gambling.

His grandfather had hoped that Dandolos would use his allowance to go into business. Instead, he became a professional gambler, attracting crowds of spectators to his card games at American casinos.  

Nick Dandolos: $4.3 billion

Between January and May 1949, Dandolos between $2-$4 million – up to $46 million today – during a poker match with professional player Johnny Moss (pictured far left).

By the 1960s, Dandolos was reportedly almost broke, playing $5 poker games in California for fun. Estimates suggest he lost over $500 million in total before his death in 1966, the equivalent of a whopping $4.3 billion in 2021 money. But Dandolos didn’t waste his entire fortune; he’s also believed to have donated over $20 million to good causes throughout his life.  

Now read about the rich and famous people who refuse to spoil their children