The 10 Wildest Gambling Losses Of All Time

These high rollers weren’t exactly heading to the nickel slots. From blowing through millions in minutes to committing crimes to keep up their gambling addiction, here are the 10 biggest casino “whales” in history.

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Robert Maxwell
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Robert Maxwell ($2.25 million)
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In less than three minutes, the former media tycoon blew through more than $2 million by playing three different roulette wheels at Les Ambassadeurs casino in London. To make matters worse, there was no income to repay his debt as his successful publishing company went out of business several years later. He reportedly owed several million dollars, due to pension fraud, at the time of his death. 

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Jimmy White
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Jimmy White ($3.15 million)
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The snooker player admitted to losing more than $3 million gambling, mainly on horse racing and blackjack, in addition to spending over $300,000 on drugs. He likened his crack cocaine addiction to “sucking the devil’s dick” and also suffered from severe alcohol abuse. “Cocaine is a mental drug,” he said in his autobiography, Second Wind. “Unlike heroin and drink, your body does not need it. It is only your mind telling you to have it.”

After losing the World Championship Finals in 1994, he admitted to spending his nearly $200,000 runner-up prize within 24 hours. “I was compulsive," he admitted. “In one day it would be dogs, then horses, then cards, then casinos. I'd play in more exhibitions to cover the gambling debts but then I'd be stuck in the middle of nowhere and I'd drink because there was nothing else to do. I stopped [gambling] because I went skint. At least a few times.” Although he still plays poker for fun, White said that he no longer gambles.

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Akio Kashiwagi
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Akio Kashiwagi ($10 million)
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The sole principal of a real estate and investment business, Kashiwagi reportedly made $100 million per year and gambled money away just as quickly as he earned it. During a gambling session at the Trump Plaza Hotel and Casino in Atlantic City, he reportedly made a deal in 1990 to bet $12 million. But after blowing through $10 million, he reportedly left the casino with $2 million and claimed that they hadn’t held to their end of the deal. 

In January 1992, he was brutally stabbed 150 times with a Samurai sword. His body was found in his home in Japan on Mount Fuji, but the murder case remains unsolved. He still owed casinos millions of dollars at the time of his death. 

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Maureen O’Connor
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Maureen O’Connor ($13 million)
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The former mayor of San Diego and widow of the founder of fast-food chain Jack in the Box, O’Connor gambled $1 billion on video poker games throughout the 2000s. She ended up in the red by $13 million, sparking her decision to steal $2 million from the charity set up by her late husband in 2008-2009 to help cover the gambling losses. The foundation ultimately folded in 2009 due to her misuse of the funds.

Although she faced 10 years behind bars during her trial in early 2013, the court agreed to defer prosecution for two years and would drop all charges if she made restitution, received treatment for her gambling addiction and stayed out of trouble. Her lawyer Eugene Iredale blamed a brain tumor for her poor judgment, while a tearful O’Connor promised to pay back the city. 

 "This is a sad day for the city of San Diego," said Assistant U.S. Atty. Phillip Halpern. "Maureen O'Connor was born and raised in this town. She rose from humble origins...She dedicated much of her life, personal and professional, to improving this city." 

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Harry Kakavas
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Harry Kakavas ($20.5 million)
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The Australian real estate salesman spent nearly $1.5 billion at Melbourne Crown Casino between June 2005 and August 2006, primarily on games of baccarat. During one gambling spree in May 2006, he reportedly spent $164 million in less than six hours and even served a brief jail sentence after stealing $286,000 to keep up his habit.

He sued the casino to try and clear some of his debts, claiming they exploited his gambling addiction and even enticed him to gamble by giving him use of the casino’s private jet. But in June 2013, the High Court ruled that Kakavas was not taken advantage of. Chief Justice Robert French acknowledged his gambling addiction, but said Kakavas was a “successful businessman entirely capable of making decisions in his own interest.” 

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Archie Karas
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Archie Karas ($40 million)
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The world famous gambler and poker player owns the longest-documented winning streak in gambling history—starting with $50 and eventually racking up $40 million in 1992. But rather than quit while he was far ahead, he kept gambling and blew through all the money by 1995. He was arrested in Las Vegas in September 2013 and stood trial last May after being accused of marking cards at a blackjack table in a San Diego casino.

Although he faced three years in prison on charges of burglary, winning by fraudulent means and cheating, the judge sentenced him to three years of probation after he pleaded guilty to one count of felony burglary. Karas also had a previous misdemeanor conviction for burglary in Nevada, which stemmed from his gambling and cheating.

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Kerry Packer
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Kerry Packer ($42.6 million)
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Packer was both known as Australia’s richest man and wildest gambler. He blew through $42 million in less than a year between September 1999 and August 2000, including losing more than $21 million during a three-day baccarat-filled weekend in Las Vegas. He also racked up the largest gambling loss in British history after blowing through $17 million during a three-week gambling binge on blackjack at Crockford’s casino in London. But with a net worth of $4.6 billion at the time of his wild losing streak, his losses amounted to a drop in the bucket for his bank account. 

Packer has also had success at the tables, winning $21 million playing cards at the MGM Grand Casino in Las Vegas, and is widely regarded as one of the top card players in the world of high-roller gambling.

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Omar Siddiqui
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Omar Siddiqui ($65 million)
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A highly successful vice president of merchandising and operations for an electronics company, Siddiqui has had far less luck at gambling. He reportedly blew through $65 million by recklessly betting as much as $150,000 per hand at blackjack, spending $162 million over three years at the MGM Grand Casino and Sands Casino in Las Vegas.

However, his biggest issues came when he attempted a “secret kickback scheme” to defraud his employer, Fry’s Electronic, out of $87 million to pay his Vegas gambling debts. He stood trial in 2008 and accepted a plea, ultimately being sentenced in 2011 to six years in prison on fraud charges. 

Although Siddiqui’s attorney tried to explain that his client’s gambling addiction was the cause of his actions, U.S. District Court Judge Jeremy Fogel didn’t buy it. “Their addiction might explain why they did it, but they should never be excused for what they did,” he said. “It's the person, not the addiction, that does the deed."

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Zhenli Ye Gon
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Zhenli Ye Gon ($125 million)
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Between 2004 and 2007, Gon blew through $85 million at The Venetian in Las Vegas and $40 million at several other nearby casinos. Although he could afford it after making $350 million over the course of three years as the CEO of United Pharm Chem, he was also funneling a portion of his methamphetamine imports to the Sinaloa Cartel in Mexico. Mexican drug agents and American DEA officials raided his Mexico City home in 2007, where they made the largest drug-cash seizure of all time when they discovered $207 million sitting on the floor in U.S. hundred dollar bills. 

In August 2014, Gon was found guilty of organized crime, synthetic drug production and activities involving the use of illegal funds. He was sentenced to 25 years in prison as the leader of the operation. 

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Terry Watanabe
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Terry Watanabe ($204 million)
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The Nebraska-born businessman, whose father founded plastic trinket business Oriental Trading Company, reportedly blew through nine figures in just a single year. It was originally reported in 2007 that he had lost $127 million that year, but a 2010 review of casino records determined that he had blown through $204 million. His wild gambling mainly took place at Caesar’s Palace and The Rio in Las Vegas. He was so prolific that it actually attracted tourists from many miles away. Harrah’s Entertainment, Inc., reported that 5.6% of its gambling revenue that year came solely from Watanabe. 

Watanabe paid $112 million back to Harrah’s, but refused to pay the rest and claimed that the casinos bore some responsibility for his losses. Several former Harrah’s employees claim they were ordered to let him keep gambling even though he was visibly intoxicated, a clear violation of state law, while Watanabe alleged that the casino also plied him with pain medication.

However, he was also charged with four counts of intent to fraud and faced 28 years in prison. Harrah’s claimed they extended Watanabe $14.7 million as credit and he gambled it away. However, criminal charges were dropped after a confidential deal was made between both sides in July 2010. 

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