Last updated on June 11th, 2024
From self-made millionaires that started from the bottom to multi-millionaires by inheritance, these are the individuals that are noted for making some of the worst bets in history, with some of our contenders even losing up to hundreds of millions in the process. Being that gambling is a combination of both skill and luck, learning from the mistakes and personal experiences of these unfortunate players can serve us for real educational purposes, being that when it comes to errors, the goal is usually to never repeat them again. Except if you wish to become a member of this inglorious list with the biggest losses in casino history, which we strongly advise against.
So, let’s take a look at the five people who are responsible for some of the biggest losses in the history of casino gambling.
1. Ausaf Umar Siddiqui – $162 Million
We will begin our story with the undisputed king of biggest casino losses, Ausaf Umar Siddiqui, or shortly Omar Siddiqui, who worked as a vice president for the company Fry’s Electronics, located in Silicon Valley, California. Siddiqui is famous for gambling away a staggering amount of more than $162 million dollars in Las Vegas, in the span of just three years. However, while this record number does seem like the highlight of Siddiqui’s journey, it is still not the most shocking part of this story. That has to be the fact that Omar gambled with “borrowed” money, i.e. funds that he embezzled from the company he was working for, Fry’s Electronics, as well as his first employer.
In particular, between 2005 and 2008, Siddiqui took $70.4 million dollars from the company Fry’s Electronics and transferred that amount to the balance of the Las Vegas casino, The Venetian. During this period of three years, Siddiqui lived an ultra-luxury lifestyle in Las Vegas, going as far as to introduce himself as the co-owner of Fry’s Electronics to various people, all in order to avoid raising suspicion by the staff or other guests at the casino. Shortly after the police caught up with him and charged him with embezzlement, it was revealed that Saddiqui gambled away a total of $162 million dollars from the company he worked for.
Today, he still owes a whopping $137 million to both of his former employees. Many believe that Siddiqui actually gambled much more than this amount, however, due to the vast number of individual bets that he played throughout his career, it is impossible to get the exact amount. However, we do know that at the time when the police arrested him, Siddiqui had only $80 on his balance, which consequently means that he is looking forward to a lifetime of repaying a debt that seems impossible to repay.
2. Terrance Watanabe – $127 Million
Unlike Siddiqui who made elaborate plans and took serious risks in order to obtain a substantial amount of gambling money, Terrence Watanabe is the complete opposite, being that he inherited all of his vast fortunes from his businessman father, Harry Watanabe, founder of Oriental Trading Company. Yet, that is pretty much the only major difference between the two, considering that both their playing style and lavish lifestyle are what mostly bind them together. Oh, and the fact that they both lost over $100 million at the Las Vegas casinos over the span of their short gaming career.
Terry rose to a prominent position within the company of his father in 1977 when he become a partial owner, as well as president of Oriental Trading Company. With this change, the company went from supplying carnivals, to focusing its services on schools, retailers, churches and individual entities. However, just as the company expanded, in 2000, Terry sold Oriental Trading Company for a whopping $204 million and decided to retire with his money. Only little did everyone know, that retiring for Terry Watanabe meant moving to Las Vegas and spending $127 million of his pension at the Caesar’s Palace and Rio casinos. In fact, in 2009 alone, the total worth of the bets that Terry placed at these casinos amounted to $825 million.
The downfall of Watanabe came at his own expense/ One indicator of his reckless gambling habits is the fact that in many instances, he was losing up to $50.000 per single hand, with the losses amounting to more than $5 million on certain days. Watanabe was such a high roller, that Caesar’s had set a $17 million limit specifically for him. After losing his entire inheritance, Watanabe filed for bankruptcy in 2017 and ended up suing Harrah’s Entertainment Inc., the owner of Caesar’s and Rio. According to the lawsuit by Watanabe, he is suing the casinos for abusing his alcohol and drug addictions, i.e. encouraging him to play even after seeing that he is not in any condition to do so, while the casino accused him of writing bad checks, and accused him of being a criminal. Funny, if you consider that during the height of his gambling career in 2009, Watanabe single-handedly contributed 5.6% of the annual profits of Caesar’s Casino.
3. Zhenli Ye Gon – $125 Million
We can confidently say that the story of Zhenli Ye Gon is straight out of a Hollywood action movie, considering that it involves multi-million casino bets, record-breaking drug busts, Mexican cartels, meth trafficking, drug kingpins and whatnot. Starting out in Mexico after he moved from Shanghai, China in 1996, at the beginning of his career, Ye Gon was running Unimed Pharm Chem, a company that imports chemicals. According to the records, during his time, he operated legitimately and within the law. However, it is not clear exactly when, it is speculated that after 2002 he started re-directing the chemical imports from China, directly to the Sinaloa Cartel run by the infamous El Chapo.
After receiving the chemicals, the cartel would then use the precursors to produce crystal meth, and eventually sell it to the United States for hundreds of millions of dollars. However, everything went to pieces after the Drug Enforcement Agency (DEA) and the Mexican Federal Police raided his mansion in Mexico and found $207 million in cash in a separate room, neatly placed on the ground in the form of a cube. Ye Gon was not present during the raid, but once apprehended, he claimed that the money belonged to the Cabinet of then-President Filipe Calderon and that they were Sinaloa’s money to invest in the presidential campaign.
It is important to know the backstory of Ye Gon in order to understand how he reached the status of a high roller in Las Vegas, and consequently end up on the list of biggest casino losses in history. Similarly to our two previous contenders, in a span of just three years, Ye Gon gambled away little over $125 million cash money in Las Vegas, with the majority of this amount going to The Venetian casino. This happened starting from 2004, up until the raid on his mansion in Mexico in 2007. Ye Gon had such a gambling addiction, that he gambled away $45 million in one year alone at the Venetian, in cash, or from 2006 to 2007.
After spending the $45 million, he lost another $35 million which was a credit given to him by The Venetian casino, where during his gambling career he “left” $85 million alone. The other $40 million that he lost were spent in various smaller casinos around Las Vegas. Though interestingly enough, Las Vegas Sands (owner of The Venetian), was charged by the U.S. government for failing to report Ye Gon, and instead allowing him to play despite his status as wanted. This resulted in a $47.5 million fine by the U.S. government for The Venetian, and the termination of all executive bonuses at the casino. These massive losses eventually plummetted the stocks of Las Vegas Sands down to the ground, making for a far more costly venture than anybody expected.
4. John Daly – $50-$60 million
Needless to say, John Daly is a household name in the world of golf. And while this living legend of golf is most famous for his self-taught flowing golf swing and on-court accomplishments, Daly is also famous for having some of the biggest losses in the history of casino gambling. In another movie-like story, John Daly started playing golf in 1991, when he stepped in for a friend who was unable to attend due to the birth of his child. This certainly changed everything, considering that Daly ended up winning his first PGA ever, and set on a successful career in professional golf.
However, John Daly had one big weakness, and that was slot machines. In fact, Daly was such a slot junkie that he simply loved the adrenaline that he got from the slots in Las Vegas, up to such an extent, that he didn’t care about his losses whatsoever. In 2006, right after losing in the playoffs to Tiger Woods, Daly went straight from the golf course to the Vegas slots and gambled away a mind-blowing $1.65 million in a matter of five hours. He did a similar thing just one year prior in October of 2005 when right after winning the WGC American Express tournament and $750.000, he went directly to the Wynn Casino in Las Vegas and gambled a total of $1.5 million on a $5.000 slot machine.
In the autobiography that he published in 2006, John Daly goes on to write about his gambling addiction and openly states that he had a major problem during his career. In his book, Daly claims that during his 15-year gambling spree he lost somewhere from $50 to $60 million, which places him in the top 5 biggest casino losses in the history of gambling. Today, Daly is still playing professional golf, and is ranked 1724 by the Official World Golf Ranking, and believe it or not, he is still hitting the slots. Only according to the golfer, nowadays he plays only on slots that range from $25 to $5.000, and nothing more.
5. Archie Karas – $40 Million
Archie Karas is another exceptional casino player that qualifies for the title of the biggest losses in casino history, simply because he is said to have spent $40 million during his gambling career. What makes Archie so unique, is the fact that he managed to become a multi-millionaire with just $50 to his name. Arriving in Las Vegas in 1992, Archie took those $50, and slowly, but surely managed to gather a respectable amount of cash by participating in various cash games and a number of tournaments. In fact, he was so skilled, that he managed to obtain a loan of $10.000 from an anonymous benefactor, money that he used to play in high-stakes tournaments.
Not only did Archie successfully return the $10.000 loan in a very short time, but he also started to make millions of dollars while playing at various casinos in Las Vegas. Consequently, he was excellent at reading people, which made him a very skilled poker player, up to such an extent, that he started beating some of the biggest names on the pro tour. Yet, the winning and the confidence clearly got to Archie’s head, since he soon decided to change his M.O. altogether, and instead on excelling in a game of skill such as poker, focused solely on games that are based on chance, such as Baccarat and Craps. Not only that, but in the rare instances when he was playing poker, Archie was often arguing with the casino to allow him to bet over the limits.
This resulted in Archie losing basically all of his hard-earned $40 million from gambling in a span of just three weeks, which is one of the all-time records when it comes to the biggest losses in casino history. When asked about this infamous record, Archie simply said that “money means nothing to me, I don’t value it”, and that money cannot “buy health, freedom love, happiness”, ending with the quote, “I don’t care about money, so i have no fear, I don’t care if I lose it”. Regardless of Archie’s take on money, one thing is certain. Never change your tactics unless the situation requires it. Who knows, perhaps if Archie decided to stuck with poker and not take his chances, he might’ve ended up on a completely different list.
