Infamous Gamblers: The Biggest Losers and Cheats in Gambling History

The thrill of gambling comes from the possibility of winning big at any given time. The unknown is something that motivates some people and terrifies others. With games of skill, like poker, some gamblers manage to make a living out of it, but all successful gamblers have one thing in common: knowing when to fold. 

Unfortunately, for some, the point of enough never arrives, which leads to detrimental outcomes. Today, we uncover some of the most notorious gamblers of all time. Some lost everything because they did not fold, while others risked everything by cheating. 

These are cautionary tales of why responsible gambling is vital to the entertainment industry and shows how greed is a dead end. 

 The Biggest Losers in the History of Gambling 

The adrenaline rush from a big win or winning streak is undeniable, and some punters fall prey to massive losses. One thing the following infamous gamblers have in common is not knowing when to stop. As a result, they made headlines, and we explore what happened. 

✓ Terrance (Terry) Watanabe 

Known as the biggest whale in the history of Sin City, Terry Watanabe lost more than $200 million in Las Vegas. Watanabe inherited his father’s successful business, The Oriental Trading Company, which sold carnival supplies. He continued to grow the business and established it as an industry leader in party favours. 

When Terry sold the company, he turned to philanthropy and, due to boredom, began drinking heavily and gambling even more. Terry was a known VVIP in Las Vegas, but Wynn banned him because of his drinking problem and compulsive gambling. On the other hand, Caesars welcomed him with tailor-made packages and afforded Terry privileges no other whale experienced. Following a losing streak that started in 2007, Terry lost an estimated total of $220 million over two years. 

Known as “the house player” by casino employees, Terry played games unusual for high rollers. His slot, keno, and poor blackjack skills brought Caesars 5.6% of their total gambling revenues across all their venues in 2007. Eventually, the whale could not cover his gambling debt, and Caesars took Watanabe to court for $14.75 million in outstanding debt. They settled on $1 million, and the group received a $225,000 fine for their lack of intervention. 

✓ Leonard H. Tose 

Leonard Hyman Tose owned the Philadelphia Eagles from 1969 to 1985 and earned his fortune through a successful family business. Tose inherited his father’s trucking company, which he built up to eventually include 700 trucks and gross $20 million a year. Described as a generous man with a zest for life, Tose lost his fortune because of gambling and alcohol addiction. 

Leonard Tose sold his beloved Eagles for $65 million in 1985 and used $25 million of this to settle gambling debts. Following this loss, Tose spiralled into an all-time gambling low and lost everything. His compulsive gambling led to massive losses at Atlantic City casinos estimated at around $34 million, and during a congressional hearing, Tose admitted to losing up to $50 million while gambling. 

Although he was a successful businessman, compulsive gambling and alcohol addiction ruined his life. At the age of 81, Tose lost his lavish seven-bedroom home for failure to pay taxes. The once affluent man died at the age of 88 in 2003. 

✓ Andrew (Andy) Beal 

Notorious in the poker world, Andy Beal challenged the poker industry’s top players known as The Corporation. The billionaire banker made waves in the poker industry during a series of high-stakes games in Vegas. Beal is an American banker, businessman, investor, and fancies himself a mathematician. Soon the number theorist found his theories obsolete in the poker room. 

The professional group of poker players included Todd Brunson, Jennifer Harman, Ted Forrest, Phil Ivey, and others. Beal’s hunger for extreme thrills pushed him to a Texas Hold’em table with stake limits of $100,000 to $200,000. Beal won $11.7 million against The Corporation, one of the largest single hands in poker history. The rivalry continued for three years with Beal winning most games, but in 2004 the tables turned, and Phil Ivey beat Andy Beal, leaving him $16 million down. He vowed the end of his gambling career. 

Two years down the line, Beal forgot the expensive lesson and returned to Vegas. The Corporation and Beal sat down at Wynn Las Vegas in February 2006 and 3 days later, the banker walked away from gambling for good as he lost another $16.6 million against Ivey. 

✓ Michael Jordan 

Better known for his insane basketball skills, Michael Jordan often makes headlines thanks to his love for gambling and the poor decisions that follow. The NBA star had his basketball career cut short because of questionable dealings linked to his gambling habits. Also known as Air Jordan, the former Chicago Bulls player is considered the G.O.A.T. of basketball. 

According to friends and fellow players, Jordan’s gambling dates back to when he was a youngster. The sports legend ascribes his gambling habits to his highly competitive nature. MJ insists he does not have a problem, though. His gambling triggered an investigation by the NBA, and shortly after, Jordan retired from basketball. The abrupt and early retirement sparked rumours, although the NBA released a statement to clear him of their suspicions. 

Jordan’s former golfing buddy exposed that the basketball star owed him $1.25 million in golf bets. In 1993 Jordan testified in a case against an alleged drug dealer and gambler because Jordan wrote cheques to James “Slim” Bouler to cover his gambling debt. Teammates describe how a Rock, Paper, Scissors game quickly turned into a $100k bet.  

Jordan is a respected celebrity, but his wagering habits and events linked to it have raised many concerns. 

✓ Jim “Mattress Mack” McIngvale 

The beloved furniture store owner from Houston caught the attention of the gambling industry with his staggering sports bets. Jim McIngvale, the owner of Gallery Furniture, recently had major losses thanks to his extravagant betting habits. His losses for this year alone stack up to a breathtaking $18 million. Regardless of his betting losses, Mattress Mack remains undeterred and continues wagering on his beloved teams. 

Mattress Mack places wagers on his favourite sports teams and justifies the size of his bets by running promotions in his store. The 71-year-old business owner hedges his bets this way, according to him.  

The reason Jim McIngvale’s stupendous bets make headlines is the odds he plays. It seems Mattress Mack has a thing for extreme risks and his win in the 2021 Super Bowls has him hooked. One of his most recent losses came from a bet on College Football, where he staked $6.15 million at odds of around +130. 

 Cheating Scandals 

We shift our focus from addicts who ran out of luck to cheaters who made headlines. No industry seems safeguarded from criminal activity, and the stakes are high for gambling cheats. This list includes one of the most famous gamblers who held a record-winning streak, and casinos later uncovered his cheating tactics, stripping him of his glory. 

✓ Tommy Carmichael 

This TV Repairman from Tulsa is the most successful slot machine cheat in the history of American gambling. Tommy Carmichael did not start off as a criminal, though. He tried to make an honest living, and when he was at his lowest, a friend dangled a golden carrot in front of him. This was a tool used to hot-wire one-armed bandits. Tommy took the bait and travelled to Las Vegas. 

Tommy had a 5-year run with the jackpot triggering mechanism in the early 80s and claims that he stole $2,000 every day. Until he was caught. He served two years of his 5-year sentence and developed new bypass mechanisms once released. Tommy made a living out of tricking slot machines and later from selling the tools he made to do this.  

Slot machine manufacturers upgraded their machines constantly thanks to his developments. His knack for finding loopholes helped the industry better their security and got him onto the FBI’s blacklist in Nevada. 

✓ Josh Fields (aka JJ Prodigy) 

One of the poker industry’s biggest scammers is Josh Fields. His playing alias is JJ Poker. In 2006, JJ Poker won $140,000 in a PartyPoker tournament, but the platform discovered his cheating tactics and stripped him of the prize. He was one of the first poker players caught for multi-table cheating, and the shocker was that he was only 14 years old at the time. 

Fields’ poker skills may have been pro-level, but his lying tactics were merely that of a young boy. PartyPoker discovered a strange profile with the username Ablackcar. Following an investigation, the poker site linked the profile to Josh, who tried to fool the company by stating it was his grandmother’s profile, and he played on her behalf. 

Sadly, the skilled poker player may never find a platform willing to forgive him. 

✓ Russ Hamilton 

Russ Hamilton could easily be the most loathed character in the poker world. The 1994 WSOP main event winner accomplished a lot in his gambling career and then threw it all away by scamming players. He dropped out of college to pursue a career in poker and made good money from gambling. Hamilton won several titles as a young poker player in the late 80s and early 90s, then tried his hand at blackjack. 

Eventually, employed by a popular online platform: Ultimate Bet, Hamilton moved playing fields and became a cheating criminal. A recording released in 2013 revealed how he scammed players on the site by accessing a profile in ‘god mode’ where he could see his opponents' cards. He cheated players out of $22 million and, to this day, is unwelcome in any poker circle. 

✓ Special Mention: Archie Karas 

Archie Karas was somewhat of a gambling hero, although he is one of the biggest losers. Over the span of three years, Karas turned $50 of his own money and a $10,000 loan into a stunning 6-figure fortune. His legendary winning streak is so famous that the gambling industry named it ‘The Run’. Karas still boasts the title of the largest and longest winning streak in casino gambling history. 

Archie Karas originally made money playing pool, but his run started in Las Vegas with high-stakes pool games that turned into higher-stakes poker games. Archie turned his $10,050 into $40 million.  

Unfortunately, his hunger for big bets led to his downfall, and he lost it all in three weeks. In 2013, they arrested Archie Karas for winning by fraudulent means as the Barona Gaming Commission caught him in the act of marking cards.