Regardless of whether you are an average person or one of the wealthiest people in the world, there’s no doubt that gambling, whether it’s sports betting, casino betting, or online casino games, can be a lot of fun. For some of the world’s richest individuals, having a lot of money also opens the door to incredible bets, with many individuals placing high-stakes wagers for the excitement, for pride, or just to win even more money.
Unfortunately, sometimes, this leads to the biggest gambling losses ever. Keep on reading to learn about the most money lost gambling by some of the wealthiest people around the world, with incredible amounts that are thousands if not millions of times larger than what the average person gambles.
5. Jim McIngvale: More Than $15 Million
Jim McIngvale, born James Franklin McIngvale and also known as “Mattress Mack,” is the owner and operator of the Galley Furniture company. This company once faced hard times but grew into a massive operation. An avid sports fan, McIngvale took his earnings from his business and spent millions betting on his favorite sports. His losses have accumulated and were reported to be in excess of $15 million according to the AmericanFootballInternational.com article “$15.43M Losses: “Mattress Mack’s” Turbulent History of Sports Betting.”
However, this total has likely increased to closer to $18 million or higher after CBS Sports reported in the article “Jim ‘Mattress Mack’ McIngvale has lost over $9M betting against Georgia in last two Championship Games” that he lost $3 million betting on TCU in the College Football Playoff National Championship in 2023.
4. Charles Barkley: $20 Million
Charles Barkley is a former NBA player and was once honored with the title of being one of the 50 greatest players of all time in 1996. His incredible skills on the court opened the door to millions of dollars in earnings through his time on the court, as well as through various sponsorships with companies like Nike, Coca-Cola, and McDonald’s.
Unfortunately for Barkley, his love of gambling also led to millions of dollars in losses. The losses built up, eventually reaching a total of $20 million, according to the Lineups.com article “Charles Barkley Speaks Out About Gambling Addiction, His Time in the League With Michael Jordan.”
3. Archie Karas: $40 Million
What starts off as an incredible tale ends as one of the worst gambling stories of all time. Born into poverty in Greece, Archie Karas left home after his father threw a shovel at him. He worked his way to Los Angeles, where he waited on pool tables and worked on his pool skills, eventually becoming a skilled pool shark. While he was initially able to make a decent living off his pool skills, people soon caught on, and his winnings began to dry up.
He turned his attention to cards and, over time, became quite the skilled card player. During a particularly successful run playing a variety of gambling games that started in 1992 and ended in 1995, Karas was able to make himself $40 million richer.
However, he once again found that people were unwilling to play against him, so he turned to games of pure chance. Unfortunately, luck was not on his side. Within a few weeks, he lost $11 million playing craps and $17 million playing baccarat. He took a break but soon returned to gambling, losing the last of his fortune trying to repeat the success he had between 1992–1995.
2. Terrance Watanabe: $204 Million
Terence Watanabe is an American businessman who inherited the Oriental Trading Company from his father. The business supplied various goods, including arts and crafts, party supplies, school supplies, and toys. In 2000, Watanabe sold his stake in the company to private equity firm Brentwood Associates, choosing instead to pursue a life as a philanthropist.
Unfortunately for Watanabe, his passion for gambling got the better of him, leading to a gambling loss of $127 million at Caesar’s Palace and The Rio in 2007. According to the PokerListings.com article “Poker’s Greatest All-Time Whales: Terrance Watanabe,” his losses for the year totaled $204 million.
1. Harry Kakavas: Almost $1 Billion
The biggest loss on this list goes to Harry Kakavas, an Australian real estate agent who made a fortune selling properties on the Gold Coast. Unfortunately for Kakavas, the more success he found as a real estate agent, the more he lost betting at the casinos.
According to The Sydney Morning Herald article “Casino did not exploit man who spent $1.5b, rules High Court,” Kakavas made A$1.47 billion (Australian dollars) in bets at the Crown Casino in just over a year. In one gambling session that lasted five and a half hours, Kakavas spent A$164 million (approximately US$105 million) at the casino.
0. Michael Jordan: Unknown
It’s public knowledge that Michael Jordan loves to gamble. When the subject of gambling came up in the documentary “The Last Dance,” Jordan responded, “I have a competition problem, a competitive problem.” He described gambling as a hobby of his. “I enjoy it, it’s a hobby,” he said. “If I had a problem, I’d be starving. I’d be hawking this watch, my championship rings; I would sell my house. My wife would have left me, or she’d be starving. I do not have a problem. I enjoy gambling.”
And enjoy gambling he does. While there’s no official number around Michael Jordan’s gambling losses, according to the SportsGamblingPodcast.com article “Michael Jordan’s Worst 5 Gambling Losses,” he’s lost $5 million on craps, hundreds of thousands, if not millions of dollars, on golf bets, and even $100,000 on a game of rock, paper, scissors. However, it wouldn’t be surprising if the people Jordan has managing his finances have claimed back gambling losses to minimize the impact of his gambling hobby.
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