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You are gambling when you play a game of chance or skill and wager something valuable in the hopes of winning a prize. People who gamble frequently take financial risks to gain a more significant sum of money, even if there are losses too. Well, such history is written at the great gaming online casino brands.

Typical gambling activities include:

  • Games of chance like LOTTO 6/49 or LOTTO MAX
  • Instant games, such as scratch-off tickets
  • Nevada tickets and bingo games
  • Games involving dice in sports
  • Slot machines and table games are examples of casino games
  • Play cards
  • Horse Racing
  • Lottery video machines

Here we have mentioned the five craziest gambling losses:

1. $127 MILLION for Watanabe

Terrance Watanabe acquired the Oriental Trading Company from his influential business father after his death in 1977. He sold the business in 2000 to focus on Baccarat and Blackjack, albeit he was more interested in gambling than business.

In 2007, Watanabe went for an entire Las Vegas gambling binge, primarily at Caesar’s Palace. He placed a stunning $835 million in wagers and lost $127 million. According to sources, according to sources, Watanabe’s agonizing losing streak may have been the longest Las Vegas has ever seen.

Watanabe had other addictions besides gambling. According to witnesses, he was using cocaine and drinking two to three bottles of vodka daily. The company Caesars Entertainment,

2. ARCHIE KARAS: $40,000,000,000

Archie Karas, one of the most well-known gamblers ever, owns the record for the longest and largest winning run in gambling history despite being one of the most considerable losses. He had $50 in his pocket when he arrived in Las Vegas in 1992 and was penniless. At the beginning of 1995, he had turned a $10,000 loan from a friend into more than $40 million. According to legend, once he had a bankroll of $7 million, he would just spread the cash out on a table and wait for a challenger to approach him. Poker, Baccarat, and dice were his three favorite games. As Karas pleaded with the casino to allow him to bet much above the limit, he made more and more careless wagers, knowing that this enormous winning streak would eventually end. Over three weeks, he lost every last dollar of his gains.

Archie Karas is unquestionably a legendary personality in the casino industry, having gone from one of the biggest winners to one of the most significant losses.


On this list, Charles Barkley is arguably the most well-known name. The 11-time NBA All-Star, unlike the other two, was not gambling responsibly.

Considering his tremendous success as a basketball player, he gambled away nearly all his $30 million fortune. In one blackjack game, lifelong high roller Barkley admittedly lost $2.5 million. While Barkley struggled, he also seems to have taken more enjoyment from the game than many other players on this list. He participated in various casino games, including Baccarat, Blackjack, dice, and roulette. He never played intending to make a lot of money; instead, he preferred the excitement of the game. He was aware that losing was a part of the game. Barkley has learned a little bit about safe gaming over the years. Even though he has returned to it after a brief break, he no longer bets more than he can reasonably afford.


Harry Kakavas, a former Australian billionaire, lost $20.5 million, a small amount given that he bet $1.43 billion, similar to Maureen O’Connor. Over two years, he lost much money at Melbourne’s Crown Casino alone, from 2012 to 2013.

The real estate magnate attempted to sue the Crown in Australia’s High Court because they took advantage of his “pathological drive to gamble” when he was forced to deal with the gaming results. Harry, nevertheless, was deemed to be able to reason logically by the judge. He consequently lost the case. However, Kakavas had a protracted gambling addiction. After stealing $220,000 from a prominent Australian firm and using the money to feed his gambling addiction, he was sentenced to four months in prison in 1998.

Harry, a frequent player at the Crown Casino, decided that this was his lowest point and stopped going there to gamble. But he couldn’t help but return to the Baccarat tables and was later seen in Las Vegas squandering millions. Harry returned to the Crown Casino’s tables at that point, which caused the subsequent losses.

5. 13 million dollars for MAUREEN O’CONNOR

Maureen O’Connor, the only female on this list, is famous for being the mayor of San Diego at the time of her significant gambling loss. Although $1 billion was bet, it’s astounding that she managed to limit her losses to just $13 million. O’Connor’s gambling addiction was so severe that she had to borrow $2 million from her second husband’s charitable organization, which she then used to purchase only one video poker game. But if we only remember O’Connor for her colossal defeats, we do her a disservice. She did an excellent job as mayor and worked hard and meritoriously to advance her profession. She also accomplished the difficult chore of paying off her gambling debt, which was praiseworthy.