Home Life Style The Most Outrageous Casino Wins and Losses of All Time: Casinobee.com’s Roundup

The Most Outrageous Casino Wins and Losses of All Time: Casinobee.com’s Roundup

by Eric
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Casinos give a very thrilling experience to players. There is no doubt that players love winning more than losing at casinos. Many players have used real money or the casino bonus to win big and change their lives. At the same time, a lot of people have lost huge amounts at casinos and this has wrecked some of them. Casinobee brings you some of the most outrageous casino wins and losses of all time. We’ll walk you through 3 of the most outrageous winnings and losses of all time. Guess what? There is a winner who blew his huge wins away and he makes both lists. 

Top Winnings at the Casino

From $50 to $40 Million 

Number one on the list is a Greek immigrant who moved to Las Vegas with just $50. Archie Karas made a name for himself as he is known as the man who has the longest winning streak in casino history. His streak lasted from 1992 to 1995 and saw him scoop an excess of $40 million. His winnings came from poker, blackjack, baccarat, and pool.

Engineer Wins $39.7 Million 

It is extremely rare to hit the jackpot at a casino. Well, not for the young Los Angeles software engineer. Still today, no one knows his name but the 25-year-old wagered only $100 and won an excess of $39.7 million. He won it on the popular Megablocks slot machine in the Las Vegas casino Excalibur. He opted to collect his money in 25 installments of $1.5 million per annum. He has at least 5 more installments to collect. What a lucky guy. 

Newbie Wins $34.95 Million

When Cynthia Jay-Brennan made the decision to test her luck on the Megabucks slot in 2000, she was a total novice. On her ninth attempt, after failing on her first eight attempts, she won a huge $34.95 million jackpot. Cynthia Jay-Brennan quickly left her work, got married, and began touring the world after shaking hands with lady luck. She wasn’t always that fortunate, though; a few months after her huge triumph, she and her sister were engaged in a car accident that left her sister dead and left her disabled.

Top Losses at the Casino

Over $180 Million lost 

Umar Siddiqui was fired from his marketing manager role at Fry Electronics after he gambled away $65 million of the company’s money. He illegally transferred $70 million of the company’s money to The Venetian to gamble. He accumulated over $165 million in gambling debts and still had $65 million to pay to the company he was sacked from. He had only $80 to his name when he filed for bankruptcy. No one knows if he will ever be able to repay these debts in his lifetime.

Big Whale Loses $127 Million in a Year

Big whales in Las Vegas get VIP treatment in casinos but when they lose, it is mostly huge too. In 2009, Terrance Watanabe bet over $865 million in 2 casinos and lost about $127 million. He struggled with drinking and gambling addiction. Additionally, his attorney claims that Caesar’s Palace and Rio Casinos profited from this. His losses alone made up for 5.6% of the annual revenue of these companies. He got bankrupt and at some point even had to fundraise for a $100,000 surgery. 

$40 Million Gone in 3 Months

Remember Archie Karas, the man with the longest winning streak in casinos? Ironically, he is also on this list. Just 3 months after he had accumulated winnings of $40 million he lost almost all the money. He took a break from gambling when he was left with just $1 million. When he came back from his break he was able to double his money to $2 million. Shortly after that, Archie lost it all again. 


Over the years, there have been many winners and losers at casinos. Ask any of the top winners what it takes to win big at a casino and you’ll hear different answers from everyone. However, do you know what is the same? The feeling of joy and triumph when you win. Another feeling that is the same across the board is the feeling of uncertainty when you lose huge amounts at the casino. If you have good gaming habits and are able to manage your bankroll properly, then you will win more at the casinos.

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