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Journey to the World of Gambling: Success Stories and Failures in Casinos

For most regular players, big wins are like the stuff of dreams – they don’t happen very often. There are examples of players choosing online slots ie and, landing cash prizes as they discover min deposit in irish casino (LeprechaunPot). However, such instances are rare with a land-based real money casino that doesn’t allow players to place too many bets at once.

We all keep hearing about billionaires having the time of their lives at a casino table while simultaneously realizing ordinary gamblers have fewer possibilities to land a winning combination. However, big successes and failures have always fascinated us as humans, be it a tale of notable victories or glorious falls from grace demonstrated by world-famous gamblers. Here are the top stories of casino legends winning and losing fortunes in an unexpected twist of fate:

Success: Mike Ashley

The story of Mike Ashley, a multimillionaire and the owner of Newcastle Football Club, is one for the pages. One night, Mike decided to visit Fifty Casino in London, where he would bet on every combination that included the number 17 in every pattern. Black 17 was rumored to be Mike’s favorite number – the same number His Majesty’s secret agent James Bond favored at the casino table. Ashley started his bet with £480,000, leaving the casino with £1.5 million in his pocket 15 minutes later. The onlookers have reported that upon learning he had just won over a million, Ashley stood up and said: “This will do me very nicely,” and proceeded to the exit.

Failure: Maureen O’Connor

Maureen O’Connor’s story is spectacular in every regard. She was mayor of San Diego when she lost a staggering amount of money and had to deal with the consequences. At one point, the stakes were so high that O’Connor betted on $1 billion in a local casino, only to get $13 million removed from her after a series of poorly executed strategic moves. However, considering the number of bets in the first place, it is a shock that a former mayor managed to keep her losses so low. In the case of O’Connor, her gambling addiction was so serious that she once took money from her husband’s charity to pay for her casino debts.

Success: Elmer Sherwin  

Elmer Sherwin was certain he was the luckiest man in the world when he hit the winning jackpot at The Mirage in Las Vegas and walked away with $4.6 million. Since Elmer was always fond of traveling, he went on a world tour and visited places he thought he would never visit. However, this was not the last time Sherwin’s incredible luck made him the hero of the day. In 2005, he was spotted at the Cannery Casino & Hotel of Las Vegas betting at the Megabucks slot machine. This was his favorite slot, as he always won smaller prizes and left the casino elated. To Sherwin’s astonishment, he won another sensational award for $21 million. The lucky guy spent the money on supporting the victims of Hurricane Katrina and helping his children financially.

Failure: Harry Kakavas

Harry Kakavas, an Australian billionaire, lost $20.5 million when he became a frequent visitor at the Crown Casino in Melbourne. He originally gambled $1.43 million, which made his subsequent losses less dramatic. However, the loss of a larger part of his fortune did not stop Kakavas from suing the casino and demanding that they compensate him for the psychological damage. The billionaire insisted that the Crown Casino knew he had a serious gambling problem yet did nothing to stop him on the path of self-destruction. Kakavas lost the case as the court decided that he was mentally stable and fully capable of walking away from the casino whenever he wanted. The unfortunate gambler was later seen in Las Vegas, spending millions and unable to cope with his gambling addiction.

Success: Charlie Wells

This story took place over a century ago, but that doesn’t detract from its grandeur. Charlie Wells visited the Monte Carlo casino in 1892 and broke the bank of Monaco as he walked away with 1 million francs in his pocket. He started with a bet of 4000 francs and worked up until he drained the casino’s reserves dry. The witnesses reported Wells playing for 11 hours straight. He never left the table and kept winning astonishing amounts with what he called his “infallible technique.” He was later accused of cheating the casino by observing the cards. However, with no tangible proof of his machinations, some people believed that his exceptional luck was the real secret to his success.

Failure: Terrance Watanabe

Terrance Watanabe, the owner of the Oriental Trading Company, was the son of a successful businessman who knew how to manage his finances. However, his business streak did not help him when he developed a serious gambling addiction and decided that being the head of the company was decidedly less entertaining than spending his days and nights playing baccarat. In 2007, Terrance went on his grand gambling spree in Vegas, losing $127 million at Caesar’s Palace, which is said to be the biggest casino failure Vegas has ever witnessed.

Andy Macpherson

Andy Macpherson is a Brighton-based blogger, amateur golfer and photographer with a passion for capturing the essence of his surroundings. Born and raised in Hove, he has spent almost his entire life exploring the streets and beaches of Brighton, always with a DLSR in hand. When he's not out taking photos or hacking his way around the golf course, Andy can often be found gorging on Pad Thai. As a self-proclaimed foodie, Andy is always on the lookout for new restaurants and dishes to try, which is the main reason behind why he loves reviewing food places for the site.