4 Most Successful Gamblers in History


Gambling is usually considered more of a game than an art, but there are a few expert hands who have turned this pastime into a lucrative career. With smart strategies and a bold approach, these successful gamblers have amassed astonishing winnings at casinos, race tracks, and beyond.

Louis “The Coin” Colavecchio

Image  via Flickr by Mrs. Gemstone

Though some successful gamblers have made their winnings honestly, Louis Colavecchio, also known as “The Coin,” didn’t play by the rules. The jewelry store owner had access to the perfect tools and equipment for crafting counterfeit coins. He meticulously replicated the design on casino coins, then used these to hit the slots without risking his own money. Though the total sum of his winnings is unknown, his scam lasted four years. By 1998, he had “money buried all over.”

Colavecchio ultimately served seven years in prison for his counterfeiting crimes. His sentence might have been longer, but he offered to let the casinos in on his counterfeiting secrets in exchange for some leniency. Today you’ll have to play slots online or in the casino honestly to score your wins, but you can still go for the jackpot.

Bill Benter

Professional gamblers often take home high winnings, but few are as successful as Bill Benter, who took home $10 million in the 1994-95 season alone. Rather than place his bets in casinos, Benter chose to make his money on the horse races. The gambler’s wildly successful bets were more than just luck. He developed a piece of software that analyzed more than 130 variables to predict which horses were the best bet.

Though exact numbers are unpublished, Benter indicated that he’d probably made close to a billion dollars overall in his horse racing endeavor, but he asserts that he’s “not a billionaire.”

Titanic Thompson

Titanic Thompson’s astounding gambling career was based heavily on making outrageous bets for big wins. A skilled con man, one of his favorite strategies was to encourage heavy bets on his prowess on the golf course. He would play poorly for the first half of the game and lure gamblers into big bets that he would ultimately win.

Titanic would take on outlandish bets, such as wagering members of a country club that he could drive his ball the furthest in winter. He won $50,000 by hitting his ball onto a frozen pond. Though his success relied on misleading others, he was wildly successful at this gambling strategy.

Edward Thorp

Though modern casinos know how to thwart Thorp’s strategy, this master of blackjack was one of the most successful gamblers in history. Thorp is credited with developing the first system of card counting. Before casinos were wise to the strategy, they could find no way of detecting the cheat. At the peak of their run, Thorp and his wife could take home the equivalent of $70,000 in today’s money in a single weekend.

Thorp capitalized further on his success by writing the 1962 book, “Beat the Dealer,” followed by a second edition in 1966. Thorp ultimately earned a spot as one of the first seven people honored in the Blackjack Hall of Fame.

Though not every gambler can make it as big as these players, there are plenty of opportunities out there for the everyday player as well. Whether you grab a seat at the slots or head up to the roulette wheel, you’ll find a seemingly endless range of ways you can play.



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