Most Legit Historical Gamblers

Plenty of gamblers have made names for themselves through cheating or manipulation of games of chance. But there are also many who achieved fame legitimately, based upon their skill and/or luck or sometimes simply their persistence. Following are a ten of gambling’s most reputable practitioners of years past, some of them familiar worldwide, a few surprising and others perhaps more obscure.

Charles II (1630-1685) – The king who restored the English monarchy in 1660 can also be considered the father of modern gambling in the U.K. His court life was a rich mix of socializing, dice and cards that gained him a reputation as the “Merrie Monarch.” He not only created the written rules for British horse racing in 1665, but before his death, he had purged London of its illicit gambling dens and instituted licensing for legal gaming.

Giacomo Girolamo Casanova de Seingalt (1725~1798) – Best known simply as “Casanova” and famous for his exploits with women, this Venetian adventurer had always aspired to be a professional gambler. He certainly deserves credit for being the first person to describe a now popular betting progression, doubling the size of his stake following each loss until his wager eventually won. According to his memoirs, this system served him successfully at the Ridotto Casino in 1754. The practice of “doubling up on a loss” is today quite common among roulette players.

James Butler Hickok (1837-1876) – Legendary lawman “Wild Bill” Hickok had a penchant for card games as well as gun-slinging. While playing poker in Deadwood, South Dakota at the Number Ten Saloon in 1876, he was murdered—shot in the back—while holding two pair, Aces and Eights. To this day, that card combination is known as the “Deadman’s Hand” and many players still believe those cards are a foreshadowing of “bad things to come.” Hickok was inducted into the Poker Hall of Fame upon its inception in 1979.

Fyodor Mikhaylovich Dostoyevsky (1821-1881) – The Russian novelist known in the West as “Dostoevsky” was an avid gambler, who often lost large sums of money and was in debt most of his life because of it. His exploits became source material for two of literature’s greatest works, “Crime and Punishment” and “The Gambler.” By one account, some of his writing was hastened by the need to secure advances from his publisher in order to settle loans for his gambling addiction.

John Warne Gates (1855-1911) – Known as “Mr. Bet-a-Million,” this industrialist and gambler was born in Illinois but gained his fortune in Texas by manufacturing barbed wire. In frequent trips to Europe, he became noted for his high stakes baccarat, but his nickname wasn’t earned at the tables. In 1900, he won $600,000 for a $70,000 wager made at a British racetrack, mistakenly reported as a “million dollar bet.” On a different occasion, Gates won $500,000 playing poker non-stop during a train ride to New York from Chicago. And another time, he reportedly lost a million-dollar bet on which of two raindrops would reach the bottom of a window pane first, cementing his reputation.

Nicolas Zographos (1886~1953) – Blessed with a photographic memory, this baccarat savant could remember the order of all 312 cards as six decks were played. His “Greek Syndicate” virtually controlled the baccarat tables of Europe in the early 20th century. One of the Greek’s biggest wins was in 1926 when he had millions of francs at risk and was dealt two worthless court cards. Against all odds, he drew the nine of diamonds to win and it became his symbol ever after, appearing on all he owned, from a private yacht to his handmade cufflinks.

William Nelson Darnborough (1869~1958) – This little known American roulette player is considered by many to be the first person to successfully develop and apply a systematic methodology for predicting where the ball will drop. His calculations allowed him relieve Monte Carlo of an estimated $415,000 between 1904 and 1911. One of his legendary feats was winning on five successive spins by betting the number 5.

Kenneth Senso Uston (1935-1987)
– This Harvard MBA and businessman was one of the world’s most proficient blackjack players. He led a San Francisco based team of card counters to millions of dollars of winnings at the tables of Reno, Las Vegas and Atlantic City. He was so good that he also had to become a master of disguise to evade surveillance systems. When casinos eventually banned him from play, Uston published his methodology in a 1981 book entitled “Million Dollar Blackjack,” considered to be a gambling classic to this day.

Kerry Francis Bullmore Packer (1937~2005) – This Australian billionaire made his fortune in mass media, but his reputation as a gambler is legend. One story has been told of him winning 20 consecutive hands when playing high stakes baccarat in Las Vegas, with each hand worth $250,000. In 1997, he reportedly won somewhere between $20 million and $40 million at the tables of the MGM Grand. Being generous, Packer allegedly tipped a doorman $1 million. He also paid off the mortgage of a cocktail waitress. Packer’s biggest known loss was at Crockfords Casino in London, where he dropped an estimated $16.5 million. With a net worth of $8 billion, it was just a case of “easy come, easy go.”

John Patrick “J.P.” McManus (1951-2008)
– Born in Limerick, Ireland, McManus grew up around greyhounds; he set up his own betting stand as a boy. At the age of 30, he wagered successfully on the second-seed in the Cheltenham Novices’ Hurdle and won an estimated $250,000. In 2006, he reportedly won more than £1 million in horseracing bets from Scottish bookmaker Freddie Williams. Before he passed away, McManus had become a stable owner, racing his own jumpers in the National Hunt, and earning a fortune through global financing and money dealing out of Geneva.