The Legend of Pittsburg Phil

Gambling

George E. Smith, otherwise known as Pittsburg Phil, became a well-known handicapper. (Photos by Wikimedia Commons)

In the years before 1894, when the Daily Racing Form first started publishing, there was only one way to handicap horse races with past performance charts - you had to make the charts yourself. The number of people who were compiling data on horse races and making their own charts prior to the 1890s was most likely very small, but nobody was as successful at using racing data to inform his bets than a young man from outside of Pittsburgh named George E. Smith.

Smith was the son of two immigrants, a mother from Ireland and a father from Germany. His father died when he was very young, so Smith was forced to work in a Pennsylvania cork factory to help his family make ends meet.

Wage labor wasn’t for Smith, he decided, so he socked away a portion of his pay each week to fund a money-making scheme: he would buy and train two roosters and enter them in cockfights. He parlayed his success in cockfighting to placing bets on baseball games. Here, too, he had some success, and soon contemplated leaving the cork factory completely.

While hanging around Pittsburgh pool halls making sports wagers, Smith would pay attention to the calls of racing results coming in over the wire. He kept notes on each race, and eventually noticed patterns. He won a little money betting on horses he had been tracking, and decided there was an angle to exploit by keeping good notes. Smith quit his job at the factory and increased his wagers on horses. In two years he made more than $5,000 - a sum that drew the attention of his strictly religious mother.

In his defense, Smith argued that he wasn’t technically gambling, since he was using information to make an educated investment, perhaps the first in a long line of gamblers to use the “game of skill” defense to justify their vice, er, passion.

By 1885, Smith had won more than $100,000 on horse racing without ever having seen a live race. He broke the streak that year when he went to watch Joe Cotton win the Kentucky Derby. Smith eventually landed in Chicago, where he upped his action and grew to become one of the largest horse racing gamblers in America. His wagers were written about in newspapers alongside of racing recaps. He was given the moniker “Pittsburg Phil” and his legend grew as large as his bankroll.

Pittsburg Phil grew wealthy enough to start his own stable and run his own racehorses. He had trouble as a horseman, largely due to his associations and partnerships with jockeys. He partnered with the talented and controversial Tod Sloan, who himself was the inspiration for the Ernest Hemingway story “My Old Man,” only to see Sloan lose his racing license over accusations he had been betting on his own races.

Pittsburg Phil gave Sloan a loan of $5,000 to help him out after he lost his license, only to have Sloan repay him by stepping out with Phil’s girlfriend, Daisy Dixon.

Pittsburg Phil then employed the jockey Willie Shaw, but Shaw also raced under a cloud of suspicion for cheating. Eventually, The Jockey Club banned Shaw from racing for allegedly holding horses back. They also banned Pittsburg Phil from racing for paying Shaw to lose races. He denied the charges, believing The Jockey Club was merely trying to rid the racetracks of the big gamblers and that bookmakers resented his winnings. He offered $30,000 to anyone who could prove the charges against him.

Pittsburg Phil continued to bet on horse racing through the early 1900s, and his methods remained profitable. One of his more successful angles was betting on longshot mudders —horses who he thought showed a preference for heavy, muddy tracks. He was so successful at the track that he had to employ scores of “beards” — fronts to place his bets for him — to avoid bookmakers adjusting the odds based on his preferences. The Jockey Club employed Pinkerton agents to follow Pittsburg Phil around and keep tabs on his activities.

When Pittsburg Phil died from tuberculosis in 1905 at the age of 42, he was worth more than $3-million. He was interred in an opulent mausoleum in Union Dale Cemetery in Pittsburgh that he built for more than $30,000 years before his death.

HIS STATUE ON THE MAUSOLEUM

One day, years before Pittsburg Phil passed away, his friends came across him in the cemetery as he supervised the construction of his final resting place.

“Who’s it for?” they asked him.

“Me,” he replied.

“You’re not thinking of dying are you, Phil?”

“Got to some time,” he replied.

After Phil’s death, his mother, a devout Catholic and opponent of gambling, added one last detail to his mausoleum: a life-size statue of her son, a Daily Racing Form clutched in his hand.

Years after his death, the book “The Racing Maxims and Methods of Pittsburg Phil” was published. The book, based on an interview Phil gave to Edward Cole, was the first the public had ever heard of many of Phil’s methods at the racetrack. Despite the fact that he was self-taught and operating without any of the tools and reams of data available today, many horseplayers still believe his “Maxims” are gospel.

George Smith would make one final appearance at the racetrack after his death. The 1916 Kentucky Derby was won by a horse named George Smith, so-named to honor the man who owned the horse’s dam, Cansuelo II, the one and only Pittsburg Phil.

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