When a federal census worker counted his family in 1880, George J. Doyle lived with his widowed father, John, and four siblings in the poverty-stricken Five Points section of lower Manhattan. The Doyle family’s tenement, located at 86 Mulberry Street, housed 19 families, 68 souls total, all with Irish roots. The building probably had six or seven apartments, no indoor plumbing and was less than a block from Mulberry Bend — one of the most dangerous areas in the slum-infested Five Points. George, soon to be known by the nickname “Dorsey,” was 14. He and his younger sister, Katie, were still in school while the rest of the family worked at low-paying jobs.
At the age of 14 Dorsey Doyle was likely already sharpening his skills as a pickpocket and readying himself for life as a gang member and career criminal.
In 1887, when he was 21, Dorsey pleaded guilty to robbing a man of his watch and chain on the Manhattan side of the Brooklyn Bridge. He was sentenced to two years and three months in Sing Sing Prison. The prison entry for him lists six scars — most of them on his face — a testament to a life of violence, despite his youth. Sing Sing was known for whippings, solitary confinement, poor rations and a requirement of total silence from inmates. Rehabilitation for prisoners was decades in the future and many tried to escape, attempted suicide or went insane. Dorsey emerged from Sing Sing a full-blown, hardened criminal.
Dorsey was a member of the Whyos, a gang of Five Points Irish mobsters that hit its peak in the late 1870s and 1880s. While earlier New York criminal gangs spent most of their time fighting each other, the Whyos had the entrepreneurial spirit. Naturally they were involved in general thuggery, but they added extortion, prostitution and murder for hire to their menu of criminal activities. They were rumored to have a price list for the criminal services they supplied, ranging from $1 (punching) to $100 and up (“doing the big job”). By 1888, four of the Whyos members had been convicted of murder and hanged at the Tombs jail in lower Manhattan.
After his release from Sing Sing, Dorsey branched out from New York City and, in 1893, earned a three-year stay for grand larceny at the infamous Eastern State Penitentiary in Philadelphia. (Al Capone did a year at “ESP” in 1929.) By 1895 Dorsey’s flourishing career earned him spot #521 in Chief Inspector Thomas Byrnes new edition of his book, Professional Criminals of America. Byrnes described him as “well known throughout the eastern country, as he follows the races, fairs, etc.”
After an unsuccessful attempt, in 1898, at robbing a passenger of a gold watch and chain on a Broadway cable car in New York City (Dorsey shot at the policeman who eventually caught him) he received a second sojourn at Sing Sing. Shortly after his second release from Sing Sing, he and three other men were observed trying to pick pockets on an electric car in Manhattan. A mad chase by police ensued during which he jumped off the moving car and was the only man captured. He was convicted of attempted grand larceny and sentenced to Sing Sing for the third time!
At the turn of the twentieth century, with his Whyos pals dead or in prison and with a face that was well known to the New York police, Dorsey moved west. In 1908 he was arrested with another man for lifting a diamond stud off a man boarding a train in Wilkes-Barre, Pennsylvania. When he was arrested in Pittsburgh in 1915, the newspaper described him as “John Dempsey, alias Dorsey Doyle, aged 50, of Toledo.” He was one of a “mob” of clever pickpockets, all of them younger than Dorsey.
Fifty is ancient for a pickpocket — a skill necessitating quick reactions, nimble fingers and fast feet. Dorsey was never mentioned in the news after 1915, so he may have retired from crime and led a quiet, law-abiding life in Ohio. The days of the Irish gangs of New York were, after all, long gone, and no one, even a notorious criminal, wanted to risk a fourth stretch in Sing Sing.
Featured photo: Dorsey Doyle, carte de visite mugshot, circa 1892, by John Rosch. Collection of the author.