When a federal census worker counted his family in 1880, George J. Doyle was just one of the thousands of children of Irish immigrants living in the poverty-stricken Five Points section of lower Manhattan. Along with his father and four siblings, George lived in a tenement at 86 Mulberry Street that housed 19 families — 68 souls total — all of them with Irish roots. The building would have 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. In 1880 George, who was 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.
By 1880 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 mandating total silence from its inmates. Education and rehabilitation for prisoners was decades in the future and many tried to escape, attempted suicide or went insane. Dorsey survived his stint there and 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 much of their time fighting each other, the Whyos had a more entrepreneurial focus to their activities. They were, of course, involved in general thuggery, but they added extortion, prostitution and murder for hire to their menu of criminal activities. The Whyos were described to have a price list for the criminal services they offered, ranging from $1 (punching) to $100 and up for “doing the big job” (aka murder). 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. In 1893 he earned a three-year stay for grand larceny at the infamous Eastern State Penitentiary in Philadelphia. (Al Capone did a year there in 1929.) By 1895 Dorsey’s flourishing career earned him spot #521 in the second edition of Chief Inspector Thomas Byrnes’ book, Professional Criminals of America. Byrnes described Dorsey as “well known throughout the eastern country, as he follows the races, fairs, etc.”
After an unsuccessful attempt at robbing a passenger of a gold watch and chain on a Broadway cable car in New York City in 1898, (Dorsey shot at a pursuing policeman and the cop eventually caught him) he received his second sojourn at Sing Sing. Shortly after his release from prison, 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 and a colleague were arrested for lifting a diamond stud off a man who was boarding a train in Wilkes-Barre, Pennsylvania. He was arrested a few years later in Pittsburgh. At that time a 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 men.
Fifty is ancient for a pickpocket, a skill necessitating quick reactions, nimble fingers and fast feet. Dorsey didn’t appear in the news after his Pittsburgh arrest, so he perhaps he retired from crime and led a quiet, law-abiding life in Ohio. The days of the Irish gangs of New York were long gone, and no one, not even a notorious criminal, wanted to risk a fourth stretch in Sing Sing.
Featured photo: Dorsey Doyle, carte de visite mugshot, by John Rosch , circa 1892. Collection of the author.