Jack Mahaney was an American criminal, sneak thief, confidence man and gang leader in New York City during the late-19th century. He was also one of the most notorious prisoner escapees of his time, popularly referred to as the "American Jack Sheppard

Jack Sheppard

Jack Sheppard was a notorious English robber, burglar and thief of early 18th-century London. Born into a poor family, he was apprenticed as a carpenter but took to theft and burglary in 1723, with little more than a year of his training to complete...

", successfully escaping from virtually every major prison in the eastern United States

Eastern United States

The Eastern United States, the American East, or simply the East is traditionally defined as the states east of the Mississippi River. The first two tiers of states west of the Mississippi have traditionally been considered part of the West, but can be included in the East today; usually in...

 including The Tombs

The Tombs

"The Tombs" is the colloquial name for the Manhattan Detention Complex, a jail in Lower Manhattan at 125 White Street, as well as the popular name of a series of preceding downtown jails, the first of which was built in 1838 in the Egyptian Revival style of architecture.The nickname has been used...

 and Sing Sing

Sing Sing

Sing Sing Correctional Facility is a maximum security prison operated by the New York State Department of Correctional Services in the town of Ossining, New York...

. Mahaney also escaped from custody which included well-publicized incidents where he jumped from a train without injury.

Biography

Jack Mahaney was born in New York City in 1844. When he was 10, his father died and he was sent to a boarding school by his mother. He was, by all accounts, a mischievous student who was frequently in trouble at the school and eventually ran away after being flogged repeatedly by teachers. When police found him, Mahaney was in company with a gang of teenage "dock rats" and was placed in the House of Refuge. He escaped from the juvenile institution, along with a dozen other youths, and fled to the Five Points

Five Points, Manhattan

Five Points was a neighborhood in central lower Manhattan in New York City. The neighborhood was generally defined as being bound by Centre Street in the west, The Bowery in the east, Canal Street in the north and Park Row in the south...

.

Mahaney joined the gang of Italian Dave, the famed sneak thief and fagin

Fagin

Fagin is a fictional character who appears as an antagonist of the Charles Dickens novel Oliver Twist, referred to in the preface of the novel as a "receiver of stolen goods", but referred to more frequently within the actual story as the "merry old gentleman" or simply the "Jew".-Character:Born...

, whose group of street urchins and pickpockets were among the notorious thieves of the Five Points. Italian Dave had between 30-40 youths, between the ages of 9 and 15, whom he housed in a
Paradise Square tenement building. It was here that Mahaney was trained to steal along with Italian Dave's other pupils. Practicing on dummies dressed as men and women, Mahaney and the others learned how to pickpocket and snatch valuables such as purses and muffs. They were also instructed on begging and stealing from store windows and counters. Whenever a student was clumsy or otherwise displeased Italian Dave, their leader, dressed in a policeman's uniform, would hit them with a nightstick.

Mahaney was very successful in this trade and, becoming a noted pickpocket and sneak thief in his own right, was personally taken under the wing of Italian Dave and made his protege. He was also allowed privileges given to few others including going on marauding expeditions where he and Italian Dave would roll a drunk or snatch a purse. Mahaney eventually left the gang as he entered adulthood and formed his own gang of butcher cart thieves active in the Five Points. He also became a noted confidence man and swindler in his later years.