Gentleman Gerry and the upright jerker

Gerald Chapman (1887 – 1926), called the “Count of Gramercy Park”, and “The Gentleman Bandit” was an American criminal who spoke with a near impeccable English accent.

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After being convicted on a bank robbery charge and transferred from Sing Sing, he first became acquainted with ‘Dutch’ Anderson, a swindler and ‘gentleman’ crook, while imprisoned in Auburn State Prison in 1908. Following both men’s paroles in 1919, they conducted successful bootlegging operations in Toledo, Miami and New York City.

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They also managed to amass $100,000 through confidence trickery. Chapman rented an apartment in exclusive Gramercy Park and acquired a pretty English “wife” named Betty, who was as much a born lady as he was a born gentleman.

more photos of old New York here

In 1921, along with another former Auburn inmate, Charles Loeber, Chapman and Anderson began committing armed robberies. On October 24, the three men forced a U.S. Mail truck to stop at gunpoint on Leonard St, successfully taking $2.4 million in cash, bonds and jewelry. 

mail truck found here

While the police were searching frantically for leads, Chapman was back at 12 Gramercy Park, throwing dinner parties for his wealthy neighbours. In another robbery at an American Express office, the gang added a further $70,000 to their capital.

Eluding capture for more than eight months, Chapman and Anderson were eventually arrested after being betrayed by Loeber. While Chapman sat with a detective in the Federal Building on Broadway, he feigned some kind of attack, slumping in his chair and gasping for water. As the detective left the room, Chapman, with hands shackled, rushed out a window and ran along a narrow cornice. He was recaptured but the escape attempt made headlines and he was described as a modern day Robin Hood.

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In an Atlanta penitentiary, faced with a 25 year sentence, Chapman swore he would escape. He stole small pieces of cord from the workshops and braided them into a rope. From stolen cutlery he made a file and a crude hook. When he complained of stomach pains he was admitted to hospital for observation. There he persuaded a “trusty” in the same room to join him in an escape attempt.

more prison weapons found here

They filed through the bars, severed an electric cable (plunging the prison into darkness) then used a rope of bed sheets to get to the ground and over the wall. Two days later they were tracked by bloodhounds and recaptured. Chapman was shot twice as he tried to run away and was transferred to a civilian hospital. While he was there Betty came to visit him and managed to smuggle in a gun. He used it to force an intern to hand over his white coat and walked out of the hospital to freedom once more.

NOT this Betty (found here)

Chapman and Anderson joined forces again and drove east in a stolen car, committing burglaries as they went. They were foiled in an attempt to rob a department store when police arrived and blocked their exit. Shots were fired and Chapman managed to escape once more.

On 17 January 1925, Chapman’s luck ran out and he was arrested leaving the house of a doctor friend and extradited to Connecticut. During the six-day murder trial in Hartford, crowds gathered due to his status as one of the “top 10” criminals in America. The jury deliberated for 11 hours, after which Chapman was found guilty and eventually sentenced to hang. He proclaimed his innocence to the end, asking in his final appeal for “justice, not mercy”. Chapman was executed by the upright jerker** on April 6, 1926.

**The upright jerker was an execution method and device intermittently used in the United States during the 19th and early 20th century. Intended to replace hangings, the upright jerker did not see widespread use.

As in a hanging, a cord would be wrapped around the neck of the condemned. However, rather than dropping down through a trapdoor, the condemned would be violently jerked into the air by means of a system of weights and pulleys. The objective of this execution method was to provide a swift death by breaking the condemned’s neck.