Gerald Chapman, Prohibition's celebrated ‘Gentleman Bandit,’ might have escaped the gallows if he hadn't gone on a crime spree in Connecticut.
While in prison, Gerald Chapman found a mentor who taught him that acting respectable and dressing well diverted suspicion from criminal activity. Before he pulled off the biggest armed robbery in history, Chapman dressed well, lived in New York’s posh Gramercy Park neighborhood, frequented expensive nightclubs and adopted a British accent.
Newspapers nicknamed him the 'Count of Gramercy Park' and the 'Gentleman Bandit.' He was the first celebrity gangster, the first criminal the press dubbed ‘Public Enemy No. 1.’
Gerald Chapman came into this world as George Chartres in Brooklyn, N.Y. -- or maybe it was Manhattan’s Lower East Side – sometime in August 1887. As a youth he drifted into petty crime.
Police arrested him for the first time at the age of 14, and he spent most of his young adulthood in Sing Sing. He met his mentor, George ‘Dutch’ Anderson, after prison officials transferred him to Auburn Prison.
Anderson’s real name was Ivan Dahl von Teler. He had been born into a wealthy Danish family and attended Heidelberg and Uppsala universities. Then he dropped out of college in Wisconsin to take up crime. Anderson saw in the younger Gerald Chapman someone who had enough smarts and daring to commit big-time heists.
When the two men were out on parole in 1919 they formed a gang with Charles Loerber, a getaway driver who posed as their chauffeur while they plotted their crimes. Chapman pretended to be an oil baron, and Anderson his business partner. The gang quickly seized the opportunities presented by Prohibition and began bootlegging in the Midwest, arranging confidence scams on the side.
In 1921 they branched out into armed robbery. They plotted the route of a U.S. mail truck that ran regularly along a street in New York’s Tribeca neighborhood. On Oct. 24, they blocked the mail truck with two cars, assaulted the driver and made off with $2.4 million in cash, bonds and jewelry – the biggest heist in U.S. history.
They should have lain low, but instead they committed a string of robberies in upstate New York. But robbing the post office is a federal crime, and federal investigators soon hunted them down.
3rd Time the Charm
An undercover postal inspector nabbed them when he bought stolen Argentine gold notes from Gerald Chapman. He and Anderson were tried and sentenced to 25 years in the Atlanta Federal Prison.
Gerald Chapman managed to escape after three tries. During his first attempt he tried to outrun a posse of 200 men, who shot him in the arm, kidney, hip and back. Six days later he escaped from Atlanta General Hospital, only to be captured again. After returning to the Atlanta penitentiary, he promptly broke out again and made a clean getaway in March 1923.
The press ate up the story of the Gentleman Bandit, and he paved the way for future celebrity gangsters like John Dililnger and Al Capone.
According to True Detective in 1929,
Newspaper feature writers used miles of typewriter ribbon on him, and ended by creating an idealized character which combined the daring of Jesse James, the ruthlessness of the apache, Clair Raoul, the suavity of Doctor Crippen and the ingenuity of the notorious Perugia, who committed the famous theft of the Mona Lisa.
Anderson escaped in December that year.
Death in New Britain
In the fall of 1924, Gerald Chapman and another man went on a crime spree in Connecticut. They were spotted trying to rob a New Britain department store, and five police officers rushed to arrest them. In the ensuing shoot out, Chapman killed Officer James Skelly and escaped. The police captured the other armed robber -- Walter Shean, the ne’er-do-well son of family from Springfield, Mass. Shean ratted out Chapman rather than hang for Skelly’s murder.
Gerald Chapman went into hiding at the farm of Ben Hance in Muncie, Ind. Three months later, Hance did his public duty and tipped off the police to Chapman’s whereabouts. Police arrested him sent him back to the federal prison in Atlanta.
Though the federal government had jurisdiction, the State of Connecticut wanted to try Chapman for murder. In March 1925 he was extradited to Connecticut State Prison in Wethersfield for a trial that would turn into a media circus.
Ben Hance and Walter Shean testified against Chapman, and the prosecution showed that spent cartridges from Officer Skelly’s body matched Chapman’s gun. Chapman denied he’d ever been in New Britain, knew Ben Hance or Walter Shean or that he was even Gerald Chapman. The jury deliberated for 11 hours and on April 4, 1925 delivered a guilty verdict. He was sentenced to hang by the ‘upright jerker.’
“Death itself isn’t dreadful, but hanging seems an awkward way of ending the adventure," Chapman said to his attorney after his sentence came down. The upright jerker was a flawed hanging method in which counterweights were dropped to pull the victim upward. Theoretically death resulted instantly from a broken neck, but in practice victims sometimes strangled slowly.
Chapman’s lawyers argued the state couldn't execute him because he had to first serve out his federal sentence. President Calvin Coolidge solved that problem by granting Chapman a pardon. Chapman appealed his sentence all the way to the U.S. Supreme Court, but the high court ruled against him.
Eight months later, Ben Hance and his wife were killed in revenge during a roadside ambush on the Anderson-Muncie Highway. Mrs. Hance died instantly, but Ben Hance lived long enough to finger Dutch Anderson and an accomplice. Police later killed Anderson in a shootout.
This story about Gerald Chapman was updated in 2018.