Home Connecticut Gentleman Gerald Chapman, Connecticut’s Celebrity Gangster

Gentleman Gerald Chapman, Connecticut’s Celebrity Gangster

0 comment

Gerald Chapman, Prohibition’s celebrated “Gentleman Bandit,” might have escaped the gallows if he hadn’t gone on a crime spree in Connecticut.

Gerald Chapman. Photo courtesy Boston Public Library, Leslie Jones Collection.

Gerald Chapman. Photo courtesy Boston Public Library, Leslie Jones Collection.

While in prison, Gerald Chapman found a mentor who taught him that dapper dress and good manners 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 and frequented expensive nightclubs. He even affected a British accent.

Newspapers nicknamed him the “Count of Gramercy Park” and the “Gentleman Bandit.” He was the first celebrity gangster and the first criminal the press dubbed “Public Enemy No. 1.”

Gerald Chapman

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 his transfer to Auburn Prison.

Anderson’s real name was Ivan Dahl von Teler. Born into a wealthy Danish family, he attended Heidelberg and Uppsala universities. Then he dropped out of the University of Wisconsin to take up crime. Anderson saw in the younger Gerald Chapman someone who had enough smarts and daring to commit big-time heists.


Gerald Chapman in his Wethersfield prison cell. Photo courtesy Boston Public Library, Leslie Jones Collection.

Gerald Chapman in his Wethersfield prison cell. Photo courtesy Boston Public Library, Leslie Jones Collection.

When the two men were out on parole in 1919 they formed a gang with Charles Loerber, a getaway driver. He 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. They also arranged 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 and assaulted the driver. Chapman and his gang 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 then managed to escape after three tries. During his first attempt he tried to outrun a posse of 200 men. They 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. Chapman paved the way for future celebrity gangsters like John Dillinger 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

Gerald Chapman with his attorneys. Photo courtesy Boston Public Library, Leslie Jones Collection.

Gerald Chapman with his attorneys. Photo courtesy Boston Public Library, Leslie Jones Collection.sp

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 a wealthy 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 Chapman and 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. His trial would turn into a media circus.


Dutch Anderson 'Wanted' poster.

Dutch Anderson ‘Wanted’ poster.

Ben Hance and Walter Shean testified against Chapman. The prosecution also showed that spent cartridges from Officer Skelly’s body matched Chapman’s gun. Chapman denied he’d ever been in New Britain. He also denied knowing 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 then said to his attorney. The upright jerker, a flawed hanging mechanism, dropped counterweights 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.

Chapman was hanged until he was dead shortly after midnight on April 6, 1926.

Eight months later, Ben Hance and his wife were killed in revenge. They fell victim to 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 2022.

Subscribe To Our Newsletter

Join our mailing list to receive the latest artciles from the New England Historical Society

Thanks for Signing Up!

Subscribe To Our Newsletter

Join Now and Get The Latest Articles. 

It's Free!

You have Successfully Subscribed!