'Gentleman Bandit' Gerald Chapman, the First Public Enemy No. 1, Was Captured 100 Years Ago

Cornered by the police at a New Britain, Conn., department store he was attempting to rob, Prohibition-era mobster Gerald Chapman screamed, “Get down or I’ll kill you.” Then he fired three shots from his pistol, fatally wounding officer James Skelly in the abdomen. As Skelly lay dying, Chapman escaped.

That was October 12, 1924, and because of that cold-blooded murder, Chapman earned the moniker “Public Enemy No. 1” by the media and police–long before the phrase became commonplace in the 1930s for historic crime figures like Al Capone and John Dillinger.

Chapman was earlier nicknamed the “Gentleman Bandit” after learning how to fake his way in high society from Dutch Anderson, a criminal mentor he met while locked up at Auburn Prison in upstate New York. 

In between his 1919 release and his death by hanging in 1926, Chapman lived between the criminal underworld and high society, executing con jobs and daring bank heists in both the Big Apple and the nation’s heartland.

Before he became better known to the world as Gerald Chapman, he was born George Chartres in New York City on August 16, 1886. 

Chapman’s parents died of natural causes before he turned 11. He quickly became a criminal delinquent, and by the age of 21 had been featured in newspaper articles for resisting arrest, leaping from a second-story window and breaking a plate-glass window in an attempt to evade capture as police chased him.

After a first stint in prison, he was arrested again—but not before putting up a fight. He held his arresting officer hostage with his service firearm before getting choked by the landlady who owned the building where the altercation was taking place.

Chapman’s rise to international infamy coincided with the Prohibition era, which began in 1920, when alcohol was banned in the U.S.

Claire White, a historian and the director of education at the Mob Museum in Las Vegas, says Prohibition changed the economics of illegal behavior.

“You’ve suddenly got the biggest possible cash cow for anyone inclined to break the law,” White tells A&E Crime + Investigation. “Every mobster talks about how there is this gateway drug mentality. Once you realize how easy it is to get money illegally, it’s hard to get out of that mindset.”

After Chapman’s 1919 release from Auburn prison in Upstate New York, his criminal career took off. But unlike other notorious Prohibition gangsters, Chapman mostly used bootlegging “as a ruse to travel and scout out bank robberies,” according to historian David Bailey, author of Doctors Lawyers Swindlers Thieves: Gerald Chapman and the Tale of Two Gangs.

Soon he was planning what would become the biggest cash heist in American history. 

Chapman’s biggest coup was the 1921 robbery of a New York City mail truck. He started planning the heist with information from a former postal service employee about a U.S. mail truck carrying large amounts of cash regularly on an unguarded route in Midtown Manhattan, Bailey says.

After scouting the vehicle for weeks, the bandits staged their holdup and made off with more than $2 million (equivalent to more than $36 million in 2025). Most of it was in cash and there were some bonds and checks.

White says, “In that time, there were no Brinks armored trucks. Postal heists used to be very lucrative.”

Chapman and his accomplices were arrested two years later in large part because they left a paper trail for investigators by cashing checks they stole.

Chapman was convicted and imprisoned at a federal penitentiary in Georgia. Six months into his sentence, he escaped after cutting power to the prison. Authorities closed in on him the next day and he was seriously wounded by gunfire and hospitalized.

A week into his recovery, Chapman escaped out the hospital window, fashioning his bedsheets into a rope.

Chapman then spent more than one year on the lam—robbing banks, postal trucks and department stores before the Connecticut shootout led to his execution.

After the police officer was fatally shot, Chapman was arrested in Muncie, Ind., on January 18, 1925, convicted of murder for Skelly’s killing and sentenced to death by hanging.  But he could not be executed because he still had yet to serve his sentence for the postal truck hijacking. 

Following Chapman’s arrest and death sentence, he became an unexpected underdog figure—an everyman. 

The April 18, 1925, edition of The New Yorker magazine featured a story about him entitled “Our National Hero,” in which one woman declared, “Almost anyone could love this ratty little man.” The reporter editorialized that “killing a cop is not quite generally regarded as murder.”

According to the Hartford Courant, countless letters were written to the governor of Connecticut on Chapman’s behalf, with one declaring: “As long as the very rich can commit murder with almost a certainty of getting away with it I, for one, certainly do not believe in killing a man because he has not enough filthy lucre to employ a high priced lawyer.”

President Calvin Coolidge intervened by commuting Chapman’s sentence to the time he had already served so he could face the gallows. He was dead within five months, but many people who had rooted his criminal exploits did not approve.

White believes part of his appeal had to do with the social fabric of the United States, which “started as a group of rebels.”

“We were a group of people who didn’t like where we came from—whether it was the laws, religious persecution, famine, whatever,” White says. “This nation was founded by people bold and brave. So the idea of a person who can get it over on the banks or the post office, it’s very appealing.”