Criminal. He was called the "Count of Gramercy Park," and co-led a Prohibition-era gang with George "Dutch" Anderson during the late 1910s until the mid-1920s. While imprisoned in Auburn State Prison on a bank robbery charge, he became aquainted with George Anderson. Following both men's paroles in 1919, they began bootlegging operations in Toledo, Ohio, Miami, Florida and New York City, New York over the next two years. In late 1921, along with former Auburn inmate Charles Loeber, he and Anderson began committing armed robbery when, on October 21, the three men forced a U.S. Mail truck to stop at gunpoint on Leonard Street successfully taking with them $2.4 million in cash, bonds and jewelry. Eluding capture for more than eight months, the three were eventually arrested by New York police on July 3, 1922, after being betrayed by a police informant. He and Anderson were both sentenced to 25 years imprisonment at the Atlanta Federal Prison. He escaped on April 5, and later rejoined Anderson who later escaped on December 30, 1923. They were suspected by authorities to have committed several hold ups. While on a crime-spree in Connecticut, he murdered Policeman James Skelly of New Britain on October 12, 1924. He was then recaptured on January 18, 1925, in Muncie, Indiana, by informant Ben Hance. Both Hance and his wife would be found dead eight months later on August 11. Authorities suspected their deaths may have been attributed to Anderson as retribution for betraying Chapman to police. During his apprehension, Chapman fired at an officer but missed. During the six-day murder trial in Hartford, Connecticut, crowds gathered due to his status as one of the "top ten" criminals in America. The jury deliberated for eleven hours, after which Chapman was sentenced to hang. Although he proclaimed his innocence to the end, he was executed on April 6th, 1926. The killer was a popular and glamorous figure, as were many outlaws of his era. For years after his burial, women visited his grave with flowers.