Gerald Chapman was born George Chartres in August 1887 to parents of Irish heritage. Arrested for the first time in 1902 at age fourteen, Chapman was incarcerated for most of his early adult life. While serving time for bank robbery, he was transferred from Sing Sing to Auburn State Prison, and became acquainted with highly educated Danish-born con man George "Dutch" Anderson in 1908. With Anderson as his mentor, Chapman became a voracious reader and a self-styled gentleman, often affecting a British accent. Following both men's paroles in 1919, they began bootlegging operations in Toledo, Miami and New York City over the next two years.