 He was involved in petty theft as a teenager, referred to as "The Flying Dutchman", and was associated with the Greenthals and the Mandlebaums.In 1860, he was arrested after stealing a watch from a man at the corner of Broadway and Canal Street, presumably his first criminal act, for which he was convicted and spent two years in New York State Prison.During his time in prison, he became friends with noted bond robber Chauncey Johnson and joined his gang upon his release.