Sutton became a criminal at an early age, though throughout his professional criminal career, he did not kill anyone. He was described by Mafioso Donald Frankos as "a little bright-eyed guy, just 5'7" and always talking, chain-smoking ... cigarettes with Bull Durham tobacco." Frankos stated also that Sutton "dispensed mounds of legal advice" to any convict willing to listen. Inmates considered Sutton a "wise old head" in the prison population. When incarcerated at "The Tombs" (Manhattan House of Detention) he did not have to worry about assault because Mafia friends protected him. In conversation with Donald Frankos he would sadly reminisce about the 1920s and 1930s when he was most active in robbing banks and would always tell fellow convicts that in his opinion, during the days of Al Capone and Charles Luciano, better known as Lucky Luciano, the criminals were the bloodiest. Gangsters from the time period, and many incarcerated organized crime inmates, enjoyed having Sutton for companionship. He was witty and non-violent. Frankos declared that Sutton made legendary bank thieves Jesse James and John Dillinger seem like amateurs.