Born in Seattle, Washington, Stroud ran away from his abusive father at the age of 13, and by the time he was 18, he had become a pimp in the Alaska Territory. In January 1909, he shot and killed a bartender who attacked his mistress, a crime for which he was sentenced to 12 years in the federal penitentiary on McNeil Island in Puget Sound. Stroud gained a reputation as a dangerous inmate who frequently had confrontations with fellow inmates and staff, and in 1916, he stabbed and killed a guard. Stroud was convicted of first-degree murder and sentenced to hang, but after several trials his sentence was commuted to life imprisonment in solitary confinement.