Married and plagued by financial issues, in 1957 he tried to rob a Bakersfield roadhouse, was caught and arrested. Convicted, he was sent to the Bakersfield Jail. After an escape attempt he was transferred to San Quentin Prison on February 21, 1958. There he was prisoner number A45200. While in prison, Haggard learned that his wife was expecting another man's child, which pressed him psychologically. He was fired from a series of prison jobs, and planned to escape along with another inmate nicknamed "Rabbit" (James Kendrick) but was convinced not to escape by fellow inmates.