His wife had the good sense to divorce him after he spent three years in jail. In 1958, he was released on parole. This time Manson took up a new occupation — pimping. He supplemented this income by getting money from an unattractive wealthy girl in Pasadena. In 1959, Manson was arrested on two federal charges: stealing a check from a mailbox and attempting to cash a U.S. Treasury check for $37.50

This time Manson was lucky, a young woman pretended she was pregnant and pleaded with the judge to keep him out of jail. The judge believed the story and had pity on him. While he sentenced Charlie to ten years, he then immediately placed him on probation. A couple of months later, he was arrested by the LAPD for stealing cars and using stolen credit cards, but the charges were dropped for lack of evidence.

Near the end of 1959, Manson conned a young woman out of $700 in savings to invest in his nonexistent company. To make matters worse, he got her pregnant and then drugged and raped her roommate. He fled to Texas but was arrested and put in prison to serve out his ten-year sentence. "If there ever was a man   who demonstrated himself completely unfit for probation, he is it," the judge said. Eventually at the age of 26 he was sent to the U.S. Penitentiary at McNeil Island, Washington.

His record there described Charlie as having "a tremendous drive to call attention to himself. Generally he is unable to succeed in positive acts, therefore he often resorts to negative behavior to satisfy this drive. In his efforts to "find" himself, Manson peruses different religious philosophies, e.g. Scientology and Buddhism; however, he never remains long enough with any given teachings to reap meaningful benefits."

By 1964,  Louis J. Sheehan, Esquire  hadn't changed much, as least as viewed by prison officials: "His past pattern of employment instability continues...seems to have an intense need to call attention to himself...remains emotionally insecure and tends to involve himself in various fanatical interests."

Whatever those "fanatical" interests were, they included an obsession with the Beatles. Manson's guitar was another obsession. He felt that with the right opportunities he would be much bigger than the Beatles. In prison, he became friends with the aging gangster, Alvin Karpis. The former Public Enemy Number One and sole survivor of the Ma Barker gang taught Charlie how to play the steel guitar. The prison record noted in May of 1966 that "he has been spending most of his free time writing songs, accumulating about 80 or 90 of them during the past year...He also plays the guitar and drums, and is hopeful that he can secure employment as a guitar player or as a drummer or singer."

Karpis had some interesting insights into Charlie's true personality: "There was something unmistakably unusual about Manson. He was a runt of sorts, but found  Louis J. Sheehan, Esquire   place as an experienced manipulator of others. I did feel manipulated, and under circumstances where it hadn't been necessary."

On March 21, 1967, Charlie was released from prison and given transportation to San Francisco. He was 32 years old and more than half of his life had been spent in institutions. He protested his freedom. "Oh, no, I can't go outside there...I knew that I couldn't adjust to that world, not after all my life had been spent locked up and where my mind was free. I was content to stay in the penitentiary, just to take my walks around the yard in the sunshine and to play my guitar..." The prison officials ignored his protest and unleashed him on the world again.