RIDGE RUNNER CHRONICLES: Timothy Leary’s Infamous Prison Break

By Editor | July 7, 2026 |

If you routinely read my columns, you know that I often write about the 1960’s; my topics include the JFK assassination, the Viet Nam War and most recently, the story of Bernadine Dohrn and her life on the run. The 1960’s was the most meaningful period of my life and maybe yours too. But when we talk about the 1960’s, how can we ignore Timothy Leary, the “turn on, tune in and drop out” guy who was urging Americans to do drugs and drop out? I became curious about his life after learning that Bernadine Dohrn helped him escape from a California prison in September 1970. A biography about his life, entitled “I Have America Surrounded” by John Higgs, details a boatload of bizarre stories about this man. Unfortunately, I don’t have the space here to discuss them all but I will discuss one in particular—Leary’s infamous prison break. Maybe we can get to some of the other stories later.
In 1970, Leary was convicted of drug possession in California and sentenced to 20 years in the California prison system. He was then 50 years old, so in reality, this could wind up being a life sentence for Leary. When the authorities were trying to decide where to place Leary, they gave him the mandatory psychological test to determine where he would be the best fit in the California prison system. Unbeknownst to the California prison authorities, they gave him a test generally known among psychologists as “The Leary.” Yes, it was known as “The Leary” because it was Leary himself who had designed this test years ago when he was a psychologist at Harvard. He knew how to best answer this test if he wanted to be placed in the “best” prison. And because he gave all the “right” answers in the test, that is why he wound up at the minimum security prison at San Luis Obispo instead of at Folsom Prison or the other prisons where the hardened criminals were placed and escape is out of the question.
Once Leary arrived at San Luis Obispo, he immediately began scouting how he could possibly escape. He had to be deliberate in sizing up the physical structure of the prison because even staring too long at the fences could raise concerns among the guards. He finally realized that his best opportunity to break out would be to climb a wall and grab onto a telephone cable that extended from one of the buildings out beyond the border wall of the prison, a distance of more than 150 feet. This meant he would have to do this after dark and before bed checks. This also meant he would have to get himself in top physical shape to go hand over hand on that wire for such a long distance. In addition to getting in shape physically, he and his wife, who visited him in prison frequently, mapped out a plan to get him away from the prison grounds quickly once he dropped off the telephone cable beyond the wall.
On Sept. 11, 1970, Leary made his escape attempt shortly after dark. In a prearranged plan, Leary successfully “monkey-climbed the wire beyond the last prison wall, he dropped to the ground and was picked up by his co-conspiritors on the outside and whisked away in a van to northern California where, two days later, he was seated at a camp fire with Bernadine Dohrn. They were not there to roast marshmallows. They were there because Bernadine wanted Leary to go to Algeria and join forces with Eldredge Cleaver, the leader of the Black Panther Movement, so as to induce young white males to join in a planned, violent overthrow of the US government. The irony of this meeting was that J. Edgar Hoover had already declared Bernadine to be the most dangerous woman in the US and President Nixon, upon learning of the prison break, declared Leary to be the most dangerous man in the US and here they were, sitting together in front of a camp fire, taking LSD and planning their futures.
After this overnight meeting, Leary was secretly whisked to Algiers but his relationship with Cleaver soured pretty quickly. Cleaver wanted a revolution of the US government; Leary instead wanted a revolution of the mind through the use of psychedelics. Cleaver eventually “imprisoned” Leary in an attempt to get a ransom for Leary’s freedom but Leary escaped from Cleaver’s “prison” and fled to Europe and later to Afghanistan. He was eventually captured by US authorities in Afghanistan and returned to California, where this time he was sent to Folsom Prison. At Folsom Prison, he was placed in solitary confinement in a cell next to Charles Manson, and yes, they talked through the wall to each other. Eventually, Leary gained his freedom from Folsom by cooperating with the FBI in their attempt to hunt down and capture members of the Black Panther Movement.
Note: Leary was arrested more than 35 times in his lifetime. He was usually “safe” amongst other prisoners because many of them were also jailed for drug possession and they viewed Leary as a “comrade.” That changed when he became a “snitch.”
–––––––––––––––
■ Bill Hoagland has practiced law in Alton for more than 50 years, but he has spent more than 70 years hunting, fishing and generally being in the great outdoors. His wife, Annie, shares his love of the outdoor life. Much of their spare time is spent on their farm in Calhoun County. Bill can be reached at [email protected].