While escaping from prison, Timothy Leary took time to troll Ronald Reagan

While escaping from prison, Timothy Leary took time to troll Ronald Reagan

An FBI account of Leary’s escape uncovers a few embarrassing details for the then Governor

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Edited by Beryl Lipton

While Timothy Leary’s 1970 escape from a minimum security prison in California with the aid of The Weathermen is the stuff of countercultural legend, recently released Federal Bureau of Investigation files reveal a lesser-known detail of the incident: Leary’s ruthless trolling of then-Governor Ronald Reagan.

Uncovered by Paul Galante as part of our ongoing effort to crowdsource Reagan’s file, the anecdote is part of the Bureau’s investigation of The Weathermen. In January of 1971, an as-yet redacted individual with ties to the group was giving a talk to a group known as “Strategic Hamlet” at the University of California at Berkeley, and at least one FBI Special Agent was in attendance.

The individual had recently met with Leary and his wife in Algeria, where Leary had fled after his escape.

(Leary’s “psychedelic” decor had apparently left an impression.)

During the visit, Leary had given his personal account of his prison break, which the individual repeated for the audience. Leary had been sentenced to 10 years for marijuana possession and was in the process of appealing a second 10-year federal sentence, also for marijuana possession. Leary had intentionally distanced himself from his contrarian reputation and cultivated the image of the model prisoner, and it had paid off: he had convinced the authorities that “the most dangerous man in America” wasn’t a flight risk.

Among the doubters was Reagan, who, unfortunately for him, had made public statements to that effect. According to Leary’s account, he kept a newspaper clipping of Reagan defending his decision to keep Leary under minimal security and, on the night of his escape, he left the clipping - with Reagan’s remarks helpfully underlined in red - so they would be discovered the next morning.

Unsurprisingly, that detail didn’t make it into the official account of Leary’s escape.

Reagan wasn’t alone in regretting taking Leary at his word. A pair of police officers, at Leary’s advice, had apparently delayed his transfer to Monday so they could have the weekend off.

While it’s easy to chalk up this story up to some secondhand embellishments from a source that is itself a known embellish-er, it’s worth noting that Leary’s own version of the actual escape part of his escape is decidedly lacking in greatness. While some accounts try to paint Leary as some sort of action hero with a PhD, Leary’s version sounds exactly like what you’d expect from a 45-year-old academic trying to hop a fence.

Read the full account embedded below and the rest of Reagan’s file on the request page. Thanks again to Galante for finding this through the crowdsource; if you’d like to help out yourself, click here or via the button below.

*Image by Brian Crawford via Flickr and is licensed under CC BY-SA 2.0