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As a youth, Cassady was repeatedly involved in petty crime. Brierly was well known as a mentor of promising young men and was impressed by Cassady's intelligence.
He was arrested for car theft when he was 14, for shoplifting and car theft when he was 15, and for car theft and fencing stolen property when he was 16. Over the next few years, Brierly took an active role in Cassady's life.
Cassady first met author Ken Kesey during the summer of 1962; he eventually became one of the Merry Pranksters, a group who formed around Kesey in 1964 who were vocal proponents of the use of psychedelic drugs.
During 1964, Cassady served as the main driver of the bus named Furthur on the iconic first half of the journey from San Francisco to New York, which was immortalized by Tom Wolfe's book, The Electric Kool-Aid Acid Test (1968).
Cassady also appeared in Allen Ginsberg's poems, and in several other works of literature by other writers.In a beachside house just south of Puerto Vallarta, Jalisco, they were joined by Barbara Wilson and Walter Cox.All-night storytelling, speed drives in Walker's Lotus Elan, and the use of LSD made for a classic Cassady performance — "like a trained bear," Carolyn Cassady once said.The couple eventually had three children and settled down in a ranch house in Monte Sereno, California, 50 miles south of San Francisco, where Kerouac and Ginsberg sometimes visited.Cassady traveled cross-country with both Kerouac and Ginsberg on multiple occasions, including the trips documented in Kerouac's On the Road.