On Valentine's Day 1969, Jerry Rubin and fellow members of the Youth International Party (aka Yippies)—with financial help from Jimi Hendrix—mailed joints to 30,000 random Manhattan residents in order "to clear the garbage from the air." Accompanying each joint was a note debunking myths about pot's dangers.

The stunt made television news, and a broadcast journalist (with joint in hand) called the police on the air. They arrived, confiscated the joint, and told viewers, "Marijuana is a dangerous drug that can drive people insane."

Our attorney general is still peddling this nonsense.

That's one of many riveting incidents found in Pat Thomas's biography, Did It! From Yippie to Yuppie: Jerry Rubin, an American Revolutionary (Fantagraphics), revealing Rubin's paradigm-shifting approach to activism, which injected humor and theatricality into what traditionally had been worthy but dull actions. Thomas is reading from his book on Friday, October 20, at Elliott Bay Book Company.

Did It! is a coffee-table book packed with photos, documents, letters, and other ephemera that form a fascinating mosaic of Rubin's evolution from innovative leftist activist (leading the Yippies in the 1960s/early 1970s), to champion of self-help/human-potential programs (est, yoga, meditation in the mid to late '70s), to social networking early adopter (hosting business-card-exchanging salons in the 1980s, predating LinkedIn by decades).

Rubin makes an enthralling, enigmatic central figure: a Jewish ex-sportswriter from Cincinnati who was arrested for inciting a riot at the 1968 Democratic National Convention, who pranked the New York Stock Exchange by tossing dollar bills on the floor to watch brokers descend on them like jackals, who spearheaded the health-food movement, and who regularly hung out with John Lennon and Yoko Ono.

The real mystery is how such a notorious figure managed to fade from public consciousness. According to the book's author, people thought Rubin "sold out," the worst thing a 1960s radical could do.

"Jerry put on a suit and tie in the 1980s," Thomas explains in an e-mail interview. "He got written out of the history books in the 1990s, while [friend and fellow activist] Abbie Hoffman became canonized like a saint for still kicking against the pricks."

As years went by, Rubin, who died a millionaire in 1994, lost the cool luster that always adhered to the mythologized Hoffman—who lived underground for several years following a drug bust. The disparity in their reputations was part of what inspired Thomas to write the book.

"It's very much a McCartney versus Lennon type of thing," Thomas says. "One guy is considered a saint, and one guy isn't. I wanted to defend the underdog."

Rubin also figured in Thomas's last book, Listen, Whitey! The Sights and Sounds of Black Power 1965–1975. He wrote about the "synergy between the Black Panthers and the Yippies" and Rubin's friendship with Eldridge Cleaver. The Black Panthers resurface in Did It! at the trial of the infamous Chicago 8 (Rubin was one of them).

The revolutionary questions the book poses aren't just dusty old 1960s tropes. We're still wrestling with them today. Rubin came to believe that the best way to change America was by accumulating vast financial power to create a new establishment, because change can't come from below. Did this make him a cynic? A brutal pragmatist? Or, given that American politics now consists of a vicious meta-battle between George Soros and the Koch brothers, prophetic?

"Keep in mind, Jerry was born working-class," Thomas says. "He wasn't given a dime. So as he got older, he wanted what we all want: a nice house and a car. He also loved a challenge. So he enjoyed what it took to make that money, but most importantly he wasn't looking for military-industrial investments; he made money selling vitamins and health drinks! Rubin's speeches of the 1980s discussed forcing Burger King to hire more African American executives. When did the Koch brothers ever suggest that?!"

The more Thomas dug into Rubin's life, the more he realized the conventional wisdom about his subject as a betrayer of leftist causes was inaccurate. Like his Chicago 8 comrade Tom Hayden, Rubin simply became a tie-wearing Democrat.

"What surprised me is that Rubin had personal survival instincts," Thomas says. "When Nixon got reelected in 1972, Rubin became very depressed. Rather than start drinking and drugging, he turned to health food and yoga. He wasn't on Wall Street in the '80s selling stocks for Exxon; he was marketing green energy and solar panels, long before others were."

Of Rubin's many facets, his most important remains his work as a Yippie, Thomas maintains. The party fought "tooth and nail against LBJ's and Nixon's Vietnam War machine, using humor, rock 'n' roll, foul language, pranks, and theater." Their tactics—trying to levitate the Pentagon, introducing music and psychedelics into protests, media-savvy slogans, sowing disruption and chaos—seized the popular imagination and laid the foundation for Occupy and Pussy Riot.

One of Did It!'s outstanding contributions to political history is its emphasis on women's roles in the movement. Thomas says his interviews with activist Nancy Kurshan (Rubin's Yippie-era partner), key Yippie operative Judy Gumbo, and Yippie/Newsweek reporter Kate Coleman had the greatest impact on him during the writing process.

"Women were the backbone of the antiwar movement," he says. "They were generally egoless. They are successful survivors with their self-esteem intact." Thomas and his editor Kathy Wolf plan to write a book about them next.