In September 1970, the Weather Underground helped Timothy Leary escape from a federal prison. It wasn’t a natural alliance. Leary was a hippie icon, but he usually kept the Left at arm’s length, preferring psychedelic spirituality to armed revolution. The Weathermen, meanwhile, came from the most Stalinist recesses of the New Left. Their heroes included Kim Il Sung and Mao Zedong, and their methods were aimed less at blowing people’s minds than at blowing people up.

Nonetheless, Leary played his new role with gusto, issuing a “P.O.W. Statement” that reads like a parody of revolutionary rhetoric. “Brothers and Sisters,” he wrote, “this is a war for survival. Ask Huey and Angela. They dig it. … To shoot a genocidal robot policeman in the defense of life is a sacred act.”

Less than six years later he wrote another essay, this one gracing the less Mao-friendly pages of National Review. It was an unrestrained attack on the ’60s and its celebrities. The Weathermen who rescued Leary were dismissed (accurately) as a “bewildered, fugitive band of terrorists.” John Lennon was accused (less accurately) of ripping off the slogan of Leary’s aborted gubernatorial campaign in California, “Come Together.” (In fact, Lennon had written “Come Together” to be Leary’s campaign song.) Pages of bile were directed at Bob Dylan and his “snarling, whining, scorning, mocking” songs. At one point Leary declared, “Squeaky Fromme stands in a Sacramento courtroom … for believing exactly what [Dylan] told her in the Sixties” and blamed her attempted assassination of Gerald Ford on the fact that “she was unlucky enough to have owned a record player in her vulnerable adolescence.”

In 1997, reviewing a hagiographic documentary called “Timothy Leary’s Dead,” I cited those two essays as evidence that Leary was “a con man at heart, the counterculture’s own Madison Avenue huckster.” Now that I’ve read Robert Greenfield’s Timothy Leary: A Biography, I feel a little less confident about that conclusion. The book paints a deeply negative portrait of Leary, but it also reminds us of the context that produced those extraordinarily odd pieces of writing. At the same time, it makes it clear that there was more than a little Madison Avenue in Leary’s DNA.

A decade before his jailbreak, Leary was a respected Harvard psychologist known for his work in personality assessment. He was also one of several researchers around the world who were exploring the effects and potential benefits of psychedelic drugs, which still were legal at the time. It gradually became clear that where other scientists tried to maintain their traditional objectivity, Leary was an evangelist eager to spread the good news of acid and shrooms. His new enthusiasm eventually led to scandal, and he happily left Harvard behind. Soon he was preaching the virtues of LSD to every audience he could find, even as the government and the media started to view the drug as the nation’s leading menace.

Scholars today generally regard the LSD scare of the ‘60s as a classic social panic. “Of all the widely used recreational drugs,” the sociologists Erich Goode and Nachman Ben-Yehuda note in their 1994 book Moral Panics, acid “is the one taken by users most episodically and occasionally, least regularly and chronically.” It certainly poses risks, but the most disturbing rumors about its effects—that it causes chromosome damage, that it prompts teens to blind themselves by staring at the sun—turned out to be false. What’s more, the media scare arrived at a time when LSD use was at a relatively low level; the hysteria actually faded as the drug grew more popular.

What’s fascinating is Leary’s relationship to that panic. Leary has written that his best-known slogan—“tune in, turn on, drop out”—was inspired by a lunch with the media theorist Marshall McLuhan, who told him, “You call yourself a philosopher, a reformer. Fine. But the key to your work is advertising. … You must use the most current tactics for arousing consumer interest.” According to Leary, McLuhan even broke into a jingle: “Lysergic acid hits the spot/Forty billion neurons, that’s a lot.”

Leary was known to take liberties when recounting his personal history, and the McLuhan story sounds a little too perfect to be absolutely true. But the very fact that he tells it shows he was aware of what he was up to, as does his famous claim in Playboy that LSD “is the most powerful aphrodisiac known to man.” In his book The Politics of Ecstasy, Leary commented that if the Playboy interview “had been conducted for Sports Illustrated, the conscientious interviewee would naturally consider the question, How LSD Can Raise Your Batting Average.” Greenfield adds: “In other words, had he been talking to Popular Mechanics, Tim would have claimed that LSD could rev up horsepower and reduce engine knock while doubling miles to the gallon. Clearly, Tim Leary knew exactly what he was doing. In America, nothing sells like sex.”

Leary’s pitches for psychedelics oversold their benefits just as the media’s scare stories oversold their dangers. His ad campaign helped fuel the panic and, in less obvious ways, was fueled by the panic itself. Both Leary and his enemies had a stake in the idea that the boomers were becoming the Acid Generation. As the press grew increasingly obsessed with LSD, Leary was willing to ride that wave as he offered a rival narrative of his own.

Sometimes, to be sure, he tried to put the breaks on the hysteria. In 1966, for example, when it looked like a ban on possessing LSD was on the way, he testified to the Senate that the government should instead create a closely regulated system for people who wanted to experiment with the drug. Greenfield chalks this up to Leary’s habit of telling people what they’d like to hear. A more charitable interpretation is that he saw the likely consequences of a black market and hoped to minimize the damage by convincing legislators to adopt a more liberal system of controls. There’s little doubt, though, that his ultimate policy preferences were more freewheeling: almost immediately after the Senate hearings, he was rolling out the “turn on, tune in, drop out” slogan in an address in San Francisco.

You can only ride a wave so far, and eventually Leary plunged into the surf. Busted on minor marijuana charges, he soon found himself facing 20 years in prison. There’s no doubt that it was his message, not his rather petty violations of the law, that earned him his stiff sentence. One judge declared, as he ruled that Leary should be held without bond, “He has preached the length and breadth of the land, and I am inclined to the view that he would pose a danger to the community if released.” When Leary attempted an appeal, a DA argued to another judge that imprisoning him would prevent him from spreading his “messianic ideas about psychedelic drugs to young people.” Like the bottled goose in the Zen parable, it was words that got Leary into jail, and it was words that would get him out again.

Hence the “P.O.W. Statement” and the screed in National Review. Those two essays were radically opposed not just to each other but to everything Leary seemed to stand for before his imprisonment. But they were written for the same reason: to win his freedom. As Leary’s friend Robert Anton Wilson told Greenfield, “The letter for the Weather Underground when they broke Tim out of jail was the dumbest thing he ever wrote. But that was the price of getting out of prison. Writing propaganda for the Weathermen.”

And the National Review piece? It came half a decade and several lifetimes later, after Leary had passed through a topsy-turvy exile in Algeria and Switzerland and returned to the American penal system. Passed over for parole, Leary wrote the story when he realized that, in Greenfield’s words, “unless he could persuade those in power that he really did hate the sixties, he might never get out of jail.” Sure enough, U.S. Attorney John Milano offered the essay as evidence to the parole board that the prisoner really was rehabilitated. In April 1976, the same month the article appeared, Leary was freed. (One of his books reprints the piece with all the ’60s-bashing excised and with a paragraph praising Dylan inserted instead. In the introduction, Leary apologized for his earlier tone: “at this time I was alienated, a bit daft and given to occasional fits of irritation … . I particularly regret my whining complaints about Bob Dylan.”)

Greenfield covers most of this in intense detail, but there are two substantial problems with his book. One is that Leary’s ideas are almost entirely absent from it. Leary could be wrongheaded or incoherent, but he could also be sharp-witted and prescient. Even his bizarre contribution to National Review had some genuine insights hidden among the bile. In a speech last year, Eric Garris, webmaster for LewRockwell.com and Antiwar.com, recalled an address Leary delivered at the 1977 convention of the Libertarian Party. In Garris’s words, the doctor described “a network that would connect computers worldwide, allowing participants from around the globe to sign on and retrieve text, photographs, audio and video instantaneously, and to communicate in realtime with anyone in the whole world who also had a computer and a connection.” At the time, Garris noted, “We figured Leary had just done a little too much acid and his imagination had gotten the best of him.” Turns out he was onto something.

Leary himself prefaced one of his books with a comment that only a third of the ideas in it were worthwhile. But at their best, his latter-day writings offered a cheerful, funny vision of a post-industrial future, like Alvin Toffler crossed with Cheech and Chong. You’ll find none of this material in Greenfield’s book, which prefers to quote Leary at his least lucid and which skips quickly through the last two decades of his life.

The other problem is Greenfield’s blinding disdain for his subject. There is, to be sure, a lot to dislike in the man. He could be selfish and astonishingly irresponsible, especially as a husband and a father; and there isn’t much to admire in his apparent willingness to snitch on former friends as he struggled to get out of jail. But there’s something odd about a biography that almost inevitably assumes, whenever Leary’s account differs from that of another witness, that Leary’s the one who’s lying. (At the same time, Greenfield is willing to swallow obviously self-serving stories when Leary’s memoirs are the only source available.)

This book alludes to Leary’s charisma, but it never demonstrates it. By the time it’s over, the average reader might be forgiven for asking why such a man ever attracted any followers in the first place. That’s a pretty big failure in a biography of a pop icon.

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Jesse Walker is managing editor of Reason and author of Rebels on the Air: An Alternative History of Radio in America.