by Don Lattin
“Open your mouth and shut your eyes and I will give you a big surprise,” Owsley told Caroline, placing a tab of LSD into her mouth. “Come on. Let’s go meet a friend of mine.”
Owsley’s friend was Richard Alpert, who’d moved out to San Francisco after his falling-out with Timothy Leary and the rest of the old tribe back at Millbrook. Leary would soon follow Alpert out to the West Coast, but the infamous Harvard duo were merely the best-known members of a huge westward exodus. A tidal wave of East Coast refugees came to the San Francisco Bay area between 1965 and 1968. The region hadn’t seen anything quite like this since the days of the Gold Rush, back in 1849. Both events involved wild, outlaw migrations that attracted thrill seekers and people with nothing left to lose. More than a few of the midsixties migrants carried a little book in their backpacks titled The Psychedelic Experience: A Manual Based on the Tibetan Book of the Dead, written by Timothy Leary, Ralph Metzner, and Richard Alpert. The book, published in 1964, offered detailed flight instructions for initiation into the cult of LSD.
Alpert arrived in San Francisco and went straight to the Haight, just as the hippie revolution was taking form in this blue-collar neighborhood of dilapidated Victorians and struggling shops. Rents were cheaper than over in North Beach, where the edgy artists, Beat poets, and assorted hangers-on were losing their monopoly on hip. In Berkeley, on the other side of San Francisco Bay, the revolution was political and had a harder edge. It was mellow in the Haight. Golden Gate Park was just a few blocks away. Alpert offered his impressions in an article published in the Oracle.
“The Haight Ashbury is, as far as I can see, the purest reflection of what is happening in consciousness, at the leading edge in the society. There is very little that I have seen in New York, Chicago, Los Angeles, that is giving me the hit that this place is because it has a softness that is absolutely exquisite,” Alpert wrote. “We are human beings who are making a statement about how we are going to live our lives, gently and lovingly.”
On the night he met Caroline Winter, Alpert was at the Fillmore with Allen Ginsberg, who never seemed far from the sixties action. He had been there that night at the start of the Harvard Psilocybin Project. One night, stoned on the mushroom pills, Ginsberg tried to call John F. Kennedy from Leary’s house and inform the new president that world peace was at hand. That was the same night the gay poet tore off his clothes and threatened to run naked through the streets of Boston—a stoned messiah with a message of love. The beat icon was back at the Homer Street house a few months later, when Alpert had his first psychedelic trip on the snowiest night of the year. And here he was five years later in San Francisco, hanging out at the Fillmore. On this night, however, Alpert and Ginsberg were looking for something other than a rock concert. Alpert’s old pal from Millbrook, jazz trumpeter Maynard Ferguson, was performing over at the Playboy Club, so they decided to bring along Caroline Winter, who was just taking off on her very first LSD trip.
Caroline was sitting between Alpert, who was driving, and Ginsberg, riding shotgun. She was getting more and more stoned as they drove up and down the city’s precipitous hillsides. She grabbed hold of her escorts’ hands when everything started looking like it was upside down. Caroline was starting to freak out on this roller-coaster ride through the streets of San Francisco.
“This is too weird!”
“Don’t worry, baby,” Ginsberg said. “We are with you all the way.”
Caroline was blown away by the entire experience that night, and soon fell in love with Richard Alpert. Over the last decade, Alpert had had more lovers and sex partners than he could remember. Most of them were men, some of them were women, but Caroline was one of the few real loves of his life. For Caroline, however, the relationship with an infamous, older, bisexual man was intense and confusing. Meeting someone as strong and charismatic as Richard Alpert was overwhelming enough. But it was all happening in a supercharged, psychedelic state of mind. Later, as her relationship with Alpert was deepening, Caroline got the news that her father had died back in England from a heart attack. Suddenly, she felt desolate and bereft, but Richard was there to help her through the grief.
They became a couple, and the relationship got serious enough that Alpert decided to have Caroline meet his parents back in Newton. They drove all the way across the country in October 1966 in Richard’s antique Buick. Alpert’s parents were polite, but Caroline could tell they did not approve. They were glad to see that Richard had finally found someone, but couldn’t he do better than that? Caroline was more than a decade younger than Richard. She wasn’t Jewish. And to top it all off, she wore miniskirts. Mrs. Alpert did not approve of miniskirts. At the time, Alpert’s mother was battling cancer and had a greatly enlarged spleen. Caroline got the sense that the woman was not long for this world—that she wanted to spend time with her son and not with some stray girl he’d dragged in behind him.
Caroline and Richard became closer after Mrs. Alpert’s death. Both of them had lost a parent, and their shared experience deepened the bond. They rented an apartment in Manhattan for a few months, and even went up to Millbrook to see if Leary and Alpert could reconcile their estranged relationship. Tim and Richard tried to rekindle their friendship, tried to make it seem like the good old days, but Caroline could tell there was still a lot of tension between the two men. Leary presented a cheerful facade, but Caroline could see the tension behind the mask.
Not surprisingly, the Millbrook gossip centered on Alpert’s return. Not only was he back at the grand New York estate; he had shown up with this little hippie girlfriend. Caroline could see that many of Richard’s old friends were puzzled by her appearance and envious of the fact that she was so close to Richard. What’s so special about her? Oh, he’ll get over her once some young stud comes along. Caroline felt like she was on trial. She could see that their relationship was getting too complicated. At the time, Richard was attracted to both men and women. He and Caroline had agreed to have an open relationship. Caroline went along with the plan, but she was never really that comfortable sharing her love with any Tom, Dick, or Harry.
When Richard and Caroline showed up, Millbrook was in its final chaotic year. The place was so crowded that people were practically living on top of each other. Leary was struggling with mounting legal bills stemming from his December 1965 arrest in Laredo, Texas, when police found three ounces of marijuana hidden in the panties of his eighteen-year-old daughter, Susan. Four months later, a Texas jury saddled Leary with a thirty-year prison term. He was out on appeal when, just a month after that, in the wee hours of a Sunday morning, a squad of sheriff’s deputies raided the Millbrook mansion.
There had been a party the night before—dinner around low tables and cushions in the oak-paneled dining room. Bob Dylan, the Beatles, and Ali Akbar blasted from big stereo speakers. Leary and the woman in line to become his fourth wife, Rosemary Woodruff, passed around a pipe of DMT. Guests splashed blobs of colored paint on the mansion walls. Chromatic patterns undulated. Men with longish hair tended to a roaring fire while beautiful women danced about with yogic grace.
Outside in the bushes, an assistant district attorney peered into the windows with a pair of binoculars, fascinated with the psychedelic light show illuminating the house. Movies were shown of cascading waterfalls, kids jumping on trampolines in slow motion, men jumping out of airplanes, and other scenes designed to heighten the psychedelic experience. The D.A. in the bushes was none other than G. Gordon Liddy, a former FBI agent who had taken to using his first initial and middle name in imitation of his hero, J. Edgar Hoover. At first, Liddy thought the guests were watching pornographic movies. Then he realized there were no naked women in the films. But something very weird was going on in there. Sometime after midnight, Liddy and four Dutchess County sheriff’s deputies bounded up the stairs and into Leary’s third-floor bedroom. Leary and three other guests were arrested after the squad found a small stash of marijuana in one of the bedrooms. The charges were eventually thrown out of
court, but the publicity was a boon to Liddy’s law-enforcement career. Later, in one of the most delicious ironies in the amazing life of Timothy Leary, Liddy would be convicted as one of the burglars in the Watergate scandal that brought down the presidency of Richard Nixon, the same man who had called Leary “the most dangerous man in America.” Years later, to top it all off, Leary and Liddy would become friends and head out on the lecture circuit together—two ex-felons out to entertain an audience and sell some books.
Back in the sixties, however, Timothy Leary was at the top of G. Gordon Liddy’s hit list. Dutchess County sheriffs raided Millbrook a second time in December 1967 and charged their landlord and partner in crime, William Hitchcock, with conspiracy to create a public nuisance. By then, Leary and his fourth wife, Rosemary Woodruff Leary, had decamped back to the Learys’ old family home in Berkeley.
Leary and Alpert made frequent tours of the West Coast following their ouster from Harvard. In the fall of 1964, before their estrangement at Millbrook, they gave a series of lectures in San Francisco and Palo Alto where, according to a headline in the San Francisco Chronicle, they foresaw “A Day When LSD Is Like Aspirin.” Actually, they never said that. Leary told the Chronicle reporter that he thought the intellectual elite of the next generation would usher in greater use of psychedelic drugs, and the general population of the generation after that would use them to attain higher states of consciousness. Both Leary and Alpert warned that “unprepared” users could suffer destructive, rather than constructive, consequences from these drugs.
Following his ouster from Millbrook, in late 1965, Alpert went on a solo lecture tour across the United States. At an appearance in a San Francisco nightclub, Alpert paced back and forth across the stage, tossing off witticisms like a psychedelic Mort Sahl. In his more sober moments, Alpert told the crowd that LSD can produce “a religious experience without any significant side effects on the human body,” but, once again, he warned against “injudicious use of the drug.” After the lecture he took questions from an audience that included aging beatniks, protohippies, and other seekers of truth. It was a stump speech, but one that almost never got delivered. Earlier that same day, Alpert had been tripping on a beach south of San Francisco and had lost track of time. He barely made it to the club, and when he arrived, he was still very stoned. He still had this very pleasant, oceanic feeling—so much so that when he looked out into the crowd, the audience members appeared as a wonderful school of colorful fish. Alpert was laughing a lot that evening, and the levity was infectious, but few people in the crowd realized that they were the butt of Alpert’s private, hallucinogenic joke.
During the question-and-answer period, one very earnest looking fish/man stood up and addressed Alpert. It was a very technical question about endorphins, brain chemistry, and mental functioning. Alpert couldn’t focus on the words, which started bubbling from the mouth of the fish/man like he was in some cartoon. At one point, Alpert noticed that the word bubbles had stopped coming out of the fish/man’s mouth, and that he was standing there in the audience waiting for some kind of answer. There was a long pause. Alpert looked at the man, trying to get beyond all the words, but all he could see was a sweet and somewhat insecure fish standing there asking, “Do you love me?”
“Yes,” Alpert answered. “I love you.”
The crowd roared with laughter.
Next question.
At the time, Alpert was doing more than just lecturing about LSD. He was also transporting large quantities of the drug. He’d not yet come to the realization that LSD was too powerful to be played with in such a haphazard way. He was still telling himself that everything would be fine if his love went out with the acid. No one would be harmed. But Alpert was no longer personally directing psychedelic sessions whose love and safety he had control over. He certainly knew about bad trips. He had had some wicked ones himself. If he’d really stopped to think about it, he would have had to admit that he couldn’t really control what happened after he passed along a shipment. Whom was he sending love out to? The distributor? People he’d never even meet?
At least he knew it was good acid. Alpert’s supplier was Owsley Stanley. Owsley’s LSD was unveiled at a series of “Acid Tests” staged in 1965 by the novelist Ken Kesey and his band of Merry Pranksters—events that lead up to the Trips Festival at San Francisco’s Longshoreman’s Hall in January 1966. Back at Harvard, Leary and Alpert had become infamous for their LSD research, but that campaign was cautious compared with the crusade waged by Kesey and the Pranksters. Hundreds, and then thousands, gathered in backyards, halls, and auditoriums around the Bay Area to drop acid, dance, and revel under psychedelic light shows that were fast becoming the stock-in-trade of such gatherings. Jerry Garcia, the lead guitarist with the Grateful Dead, was crowned “Captain Trips.”
Something new was happening. These weren’t just rock concerts. This was something else—more like a three-ring circus with a very thin line between the audience and the performers. One of them, eighteen-year-old Dan Millman, dove off a balcony, somersaulted under strobe lights, and rebounded off a concealed trampoline. Nearly everyone—on and off stage—were blasted out of their minds, so many of them weren’t sure just what to make of the flashing figure flying through the air. (Years later, Millman would reappear as the bestselling author of The Way of the Peaceful Warrior and other New Age books.) Jerry Garcia would suddenly stop playing his guitar, staring down in amazement as strange sounds came out of speakers that weren’t even hooked up. Before his eyes, a maze of cables and wires turned into a den of writhing snakes. Poetry and other pronouncements echoed from a series of speakers set up around the hall. Kesey and company hooked up tape recorders and tape loops with strange sound delays. It made you believe in magic, far-out beautiful magic.
Two watershed events in late 1966 and early 1967—the Love Pageant Rally and the Human Be-In—would follow the Trips Festival and usher in the Summer of Love, when it seemed like the whole world came to San Francisco in search of peace, love, and another way of living. The Love Pageant Rally was held on October 6, 1966, the day LSD became illegal in California. More than two thousand people gathered in the Panhandle of Golden Gate Park, where they danced to the music of the Grateful Dead and Big Brother and the Holding Company, a local band who were featuring their new singer, a girl from Texas named Janis Joplin. The event was announced on the back page of the first edition of an underground newspaper called P.O. Frisco. The rally was the brainchild of a small band of writers and musicians who had observed a group of angry, sign-carrying hippies demonstrating outside of a San Francisco police station, protesting the recent bust of their commune. Who needs this endless confrontation with authority? Let’s try something else. Let’s change the world with celebration, not confrontation. Let’s party!
P.O. Frisco was a mess of a newspaper, but it blossomed into the legendary Oracle, which featured idealistic explorations into the personal experience and social implications of mind expansion. The Oracle was right there at the dawning of the Age of Aquarius, when a new generation began its grand experiment with Native American shamanism, Eastern mysticism, communal living, utopian revolution, sexual liberation, and ecological awareness. The rainbow newspaper, filled with the swirling and twirling calligraphy of psychedelic art, left behind the source documents for an eclectic spirituality and social philosophy that still exerts a widespread—albeit subtle—influence on American society.
P.O. Frisco published its first edition on September 2, 1966. Its lead columnist was none other than Richard Alpert, who offered readers his personal reflections on the intricacies of LSD intoxication. Alpert was living in Berkeley at the time with Caroline Winter. He was still struggling with the “old Richard Alpert” and had not yet given birth to the man who would be Ram Dass. He started his column with a confession: “There are times when I am afraid to take LSD because I am so hung up, so paranoid, distrusting, guilt-ridden, caught up in the ego tentacles of power, greed and lust.” He ended his ar
ticle with a vision of a time when people “will be high more of the time whether using or NOT using psychedelic chemicals,” when people are “so ecstatically involved in our Here and Now life that we hardly have time to take drugs anymore.”
Teacher: Marin County, California Summer 1966
It was all too far-out for Huston Smith, the MIT philosophy professor and ordained Methodist minister. He’d come to San Francisco not with flowers in his hair, but to deliver a well-reasoned paper at a reputable academic conference. Huston’s paper was titled “The Religious Significance of Artificially Induced Religious Experience.” A preconference party was to be held at a mansion in Marin County, the woodsy suburb across the Golden Gate Bridge from San Francisco, where the hosts hoped to provide some appropriate music.
They hired the Grateful Dead.
About two hundred people gathered on the grounds and around the swimming pool of an estate nestled in the foothills of Mount Tamalpais. Paul Lee, one of the conference organizers, surveyed the scene and could hardly believe his eyes. There were all sorts of people in the crowd—grandfathers, grandmothers, parents, children, teenagers—and many of them were running around naked. Owsley, adorned in a powder blue jumpsuit, was in the house handing LSD out to anyone who wanted it. He spotted Lee, a large man, and walked up to him.
“Wow, man,” Owsley said. “You have such a friendly and familiar face.”