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Rosemary Woodruff Leary was once a one-named media heroine married to one of the most infamous men of all time, the ex-Harvard psychologist and high priest of LSD, Timothy Leary. Now she’s a footnote — barely acknowledged if mentioned at all in the history of the counterculture and psychedelic renaissance of the 1960s. But my goal is right this wrong and make the world aware of Rosemary’s contributions to the culture with my book The Acid Queen, out on April 22nd.
Rosemary helped Timothy craft his most enduring slogans — “All my best lines come from Rosemary,” Timothy once said. She sewed his clothes, edited his speeches, inspired some of his most out-there beliefs, went to jail for him, ran for political office with him, and, most crucially, helped orchestrate his infamous prison escape in 1970. Here is an excerpt of the drama that led up to that fateful night that would force her underground and into the shadows.
On March 2, 1970, in Houston, Judge Ben Connally sentenced the smiling psychologist and “hero of American consciousness” Timothy Leary to 10 years in prison and a $10,000 fine for marijuana possession. “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,” Connally said.
Ten years.
The vastness of the number stunned his wife, Rosemary. Ten years meant no children. Ten years meant no house in the woods. Ten years was three times the length of their marriage, twice as long as they’d known each other. A lifetime, really. Her legs buckled.
An Associated Press reporter, one of the many national news outlets now covering the trial, documented how stricken Rosemary appeared.
Ten years.
Then another shock: no bail pending appeal. The court based the decision on Timothy’s persistent advocacy of narcotics, recent arrest in Laguna, and the dual drug-related deaths of Charlene Almeida and John Griggs. “Whether or not Leary bears any liability at law for these deaths, these persons would, as a matter of simple, factual cause and effect, in all probability have been alive today had Timothy Leary not been at large during the latter part of the year 1969,” the bail denial report read. Outside the courtroom, Rosemary’s black long-sleeved minidress hung off her body. She wore the League for Spiritual Discovery’s beaded LSD medallion necklace and rose-colored bug-eye sunglasses that highlighted the redness around her eyes. Her hands shook as she read aloud the statement Timothy had scrawled on a piece of ripped-out notebook paper. “These are the times,” Timothy had written, paraphrasing Thomas Paine, a British philosopher who supported the American Revolution, “which test the depth of our faith, trust, and patience. Love cannot be imprisoned.” The word “faith” was nearly unreadable, smeared by Rosemary’s tears. Facsimiles of the note appeared the next day in the underground press with the parts where her tears had fallen highlighted for effect. The headline read, Rosemary wept.
“What do you plan to do?” a reporter asked her.
“I plan to use every means to free my husband and myself and our son and our brothers and sisters from the strictures of these laws, which deny our rights as guaranteed to us under the Constitution. I feel that Judge Connally is right: My husband is a menace. We are all menaces to the community which makes a mockery of the Constitution of this country.”
Five days later, the judge sentenced Rosemary to six months in prison with five years’ probation for marijuana and LSD possession. She was released on appeal bond. Jack would begin a compulsory ninety-day psychiatric evaluation in the California Institution for Men in Chino, a rough place known to be brutal to younger inmates for the same possession charges. The sentences were light compared with what would befall Timothy Leary.
Timothy’s Laguna sentencing followed. Groups of hippies answered Rosemary’s invitation and flocked to the courtroom. They adorned Timothy’s defense table with pink and white carnations, red roses, and two orchids, led prayer and drum circles outside, and chanted inside the courtroom — an unintentionally similar spectacle to that of the Manson Family trial. At various points, the judge threatened to throw the crowd out for being too rowdy. At least one person declared how high he was on LSD.
The Orange County judge Byron K. McMillan stood before them all and laid down the hammer: Leary was “a pleasure-seeking irresponsible Madison Avenue advocate of the free use of LSD and marijuana.” Judge McMillan denied Leary’s bail request and sentenced him to the maximum: another 10 years.
Rosemary examined her face in miniature in the pools of Timothy’s eyes. After denials of visits based on her own criminal record, an airline employee strike, and then, finally, a postal workers strike, which prevented written communication from reaching Timothy for days, she was finally able to visit him on March 19, 1970, for the first time in two interminable weeks at the California Institution for Men in Chino.
In the visiting room, the gray hue of the fluorescents gave his face a shadowy, forlorn quality. His eyes were red. She had never seen him cry before. Rosemary grabbed for the phone as they made fish faces at each other. Their phones hadn’t yet connected.
They placed their hands on the glass, fingertips to fingertips, palm to palm. “Here you are with me always,” she wrote to him upon her return home. “I feel you inside myself, my very self.”
When the phone finally cracked back to life, she heard his words: “You’ve got to free me. You’ve got to get me out of here.”
Rosemary tried to tell him about the lawyers and the fundraising and the media, but he interrupted her. “Don’t trust the lawyers. You’ve got to free me. You do it.”
“How?” she asked.
“I don’t care how.”
“I will,” she said. She was crying now, too. “I will free you, my love.”
ROSEMARY’S EXISTENCE OSCILLATED between prison visits and a coordinated effort to raise awareness and funds and galvanize grassroots support for Timothy’s defense: interviews with television shows, local radio stations, and underground newspapers, inquiries into Timothy’s literary estate and opportunities for more writing and movie deals, making sure she paid the water and electricity bills on time while also checking on Timothy’s children. The right side of her face flared red with acne thanks to the hours spent on the phone as she racked up $400 monthly telephone bills. Rosemary joked that she deserved a “Stand By Your Man Award.”
Owing to the draconian length of Timothy’s sentencing, and also to Rosemary’s newfound mediagenic powers, the vast majority of outlets sympathized with the Learys. The papers ran full-page appeals for Timothy’s defense fund signed by John Lennon and Yoko Ono, Allen Ginsberg, and the Magnificent Seven actor James Coburn.
She met reporters at the redbrick Victorian law office of Kennedy & Rhine, which was handling Timothy’s Laredo appeal. The location of her media interviews telegraphed her revolutionary state of mind.
Michael Kennedy, a sandy-haired and handsome 33-year-old superstar lawyer of the political left, shared Timothy’s innate distrust of authority, prided himself on attracting clients who, as he put it, were “anyone who the government didn’t like.” The New York Times christened him the “patron lawyer of unpopular causes,” and his philosophy seemed to be that if you weren’t pissing off people in power, you weren’t doing your job.
Rosemary bonded with Kennedy’s larger-than-life second wife, Eleanora, who was almost a decade younger than Rosemary, but acted as her fairy godmother, sprinkling money and sisterly advice. Eleanora was once a buyer for Saks Fifth Avenue department store so she knew how to ensure that Rosemary presented as gracefully as possible while hopscotching around the country to raise money.
The San Francisco Chronicle christened her “the surrogate monarch of psychedelia.” She educated The New York Times on the foundations of their religion: “The proper place to experiment with new substances is one’s body. You shouldn’t violate someone else’s body, either a patient or a guinea pig. All Tim has done in the last few years is publish the results and findings of those experiments on himself.”
The smitten male interviewers seemed content to let Rosemary frame her story. During one recorded interview, she told a Berkeley Barb reporter what the headline of the piece should be: no time to turn on or a saint in chains. (Newspaper editors chose the latter.)
Rolling Stone published two profiles of Rosemary, describing her as “the Public Figure.”
She had learned from Timothy how to use her innate talent for quips to manipulate an audience and spin a media narrative. Timothy even called her “the media heroine, the grass widow.”
“She’s so mellow, Rosemary Leary. You know how on acid things come to you in waves? Well, that’s how Rosemary comes on. But the waves are gentle, more like ripples on a placid lake,” the reporter Rick Heide wrote in the Berkeley Barb.
And she wielded Timothy’s time-tested Marshall McLuhan route of communication: positivity. “We’re rarely afraid,” she told them, “and Tim never. Tim seems very serene and relaxed. He’s been practicing a great deal of yoga these days.”
As the philosopher Irwin Edman wrote, “It is myth, not mandate, a fable, not logic by which people are moved.”
ROSEMARY’S EFFORTS IN FRONT of the camera to drum up interest and raise money for Timothy’s defense distracted from a second, secret strategy underway, which offered the most cinematic solution to Timothy’s legal woes: a prison break.
The theater of the absurd that followed in the late spring and summer of 1970 blended melodrama with mythology — where the primary actors barely touched center stage, hiding in plain sight, while the understudies took on starring roles in Timothy’s escape.
The first step toward freedom occurred with Timothy’s prison transfer from Chino to California Men’s Colony (CMC), a minimum-security facility for elderly, nonviolent prisoners. After nearly two months of incarceration, prison psychiatrists had allegedly used Timothy’s own Leary Circle personality test from his pre-psychedelic era as a research psychologist on its creator. Timothy knew what to say to make the psychiatrists view him as a nonthreat — a doddering, middle-aged hippie with no fight left in him. The results led them to approve a relocation to CMC’s much cushier institution of golf courses and vegetable gardens. CMC also allowed for unsupervised visits, which meant that he and Rosemary could embrace and speak freely in private.
Rosemary hitchhiked to the prison wearing a simple crepe and silk shawl to comfort her husband, brushing aside fears about the Zodiac Killer operating in the area. Timothy immediately started whispering plans of escape in her ear.
He asked Rosemary to hire a helicopter with a grappling hook to scoop him out of the prison yard. Or maybe she could somehow get her hands on a yacht waiting offshore to ferry him away? Or a submarine? Rosemary’s dual role was to carry on his legacy on the outside and reconcile his fantasies with reality on the inside. She reminded him how many naval and army bases surrounded them. “I mean, I was a superwoman living on carrot juice in those days but even so I wasn’t able to manage things like that,” she said. She still held on to a shred of hope that they could do this legitimately — without breaking any more laws.
MICHAEL AND ELEANORA KENNEDY WOULD later insist that they had nothing to do with orchestrating or executing the escape. Kennedy’s close friend and sometime co-counsel Michael Tigar wrote in his own biography that Timothy later pointed a finger at Kennedy, calling him the mastermind, in order to seek revenge after their future falling-out. Rosemary remained mum about the Kennedys’ involvement, though there are references to secret meetings with them all over her letters.
Here are the facts: Michael Kennedy provided legal counsel for all three escape conspirators — the Learys, the Brotherhood of Eternal Love, the so-called “Hippie Mafia,” and the Weather Underground, a militant group of far-left Marxists— and he is the one conceivable linchpin among them.
Bill Ayers, a key member of the Weather Underground, recalled that Kennedy acted as middleman between the Brotherhood of Eternal Love and the Weather. “We met with Michael one day and he said, ‘These folks are interested in getting Tim Leary out of prison, and they wondered if you all would be interested in helping if you had any capacity to do that?’” Ayers said. The Kennedys themselves even admitted to deploying less than aboveboard tactics for special clients. “We helped the Weathermen in any way we could,” Eleanora said in a documentary later, “legal or illegal.” “We do our best work in the dark,” Michael added.
Motivations aligned, however unlikely, for the Weather Underground, who were enticed by the potential for unrest, the publicity, the training for other future prison breaks, and $25,000 in a paper bag supplied by the Brotherhood and exchanged on the Santa Monica Pier.
ON SEPTEMBER 1, ARIES — the astrological sign of the ram, the perfect code name for pugnacious Michael Kennedy — alerted Rosemary that a member of the Weather Underground would be in touch. In the meantime, she should pack and be ready to depart at a moment’s notice and await a call to meet in person — no details shared over the phone they all knew was tapped. Rosemary endeared herself to the Underground contact with one demand: “I need two pounds of red henna hair dye from Kiehl’s.”
“Rosemary made a big impression on us,” Jeff Jones said. When Jones changed his identity years later, he ran into other members of the Underground, also underground, shopping at Kiehl’s. Give up your identity, sure, but not Kiehl’s naturally scented soaps.
With that edict approved, Rosemary connected with Bernardine Dohrn, whom Rosemary called Pam, and visited a wig store in San Francisco. Rosemary tried on a feathery Keith Richards number that reminded her of a fancy bird plumage. Too stylish. Bernardine picked out a blond one, curled and short like June Cleaver, a typical Eisenhower-era housewife. When Rosemary put on the wig and looked in the mirror, she saw her midwestern cousins staring back at her.
Rosemary adjusted her new wire-rimmed glasses. Her scalp itched under the wig hair. “Oh lord must I look this way? Fresh from the beauty shop plastic lady. The longer I looked the less I liked her,” she wrote. They bought a push-up bra and a smart short dress. She called herself Miss Priss.
Bernardine and Rosemary visited a department store where a clueless salesgirl helped Rosemary, in her new wig, apply makeup — orange-pink lipstick that worked in all the wrong ways, dark brown eye pencil, and false eyelashes. Rosemary hadn’t worn this much makeup since her modeling days.
She made up a story about this new face in the mirror. Sylvia was a 28-year-old, good little Catholic girl who had only just moved out of her parents’ house. She worked as a secretary at a law firm and was having an affair with an executive. This, Rosemary could work with. She couldn’t believe how easy it was for her to slip into another person’s life. Rosemary then boarded a plane to Chicago to secure identification. The Weather Underground had already supplied Rosemary with a birth certificate from a child who had died in infancy named Sylvia E. McGaffin — a particularly ghoulish detail considering she was putting off the second phase of her fertility surgery to leave the country with Timothy. A new name mired in loss.
With a birth certificate, you could forge a new identity — a laminated student card, a library card, a driver’s license, and then, ultimately, a passport.
The import of this moment — the finality of truly giving up herself — came to her here, in full disguise as Sylvia, in the passport office inside the coldly modern steel federal building in downtown Chicago. All the humor and excitement of the previous day gave way to a feeling of emptiness. This was it. She filled out the forms using national holidays for her parents’ birthdays so that she could remember the answers if questioned.
Rosemary restrained herself from scratching at her wig. The other selves — the women that she might have been, the lives that she could have lived — suddenly passed through her mind’s eye: finishing a shift at a bakery, loading books on the shelves of a local library, waiting for her professor husband to come home after a day of lectures, holding her babies, riding a bicycle to her house near the shore. I want to go home, she thought. But home didn’t exist anywhere. Not anymore.
“I was now a fugitive,” she wrote.
An officious woman talked on the phone and held her hand up as a sign for Rosemary to wait. The woman lowered the phone and lifted her eyes and said, “Name, please.”
Rosemary felt her cheeks flush. Her mind faded to black. Her name. Her name. What was her name! She couldn’t conjure any appropriate words. She felt the sweat form around her brow and found herself flailing, literally. She had thrown her bag into the air. A diversion. Not a graceful one, but it gave her a beat. As she collected her things, she bent down to pick up the contents on the floor, praying that her brain would start working again. Think.
As she stood up, the words found her: “I am Sylvia McGaffin.”
ROSEMARY MADE AN APPOINTMENT to see a dentist, a luxury that would not be available on the run. She had already said her goodbye to Timothy in person. His final prison letter to Rosemary read, “Sunday . . . perfect . . . perfect . . . perfect . . . what fun to see your mind in action . . . your metamorphosis.”
She returned his letter with a coded message giving the green light to the escape by using her fertility surgery as shroud:
BELOVED,
OPERATION TOMORROW DOCTORS FEEL BEST NOT TO WAIT TOTALLY OPTIMISTIC ABOUT SUCCESS AND NEW LIFE DON’T WORRY I’LL BE BRAVE WON’T BE DOWN TO VISIT SUNDAY BUT WE’LL BE TOGETHER SOON I AWAIT YOU I LOVE YOU CONTACT ME AT THREE TREE RECOVERY CENTER.
YOUR MATE
There was no going back now.
ON SEPTEMBER 12 1970, Timothy, rangy and supple from months of yoga and handball, somehow pulled himself up a telephone pole and then along a high wire over a 12-foot chain-link fence wrapped in double strands of barbed wire. He followed railroad tracks to a small parking lot off Highway 1 surrounded by three trees. Twenty minutes later a car arrived and, as planned, put its right blinker on.
“Are you Nino?” the driver asked.
It was his new code name. Timothy got into a getaway car, driven by a Weather Underground contact. Along with his eyeglasses, his ID, and his meditation beads, he carried one possession: Rosemary’s letters.
Timothy wrote the following message, released by the Weather Underground to the straight and alternative presses: “I offer loving gratitude to my Sisters and Brothers in the Weatherman Underground who designed and executed my liberation. Rosemary and I are now with the Underground and we’ll continue to stay high and wage the revolutionary war I am armed and should be considered dangerous to anyone who threatens my life or freedom.”
Meanwhile, halfway across the country, the FBI director, J. Edgar Hoover, launched a manhunt and an investigation into the break-out, telling a group of reporters, “We’ll have him in 10 days.”
From THEACIDQUEENby Susannah Cahalan, to be published on April 22, 2025 by Viking, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2025 by Susannah Cahalan.
