Writing the Psychedelic Odyssey of Rosemary Woodruff Leary
An Interview with author Susannah Cahalan
Susannah Cahalan can pinpoint the moment when she decided to write the story of Rosemary Woodruff Leary’s life. She was walking down a tree-lined street in Brooklyn, contemplating her next book project. Should she write Rosemary’s biography, or take a well-paid ghostwriting job?
As she pondered her professional dilemma, Cahalan found a piece of paper that featured a striking image: an owl with mushrooms growing out from its head. She later learned that owls appeared in Rosemary’s diary and writings. When Rosemary left Timothy Leary in 1971, she even dreamt about an owl clawing out her eyes. Cahalan did not then know Rosemary identified with the owl of Athena, however, she did know she would write Rosemary’s biography.
The Acid Queen: The Psychedelic Life and Counterculture Rebellion of Rosemary Woodruff Leary (Viking 2025) is the enigmatic story of Rosemary Woodruff Leary’s life—a story that has never been properly told. Rosemary’s posthumous memoir, Psychedelic Refugee, was published in 2021, but was never finished. It contains many gaps and elisions because Rosemary was afraid of incriminating people who helped and protected her while she lived underground for some twenty three years.
, a veteran New York City reporter and author of a Brain on Fire: My Month of Madness (2012), has carefully pieced together the missing parts of Rosemary’s mysterious underground years; we now know where she lived and how she managed to survive while on the run from the FBI, the Bureau of Narcotics and Dangerous Drugs (BNDD), and the law enforcement arm of the Nixon Administration. The tale of how Rosemary manages to escape detection and outwit her captors is as dramatic as any John le Carre novel.If being on the run from the law was a major theme in Rosemary’s life, the other dominant narrative thread is her topsy-turvy love affair with Timothy Leary. Rosemary and Leary’s lives converged when the charismatic Harvard professor became famous for his advocacy of conscious-expanding drugs in the mid-1960s. In 1965, the couple fell in love at the Millbrook commune in upstate New York which served as a cultural incubator for the younger generation’s interest in meditation, Eastern religions, and elaborate set and setting experiments.
However, after five months of psychedelic bliss, Timothy and Rosemary’s love affair was interrupted in December 1965 when the couple drove from Millbrook to Mexico for a much needed winter vacation. After being turned away at the Mexico border, Leary, Rosemary and his two children were arrested at the Texas border for possessing a miniscule amount of cannabis. Eager to make an example of Leary, the Texas judge initially gave the psychologist a sentence of thirty years in prison and a fine of $20,000. The infamous Laredo bust marks the beginning of a tumultuous conflict with US law enforcement. Rosemary’s romantic connection to Leary meant she was subjected to police surveillance and harassment.
After the Laredo arrest, the most significant event in Rosemary’s life is undoubtedly her decision to aid Leary’s escape from the California Men’s Colony in San Luis Obispo, California in 1970. Although the prison break was actually successful, Rosemary’s willingness ‘to aid and abet’ the psychologist’s unlikely escape meant that she was compelled to live underground for two decades.
The Acid Queen unveils the untold story of Rosemary’s extraordinary underground years: her fraught break up with Leary in Switzerland in 1971; her clandestine years in Sicily, Afghanistan, Colombia, and Costa Rica with her lover and confidant John Schewel; her dramatic return to the United States on water skis; her incognito existence as ‘Sarah Woodruff’ in Provincetown, Massachusetts; and her reconciliation with the psychedelic icon at the end of Leary’s life.
We know a lot about the psychedelic icons of the 1960s and 1970s—Leary, Ken Kesey, Hunter S. Thompson—but we don’t know enough about the psychedelic women who were often overshadowed and, in some cases, forgotten. Although some people are eager to write off Rosemary as a fame adjacent fashionista, Cahalan’s biography establishes Rosemary’s importance as a counterculture heroine, psychedelic pioneer, and victim/survivor of the War on Drugs.
As a scholar of Timothy Leary’s early psychedelic writings, I was intrigued when I first heard that a biographer was finally bringing Rosemary’s story to light. I spoke with Susannah just before she embarked on her Acid Queen book tour of the Northeast and San Francisco.
Penner: You have written two books about psychiatry, and the treatment of madness in the postwar era. The biography of Rosemary Woodruff Leary is a quite different ‘animal.’ Did you enjoy writing this biography? Did it require a different approach than your other books?
Cahalan: It was a very enjoyable experience. I would say I miss it already. It was immersive. Rosemary is from a different time period. She had a lot of intense feelings and relationships that I have never experienced, so it was amazing to really dive in to her world. Along with interviewing her friends and family and tracking down every single newspaper article written about her, I also wanted to get really close to her, so I did a lot of wacky things. I threw her tarot cards. I threw her I-ching. I did her style of yoga. I did her breathwork. I really wanted to embody her. I think being in Rosemary's world opens me up to a lot ways of approaching writing that I would never have taken seriously when I was a reporter. I talked to mediums and really went to another level to connect to her. I think she rubbed off on me during the creation of this biography.
Penner: I've been interested in Rosemary’s early years in New York in the early 1960s. There seems to be a pattern. She often ends up with these jazz musicians, but they also seem kind of abusive and they have addiction problems. Why did Rosemary often end up with this type of man?
Cahalan: I don't know if I have the answer to that question. The thing they have in common is they're kind of great men and they all have some kind of talent. Even her first husband was an Air Force guy and a shining star in St. Louis. I think she had a bit of the Jungian golden shadow: she was attracted to great men who had narcissistic traits. Maybe because of the context of her times—the limitations that were put on women—she wasn't able to shine in the way that she felt she should, so she found men that she could kind of shine through. And I think they resented Rosemary's greatness, too. In a way, it was a competition and she was seeking out men that wanted to keep her down and destroy her. And that's not unique to Rosemary. Women still do that today. I feel that that's a pattern that was repeated in her life.
Penner: I see her discovery of psychedelics as a key moment that dramatically changes her trajectory in life. What did psychedelics offer her?
Cahalan: I think it all stems from this moment in her youth when she had a mystical experience without substances. But she had this feeling like everything was on a grid and she was plugged in and electricity was all around her. I think a lot of people have an experience like this one, but they don't remember it. Many people who consider themselves to be like seers or healers, sages, and shamans report having spontaneous mystical experiences. And that happened for Rosemary. I think it was profound and she never forgot it. She was a seeker and she was looking for meaning. The life that she was leading didn't have much meaning. She really saw herself as a great character in history, but obviously the path she was on was not going to lead her there.
Enter psychedelics and they offered her the ultimate experience. The first time she did peyote, it was because of Charles Mills [a jazz musician and composer], whom she was dating at the time. He wanted someone to come with him on the journey. However, the first time she did LSD was with another woman, so that's an interesting shift. And that was a totally different experience. I mean, she became a seagull. She flew around the Statue of Liberty; it was a very free and exhilarating experience. It was really transformative and she connected her experience to that moment in her youth.
Penner: Meeting Timothy Leary also certainly alters her life in profound ways. How would you characterize the moment when they converge?
Cahalan: So good. I think they were, again, like the idea of an electrical grid: they are plugging into each other. I don't want to sound cheesy, but there was a soulmate kind of element there where they were really finding each other's match. She immediately thought that he was charismatic and handsome and exciting, but he also immediately gave her that feeling of meaning. Yes, she was beautiful and smart, but he also saw someone who was on his level. He didn't look down on her because she didn't graduate from high school. He really saw that she was a great intellect. And that she had lived a real and complicated life. She understood poverty. She understood way more about living in New York City and going to smokey bars than he ever did. Timothy writes about how she was able to laugh at him and see the absurdity of life.
Penner: I am also fascinated by the honeymoon stages of their relationship.
Cahalan: I wish for her sake that it lasted longer. I like when she was his Pygmalion and becoming ‘the queen of set and setting.’ However, that really only lasted a few months because then they had the Laredo bust in 1965 [when they were both arrested and thrown in jail]. That event really threw things into a stark perspective. The problems started to emerge very early on in their relationship, but five months can be transformative. I mean, ‘five months,’ she said, and I'm paraphrasing, ‘those five months were enough to withstand so much.’
Penner: One of the more fascinating parts of your book for me was the concept of ‘ego inflation’ and that it can be induced by LSD. In your account of their relationship, you argue that it was a key part of Timothy Leary and Rosemary's experience. Are you suggesting that it explains why they were so bold and fearless in their personal lives ? They do many crazy things together, like busting out of a medium security prison.
Cahalan: I wouldn't say ‘ego inflation’ is the only reason. I think there are a lot of factors. Although there can be good things that come from ego inflation. For example, if you do feel powerful and you feel like you have some gift to give the world you will do things you believe in. But, I think, even more than the ego inflation, it was ‘true belief.’ They really did share this belief in psychedelics as a way to augment the psyche, heal the world. ‘True belief’ really enabled that behavior, but ‘ego inflation’ actually got in their way sometimes when they went too wide—too evangelical. They were spreading the gospel of LSD without taking on any responsibility—that maybe it was not for everyone. Maybe the things they were promising—like healing racism—maybe that’s over-promising. And so to me, the ‘ego inflation,’ as much as it propelled them to be strong in their beliefs also really tripped them up.
Penner: When reading your biography, I was surprised by how often Leary and Rosemary's relationship was interrupted by affairs with other people; they both take lovers openly and then come back together. In the end, I think there were three weddings and almost a fourth one at the end of their lives.
Cahalan: Yes, she ended up proposing to him at the end of his life. I love that twist.
Penner: Why did they keep coming back to each other?
Cahalan: I can tell you why Rosemary kept coming back to him, but why Timothy kept coming back to Rosemary is speculation. I can’t talk about that. But Rosemary repeatedly said, ‘I was mated to him’; she really felt that, even though she'd been married to other men before. This was a ‘for life bond’ and I think that she was a woman of her word. She had a lot of integrity and felt very strongly that this was ‘her person.’ But, obviously, Timothy behaved in ways that made that impossible. In the end, she really stuck to that and clung to the idea that ‘I am his forever.’ I don't think that it was the same for Timothy.
Penner: It seems like Rosemary's a little more capable of what I'm calling ‘free love.’ She seems more able to untangle herself from the affairs she's having—to separate sex from love—than Timothy, who comes from a different generation. Do you agree?
Cahalan: I think that's a really interesting question. I think you are right about Rosemary because she did talk about sex as kind of a tool. In her teenage years and in her years with Leary, she saw her sexuality as a ‘superpower’ she could deploy. At a certain point in her later years she lost that ability to use sex as a tool. Timothy had a hard time with the lack of monogamy, even though it suited him just fine at times. However, he was from a different generation. He was 15 years older than her. And you can't just shake that out of someone. Maybe not anyone.
Penner: While reading your account of Rosemary's journey, I was struck by how at certain moments Rosemary seemed more reflective than Leary when tragedy strikes. And she seemed to have some reservations about psychedelics that Leary did not seem to have at that time. Do you agree?
Cahalan: Yes, the main thing she said repeatedly was that there was a responsibility when ‘you turn somebody on.’ She compared it to Frodo and ‘the ring’ in Tolkien’s Lord of the Rings. And this is reflected later, too, when she taught a class at the University of California, Santa Cruz, to young students at the end of her life. She was very circumspect. She was not an out and out advocate. Because LSD offers such a great reward there has to be some kind of risk involved and she was very much aware of that. She was very much cognizant of the fact that maybe not everyone's equipped for that kind of experience.
Penner: Rosemary's life cannot be divorced from the War on Drugs. After meeting Timothy, she was hounded by the law enforcement, BNDD, and the Nixon Administration. Could you comment on how the War on Drugs shaped the trajectory of her in life?
Cahalan: As we said earlier, she had five great months with Leary and then the arm of the law came down on that fifth month in Laredo. And that's a hinge moment for her. She knew that was the moment when everything would change. And then from there, she went to jail for not cooperating with a grand jury. There's also other arrests and constant raids. Her movements, her thoughts, her money—all of that was being shaped by the War on Drugs. And then to be on the run for 22 years—even though it was for a variety of reasons—the reality is that she would not have been “on the run” had it not been for the War on Drugs. And we have to mention the extreme measures that were taken—the extreme sentencing involved for small amounts of marijuana. Her whole adult life was dictated by that for sure.
Penner: At the moment, there's definitely a lot of interest in the psychedelic women from the 1960s and 1970s. How does Rosemary’s experience contribute to our understanding of this time period ?
Cahalan: I think that there is this narrative right now that stems from the medicalization about how psychedelics can provide healing. But I think that there is another story from the underground that's maybe getting lost in that medical narrative. For example, the wisdom that is being passed along through women who acted as midwives to the movement. Women were often the ones who were taking care of things, feeding people, or if someone had a bad trip, they were the ones to take care of them. I'm generalizing, but a lot of times those jobs went to women, so they have a lot of institutional knowledge that was passed down, probably orally because there was a lot of stigma associated with women taking psychedelics. The stigma was there for men too, but more so for women.
Penner: how does Rosemary and her story speak to our cultural moment right now in in 2025?
Cahalan: I think it's a reminder. As you hear these things like ‘patenting the pillows of the psychedelic experience’ and how hedge funds are getting into psychedelics. Rosemary's perspective about how psychedelics changed her is amazing. I am quoting, ‘I can’t say that I believe in anything specific, but I can believe in a certain kind of joy that overcomes me from time to time. And I do believe that joy, or that sense of grace, if you will, has something to do with my experience with psychedelic substances. It made me aware of another reality than this reality that we experience in our daily lives. The fact that we have blinders on and don’t pay attention to it. So, I’m more inclined to pay attention to beauty… I believe everything and, at the same time, almost nothing, but it leaves me in a comfortable place.’ It's a fascinating perspective. And you can't commodify that statement. You can't sell that on the S&P 500. You can’t teach a class about that one.
The Acid Queen is out now.
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