Today's guest is Susannah Cahalan, whose new book is The Acid Queen, a biography of Rosemary Woodruff Leary—muse, fugitive, and heavily indicted co-conspirator in Timothy Leary's psychedelic revolution.

She talks with Reason's Nick Gillespie about hippie communes, outlaw drug smuggling, the war on drugs—and how the '60s counterculture, in its best moments, ran experiments in radical individualism, using personal freedoms to build voluntary communities rooted in altered consciousness and aesthetic liberation. The Acid Queen helps explain how the personal became the political, why libertarians should care about the messy legacy of the counterculture, and what comes next in drug policy, especially regarding psychedelics.

This conversation was recorded at a live event in New York City. Go here to find out about upcoming events. Go here to sign up for Reason's NYC events newsletter.

0:00—Introduction

1:15—Who is Rosemary Woodruff Leary?

7:02—How did Rosemary meet Timothy Leary?

9:57—Why America was ready to experiment with psychedelics

15:12—Rosemary's connection to John Lennon and Yoko Ono

16:11—How Rosemary and Timothy Leary became outlaws

21:07—The jailbreak of Timothy Leary

28:45—The political speech of Timothy Leary

31:45—Why Rosemary and Timothy split up

35:31—The final years of Rosemary

40:08—The reconciliation of Rosemary and Timothy

42:54—The common thread between Cahalan's books

46:18—Labeling in mental health

48:34—Cahalan's experience with psychedelics

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Transcript

This is an AI-generated, AI-edited transcript. Check all quotes against the audio for accuracy.

Nick Gillespie: This is The Reason Interview With Nick Gillespie. Thanks, everybody. We're at the Psychedelic Assembly, which co-sponsors this event. Susannah Cahalan is the author, most recently, of The Acid Queen: The Psychedelics, Life, and Countercultural Rebellion of Rosemary Woodruff Leary. Susannah Cahalan, thanks for talking to Reason at the Psychedelic Assembly.

Susannah Cahalan: It's such a pleasure to be here—and especially at a place that Rosemary would have loved so much.

Yeah, this has her vibe all over it. Why don't you, just very briefly, tell us who Rosemary Woodruff Leary is?

Sure. So, Rosemary Woodruff Leary—as much as I hate to start with Timothy Leary, we are starting with him—she was the third or fourth wife, depending on who you ask and how seriously you take divorce records from Mexico. She was a seeker. She was someone who was very much a behind-the-scenes character who was propping up Timothy Leary, working with him behind the scenes, on his speeches, sewing his clothing, really helping him create an image.

She was also very much a true believer in the role that psychedelics could play in not only expanding consciousness but actually making society better. She was called the Queen of Set and Setting.

Explain what set and setting is. Because when you're talking about Timothy Leary and set and setting, that carries a wallop. Explain that for us.

It does. One of my favorite things that Timothy Leary wrote about—this is pre-Rosemary—was the concept of set and setting. I'm going to reduce it very much down to its essence, but it's the mindset that you bring into a trip and it's the environment. Rosemary was very good at making people feel grounded and supported. She was great at beautifying spaces. She knew what colors to make the throw pillows, to position people properly to make sure they channeled and augmented their trips. That's why she earned that moniker.

Leary was born in the early '20s. She was born in 1935 in California and then ended up in New York?

She was born in St. Louis.

Oh sorry, in St. Louis. Then she is in California at some point, right?

Yes.

In any case, she shows up kind of at the end of the Beatnik scene—or the Beat scene—in New York. What was going on there? Who was she? We'll get to how she meets Leary and how they become the king and queen of Millbrook—the upstate estate where Timothy Leary, Richard Alpert - who became Ram Dass - and Ralph Metzner really created the text that started the '60s version of psychedelia. But what was she doing in New York?

She was born in 1935, as you said, from St. Louis. High school dropout, very beautiful. Was in an abusive marriage at 17, and left that, after she lost a baby, boarded a train to New York with no money in her pocket and no degree. Was recruited and spotted by Eileen Ford and began modeling.

Of Ford Models?

Of Ford Model Fame. And she then did what was like the second-sexiest occupation you could do at the time: airline stewardess, which was apparently harder to get into than Harvard. You had to be less than 120 pounds, x, y, z. So she fit the bill, and there she met her second husband, who was a jazz accordionist and a Holocaust survivor.

She knows how to pick them.

Oh yeah. He was an intense guy, I've heard. I did not meet him myself, but I interviewed several people who said he really didn't take anyone's shit, and people respected him—especially Miles Davis, who was a big fan of his.

Interestingly, I've actually listened to his work. You can find Matt Matthews on Apple Music, I think, and it's really good—shockingly good, jazz accordion. She met him and married him, and was instantly involved in the jazz scene that was going on in mid-'50s in New York City. And began rubbing shoulders with the early Beatnik scene—with Jack Kerouac and kind of rubbing shoulders with these interesting writers, artists, and scoundrels of the era. That's when she started really experimenting with drugs.

What drove her to that? Because this is a fascinating demimonde which gives rise to the East Coast version of the '60s counterculture. What was she seeking that she wasn't getting in St. Louis?

I think that's such a great question. She had always talked about herself in these mythic terms. She saw herself as someone who was going to live a great life—with a capital G, Great. She wasn't going to find that in her small town in St. Louis. And even though St. Louis is a city, she wasn't going to find that there.

She was attracted to "great men," as she liked to think of them—these genius archetypes. That's what she found in New York. Through being in this scene, being a part of the music scene — even though she wasn't a musician or necessarily an artist outright, she was able to express some of those sides of herself and express those "great" parts through the men that she picked.

Let's talk about how she meets Leary and ends up moving to Millbrook, the upstate estate where Leary and his peers kind of repaired to after getting bounced from Harvard in the mid-'60s. How did she meet him, and how did she come to live in Millbrook?

She took a little bit of LSD before she went to a gallery opening, in downtown. There she saw the man of the hour, Timothy Leary. They were fresh off The Psychedelic Experience…

The book…

…which was a seminal guide that is quoted in a famous Beatles' song "Tomorrow Never Knows." He was really pontificating and enjoying the spotlight there. They both were immediately attracted to each other. They both write independently of that immediate pull.

She was intrigued, but she was divorced, again, and dating another jazz musician—who was very abusive, but she was in love with him. So at that time she didn't decide she wanted to go with Leary. It was later, when she decided to go with friends to visit Millbrook.

Millbrook, for people who don't know, is a 2,000-acre rich estate — wealthy landowner, old-school estate—in Millbrook, in a very fancy suburb in upstate New York. This is a place that has about twelve buildings, including an indoor tennis court and a bowling alley on the grounds.

Timothy Leary was dating, briefly, the sister of two brothers who owned that estate. Through her—an amazing woman named Peggy Hitchcock—she managed to secure that house for $1 a month for Timothy Leary and his fellow ex-Harvard psychologists.

Who eventually created something called the League of Spiritual Discovery, and I mean, that is really—if there's a place where what we think about when we think of the psychedelic '60s where it comes from—it's that.

Absolutely. The experiments weren't just psychedelic in nature, but they obviously did experiment very heavily with using psychedelics—using them in high doses, using them over long periods of time, using them with a person, solo. All sorts of different psychological experiments that Timothy was bringing from his time at Harvard and, before that, working on interpersonal dynamics.

They would not only do that, but would also experiment with your food—dyeing the eggs green, just trying to get you out of the stultifying present and really become aware of your surroundings. A gong would bang. They were constantly— at that point, you had to go to your journal and present how aware you were by writing it down. It became this exercise, like a Gurdjieff kind of exercise, in awakening and being very present.

Can you set the scene a little bit for what was going on in postwar America where this type of thing was even taking place and then was about to burst out into everyday culture? Were people feeling repressed? Were they feeling stultified? Why? And then why were they ready to, "Ok, I'm going to go to this crazy place upstate and take a bunch of drugs and eat green eggs?"

You know, it's an interesting time. I think there's a lot of overlap with today. But it was coming out of 1950s America, coming out immediately after the atomic bomb. There was a lot sense of insecurity. Some people responded to that insecurity and fear by doubling down—having a lot of children, being very family-focused. And other people started questioning the nature of their reality and the role of society.

It was the same time you had the rise of vast intellectualization that was happening in America where you had cheap paperbacks, foreign translations, and art house cinema. All these things were happening at that time. And that was really the Beatnik movement. And the next kind of step was: How do we apply this not only to this little Beatnik world, but to society? Psychedelics seemed to be one of the ways people were exploring "how do we change our consciousness and, thus, the rest of the world?"

And I suspect some people in the audience get a sense of this too, when you talk about—ok, so they're tripping, and then a gong sounds, and they write in their journal, and they eat food that is dyed weird colors. There is a dimension to Millbrook where it is—it's either the greatest thing ever or it's the beginning of, you know, the People's Temple.

Like a bad movie. Yeah, yeah, exactly.

How did it go in and out of that kind of focus?

Well, it was both—like all things, like many things are. It was Nina Graboi, who was a female psychonaut of that era—a little older than the rest, kind of like a mother figure—she said that Millbrook had many faces. And I think that's very true.

I think it did change. A lot of times, women had a very different experience than men did there. In some ways, yes—this idea of expanding consciousness. I think there was authentic belief there. They were trying vegetarianism, communal child-rearing, all sorts of these different ways of building a new society, because they felt that the society as it was, was stuck, was retrograde - or whatever word you want to use. It was regressive. It was stultifying, all the words.

But I think this was an opportunity for them. So there's that side. But then the old social hierarchies were still observed in the house. There was very human-based behavior that occurred. Women were oftentimes still left— Peggy Hitchcock, actually, had a great line where she said, "At the end of the revolution, there was always the question, who's going to do the dishes?" And at the end of the day, the women were doing the dishes.

They were still kind of caught up. Rosemary described how Timothy—despite all of his talk of revolution of the mind and was going to upend society—was the kind of man who put his hand out and expected to have a martini glass put in it.

And she—part of the function that she served was to do that. 

Absolutely.

She kept the rooms clean, or helped organize that. Organized the feeding of, you know, hundreds of people sometimes.

And you know, it's funny. It's been an interesting thing, talking about Rosemary in today's culture, where there seems to be this idea that either you have to be a trad wife or you're a girl boss. And she wasn't either of those. Yes, she was stuck with a position that oftentimes she resented. But she actually did really enjoy taking care of other people. That was a genuine thing, and she was really good at it. She was genuinely really good at taking care of people and beautifying spaces too.

Yeah, and that—I mean, it's interesting. After reading this book, I caught a recent documentary about Anita Pallenberg, the model and actress who ended up married to Keith Richards of the Rolling Stones for a while. It talked about how much she added—first to Brian Jones' look, and then to the Stones more broadly.

It's kind of fascinating. We tend to overlook the accessorizing of the cultural revolution. Where did Rosemary's sense of taste come from?

Oh, that's such a great question.

Because she wasn't educated in any of that.

She wasn't educated. Her mother did sew, and I think—according to her brother, who was very wonderful in helping me put this together—I think she had a great eye. Maybe that's something she was born with. She had a pull toward things that were unusual and exciting, and her eye caught those things.

I mean, even just the men she picked, but the clothing she'd wear. There was always something beautifully done. She never indulged in the tie-dye or the cliché. She always was interesting and exciting, and if she wore it today, you would be like, "Oh, she's a very well-dressed woman." There was something kind of classic and exciting in the way she styled herself, and she extended that to Timothy as well, in the styling of his look.

You do an extended reading of a famous photo of John Lennon and Yoko Ono singing in Toronto, in their bed, and Timothy Leary is there, and so is Rosemary. It is amazing when you look at all of these people—most of whom are in kind of period drag, right? They're very much of the time and the place. And then you look at Rosemary, who is kind of in the center of the photo, but looking slightly off. She looks incredibly contemporary.

You know, it's so funny that you say that. That photo—there are a few things that made me realize I really wanted to do this book, and that photo was one of them. Not just because it's John and Yoko in the famous bed, in the white, and there she is. You never noticed her before. Your eyes kind of glance past her. 

But she's looking at you, the viewer. I mean, she's looking directly at the camera. And there is this sense that she's out of time—almost like she's Photoshopped in. And of course she's not, but she gives that impression. I think maybe there's something about her style and her sensibility that was a little bit out of time.

So she also was up for just about anything, because after a short period at Millbrook—describe what happens when she and Tim Leary and Leary's kids start traveling. And, I mean, very quickly they become literal outlaws.

Oh yeah. I mean, the law was down their neck from like six months into their relationship. They got arrested at the Laredo border bringing marijuana into Mexico right at the beginning of their relationship—not wise. Not wise.

That is so strange.

I love the list—I had a list of what they confiscated—and they were obsessed with the brown flour, like the, you know, the brown bread flour. "Who has this wheat flour? What sort of thing is this?" So, it wasn't a good idea to bring the little amount of marijuana that they did.

That was the first time. Unfortunately, the marijuana was found in Timothy Leary's daughter Susan's underwear—she was hiding it. And that did not look good for anyone involved. So that was first, and that was, I think, five or six months into their relationship. So from the beginning, the law was after them.

Then there was raid after raid of Millbrook, led at one point by G. Gordon Liddy, who was one of the plumbers of Nixon's Watergate.

And would eventually do a college tour with Leary in the '80s.

Yes! It's wild. That stuff is wild. But that was always part of their relationship. I think the first five months were this— she really sees — as many first five months as any relationship. But especially for her, was idyllic, because they didn't have the threat of incarceration constantly chasing them.

There was another arrest in California. Millbrook was a failed experiment, ultimately. And the very wealthy brothers who owned it didn't want the issues related to dealing with the kind of vagrants who were coming on the property. 

What went into the failure of the Millbrook experiment? Part of it was that they were constantly being surveilled by police, but that's not the whole story. Why did it not work?

So much pettiness. Lots of infighting. There was an ashram on the grounds. There was the League for Spiritual Discovery, which was Leary's religion that he incorporated. And there were just competing personalities, egos—lots of inflated egos—which can be a byproduct of excessive use of psychedelics.

And people take psychedelics to dissolve their ego, but somehow it's more like one of those sponges that grows when watered, right?

Exactly. And it can go in any direction—amplification of various things can happen with psychedelics. And in the case of a lot of these dudes who were hanging around Millbrook, there was a lot of amplification of ego.

There was a lot of fighting. It was expensive—even though it was only a dollar a year, Leary still had to work on feeding everyone. I think at one point, he was paying for everyone's doctor's bills. There were a lot of STDs going around at that time, so a lot of doctor's bills. So, you know, there's just humanity in tight spaces—even though it wasn't a tight space— still you have those issues you're trying to escape.

Where do Rosemary and Timothy end up escaping to, most famously?

So they end up in California, where you would expect them to. They ended up under the auspices of the Brotherhood of Eternal Love—fascinating group, wonderful name. Rolling Stone described them as a hippie mafia. They were surfers who used hollowed-out surfboards to transport their heroin—basically—from Afghanistan, and hash from Afghanistan. All sorts of drug smuggling operations in Mexico.

And their dream ultimately was to—they were using, by their lights, they were using their drug smuggling operation to fund a plan to dose the world for free. 

Turn on the world. Put it in the water supply. That was the ultimate goal. They got pretty close. They had some pretty amazing chemists working for them, and they were able to get several million doses ready for that.

Rosemary and Timothy ended up under their care. They really were taken care of because Timothy's The Psychedelic Experience and his book How to Start a Religion were key cornerstone texts for the Brotherhood of Eternal Love.

The head of the Brotherhood of Eternal Love — a guy who passed away from, apparently, an overdose of psilocybin—which I think may be impossible—but that was the official coroner's report. He was a real devotee of Timothy Leary and another real believer, as well.

I mean, they did things like laundry Timothy Leary and Rosemary's silk robes. They'd take them to the dry cleaner, make sure they were properly taken care of. They put them up in beautiful homes and really took care of the couple as royalty.

But the law came for Timothy and Rosemary there as well, and they were arrested in Laguna. That was their second major drug bust.

And Leary ends up going to prison, right? And the Brotherhood of Eternal Love—and Rosemary's involved in this—decides to break him out of jail. Can you describe how that happened and what Rosemary's role was?

That's a wild story. At the time, I think it's important to say, he was running for governor against Ronald Reagan of California.

And his slogan was "Come Together," which—

Which Rosemary came up with.

Yeah, there's—

"Come together. Join the party."

And there's confusion or debate over whether or not Tim Leary was involved in the John Lennon Beatles song.

Oh, he was.

Right, but I mean, they ended up arguing.

Yes, I'm sure they did.

But it's Rosemary's slogan.

Rosemary's slogan. And John Lennon was supposed to write the campaign's song but got arrested before that was ever a thing, and he just wrote a real song.

Timothy Leary was sentenced—two different… So Laredo was this very long legal saga. It ended up going to appeal, then it was retried. He gets convicted there. He gets convicted in Laguna. In total, he's facing 30 years in prison for marijuana possession.

And of tiny amounts.

And not a lot of amounts at all—I mean, probably could fit it all in your hand. And there was LSD, but it wasn't illegal yet. And Rosemary's Ritalin as well, which was also not illegal. But he was a political enemy, and he became a kind of figure. It was interesting because before he was imprisoned, he was kind of a bit of a joke in the counterculture. He was a lot older than the youth revolt happening on the New Left, and he was seen as kind of out of touch.

Then, when he went to prison, he became a bit of a martyr, and the New Left rallied around him. And managed to work with a very famous lawyer named Michael Kennedy and with Rosemary to orchestrate an escape.

That involved Timothy preparing himself… According to Laura—and I believe this, I think it's been well documented—Timothy is a trickster, so you always have to doubt. But apparently, he had come up with a personality assessment before his foray into psychedelics, when he was at Kaiser in California.

He was a psychologist working for Kaiser Health.

Exactly. Doing a lot of work on personality and interpersonal dynamics. And he apparently came up with something called the Leary Circle, it basically shows how you will act in a relationship with another person—will you be an aggressor, will you act as a victim?

Apparently, that test was used on him in the jail, and he managed to convince the authorities that he was not a threat. They gave him a very toney, cush, low-security prison in California called CMC West. Apparently, a lot of older inmates ended up there. It allowed him the opportunity to climb—like a very long pole—and go across barbed wire. Very cinematic escape.

But Rosemary was the one who was facilitating all this. She was carrying the messages. Which was amazing—I got to see letters that had never been seen before, that were used by the FBI to decode this later. They spoke in all these different code words. I got to see those letters, which was really exciting, and see the real kind of role she played in this escape. She worked with the Weather Underground—and eventually the Black Panthers.

How did she feel about going underground? Because in a way, this is the ultimate adventure—especially if you're kind of pinning your future to a great man who, of course, is going to be attacked because mere normal people can't really appreciate him. But how did she feel about all that?

That was really a line in the sand for her. At that time, before his arrest, she was begging him to walk away from the limelight and start a family. They were trying to start a family, and she couldn't conceive. But she really wanted to— she had gotten so close to fame and seen what it was really about, and I think she found it pretty repulsive. She wanted to get away from it.

But when he was in prison, she became the face. That was when she got her moniker from Allen Ginsberg—The Acid Queen. She became the person who took every media interview. And when she decided to finally throw her hat in with the revolutionaries and do this extremely illegal act that would make sure she probably wouldn't come back to the United States, she knew she was erasing herself at that point. She knew that was going to be a line that once crossed, you couldn't uncross it.

In her diary, she writes about how she had this image of all the lives she could have had, had this not happened. Simple things—like walking to the library or she saw herself working at a bakery. All these different paths in her life that could have happened, and didn't.

She helps facilitate connections from the Brotherhood of Eternal Love to the Weather Underground. Leary gets out, and they go to Algeria, where they hang out with the Black Panther Party in exile, headed by Eldridge Cleaver. What is that like?

Unhappy cohabitation, to say the least. Leary was still very out of touch. He didn't have his hearing aids—he wore hearing aids. There was a kind of conspiratorial vibe to the Panther International headquarters because Algeria was uncomfortable with them being there. Algeria was also working on a deal with the U.S. on the sidelines. They picked Algeria because there wasn't an extradition treaty. But it was an uncomfortable place for Eldridge Cleaver.

He was obviously being—we know from the FBI work—he was being targeted. There were a lot of undercover agents and narcs.

Well, this is a weird thing about the counterculture, right? Fully half the people at any place were government agents.

I have the FBI files—the Leary FBI files—and when I say that every page is redacted, I mean every page is redacted. I remember reading that something like 40 percent of the Black Panthers were undercover agents. So, he had reason to be paranoid, let's say that. But he was very paranoid.

And I mean, Cleaver—however he ended his life—this was arguably among his very worst moments. And the Panther Party also replicated the gender dynamics in an even more extreme form than what you might have seen at Millbrook.

Absolutely. His wife, Kathleen Cleaver— Anita Hoffman, was there, she was married to Abbie Hoffman, she really was disgusted by the rampant misogyny that she witnessed. She actually escaped out of a bathroom window and returned to her husband, Abbie, who was also on the lam in Paris.

But yeah, it was not a happy place for the Learys. The Panthers did not believe in psychedelics or LSD—especially not Eldridge Cleaver. He had had bad experiences with LSD. And Leary just couldn't wrap his head around the fact that it wasn't his playground.

He and Rosemary would go off in the sand dunes and run around naked. It was a Muslim-majority country—this was not appropriate…

That had a Marxist Revolution—government…

Exactly…the French occupation— the occupation was seen as the—seen as a tool of the occupation…it was just a nightmare. So Eldridge and company actually kidnapped Rosemary and Timothy and holds them hostage for a week or so.

Did they also get them—Rosemary's life is interesting partly because she goes along and then ends up in weird situations. But at a certain point in Algeria, Leary—who had always been kind of beyond politics—he would be the last person you would expect to endorse this or that candidate, because he always said these were all just menopausal men who needed Geritol and were killing other people because…

Because you should only talk politics, unless you're on all fours.

But then he gives a very political speech, right? At the behest of the Panthers. What is that about?

Rosemary talks about this. Rosemary was actually— I think that she was radicalized before actually getting to the Panthers, when she was with the Weather Underground. She was with Bernardine Dohrn, and she really liked Bernardine Dohrn and really respected her—really respected what she was saying about women. At one point, even thought about leaving Leary to join the Weather Underground. But when she called them—

I'm not sure that would have ended well.

When she called them—she's underground at that point, while she was in Paris before they went to Algeria—they asked her, "Can you type?" That was the one question they had for her. And she thought, "That was the exact job I was escaping in St. Louis. I'm not going to do it for the Weather Underground."

So she ended up going to Algeria and reunited with Leary and the Black Panthers, which ended badly, obviously.

And then talk about how they get out of Algeria, and then they ultimately split up. Leary comes above ground, but Rosemary is underground for over two decades.

Yes. Eventually, they were able to convince Eldridge to pass along their fake passports so they could attend a lecture in Copenhagen. It ended up being kind of a front—they were going to be arrested in Copenhagen. They get word from a mutual friend that the cops were already there, so they go undercover in Switzerland, a neutral country.

There, again, they get aid from a very shady character—an arms dealer named Michel Hauchard. Hauchard really wants to get his hands on Timothy Leary's book in progress about his prison escape, and manages to orchestrate another arrest of Timothy Leary, leaving Rosemary once again in the role of the media heroine and the face of the movement. She has to raise money for Timothy, and she was just exasperated by then.

When they were with the Panthers, they were at their closest—because they only had each other. But she saw him as very pathetic, a pathetic figure. He was frightened. He was cowed by the experience. He looked old. She pitied him in a lot of ways. That was their dynamic where she always would say that was something that called to her, taking care of him.

But once in Switzerland, among the jet-setters there and the socialites, I loved her detail talking about the price of shipping priceless art overseas, and allowing their dogs to eat off their plates at the table. That was the kind of vibe she was in. And she saw, what she said was, the limits of his mind. 

At that point, she couldn't unsee it.

Once she got him released from prison again, she left him. And that became the schism between them.

Leary's next few years are well known—including him ultimately being arrested, and then cutting a deal. He argues that he did not name anybody who wasn't already known, and things like that, but…

Well, he did name Rose. I mean, he said—

So yeah, explain that. Because part of the pathos of the book is that Rosemary gets simultaneously erased from history, but also she ends up having all these legal charges against her.

She becomes the target. What happens is Timothy is arrested in Afghanistan with his new "perfect love," Joanna Leary—his words. They know that Rosemary—she would call herself "the computer," she had all the information. 

Timothy Leary was giving up the information, but Timothy Leary alone on the stand wasn't going to hold water. They needed Rosemary. And Timothy was very ready to give her up. He decoded all the letters to the FBI. He gave up all the people who were involved. He even tried to bribe her mother to get her whereabouts so he could cut a better deal for himself.

Rosemary refused to cooperate. She went further underground—first going deeper into Europe, in Sicily, and then ending up in South and Central America, where she lived for about three years.

Throughout this whole time, she refused. There were opportunities for her to come forward, but she was scared—really of jail and prison. She had done some jail time earlier when she, again, was not speaking against Timothy. She was in contempt of court, back at Millbrook when they were investigating the house. She didn't want to do that.

But she also had a great sense of integrity and pride in her own sense of morality and justice—that I think was lacking in Leary.

Explain how she eventually comes back above ground. And how does she spend her life? I mean, she died in 2002 at the age of 66. Leary had died a few years before that, and they had reconciled. We'll get to that in a second. But how does she come back above ground? These stories are all played out now, but there was a moment—starting in the '70s through the '80s and '90s—where '60s radicals would float back to the surface.

Yes, and she watched it. I have all the clippings of the people she was watching. It always interested me—why she stayed so long.

She ends up—it's an apocryphal story—but she claims that she water-skied back into the country in 1976 on a drug-smuggling boat. I don't think that was true, but you know what? More power to her. I love her.

She ended up coming back via Florida and ended up going all the way up to Cape Cod, where she lived for 23 years running a bed and breakfast—or a kind of hotel—at the edge of the world in Provincetown, Cape Cod. There is where she lived under an assumed name. Very few people knew her story. She lived a very simple, quiet life until she got word of Timothy Leary's daughter's suicide.

That opened up all the spigots that she had closed about all the emotion she felt for Timothy. At that point, she made contact with him again. She was very fearful of making contact with him. She was scared of him—scared of what he could do to her reputation, what he could do to her legally. And I think she was also tired and kind of resentful of the mythology that she had helped create.

So legally, she came back and she didn't serve any time, right?

She paid $1,080—which 108 is a very important number, and she felt vindicated by that.

She was able to convince the judge that she was A) not a threat, and B) that she was overtaken by this guru, Timothy Leary. He bought it. And she hated saying that.

Her close friend David Phillips, who was with her during that time, said, "I think there was a little grain of truth about that" And she wouldn't admit that it was true.

It's kind of fascinating—the number of people who, you know, she was on the FBI's Most Wanted list for years—and then when they resurface, it's like, "all right, you can just go back into the general population."

Even people like Bernardine Dohrn, who I find despicable and risible from a political point of view—in the end, she really didn't have to pay anything. You come back. Abbie Hoffman…

Even Eldridge Cleaver, he was arrested for murder.

Right. Yeah. It's interesting that there's—particularly around the '60s—and with Leary especially, the whole War on Drugs. Nixon zeroed in on him as the most dangerous man in America. And then it's kind of like, ok, it sounds—

And then he's, you know, your friendly satirist on the night shows. But kind of—I mean, his power was…

It was interesting. He had this vision—the first time he did acid—people who know who Michael Hollingshead is… The first time he did acid was with that kind of British trickster. He had a vision of himself as a clown. And that's kind of where he ended up, at least in the '80s.

It became that terrible image for him. And he was really affected by it. He became that. And he became that in the culture too. And it was in the '90s—I think that changed a bit. The internet—

Right. Well, he was simpatico with the kind of burgeoning internet world and techno-optimism. He started talking about how personal computers and the internet were the new acid.

Yes, exactly. And for all the things—people do like to speak ill of Timothy Leary, and it's easy to do that once you know some parts of his biography—but he was very prescient. He saw a lot of things coming that we take for granted. He would say things like, "Oh, I'm going to get my brain uploaded to the internet." And people laughed. Or, "There are going to be whole departments at major universities dedicated to the study of psychedelics." And it was like—he saw a lot of the future, which you can't discount.

How did she reconcile with him? Because Timothy Leary treated a lot of people badly—particularly women who he married. And she, arguably, worse than any of them. How did she reconcile with him?

I think, well, A) she said, "I was mated to him." And that, to her, as much as they were in many ways not well-suited to each other, temperamentally, she felt that he was her soulmate. I think it was kind of that simple.

But I also think that when she saw the loss of his daughter, she took some of the blame on herself. I think she had a sense of what that loss meant to him. And I think maybe—there is a heart-opening that can happen with long-term psychedelic use and I think she was representative of that.

One great thing about the book is, if you've read a lot about the '60s counterculture, including the way it moves into the '70s, it's just a different perspective. It's by a major participant whose eyes we haven't seen through before.

From a contemporary point of view, it is hard to get past the sexism, which is everywhere, all the time. How do you tease—what is the message that you might bring to a contemporary boy or girl reading this? How do you factor that in? Because she, in the end, was giving—after Leary died, she had annual parties where she would give away parts of his ashes with glitter in it, so that when you threw it up in the air—

Yeah, it's true. I saw something—

She remained committed to the bit, even though she was part of a system that treated her so poorly.

I think she believed in him. And I think, in many ways, she believed in some of his mission—not the vast, evangelical promotion of psychedelics that he was championing, but she did believe in that.

The thing I hope people take away from it is that she was complicated. She doesn't fit into these ideas of what a woman should be or how she should use her power. No, she was more like all of us—who are complicated. We sometimes pick people who aren't great for us. Or we love people who are damaged and damaging. And that doesn't make her any less worthy of a biography. I think it makes her really exciting. As a biographer, that's very exciting to me.

Well, I mean, it is—again, it's a dimension that I just have not encountered in this way before. I think it's a huge contribution to discussions of the psychedelic movement but also, more broadly, the counterculture.

Let's talk about how it connects with your other work. Your first book, which was a cultural phenomenon, was Brain on Fire, which is about how you contracted a form of encephalitis. You were days away from being locked up in a mental institution for the rest of your life when a doctor realized what you had—and that it could be treated not through psychiatry but through medical interventions.

Your other book—and this is the first one of yours I read—was The Great Pretender from 2019, which is about David Rosenhan, who was at Swarthmore at the time—an academic psychologist who, in 1973, published a paper called "On Being Sane in Insane Places," which was a stunning takedown of mental institutions in America. And you reveal it to be an utter fraud.

What is the continuity between those two books and this one?

In some ways, I think of it as they are very closely aligned in my mind. Just in terms of very concretely—I talk about psychedelics in all three of the books. Obviously, the most in The Acid Queen. In the first book, in Brain on Fire, I talk about ketamine. The same receptor of the brain that was affected by my immune system, targeting my brain, is also the target of ketamine.

And in my second book, I talked about Humphry Osmond and the use of LSD. He actually insisted that his architect take LSD to try to understand what it's like to go mad. So that was when it was a psychotomimetic, understanding madness.

I'm interested in altered states. I think consciousness, I think the way our brain/mind shapes reality is fascinating to me. Obviously, psychedelics has a lot to do with that. But we were kind of talking before— I think there is something to the idea of institutions and how that shapes the role of labeling, and the real-world implications of those roles of institutions in everyday person's reality, if that makes sense.

Just to linger on that a bit, particularly thinking about The Great Pretender and David Rosenhan, who is one of the great critics of mental institutions and labeling—basically, what he was arguing in this paper, where he had pseudo-patients show up at mental institutions describing vague symptoms, was that because of the context, they would be labeled mad.

Is he wrong? Even though he totally faked his data.

Here's the deal with that—which I think also connects to Rosemary and the idea of being complicated. This story is obviously more nuanced, which I'm fascinated by.

He was right about so many things in that paper. And it wasn't fully fabricated. He had his own experience. There was one pseudo— they were called pseudo-patient, people who went undercover — who I was able to find. With some issues. Totally flawed study, but one that also had a lot of truth to it.

So it's hard to wrap your head around the idea that something that could be made up…

So this is like when people say, "Well, O.J. was guilty, but the LAPD framed him." 

Right.

It's one of these weird scenarios…

That can both be true at the same time.

In terms of the labeling question—we now live in a golden age of labeling, both by institutions and psychologists and medical experts, and ourselves. I don't know how many times I've talked to people who are like, "I'm on the autism spectrum—I self-diagnosed."

How should we orient ourselves toward labeling? Should we be more free with them? Should we be more careful? Should we be more suspect with them?

I mean, personally, I'm someone who's very circumspect about labeling—especially if it's an institution doing that labeling. Because as we know from the history of science and medicine, things shift all the time in terms of how labels are viewed, how they're given services, how they're treated.

So I'm always a little bit hesitant. However, a label saved my life. I got the right diagnosis at the right time, and without that, I wouldn't be here today. 

So again, it's nuanced. It's complicated. There can be great work there and very bad work there too.

It seems to me—and I'm teasing out a libertarian message in your work—that labels that are totalizing, or institutions that are totalizing, are problematic.

Because all our knowledge is provisional and contingent, and it's going to change—both with new information and with perspective and experience.

Right. Like the DSM is a working document. It was meant to be something that was supposed to change over time, but it's been—as they say—reified. It's been made concrete in a way that it wasn't meant to. And that can happen with labels as well.

Right, and that's a particular—I guess both in Brain on Fire and The Great Pretender—that's part of the negative outcome. You talk about how therapists in particular now just kind of do checklists rather than have a basic conversation with people. You miss a lot of information, even as that other approach might allow things to scale.

Seeing the humanity in another person—even if there is a hierarchy in terms of being a clinician and being the patient. And I think—to bring it back to Rosemary—but there is a hierarchical imbalance between the person who is guiding and the guided. And that's something I'm very interested in as well.

• Producer: Paul Alexander
• Audio Mixer: Ian Keyser

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