The Stonewall Inn was a dump. This is according to Jay Toole, a veteran of the now mythical uprising. “It was dark, smelly. You never drank any mixed drinks there ever because they hardly had any running water, so glasses were always washed in dirty water.”
Toole was living nearby in Washington Square Park after her parents threw her out of the house at the age of 13. She and the others who were sleeping there heard what was going and rushed over, beginning “one of the best nights I’ve ever had,” she says. “It felt so empowering to be able to yell at a cop and not get beat up…Just to yell at them and scream at them and throw things at them and see them scared. You could see it in their eyes that they were scared. And it must have surprised them that they were scared of a bunch of gay people, like ‘What the hell?’”
While living in the park as a teen, Toole dated another girl, Linda. She’d come into the park and Toole would make sure to “let the other butches know, ‘She’s mine.’” They dated and Toole quickly fell in love, even buying her a ring, but they lost touch after Linda’s parents had her put away for being a “wayward girl.” Their love story ended there, at least for the next 55 years. Then 2019 came around and Linda reconnected with Toole over email after seeing her in a video online commemorating the 50th anniversary of Stonewall.
“I got on a plane and went to Florida so fast to see her that it made my head spin. And now she’s back up here in New York with me and now we’re snowbirds.”
Jay Toole talks in our interview about surviving on the streets of New York City, the Stonewall uprising, and reuniting with Linda after 55-years apart.
This interview has been edited and condensed.
Jeffrey Masters: I want to start with when you were thirteen and kicked out of your family’s home for being gay. What kind of understanding did you have of your own queerness at that age?
Jay Toole: I think I’ve always known I liked girls, since maybe eight or nine — my first kiss, then a crush on my nun. I always felt there was something strange about me, that I didn’t like little boys. I think I always knew it was girls I wanted to be with.
JM: At thirteen, were you identifying as gay?
JT: When I first came out — I had this friend, none of the other kids were allowed to talk to me. When I was twelve, my mom had a severe mental health issue, did something wrong in the neighborhood, so the kids weren’t allowed to play with me anymore. But this one girl, from a different neighborhood, became my friend. She brought me to her house and we walked down this long hallway with a bunch of rooms — she had a gazillion brothers, this is my brother Bob, and John, and Jim, and Jack. We got to one room, and she said, “This is my sister Florence.” I stopped dead in my tracks and stepped back to look — there was this person named Florence with an Elvis Presley curl coming down, dressed in boys’ clothes.
I went to that house every single day just to see this person. I wasn’t quite thirteen yet. Eventually she called me in, and later she and her best friend took me to the Village, to a barbershop that’s still there, and got me my first haircut — a flattop.
JM: What is a flattop haircut?
JT: Almost like a crew cut, only a little shorter, brushed back a bit.
JM: Did you like it?
JT: Oh my God, yes. They bought me a boy’s shirt — I can still see it, a maroon short-sleeve shirt, black dungarees, some sneakers. I went home, and my father took one look at me and said, “Get out, get the fuck out.” So I ended up on the streets at thirteen, at Washington Square Park. Lived there a long time, in the bushes, on the benches. This was 1963, ’64, somewhere around there.
JM: Was it just generally known that if you had nowhere to stay, Washington Square Park was where you went?
JT: Those two butches had already brought me to the Village a few times, so I knew there were people like me down there, knew where the park was. I didn’t talk to anybody for days, though, I was scared shitless — in those bushes with the rats and squirrels. Then some other kids came over, asked if I was hungry, and I joined that little family. There were so many homeless queer kids out there, still are today, though they don’t hang out in Washington Square anymore. But back then that one section of the park was just queerness, and everybody had their own little family sections. It was amazing.
JM: That family welcomed you in?
JT: They did. Taught me how to survive out there — how to make money, get food, steal, rob people. It was pure survival, no judgment involved. I hope none of you listening judge it, because kids are still doing this today, still on the streets, surviving however they can, same as I did fifty-something years ago.
JM: Do you feel like people judge you for that?
JT: For a long time I did — when they’d hear my story, about jail, all the arrests. I thought it would scare people off, that they’d think, she’s still that person, better stay away. But I got over worrying about it pretty fast.
JM: I would think that living on the street would be lonely, but it sounds like you had a family, a community.
JT: For many years, yes, a community of homeless queer kids. I was homeless over twenty-five years total, and as I got older, moved away from the Village, the drug addiction took me to places that were terribly lonely. There was one stretch, 25th and 3rd Avenue, where I didn’t talk to a single person for over a year — not a word. I was lonely. This poor woman was walking down the block one day, and I ran up to her and said, “Talk to me.” Scared the hell out of her, she bolted around the corner. Homelessness takes you places you don’t want to go. People don’t think about the different mentalities, the predicaments homeless people go through, and it’s not because we want to be homeless. Back then there was nothing for us — today there’s the Ali Forney Center, the Center itself, but back then, nothing, nowhere to ask for help. As a kid, queer elders would come through the park, give us food, money, sometimes take us home for a shower and a meal — sometimes out of pure kindness, sometimes for sex. And that was okay. That’s how we lived.
JM: Was the majority of the park queer, or just your section?
JT: If you walked in off MacDougal, past the little round fountain, that one lane going up the middle of the park was completely queer. To the right of that, drug addicts and alcoholics, mostly men — not that we weren’t also drug addicts and alcoholics. We never went to the north part of the park, because we knew we’d get arrested, that’s where families were with their kids. We stayed away from that part entirely.
JM: Did it feel safe?
JT: Safe within that one segment. You never went to the bathroom alone, always with your crew, because you never knew who was waiting in there, who’d come in behind you. A lot of queer people got raped, beaten, in there. The cops never bothered us, though — didn’t care, we weren’t causing problems, just sleeping, doing our drugs, not bothering anybody.
JM: How did you afford drugs and alcohol?
JT: We robbed stores, robbed people — I became a very good pickpocket. Some restaurants on MacDougal hired us to bus tables for food. And I got a job with the mafia — they ran a pizza place right off West 3rd, and me and a friend ran numbers for them. If you don’t know what that is — it’s like buying a lottery ticket today, but there were no computers, people would come up, tell us their numbers, we’d write it on a slip of paper, take their fifty cents or a dollar, and that money went back to the mafia. If their number hit, we’d bring back their winnings.
Funny story, me and my friend decided it’d be a good idea not to bring the money back one time. We took it and got the whole park stoned, spent every dollar. Next night, one of their guys shows up in the park, and we took off running. Around nine, ten at night, and all you could hear was pop, pop, pop. If he’d wanted to kill us, he would have — he just wanted to scare us. Next morning we were on our hands and knees, literally, in front of that pizza shop, waiting for them to open. When he walked in I said, please don’t kill us, we’ll get your money back. They didn’t kill us — instead, they gave us a job dealing heroin in the neighborhood.
JM: Was that to pay them back, or make your own money?
JT: To pay them back. Didn’t mind, since I was already a heroin user by then — we’d tap the bags and use it ourselves. Years later, ’65, ’66 maybe, I ran into him again, and he said, “You looking for a job?” I said, yeah. He said, “I’m running a lesbian bar, a speakeasy, want to be the bouncer?” I said, sure.
JM: What was the bar called?
JT: Cafe Bohemia, 15 Barrow Street.
JM: You must have been young to be a bouncer.
JT: I was — chickenshit, honestly.
JM: You wouldn’t intimidate me at the door.
JT: Back then, man, I would have. You’d walk into the front of the bar and it looked like a regular bar, but then you’d open this door into a lesbian nirvana. I’d sit up on a stage, jukebox in the corner, tables everywhere. It was illegal to serve us alcohol, so it was bring your own. When the cops came to raid it, the guy up front would hit a button under the bar, a red light would go off in the back room where I was, and I’d make sure no two girls were dancing, no alcohol visible on the tables, jukebox off — just make everybody as safe as possible. But once the cops walked in, you knew someone was leaving with them. You just hoped it wasn’t you.
JM: Did you even have an ID?
JT: I did. It wasn’t mine. Passed as a guy named Melvin.
JM: With your short hair and button-up, you were going by Melvin?
JT: Yeah, chest binder and everything. They just figured I was a short, young guy.
JM: Thinking about the bathroom not being safe, and sleeping on a bench in the park — what happened when you got your period?
JT: Luckily for me, I only got it for about half a day, so it wasn’t a huge issue. But a lot of the girls used white socks, since nobody could afford Kotex — we’d steal white socks. Nobody’s ever even asked me that question before.
JM: I didn’t know if it was appropriate. Amongst that family in the park, was there dating, hooking up?
JT: Oh yeah, of course. The woman I’m with now, I met her in ’64, ’65, at Cafe Bohemia. When she came into the park I’d say, “There’s the girl,” so the other butches knew, don’t touch, she’s mine. We were together a while, until, because of some police interference, her family had her put away as a “wayward girl.” I thought she’d stopped loving me, that she just wasn’t coming back, so I moved on. Then in 2019 I get an email — I’d done an interview for Democracy Now!, she saw me on it, and wrote, “Are you her? Did you live in the Bronx? Did you have monkeys?” I wrote back, yeah, that’s me, is this Linda?
And we got back together, fifty-five years later, living together now, because of some stupid stuff that happened decades ago. Our love was just there, instantly — I got on a plane to Florida so fast to see her it made my head spin. Now she’s back up here with me, we’re snowbirds.
JM: You met this woman in the ’60s, had a crush on her, and now you’re actually together?
JT: I was in love with her, bought her a ring. Getting tattoos was illegal back then, but there was a guy who’d come through the park giving free ones — so I bought her a ring, and he married us. Then we had an argument, and she threw the ring in a mailbox on MacDougal and 8th Street. I sat there all night waiting for the mailman to come get it back. I was in love with her. Still am.
JM: How old were you back then?
JT: I think I was seventeen, she was sixteen.
JM: It’s mind-blowing that this happened with this girl as a teenager, and now you’re together decades later.
JT: It’s quite the love story. Never give up. We never really broke up, never had one big argument, it was just outside circumstances that kept us apart. Maybe that was for the best, honestly — we probably would’ve killed each other back then.
JM: When you mentioned Florence, at thirteen, you said she “brought you out.” Was that a sexual experience?
JT: Yes. And I knew right away I didn’t like being on the bottom — I just knew. It felt wrong, and it stopped right there.
JM: At thirteen you were kicked out — you must have stopped school around then too.
JT: Second week of sixth grade is when I stopped. My vocabulary isn’t great because of it. I wish I could write more, but I get stuck, thinking, you don’t have the education to sit down and write something — I know that’s all on me, though. When I was in my sixties, dying, I ended up in the New York City shelter system, got better, and they suggested I get my GED. I did, and I passed.
JM: What do you mean, you were dying?
JT: Living on the street that long — I was on 34th Street and 6th Avenue by then, in a box with other queer people, couldn’t walk anymore, people had to carry me. There’s a church on 9th Avenue and 28th Street that’s amazing, feeds the homeless every single day. But I wasn’t eating, just wasting away. They carried me to a Project Renewal van, and they told me flat out, you’re dying. Put me in the shelter system, which every queer person in New York knows to avoid, because it’s not safe for us. And it wasn’t — I was beaten by security guards in there, thrown down a flight of stairs. I also used to buy crack from the social workers, there was a shelter in Brooklyn we called BWS, and we bought our crack right from staff there.
JM: From staff members?
JT: Social workers, maintenance men, all of it. It was notorious back then. This was the eighties. I went in for real in ’99, that’s when I actually started getting better.
JM: Living on the street for close to thirty years — how did that imprint on you? How does it still show up?
JT: I can’t walk past a homeless person without giving them money or a cigarette, because I know what it’s like to be out there, invisible. People walk past all day and just don’t see the homeless. I tell people, you don’t have to give money, just walk by and say, hey — you don’t need to give anything, don’t need to stop and have a whole conversation, just let us know you’ve seen us, that we’re not invisible.
JM: I think our ability to walk past a homeless person and just carry on with our day is a scary fact of being human.
JT: It’s sad. Back then, in the throes of alcoholism and addiction myself, it probably didn’t bother me as much. Looking back now, out of homelessness maybe twenty years — it was lonely, and you learn not to trust anybody. It took me a long time to trust people again, to hold a real conversation. When I became a co-founder of Queers for Economic Justice — dumb luck, honestly — Amber Hollibaugh and Ignacio Rivera pulled me into a room and said, “How come you never say anything?” I said, because you’re all using these huge words, I have no idea what the fuck you’re talking about — I’d go home and look things up in the dictionary just to keep up. I give them so much credit, from that day forward they simplified how they talked, explained things to me. I was just lost in all their big words.
But Queers for Economic Justice is what put me on that political, social path, made me start really looking around, realizing what was wrong. I first knew something was wrong when the shelter system in New Providence, where I got my GED, gave me a diploma, and once I sobered up in there, I really looked around and saw how bad these shelters actually were. I started collecting soda cans people left, washing them out, cashing them in, so when a new girl came in without a toothbrush, I could get her one. If somebody got sent to Bellevue, I’d go visit right away, bring candy, snacks. I wanted to treat people the way I wished I’d been treated, and wasn’t. Never wanted anybody to feel the way I did, and I tried my best not to let that happen to them.
JM: What was the process like, finally getting off the streets for good?
JT: I was dying, and they put me in a place in the late ’90s — a good shelter, for once, shelters are usually terrible, but this was one of the better ones, queer director, cool social worker. I kept leaving to smoke crack and coming back, and she’d never lecture me, just lean in and say, “It’s your choice.” I’d never really heard that before, that it was my choice. One night I went out, and some kids in front of Madison Square Garden said something derogatory to me, I said something back, and they beat me with small pipes — one of the worst beatings of my life. Went back to my shelter, they put me in the hospital. Walking up 34th Street beforehand, covered in blood, nobody even asked if I was okay. Finally a rookie cop near Grand Central grabbed me, got me to a hospital. Waking up there, bandaged up, it hit me — it’s my choice, I don’t have to keep going out there and getting high and beaten, maybe killed, like so many people I knew who were killed out there.
When it was time to leave, I called my social worker and said, I don’t want to use anymore, can you send someone to get me, I don’t want to come back alone. Nobody was available. This was June of ’99 or 2000. I had a few dollars in my pocket, walked the whole way from the seventies at Presbyterian down to the forties, telling myself the whole way, you could buy a six-pack, you could buy a couple hits of crack, it was only two dollars a cap back then — and kept saying, no, wait till the next corner. Made it back to the shelter without using, and never touched crack, heroin, or pills again.
JM: Did the shelter help you find housing after that?
JT: They did — a program, I don’t know if it still exists, got me a huge apartment in Brooklyn, and I stayed there for years. That’s when I went to school to become a substance abuse counselor, passed everything, was top of my class, but never actually sat for the final exam, because I realized I didn’t want to sit behind a desk helping one person at a time. I wanted to go back into the streets, the shelter system, help as many people as I could. I used to give tours, actually — hopefully I’ll start them up again next summer — starting in 1963, walking through what the Village looked like, smelled like, tasted like back then.
JM: What did it taste like?
JT: Good, mostly — sometimes crap. Crap when the cops grabbed you, when you took a beating, or when you ended up in the Women’s House of Detention, which I did, plenty of times.
JM: The Women’s House of Detention is pretty famous — I don’t think many people outside New York have heard of it.
JT: I think it was a ten-story building.
JM: It was open from the thirties into the seventies, mostly women imprisoned there.
JT: That place was a nightmare and a playhouse, all in one. I spent time there — got arrested a lot.
JM: Why a playhouse?
JT: In the movies you see them pull a lever and the doors slam shut. It wasn’t like that — the CO would walk down and manually close your gate, and everybody smoked filtered cigarettes in there, even if you didn’t outside, because you’d break off the filter and jam it into the lock mechanism. It would sound like it was locking, but it wasn’t. Four tiers, cell blocks A through D, with a long corridor down the middle where the CO would sit at night, and once she dozed off or got distracted, we’d pop our doors open and go visit our girlfriends. That was the playhouse part, always something going on. The nightmare part was the intake physicals when you first arrived — horrendous, I don’t know if it was worse for butches specifically, but it was terrible, and I can still feel it in my bones telling you this.
JM: I should mention, the historian Hugh Ryan has a book coming out about the House of Detention.
JT: Yeah, he’s a buddy of mine.
JM: My understanding is the House of Detention was almost like a queer gathering place in its own right — like a Stonewall of sorts, a presence in people’s lives.
JT: The building itself was a presence, yeah. And inside, your own little community, your cell block, mostly queer for the length of your stay, one way or another. Sex, yes, and looking out the windows down into the Village — I was usually on the side that looked out over Wellens Drugstore, at 8th and 6th, and Nedick’s, where all the lesbians would meet up on weekends, everyone knew, meet at Wellens. From jail I’d look down and see them all gathered there and think, look at those idiots. Took me years to realize — wait a minute, they’re outside, I’m inside. I’m the idiot. My arrests were for not wearing the required three articles of “female” clothing, drugs, armed robbery, you name it.
JM: I’d be fired if we didn’t talk about Stonewall. Before we get there, can you describe the bar itself?
JT: What a dump, honestly, back then, and not much better now. Dark, smelly, you never drank a mixed drink there, because there was barely any running water, glasses got washed in dirty water, you didn’t know what was in the bottles they poured from — so you brought your own.
JM: No way.
JT: Bartenders were friendly, though. It’s one section now, but back then it was two — you’d walk in the front, and about halfway back you could swing into a second room, where most of us hung out. Music always blasting, people dancing. It was home, somewhere we could be ourselves, hold each other, dance together.
JM: The night the uprising began, you were in the park when you heard about it?
JT: I was. A bunch of us, sleeping in the park, early morning, one, two a.m.
JM: Do you remember specifically what you heard? Police raids weren’t uncommon — what made you sense this one was different?
JT: No cell phones back then, everything was word of mouth, and you couldn’t keep a secret in the Village if you tried. Word came into the park — something’s going on at Stonewall, something’s going down. Just something in the way it was said, felt different from an ordinary raid. We went up there. By the time I got there, people had already been arrested. I remember a lieutenant yelling at the crowd to get back, and nobody moving, and someone threw a bottle, and he starts screaming, whoever threw that, come out, you’re under arrest — like anybody was going to just step forward. The whole street was screaming. It felt so empowering, being able to yell at a cop and not immediately get beaten for it, even though plenty of people did get beaten that night. Just yelling, throwing things, watching them get scared — you could see it in their eyes, and I think it surprised even them, being scared of a bunch of gay people.
JM: It sounds like utter madness, but fun madness.
JT: It was. One of the best nights of my life, honestly, in that particular way. Looking back, for that one moment, even people who didn’t necessarily like each other came together and said, enough, you have to stop beating us, stop arresting us, just let us live. Being homeless and an addict, we were fighting for our lives against cops every single day already — I’ve had ribs broken multiple times by police — fighting for who I was. This is who I am, I’m not changing.
JM: Once you finally got that first apartment in Brooklyn, in your 50s, did it take a while to adjust?
JT: I lived there a month with no lights on, too embarrassed to ask anyone how to even turn them on. When I finally went to the electric company, nobody had told me I needed to bring a lease, needed credit — didn’t know any of it. Working in the shelter system later, doing QEJ work, we’d go over activities of daily living with people leaving — this is what you need to know, don’t get stuck, because if you’ve been homeless that long, you genuinely don’t know how to run a washing machine. I didn’t even know what a cell phone was. We were living on 31st Street, near Bellevue, and one day we saw people walking down the block talking to themselves, and figured they must have let everyone out of Bellevue — didn’t realize they were just on cell phones. That’s how disconnected you get, out there. All you know is your homeless family, and all any of us knew was, survive.
JM: If someone’s kicked out of their home today, nowhere to stay, no shelter that feels safe — do you have suggestions?
JT: Unfortunately the shelter system is really the only widespread option, and I’m not advocating for it, they’re not good. But if you’re queer, reach out to the Center, Coalition for the Homeless, definitely the Partnership for the Homeless — Anya’s queer there, and she’ll help, always has her hand out. She’s the one who pulled me out of homelessness in the end.
JM: Are there parts of living on the street you miss?
JT: Yes.
JM: Like what?
JT: Not having to pay bills — now I have to keep everything organized, or I’d lose track. I miss the air, sleeping outside in it. That’s about it, really.
JM: When was the last time you slept outside by choice?
JT: Went down to see Linda, and we slept on a trampoline — in our 70s, on a trampoline, are we insane? Couldn’t sleep on the ground anymore, it’s brutal on the body. The people I see out there now, and there seem to be so many more, the kids especially, it breaks my heart, talking to them — thrown out for the same reasons I was. We know better as adults, we just don’t do better. People need to know this history — even though it’s my history, it belongs to so many more people than just me. It’s our history, and people need to know what it was like, and what it’s still like out there today.
Click here to listen to the full interview on the LGBTQ&A podcast.
LGBTQ&A features interviews with the most interesting lesbian, gay, bisexual, transgender, and queer people in the world. Hosted and produced by Jeffrey Masters. @jeffmasters1
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