‘The Women’s House of Detention’ Illuminates a Horrific Prison That ‘Helped Define Queerness for America’

Photo: Irving Haberman/IH Images

Most articles about the legendary LGBTQ activist and “bad-ass Super Butch” Jay Toole lead with the fact that she’s a Stonewall veteran and feature her account of those six days that changed American history. But Toole also has some pretty shocking and important stories to share about another historic building, just 500 feet away from the Stonewall Inn: the Women’s House of Detention.

In an interview with author Hugh Ryan, Toole described one of the many times she was taken to the prison while she was living on the streets. Incoming detainees were brutalized with physician-administered forced enemas and cavity searches, and during one particular assault, she said, “It felt like his whole arm went in there.” Toole was left “covered in blood” and immobilized by pain.

“And they didn’t do nothing,” she told Ryan.

According to one 2017 study, more than 40 percent of the people held in America’s women’s prisons are queer, and, as Ryan notes, this figure was surely even higher in years past, when jails could contain people arrested for “crimes” like wearing pants. The House of Detention, which stood in New York’s Greenwich Village from 1929 to 1974, once held famous queer women including Andrea Dworkin and Angela Davis, but despite its history, the prison has slipped out of local memory. (One of its most prominent pop culture representations came via a little-seen and widely panned 2004 David Duchovny movie about a straight, white boy.) Though it’s been treated as a footnote to more celebrated LGBTQ sites of resistance, the facility, Ryan writes in The Women’s House of Detention: A Queer History of a Forgotten Prison, “helped make Greenwich Village queer, and the Village, in return, helped define queerness for America.”

“These files are incredible. I found wedding rings in these files. I found photos, love letters, poems.”

While working on his first book, When Brooklyn Was Queer, which examined the borough’s hidden LGBTQ history, Ryan noticed that more than one of the figures he profiled had been arrested and taken to the House of Detention. Then, he noted the prison popping up in queer history after queer history. “Suddenly it was like the House of Detention was jumping out at me everywhere,” he said. “I was looking through Audre Lorde and there it was, and I was looking through Joan Nestle, and there it was.”

He was determined to tell the story of the prison not from the institution’s perspective, but via the women and transmasculine people whose lives it upended. For the necessary biographical details, he turned to the Women’s Prison Association, which funded social workers at the House of D, as the prison was known to locals. Its archives are held at the New York Public Library, and in them Ryan found a treasure trove.

“These files are incredible. I found wedding rings in these files. I found photos, love letters, poems,” he said. “Some of these files ran like 500 pages and covered 40 years. It was shocking.”

Ryan first wrote about the life of of “Big Cliff” Trondle, whose early arrest for “masquerading in men’s clothing” caused him to write to President Woodrow Wilson and ask that he not be forced to wear a dress to court, in When Brooklyn Was Queer. However, Trondle disappeared from the historical record during his youth, until Ryan found his WPA records. “The moment where I found Big Cliff’s file, I actually yelled out loud in the library,” Ryan said. “I wasn’t even looking for it. It was just there all of a sudden. And I was like, ‘Oh my God, this is the next 30 years of his life.’”

Using these and other historical records, Ryan skillfully brings Cliff and other detainees to life. There’s Charlotte and Virginia, young women who met at the House of D in the 1930s and fell in love, despite authorities’ efforts to split them up and make them despise their sexuality. (“I guess I tried to push something aside that can’t be pushed aside,” Charlotte wrote in an aching letter to her social worker.) There’s Louise, a queer Black teenager, who was clever, talented, and dreamed of Paris and a life on the stage, but had to contend with authorities who deemed her “slovenly” and psychopathic. Big Cliff ultimately spent decades entangled in the legal system, facing heroin addiction and engaging in survival prostitution, before he was murdered in 1942 and buried in an unmarked grave paid for by his fellow sex workers.

Ryan uses the experiences of these figures, and many others, as an entryway into the history of the facility and to offer context to the trends in the American legal system and culture that shaped prisoners’ lives. Many were locked up for acts that are no longer considered criminal, but that represented challenges to prevailing standards of femininity.

In the prehistory and early days of the House of D, men in the criminal system tended to be accused of “crimes against people, like murder or rape, or crimes against property, like arson or robbery. Women’s justice was about immorality,” said Ryan. “And so it focuses in on things like disobedience, how you dress, if you smoke, if you are a threat to become a prostitute. It’s all about how women can damage the social order because it’s, in fact, social control.”

Charlotte was imprisoned as an accused “wayward minor,” a charge that, in New York, could be applied to “incorrigible girls”—and only girls–for decades. Many early detainees were arrested for prostitution under rulings that defined it as “the common lewdness of women.” (“The element of hire or money,” a magistrate noted, “does not appear to be essential.”) For years, only women were targeted in vagrancy prostitution cases, as while selling sex was considered a crime, buying it was not. Eventually, authorities expanded the net to ensnare gay men accused of being sex workers, too.

In the World War era, during a panic over the threat disease-carrying, promiscuous women supposedly posed to soldiers, women who were found to have STIs were incarcerated until they were deemed cured—even if that meant being held in prisons like the House of D past the end of their criminal sentences. Across the country, tens of thousands of women were incarcerated under this policy, and some were forcibly sterilized. Then, in the hyper-conservative postwar period, the state cracked down on LGBTQ people. One woman profiled in House of Detention was arrested simply for writing a letter to her girlfriend in which she defined the word “lesbian.”

Still, in the face of horrifying conditions that included food tainted with rodent droppings and widespread forced medication with thorazine, those held at the House of D made friends, built communities, and fell in love. Ryan describes one sociologist who studied the facility in the ‘60s, and who first thought there were a surprisingly high number of Black Jews in the prison. She later learned that, as religious symbols were the only jewelry permitted in the House of D, the Star of David necklaces she saw on Black women were actually highly-prized gifts from their Jewish girlfriends.

The prisoners also made history. Former detainees attended Mattachine Society lectures, and, with the Stonewall Inn visible from the prison windows, participated in the 1969 rebellion. They set fire to objects and flung them from the prison windows and onto the city streets below, chanting, “Gay Rights!” Still, the uprising that would help reshape much of gay life in America had limited effects for some of the doubly or triply marginalized queer people who were most likely to end up in the House of D. “For some in the community, [Stonewall] felt like a turning point,” Toole told The Nation in 2019. “For homeless street kids, for me and the folks that I was hanging out with, it didn’t. Because we had to still survive on the streets, and nothing really changed for us.”

“Jails and prisons are designed to break human beings, to convert the population into specimens in a zoo.”

Though the lovingly-rendered tales of the House of D’s little-known prisoners form the heart of Ryan’s book, he also profiles its famous detainees and explores the ways in which their experiences at the institution influenced their lives and politics. During her 16 month imprisonment from 1970 to 1972 Angela Davis’s only stints in general population occurred at the House of D, which meant, as Ryan puts it, that the prison represented “the only time she had regular, direct contact with other imprisoned women.” She talked to them about Communism, helped start a bail fund and, when she was placed in solitary confinement, other prisoners joined her on a hunger strike that succeeded in getting her returned to the general population.

Her experience at the prison helped make Davis one of the world’s most famous prison abolitionists. “Jails and prisons are designed to break human beings, to convert the population into specimens in a zoo,” she’d later write in her autobiography, “obedient to our keepers, but dangerous to each other.”

Andrea Dworkin first became a national figure when she went public with her account of receiving the kind of violent and bloody genital exam inflicted upon Toole and so many others. Unlike Toole, who was poor and unhoused, Dworkin was a Bennington College student who arrived at the house of D after having been arrested at a 1965 Vietnam War protest. The world took notice, and her grand jury testimony about the assault hastened the prison’s closing seven years later. Ryan notes that Dworkin only began writing about pornography after facing rejection with her initial book proposal about the prison system. To her, the two issues were intertwined. “Pornography and prisons were built on cruelty and brutalization; the demeaning of the human body as a form of punishment; the worthlessness of the individual human being…”

Prisons tend to open amid promises of reform, before enduring decline and eventual closure. That’s what happened to the House of D, which was torn down in 1974. These days, the site where the prison once stood is the lush Jefferson Market Garden. Originally, Ryan reports, members of the community wanted the garden to be private, and though these efforts didn’t succeed, it still has an exclusive feel. “There are volunteers of the garden who keep it really nice, but they also sit at the entrance when you come in,” said Ryan, “So you feel a little surveilled.” It’s also surrounded by high gates, all of which make a place once designed to contain street women, the poor, Black, queer, and gender non-conforming, now feel intended to keep many of those very people out.

Criminalized people may no longer be detained, or much welcome, in the now-tony Greenwich Village, but they fill the facilities on Rikers Island, which is nearing the end of its own trip around the prison life cycle. If it closes as planned within the next five years, Rikers is to be replaced with institutions located on the streets of the city, as the House of D once was. It seems likely that these facilities, too, will be touted as more enlightened institutions, before declining into cages filled with indignities and abuse.

Ryan says that, before his work on The Women’s House of Detention, he was a liberal when it came to jails and prison. “I would have told you that prisons were bad and they needed to be improved,” he said. “Watching this history unfold decade after decade, through liberal administrations and conservative ones, just showed me that that is impossible, that reform is never going to work, that abolition is really the only way forward. The way that the criminal, legal and prison system exists right now is to act as a stopgap and a valve on every other system that is actually broken.”

“We don’t want to provide health care or mental health care or housing or public benefits or education or job training,” he added. “It’s not about justice and it’s not about rehabilitation. It is to put away the people that we refuse to care for in any other way.”