In the 1960s, before rainbow flags and equal signs on SUV bumpers, gay and lesbian visibility came primarily through gender bending. Occasionally, queerness might attach to an individual in the public eye. Bayard Rustin's arrest on sex charges was widely publicized. Allen Ginsberg's sexually explicit poetry provoked outrage. Marlene Dietrich and Greta Garbo played roles that suggested lesbianism but that's because they wore men's clothes. Lesbian moviegoers might hope that, maybe, they were lesbians in real life. I'll never know whether the young men I saw that day in 1963 were gay. But crossing gender boundaries – especially through dress and hair style – was so closely tied to homosexuality that it didn't matter. I saw them and I knew: they were what I felt I was. I came back to Times Square many times, hoping to find someone else who was queer. Eventually, I did. Those street fairies, as they were widely termed in those days, helped me discover gay life.

My experience was not unique. Recalling her days in New York in the 1950s, Joan Nestle, a founder of the Lesbian Herstory Archives, has written that butch-femme couples 'made lesbians culturally visible.' She describes these couples, who 'often provoked rage' when they appeared on the streets, as models of courage. Histories of lesbian life in San Francisco, Detroit, and Buffalo all make the same point.

We don't have a book-length account of lesbian life in Chicago in the decades before Stonewall. But we are blessed with a richly detailed study of the culture of drag performance and street fairy life. Esther Newton, who is one of the great figures in contemporary queer studies, was a graduate student in anthropology at the University of Chicago when she decided to do her dissertation on a gay topic. Mother Camp, the book she produced a generation ago, was based on field work in Chicago and Kansas City in 1965 and 1966.

'Drag,' Newton wrote then, 'symbolizes gayness.' She described drag as 'an open declaration, even celebration, of homosexuality.' Those who cross-dressed, she argued, were effectively saying 'I'm gay, I don't care who knows it; the straight world be damned.'

When Newton made her observations, drag was a big part of gay bar life in Chicago. In 1966, seven gay nightspots had full-time drag shows, employing roughly thirty performers. At a time when much of Chicago life was racially segregated and Martin Luther King, Jr. was planning massive protests, many of these performers were African Americans. Drag shows packed in patrons on weekends; 200 or more might press into the space. Some bars with drag shows were located near each other, and the crowds moved back and forth during an evening in order to catch all the shows. The experience helped create a sense of community.

Most of the time drag shows were pure fun. Performers did hilarious impersonations of older showbiz figures like Mae West or Sophie Tucker. They bantered with the audience, using the people in front of them as material for their jokes. But sometimes a political message surfaced. Newton described impersonators who referred to the fact that Illinois, alone among the fifty states, had repealed its sodomy law. One spoke to the audience about the Mattachine Society. 'If you think we're not gonna march,' he said, 'you're out of your mind.' This was before Stonewall.

Gender crossing in these bars was confined to the stage. At night's end, the performer removed jewelry, make up, and gowns, and returned to male clothing. Among bar patrons, any gender crossing was risky business. It was against the law, and police were eager for arrests. Bar managers kept customers in line.

But outside was another matter. There, Newton reported, young gender crossers made the streets the site of their performance. Like the street fairies I saw in Times Square, they presented themselves for anyone to see. They were most visible in those neighborhoods with a reputation as gay; in fact, their presence helped mark a neighborhood as queer. They could also be found in areas that attracted johns looking for prostitutes.

Life for a street fairy was difficult and dangerous. To challenge gender boundaries openly made it hard to get a job. Many had to support themselves through prostitution. Add this to their violation of the laws against cross-dressing, and one could say, as Esther Newton did, that they lived 'outside the law ... in continuous interaction with the local police.' Police harassment often meant long arrest records.

Fragments of evidence about James Clay highlight just how vulnerable street fairies were. A twenty-four year old African American who lived on the West Side, Clay already had 12 arrests by 1970. Charges included impersonating the opposite sex, solicitation to commit prostitution, battery, resisting arrest, aggravated assault and attempted murder. A hardened criminal, right? Wrong! All of these are charges that easily stem from the efforts of a transperson of color to make a living on the streets. Clay likely made the mistake of soliciting plainclothesmen; he likely tried to escape, which translates into resisting arrest. And, to make sure of a conviction, police officers could define physical resistance to them as aggravated assault or attempted murder, which then got plea-bargained down. Clay's twelve arrests resulted in three convictions between 1965 and 1969. One of his arresting officers was James Finnelly.

In the wee hours of the morning, the day before Thanksgiving 1970, Finnelly and his partner, Thomas Bolling, spotted Clay, who was wearing women's clothing, flagging motorists. They gave pursuit and chased Clay into a building. Clay managed to shake them off and escape. In an unmarked car, the two officers kept cruising the neighborhood near Madison and Francisco. They found Clay, who had changed into men's clothes, and tried to arrest him. Clay got free again, but this time Finnelly and Bolling fired eight shots into his back.

The Sun-Times and the Defender carried stories about Clay's killing, and both papers wrote in ways that suggested doubt about police veracity. But no witnesses came forward. The recently formed Chicago Gay Alliance called for an FBI investigation into the slaying, arguing that Clay's civil rights had been violated. But the FBI refused. CGA wrote that 'street transvestites are the most up front part of our community ... Cops use transvestites to take out their hatred for those of us they can't reach so easily ... James Clay was a Gay martyr.' Clay's killing helped provoke the formation in 1971 of the Transvestites Legal Committee, which may have been the first transgender political group in Chicago.

Postscript: Thirty-five years after the killing of James Clay, Amnesty International released a report, Stonewalled, that looked at police practices in Chicago. 'Transgender people of color,' it concluded, 'are especially at risk of police abuse.' Much has changed since 1970. And much hasn't.

Copyright 2008 John D'Emilio