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Convention, held in Chicago in August 1968, and the election of Harold Washington as the city’s first black mayor in the spring of 1983.

      Chicago was the birthplace, in the 1920s, of the nation’s first, short-lived gay-rights organization, which quickly collapsed because of police harassment, and it was one of only four cities—along with New York, Los Angeles, and San Francisco—where the first annual gay-pride marches were held in the summer of 1970. Yet it was never one of the coastal gay meccas—like San Francisco and New York—that was so open to gay mobilization as to be unrepresentative of urban America as a whole. Indeed, Chicago may also be the largest American city without a strong popular association with homosexuality. Chicagoans sued for the right to operate a gay bar later than did their counterparts in New York and San Francisco.22 Of the five most populous U.S. cities in the 1980 census, Chicago was the last with a gay-rights ordinance, passed in late 1988.23 Gay politics there drew on local frames, events, and demographic shifts. Chicago, in short, offers the advantage of studying a large city with national importance that still claims a degree of representativeness that its coastal counterparts cannot.

      This book introduces the reader to women and men who created a social movement far from the coastal meccas—where, after all, only a small minority of the nation’s gays and lesbians lived. As gay Chicagoans struggled to respond to police crackdowns in the 1950s and 1960s, they turned to the criminal lawyer Pearl Hart, a radical Jewish woman from Michigan who had graduated from John Marshall Law School in the Loop before World War I. In the 1930s, she defended prostitutes in Chicago’s Women’s Court and helped found the left-wing National Lawyers Guild, and in the early Cold War she became nationally known for defending leftists charged under the Smith Act. Hart also defended countless gay men arrested in Chicago’s gay bars and tearooms. Beginning in the mid-1950s, when she was in her mid-sixties, and for two decades, she advised nearly every Chicagoan who struggled, against the powerful forces of the closet and of a conservative era, to forge a homophile movement.

      In the 1970s, Chicago’s most vocal and passionate champion of enacting gay rights legislatively, Cliff Kelley, emerged not out of the gay-liberation movement but out of the 1969 Illinois constitutional convention, and the broad movement of civil rights challengers to the regime of the Jim Crow North. Kelley, a brilliant black liberal iconoclast, was born in the South Side’s Washington Park neighborhood during the flood of black migrants seeking industrial jobs during World War II. Witty, idealistic, and intellectual, he introduced his gay-rights ordinance year after year, holding hearings, tweaking his arguments. At one point, Kelley, who said he was straight, told a newspaper reporter that he couldn’t enact gay rights in the city council because some of his colleagues “have masculinity problems or are secret bigots.”

      Kelley’s virtues were characteristic of his native city, and so too was the vice that brought about his political downfall. After sixteen years of service as an alderman, he was indicted in 1986 for accepting bribes from waste contractors doing business with the city, pled guilty the following year on a lesser mail-fraud charge, and served nine months in a minimum-security federal prison. After his release, he reinvented himself as a radio talk-show host, where he could be heard for many years on WVON-AM radio (“Voice of the Negro”), Chicago’s sole remaining black-owned station. In 2000, he moderated the only campaign debate between the incumbent, Congressman Bobby Rush, and his challengers, Donne Trotter and Barack Obama.

      Kelley’s tragic flaw may have been as implausible as his heroic advocacy for gay rights. Perhaps, in a larger sense, it was nothing if not Chicagoan. We turn now to the place where these paradoxes emerged: the contradictory landscape of the postwar city.24

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      A Little World Within a World

      “I MOVED TO my own place when I was eighteen, to a building near Clark and Division, which was the place to live if you were gay,” recalled John, a gay man, in 1983. The year to which he referred was 1950. The previous year, John’s priest had been shocked by his disclosure at confession that he had had a sexual encounter with another teenage boy. John added that once he moved to Chicago’s Near North Side, “When you applied for a job, you hesitated to give an address in that area. Quite often I gave my parents’ address to avoid remarks like ‘The queer North Side, eh?’ or ‘Is that near Clark and Perversion?’”1 Though Americans had long viewed cities as dens of iniquity, foreignness, and political radicalism, as whites began to move to the suburbs in the 1950s, sensational depictions on television and in movies cemented the cities’ reputation as dangerous. In novels and in newspapers, cops and G-men did battle to reclaim the urban jungle from dangerous criminals and sex fiends.

      But cities were also places where blacks and gays could develop communities. African Americans left the Jim Crow South for Chicago in large numbers, with nearly half a million crowding into the South Side’s “black belt” by 1950. As the boundaries of the black belt threatened to burst into the surrounding white residential areas, violence flared, yet African Americans found the chance for better work and pay in Chicago than in the places they had left behind. Gay men and women also found work, friends, and ways of living that were impossible in the small towns or the provincial urban neighborhoods where they had grown up. When sexologist Alfred C. Kinsey first traveled from Indiana to Chicago in the summer of 1939 in search of homosexuals to interview for a possible research project, he found himself swept up in a dizzying array of parties, clubs, and bars, “which would be unbelievable if realized by the rest of the world,” he wrote to a colleague.2 Almost three decades later, one Chicago lesbian went so far as to lament how deeply involved younger lesbians seemed to become in the city’s queer communities: “[J]ust because they’re homosexual, the gay life becomes everything.”3 Many men and women were afraid to dip their toes into the gay world, but urban America offered many others access to a limited degree of freedom.

      The most visible gathering places for gays and lesbians in 1950s Chicago were in the two main entertainment districts, north and south of downtown. On the South Side, just north of the historic black commercial center of Bronzeville and a block from the city’s first high-rise public-housing project, which opened in 1950, the jazz trumpeter “Tiny” Davis, known as the Female Satchmo, opened a jazz club with her partner Ruby Lucas. At Tiny and Ruby’s Gay Spot, later demolished to make room for the Dan Ryan Expressway in 1958, Davis recalled, “The daddies are daddies and the fems are fems.”4 At Big Lou’s, a Rush Street lounge on the mostly white Near North Side, a police officer in early 1952 reported “observation of effeminate men and mannish women in the place, males dancing with males, females dancing with females, and undue demonstrations of intimacy between women at the bar.”5 Between the two places, at the Town and Country Lounge in the basement of the Palmer House hotel in the central Loop commercial district, predominantly white gay men gathered for cocktails, often under the noses of straight hotel guests, and well-heeled men mingled with male window dressers and “ribbon clerks” working in downtown department stores.6

      As gay enclaves developed, a small number of Chicagoans, mostly gay men but some notable women as well, launched tiny organizations aimed at improving the status of homosexuals. Chicagoans founded in 1954 the first chapter outside California of the Mattachine Society, the pioneering national “homophile” group in the postwar era, which advocated greater acceptance of gays and lesbians, their successful social and cultural “adjustment” in American society, and more sympathetic views of their lot on the part of experts. Homophile groups sought to improve the status of the homosexual in American society by holding discussion groups; meeting with sympathetic doctors, lawyers, pastors, and scholars; and publishing newsletters and magazines. The homophile movement also discussed the need to reform criminal laws against same-sex acts.

      In many ways, the federal government drove the state repression of homosexuality in the quarter century after World War II. In the so-called lavender scare, officials investigated and purged gay and lesbian federal employees, beginning in 1950. That year, Senator Kenneth Wherry of Nebraska launched an investigation of gay employees in the State Department, sparking a wave of hostile press attention that coincided with the anticommunist panic in Washington and Hollywood. In a 1953 executive order, President

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