Chicago Whispers: A History of LGBT Chicago before Stonewall

3. Chicago’s Cesspools of Infamy

19 3 Chicago’s Cesspools of Infamy From the Civil War until the Vice Commission Report (1911), Chicago was infamous for its debaucheries, orgies, and all manner of vice: the secret rooms at Roger Plant’s Under the Willows sex complex in 1861, through the “nauseating spectacle” of female impersonators at Alderman “Bathhouse ” John Coughlin and “Hinky Dink” Kenna’s annual First Ward Ball, to the Levee “Red Light” District and the sins of Riverview amusement park. Chicago became a major manufacturing center for the Union army during the Civil War, supplying meat, leather, and weapons to grease the cogs in the modern military machine. Job opportunities attracted thousands of single men to the city, and coupled with off-duty soldiers from Camp Douglas on the South Side, this led to an increase in brothels, saloons, cheap theaters, and opium and gambling dens. The most infamous of these vice dens was on the corner of Wells and Monroe Streets. Roger Plant opened his resort at the onset of the war in 1861, and with the characteristic whimsy of this diminutive Englishman from Yorkshire he named the establishment Under the Willows. Local Deputy Superintendent of Police Jack Nelson called it “Roger’s Barracks” because with its tunnels, secret rooms, and alleyways, it was impenetrable. Not that he made any serious effort to bust it, however. In January 1868 Nelson became embroiled in a bribery scandal, and when Plant was called before the Common Council appointed to investigate the corruption, he refused to Chicago’s Cesspools of Infamy 20 answer the question, “Did you ever give Deputy Superintendent Nelson any money?” The case was dismissed. Under the Willows opened as a two-story building, but as the war progressed it grew to sixty rooms and stretched half a block. It comprised a saloon, private cubicles and rooms, and at least three brothels. “The wickedest place in the world” provided every vice, including “male degeneracy”— male prostitutes rented cubicles to perform the “infamous crime against nature.” While Plant lorded over the saloon, his 250-pound amoral Liverpoolborn wife held court over the brothels, which included a room where kidnapped teenage girls were “broken-in,” that is, gang-raped, then sold to bordellos around the city. Barely five feet tall and weighing a hundred pounds, Roger Plant never shied away from a brawl; he was known to use his teeth and anything else that came to hand. And yet he was no match for his overbearing wife, who, during marital disagreements, would hold him by the throat at arm’s length while his fists flailed in midair. Plant was rarely out of the news. In April 1864 he was arrested, along with his wife, a Mrs. Filkins, and Josephine Neary, for running a disorderly house. There were between eighty and ninety others arrested at the barracks that night. Plant was fined a hundred dollars, brothel keeper Neary forty dollars, and the others between five and fifteen dollars; those who couldn’t pay were sent to crush rocks at the Bridewell, a one-story 100-by-24-foot wooden prison built in 1851. The exact number of children the Plants sprouted is unknown, but it’s thought to be around fifteen, all of whom were seasoned thieves from an early age. In 1868, having raked in a considerable fortune, Plant closed Under the Willows, bought a country house, and retired to a life of respectability as a landed proprietor, claiming it was a better moral environment for his children. It seems the rural life and pious climate failed for at least three of his offspring. British journalist William T. Stead noted in his book If Christ Came to Chicago (1894) that Roger Plant Jr. owned three saloons and two brothels, while two of his sisters, Daisy and Kitty, ran adjoining brothels on South Clark Street. Vice in Chicago showed no signs of abating after the Civil War, and by the late 1870s prostitution was so established that gossip sheets about the brothels appeared on the streets. These were published by Shang Andrews, and in his Chicago Street Gazette one intriguing item from September 15, 1877, read: “Ada Huntley is now happy—she has a new lover—Miss Fresh Chicago’s Cesspools of Infamy 21 from Pittsburg.” Andrews also published The Sporting Life, a paper that in June 1878 was taken to court for indecency because it reputedly contained same-sex personals. In 1882...