Boys Enter the House

by David Nelson

  At the time, he was not necessarily alarmed by Tex’s anger. Robin too, was irritated by Garth after his return from abroad. “He’d spent too much time having tea in England,” he joked.

  With Garth out, Robin moved into the townhouse. For a time, the townhouse cycled through a series of gay men, including a man named Jim, who became Robin’s first boyfriend.

  Jim decided they should move out together, and not long after, the others left the townhouse behind as well. Nevertheless, Robin remained connected to his roommates, including Tex, even though he was often petty, manipulative, and eccentric. “He used to pay us to go over to clean his apartment,” Robin said. “His bedroom would literally be filled to the level of the bed with just clothes and trash and food jars.”

  It was at Tex’s new apartment that Robin met another young man—a new student at the conservatory—Craig Conner, who had just arrived from out west. “Oh man,” Robin said. “He was so beautiful and so sweet and so kind. He was just gorgeous.”

  Craig had arrived at the conservatory as a piano student under the tutelage of Tex Richardson. Most recently from New Mexico, he was also a talented baritone. Music was woven into the very fabric of his life.

  Now, in some ways, Craig would weave himself into the fabric of their lives.

  Once upon a time in gay Chicago there was a vibration happening in the city. It began as a tremor but grew into a groundswell that reshaped the city’s neighborhoods.

  In the years following the unfinished civil rights struggles of the 1960s, a vocal and burgeoning LGBT community had begun to take root in Chicago, helped along by activism, increased media representation, and a rising sense of pride.

  Before then, the gay community of Chicago was a mostly disjointed collection of secret pockets all around the city. Public perception at the time viewed anything other than heterosexuality as deviant, psychotic, evil, and often linked to criminality. In Chicago 1924 the trial of Nathan Leopold and Richard Loeb—two young men from well-to-do families accused of murdering Loeb’s fourteen-year-old second cousin—caused a sensation with its homoerotic undertones.

  Coded words and phrases, signals such as a pinky ring or carrying a sexually suggestive book allowed men and women to discreetly signal desire for same-sex encounters. Hushed moments of romance and lust unfolded in a range of unofficial safe spaces: the lakefront, movie theaters, parks, hotels, and a scattered profusion of taverns and clubs

  The South Side, welcoming waves of Black Americans during the Great Migration, was also home to a plethora of gay-friendly locations: the Plantation Café on Thirty-Fifth, the Pleasure Inn on Thirty-First, and the Cabin Inn on Cottage Grove with its chorus line of black men in drag. Black-and-tan clubs, running loose with jazz till dawn, welcomed both gays and lesbians warmly.

  Gay havens cropped up elsewhere too: Waldman’s Restaurant & Bar on Michigan Avenue, Diamond Lil’s on Rush Street, the Ballyhoo Café on Halsted, and the Rose-El-Inn (popular with lesbians) on Clark.

  For decades, the Coliseum Annex, host to an array of political conventions, also held magnificent drag balls each year on Halloween. A ball in 1932 brought in an estimated one thousand people. Looking to match this success, Alfred Finnie, a black male sex worker and nightclub bouncer, began his own drag ball on the South Side, a tradition that lasted for several decades.

  Emerging from the aftermath of the Great Fire, a red-light district in the South Loop known as the Levee became an oasis for men and women of all different sexualities. A two-year sting operation culminated in mass arrests and raids in the Levee in 1912.

  In the years during and after Prohibition, vice squads roved the city, raiding and closing establishments. Undercover police officers entrapped gay men in public restrooms.

  But a quiet rebellion unfolded in the city. Debates on human sexuality waged in the back rooms of the Dill Pickle Club, near Washington Square Park, better known by its nickname, Bughouse Square.

  Some of the city’s most notable artists, politicians, and social activists wove LGBT themes into their work as they fought tirelessly against homophobia.

  In 1924 Henry Gerber, a German immigrant who’d previously been committed to an asylum for homosexuality, founded the Society for Human Rights in Chicago. Jane Addams, a leading suffragette and cofounder of the ACLU and Chicago’s Hull House, spent forty years with her companion and fellow philanthropist Mary Rozet Smith.

  Later, Valerie Taylor created a new genre with her lesbian pulp fiction novels The Girls in 3-B and Return to Lesbos. Partners Chuck Renslow and Dom Orejudos altered the conception of masculinity and homoeroticism—Renslow through photography, and Orejudos through his choreography and dance. Together, they founded gay bars, bathhouses, and events like the International Mr. Leather competition. Tony Midnite became an early drag queen icon, performing with defiance and flair in the 1950s and beyond.

  These individuals—and many hundreds more—chiseled away at the glacier of homophobia encapsulating society. While public perception was slow to change, after World War II attitudes began to warm.

  Although some of their conclusions are debated today, the Kinsey Reports lengthened the sexual spectrum for human beings. Alfred Kinsey himself had drawn on research from gay men on Rush Street in Chicago.

  Now, in the 1960s, with the rise of the civil rights movement, the LGBT community’s voice was amplified too.

  The 1969 Stonewall riots in New York City had triggered a new movement of gay liberation across the nation. For two nights, police clashed with growing crowds. The ongoing incitement from police coupled with the activism and violence already in place during the 1960s created a flashpoint for the gay liberation movement.

  The next year, to mark the anniversary, throngs of marchers gathered at Stonewall. In solidarity, similar marches took place around the country. Since then, gay pride marches have only grown in attendance and pageantry.

  In Chicago the early gay pride parades originated at Bughouse Square, once the sight of spectacular public debates and discourse among Chicago’s greatest minds and creatives. Silhouetted by the grand Newberry Library, famous thinkers like Carl Sandburg and Clarence Darrow sparred with other soapbox orators over the important issues of the time. Perhaps because its debates drew more progressive, radical voices who often led bohemian lifestyles, Bughouse Square had also become a meeting point for “cottaging” gays.

  Later, organizers moved the start of the route to the intersection of Clark and Diversey, the new magnetic pole for gay Chicago.

  These two locations—emblematic of the progress of the LGBT community, specifically homosexual men—were also places where money often changed hands in exchange for sex. In the blinking light of marquees and neon bar signs, men bartered and haggled for a touch of flesh, a body against a body.

  And for many of the boys, whether straight or gay or questioning, these locations became a part of their tragedy.

  Billy Carroll was wheeling and dealing. In recent years, his friends had started noticing the amount of money he’d had on hand for things like athletic equipment or gourmet meals. “It was never really said where the money [came] from,” Gene Anderson said.

  In some ways, Gene knew Billy the best. Their parents had known each other, so they’d grown up together, born just three days apart. Gene was one of the few to finally learn the secret of Billy’s money.

  “The first time I went with him, he went to Yankee Doodle Dandy down there on Diversey,” Gene said. “He bought some pills.… A big jar of them, like a hundred of them.” Gene believes they were either Quaaludes or Placidyl, both hot sedatives at the time that were known for helping insomnia.

  Billy would get a deal on the pills, then resell for profit.

  As Billy went about his business, he explained the other dynamics of the scene. He pointed to a man named “Harvey,” and said, “You let him suck your dick, he’ll give you $50.”

  The men, known as “chicken hawks” or “hawks” or simply “johns” in the slang of the streets,
would strike deals with boys, or “chickens,” they picked up outside or near the corners of Broadway, Clark, and Diversey. Either party could be any age, but typically hawks skewed older, anywhere from thirties to seventies, while the chickens hovered in the middle teens, though sometimes were as young as nine.

  Years earlier, most activity had happened in Bughouse Square, the patch of land in front of Newberry Library near the loop. Life magazine ran a 1964 photo essay about gay life in America that mentioned men meeting at Bughouse Square in Chicago. For years, Bughouse served as the main location for male hustlers plying their trade.

  The Tribune ran readers’ letters lamenting the lost era of Bughouse as a place for public debates and lectures. In the late 1960s police referred to it as a “jack roller’s haven.”

  “Everybody could go down there, you could hustle, you could meet a few johns, do a few tricks, make your money and go home,” said Gene. This was where Billy had started.

  Around 1973 or ’74, police began taking action around Bughouse, clearing out or arresting men and boys that frequently met in cars or the shade of the park’s trees. Bunco squads consistently hit Bughouse, and while activity continued in the area for a while (including two nearby theaters playing X-rated male-oriented films) most sexual commerce moved northward to Clark and Diversey.

  Inside the Yankee Doodle restaurant just south of the intersection, deals went down for drugs or sex all around Billy and Gene. After a hawk and a chicken found one another, Gene explained that the hawk would “buy you your meal, and you’ll negotiate where you’re gonna go.”

  Once the meal was eaten and the price set, the hawk and the chicken would head out together. There were several places they could go. Next door to the restaurant, a bus garage offered shelter with its alleyway. If it was already busy, a pair could find another alley, or a gangway or an abandoned car or an old mattress in a quiet lot.

  Oftentimes, clients offered the use of their own cars, where the boys would ask the men to take the keys out of the ignition and join them in the backseat. It was rare, but if prices were good and circumstances just right, a boy might go home with a hawk.

  Most times, though, the encounters finished quickly. “Ninety percent of the sexual solicitations were for oral gratification,” Gene said.

  Prices of course varied, but most chickens set their starting price at twenty bucks for oral or manual copulation, though many tried to push it to fifty bucks or higher. “So if five of us all went down there, we could all make a hundred dollars, have dinner, and come home in one afternoon,” Gene said.

  Typically, transactions happened any time after four in the afternoon. By nine o’clock at night, shops closed and these types of meetings drew far too much attention. But when the workday ended, johns would come by in their cars, “wheeling around the corners one after the other like riders on a carousel,” according to the Tribune.

  The men themselves held good jobs that paid well—at least enough to afford an occasional encounter in New Town. “These guys, most of them had wives and children out in the suburbs,” Gene explained.

  But there were local clients too.

  A well-known priest from Uptown often made the rounds among the boys, paying as steeply as a hundred bucks to perform oral sex on them.

  Notable among regular clients was a city police officer, who, according to Gene, worked in a lost-and-found department and frequently sought Billy out. For a hundred bucks, Billy would go back to the officer’s home, a rare occasion when a man brought a boy back to his personal space. The man, a masochist, enjoyed when Billy used rubber gloves or a belt strap to beat him.

  “Harvey,” the man Billy had pointed out to Gene, had previously made overtures for Billy to come live with him. With his parents’ drinking and fighting increasing back in the apartment, Billy had given it serious consideration. “He had told Violet, ‘First chance I get, I’m outta here,’” Gene explained.

  Gene met Harvey again one evening when he’d taken the boys out for dinner. Afterward, they’d driven around the Clark and Diversey area a bit before dropping Gene off near the lake. He said good-bye, and Billy and Harvey drove off together.

  For a young boy looking to escape disruptions at home or find a way to make it financially, Harvey’s offer was attractive. Gene remembered another boy, Marty, from the Uptown neighborhood, who had lived with two older men separately throughout his youth. Marty, though, hadn’t even been going down to the hustling hot spots—he’d come into the offer organically during his day-to-day life.

  Even Billy Kindred, bouncing from place to place in the years before he disappeared, had previously been a “house boy” for a wealthy gay couple in New Town. He would stay in their home whenever they traveled for work.

  Although the arrangement between Harvey and Billy Carroll never happened, there would be other offers. Billy had also caught the eye of a “Bill Mango,” a kind navy man reporting to the base north of the city and living off the final train stop in Skokie.

  “He loved Billy a lot,” Gene said. Mango used to say Billy’s favorite song was “Magic” by Pilot, number five on the Billboard Top 100 during the summer of 1975. “That was Billy’s song.”

  Mango was a frequent visitor to the boys at Clark and Diversey. Gene guessed that Mango had had every one of them over the course of all his visits. Perhaps because he was such a frequent visitor, Mango soon found a different boy to fixate upon. Not long after, that boy moved in with him.

  Primarily, the purpose of sex work in the lives of these boys was financial betterment. For Billy Carroll, there was financial betterment for the incidental purchases in his life—fancy food, sports equipment, gym memberships—but he continued to gravitate to the life as a way of escape from his home situation. Other boys sought out sex work for a myriad of other reasons, either for financial stability, sexual exploration, personal rebellion, or even a sense of familial belonging among other sex workers.

  Back at home, or in their neighborhoods, the boys often faced discrimination over their sex work. “If you went to Bughouse, it was a secret,” Gene explained. “If you went down to Clark and Diversey, you didn’t say anything either. You didn’t want your other friends to know.”

  Over the years Billy introduced some of his closest and most trusted friends to his activities, which sometimes even occurred north in Uptown.

  In June 1975 Mike Bowling and his friends were at the Lunch Pail restaurant on Wilson Avenue eating hamburgers when Billy flashed a wad of bills at him. “He must have had forty bucks on him,” Mike recalled.

  “Man, I could fix you up,” Billy told him, explaining what Mike needed to do.

  Mike agreed.

  Not long after, he followed Billy’s instructions to a house on Margate Terrace, not far from McCutcheon Elementary School, where the boys had first met. A man greeted Mike at the door and took him inside. Mike knew nothing about the man, not even his telephone number.

  “You want a beer?” the man asked.

  Mike said yes, knowing this was part of the deal.

  Inside the apartment, the man waited as Mike drank the beer. When he’d consumed enough, Mike stood up and fulfilled the desires of the john by letting out a burp. He continued doing so until the man was satisfied, standing around a corner and “playing with himself.”

  When he’d finished, the man paid Mike twenty bucks.

  Mike returned frequently to make more money. But during these visits, he was never asked to take off his clothes or do anything sexual himself, aside from fulfilling the man’s specific kink.

  With other clients, too, Mike—who is straight—kept a distance, preferring instead to enter into seemingly nonsexual situations facilitated by his friend Billy Carroll. According to Gene Anderson, Billy’s role was that of a “sugar hawk,” or the boy who leads others to clients.

  At the Uptown Theatre one day, Billy introduced Mike to another guy, Andy, who’d been unsuccessfully trying to get Mike’s attention on his own. “I dropped popcorn in fro
nt of you,” Andy told him. When nothing else seemed to work, he’d gone to Billy to fix them up. Andy noticed Mike’s army combat boots. He offered Mike thirty dollars to lick his boots. Mike agreed and put his feet up on the back of Andy’s chair.

  Other times, Andy had him over to his house in the Old Town neighborhood. In the privacy of his apartment, Andy would ask to feel Mike’s muscles for a bit before asking the teenager to smack him around while he masturbated. Mike never took his clothes off, but he made sure to also wear his combat boots each time he came over.

  Andy owned beauty parlors all over the country, so he could easily afford the frequent fifty-dollar visits from Mike. “He was really cool,” Mike said. “He was a really nice guy.”

  When the men did ask to cross Mike’s comfort zone, he turned them down. At the corner of Racine and Wilson in Uptown, Billy attempted once to put him with a man paying as steep as a hundred bucks for both oral and anal sex.

  “No, I ain’t doing that,” Mike said.

  Given the varying ages of the boys and the varying ages and circumstances of their clients, many of these encounters or relationships occurred outside the confines of what can be considered sex work. These relationships were improper both legally and ethically. Perhaps they occurred in parallel in these neighborhoods as a result of society’s conjoining of homosexuality and pedophilia. Bughouse and Clark and Diversity were two of the areas these older men knew they could find young men and boys.

  In other situations, clients interacted and paid the young men without incident, and the sexual encounter occurred consensually. For these encounters, Bughouse and Clark and Diversity were also the two most likely and safest places for sexual encounters between young men and clients.