Kent Fly was bobbing on his feet in front of the Pearl art supply store on Chicago, announcing that a sale was going on inside even though it had ended. It was early March, and a cold wind whipped down the street. Fly, who had a crack running through his lower lip, was dressed in a black vinyl shell with a sleeve that had been ripped during a fight. A hood belonging to some long-gone jacket covered his head, and he had his hands stuffed in the pockets of thin tan pants. “I ain’t got no gloves,” he said.
until he saw a woman approach. “Help the homeless,” he said.
“For the bulk of people, homelessness is a relatively brief experience,” says Brooke Spellman, director of the city’s Family Support Division of the Human Services Department, which encompasses services for the homeless. “It’s a transitional stage they grow out of.” But Fly, who’s at once dim and crafty, has been a resident of the public way for nearly a dozen years, longer than most of the other homeless people in Chicago. He does get off the street, though it’s usually because he’s in jail. He’s been arrested scores of times, mostly for misdemeanors, and he swings in and out of the justice system with a startling blitheness.
Oliver says Fly can get away with selling the extras “because we don’t have the resources to police adequately illegal vendors.” And the police usually have better things to do than make arrests for failure to have a StreetWise badge. When Fly can’t get extra papers, he just asks for donations.
In early 1999 Fly was riding the Howard el when another passenger noticed that he seemed to be in pain. “The man asked me what was wrong, and I said, ‘My feet is cold,’” he says. “The man asked to see my toes, and they turned out to be black. He was a white guy, a nice fellow, and he gave me $20 and took me to the hospital for frostbite.”
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Last year he was arrested 25 timesfor disorderly conduct, criminal trespass, prostitution (the oral-sex charge), battery, assault, and possession of crack. The year before, he racked up 24 arrests. In 1998 he was arrested just 11 times, but only because he wasn’t let out of the penitentiary until August. He’d been arrested in October 1997 in an abandoned building in Cabrini-Green carrying a Ziploc bag containing crack and found guilty after a bench trial in January 1998; he was sentenced to two years in prison but got out early because of good behavior and credit he’d earned for days already logged behind bars.
Lisa Lefler, manager of the Shell station at Chicago and Orleans, knows Fly as “Foots,” the name her employees gave him because of his uneven gait. Fly begs from Lefler’s customers, frequently sweetening his requests by offering to pump their gas. “He’s been a pain in the butt to me,” says Lefler. “When Iask the guy to get off my property, he just looks at me and smiles. Then he limps away.” He often returns as soon as he notices Lefler pulling away in her Cadillac. “We’ve called the cops on Foots probably 50 times and had him arrested ten times,” she says. “He’s my worst experience in 11 years with Shell.”
