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.

Fly is 38, yet he looks older. He’s balding, with gray hair and a gray beard. He’s bowlegged, and his toes have been amputated, which makes him hobble.

“Help the homeless, my brother,” he said to a longhaired man scurrying into Pearl. The man took the wrong door, and Fly, a veteran panhandler skilled at being agreeable, directed him to the other one. “This side, sir,” he said.

Fly broke into a soulful version of the song “I’m Crying”

until he saw a woman approach. “Help the homeless,” he said.

The woman responded with a tight smile.

“Maybe you can help me when you come out,” he said, but she’d already gone inside.

He cupped his hands around his eyes and peered through the window, scouting his prey in the store aisles. Soon the longhaired man reappeared. “Sir, a little help,” Fly said. But the man beat a hasty retreat.

“I need $10,” Fly said, sighing. He explained that it would go toward the cost of a room at the New Ritz Hotel, at 11th and State, where he often spends the night. The sun had begun to fade, and Fly hadn’t yet secured enough money.

“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.

“Kent talks like he’s never done anything wrong,”

says Jerry Fluder, a police lieutenant who heads the community policing program in the 18th District and has known Fly for years. “He is real good at making it on the streets. He has an upbeat personality, and he doesn’t seem unhappy at all with the lot he’s pulled.”

Fly likes to panhandle along a route that runs west on Chicago from the Pearl store, at Franklin, to the Shell station at the corner of Orleans, then swings north a half block to a building that houses a Bally’s Total Fitness. Sometimes he materializes on Rush Street, at the Jewel at Clark and Division, or outside the rock-and-roll McDonald’s. His usual hours of operation are from noon until dusk, but you can look for him for days at the regular times and find no trace of him.

For three months in 1993 Fly was licensed to sell StreetWise, but he lost his badge for violating the rules, which require vendors to use “professional language and attitudes” on the job, cooperate with other solicitors, and not be on drugs while working. StreetWise executive director Anthony Oliver says the paper has no record of why Fly lost his badge, but Fly has a version: “I was at 69th and the Ryan in a McDonald’s, and this dude gave me a dollar for a paper. Ihad one in my hand, and he said, ‘Keep the paper.’ But then he called to complain because he said Iwouldn’t give the paper up, and somebody came to McDonald’s and took my badge. I’ve been selling without a badge since then. My friends give me extra copies.”

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.

Fly speaks in a halting manner, and he can be testy when confronted. Yet he can also be engaging, with an aw-shucks smile and a courtly, subservient way of addressing potential customers or donors. “A lot of people help me out because I’m a nice person,” he says. “That’s the thing.” He has regular patrons, particularly when he’s trolling the Rush Street area. “I don’t know their names, but I know them when I see them,” he says. “I remember faces, not names. They’re white, and they call me Fly, not Kent.”

Fly says many people who buy the paper give him more than a dollar, and some are very generous. “A dude gave me $20 on North Avenue last night. I bought a steak at Ronny’s Steakhouse, and I went and got a room at the Ritz. Once I was up north on Dearborn, and a Mexican dude with a three-piece suit came by. He and his wife, in a black-and-white dress, were celebrating their seventh wedding anniversary. I said, ‘StreetWise. Help the homeless.’ The man said, ‘How much do you need?’ Isaid, ‘One hundred dollars.’ And he handed it to me. If I’d have asked for more, he’d have given it to me.”

On a good day, Fly grosses $100, though his usual take is around $50 to $60. He also gets a $494 monthly disability check from the Social Security Administrationthough it’s stopped when he’s in jail. The check is sent to him through one of his half sisters.

Fly uses his panhandling money to buy mealshe favors quarter-pounders with cheese, fries, and a drinkand drugs. “I go into the projects and buy drugsI know what cribs to go to,” he said in late January, listing addresses in Cabrini-Green where he’d bought and smoked crack and marijuana. But a few weeks later he said he’d been off drugs for a year. “I don’t buy that shit now,” he said. “Ijust don’t.”

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.”

Fly was hospitalized for two days, and his toes were amputated. He spent a month at a rehabilitation center learning to walk again. “A woman at rehab took me to a Chinese restaurant,” he says. “She told me I could order anything I wanted.” He doesn’t know who paid for his treatment but believes it was the passenger who took him to the hospital.

When he’s panhandling, Fly keeps an eye out for the police. “They always bother me,” he said one afternoon while huddled in the doorway of the Orleans Street Bally’s. “They tell me Ihave to move on.” But he readily admits they often do more than that, saying, “I’ve been arrested thousands of times.” Police records show that since 1981 he’s been arrested 185 times, frequently on multiple chargesalmost certainly the record for a homeless person in the city.

Most of the charges are for misdemeanors or quasicriminal violations related to vagrancy. He’s been hauled in for hassling someone when he was panhandling, giving a store owner a hard time, and selling StreetWise without a license. In February 1997 he was nabbed for offering to perform oral sex on an undercover officer for $40, and three years later he was cited again when he approached the same officer with the same offer. He was arrested in October 1999 at Bally’s after being “warned numerous times by security, police and Spectrum [the building’s owner] to not be on the premises.”

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.”

Misdemeanor cases involving Fly routinely turn up in the misdemeanor court at Belmont and Western. Fly tends not to show up for hearings, and then a warrant is issued for his arrest. When he comes to court his case is made by an assistant public defender, for whom he’s merely another name on a long list. The only lawyer Fly mentions by name is a private attorney who represented him 20 years ago and with whom he’s had no contact since.

Judge Mark Ballard, who has heard many of Fly’s cases, considers him “a pest” but is amused by his manner. “Ah, judge,” Fly has told Ballard, smiling, bowing his head, and rocking on his feet. In Illinois a misdemeanor carries a maximum penalty of 364 days in jail and a $2,400 fine, but Fly escapes heavy punishment by pleading guilty in exchange for a reduced or suspended sentence. “I always plead guilty because I did it and I don’t want to lie,” he says. “So the judge will give me a sentence of time served or it’s an SOL”meaning “stricken off with leave to reinstate,” legalese for a dismissal, usually granted because the complaining witness or the police officer hasn’t come to court.

“In the end, being arrested doesn’t mean anything to him,” says the 18th District’s Jerry Fluder. “The worst thing that happens to him is he’ll have a place off the street to stay for a few days, and he’ll get meals. He’s using the system.”

When he’s not enjoying the county’s hospitality, Fly stays overnight at the New Ritz or, he claims, with Laura Ball, “my ex-lady.” He also claims that he and Ball have a daughter and a grandson. “I don’t know my grandson’s name,” he says. “I ain’t been told it yet.” Ball, who lives in Cabrini-Green, says she knew Fly when they were both young and living on the south side. “But I had no relationship with him,” she says. “Idon’t have no daughter by him, and he doesn’t stay by me.”Fly also claims he has two daughters with a woman who now lives in California, though he can’t remember her name.

Fly sometimes says he has lots of friends and girlfriends, but at other times he says, “I’m by myself a lot. I don’t like to be with anybody.” And he often lashes out at his associates. “That black nigger, I don’t like him,” he said one afternoon outside Pearl. “And the other one over there is crazy.”

On the weekend Fly usually stops in to see a woman I’ll call Pat Redmond, his youngest half sister, a bank clerk who lives with her two boys in a south-side high-rise. Redmond lets her brother sleep on her couch, and she feeds and cares for him. “People say, ‘Why do you put up with Kent?'” she says. “He’s my brotherwe grew up together. I hate to see him out there on the streets.”

Yet Fly taxes his sister’s devotion. “You can see that he’s filthy,” she said one morning in her small kitchen. “I try to get him to take a bath, because he leaves an odor here. All those germs he picks up are jeopardizing my kids. I got him to take a bath yesterday, but he needs to do that every day.” Fly insists that he showers daily.

It irks Redmond that Fly asks for money for washing the dishes and that he sells off the shoes, jeans, pants, and sweatshirts she buys him. And she says that when she slips him a little money he misuses it. “I gave him money yesterday to clean out the trunk of my car,” she says, “but once he got it he went over to the projects along State Street to spend it on drugs.” She also gets tired of Fly’s fits of anger. “Kent has a temper,” she said in late February. “If he can’t get what he wants, he just goes off on you.” As soon as she stopped speaking, Fly got up from the couch and asked for a couple bucks for the el. Redmond said no. “I need carfare!” he shouted at her and slammed out of the apartment.

Fly has six siblings, but Redmond is the only one who routinely takes him in. She’s also the person he calls when he lands in jail. “He calls me collect,”she says, “I tell him, ‘What do you want me to do?'” She says she can’t afford to bail him out.

Kent Lewis Fly was born in 1963 in Shaw, Mississippi, a poor community of bean and cotton growers 25 miles north of Greenville. His father was Truly Anderson, a truck driver, and his mother was Henrietta Fly, who would later marry a construction worker named Willie Silas.

In a court report prepared before a sentencing in 1998, Fly described his childhood as “good” and said he saw his father every week. “I was glad to stay with him,” he says. Anderson died a couple of years ago, when Fly was in jail. “Iwanted to go to his funeral,” he says, “but they wouldn’t let me.”

Fly’s relationship with his mother wasn’t particularly warm. “They were 50 percent close,”says Bobbie Jean Hardy, another of Fly’s half sisters. “She and my stepfather had problems. She didn’t talk to Kent in the usual way. It was ‘Kent, don’t be doing this and that’ instead of real talking between mother and son.” She says Fly was much closer to his maternal grandmother, who also lived in Shaw.

Fly didn’t get along with his stepfather. “I didn’t like him a lot,” he says. Hardy says Silas treated the children who weren’t his own differently, especially Fly, who had learning problems. She says Silas would tell him, “Get away from me, you crazy boy. You ain’t got no sense.” Silas also verbally and physically abused his wife and the children. Fly says that one night when he was a teenager he and one of his brothers got into a fight, and Fly drew a knife to defend himself. Silas hit him in the head with a two-by-four.

Hardy describes the young Fly as “a good neighborhood kidmowing people’s lawns, taking out their trash. Anything that needed doing, he’d do, even if he wouldn’t be paid. He was more settled back then.” Pat Redmond describes him as “playful, fun to be with.” Cynthia Hawkins, the current Shaw city clerk, remembers him from high school, where he was in classes for kids with learning disabilities. “He was nice,” she says. “His attitude was pleasant. He was real bowleggedhis legs were so wide you could crawl through them. Kids would pick on him, ’cause kids can be nasty, but that didn’t seem to faze him. He laughed it off and kept going. He also would get into little things at schoolthis or that, being disruptiveand he’d have to go down to the principal’s office. And he did a little stealingpicking up gum in the storebut it wasn’t like he broke into a building or anything. Just little misdemeanors.”

Fly says he dropped out of high school when he was a junior so that he could have an operation to correct his bowed legs. “They broke my legs and then fixed them,” he says. “I had to stay home because I had casts.” When he could walk again he took a job pumping gas.

In August 1980 Henrietta and Willie Silas brought their children to Chicago to join other members of the family, settling into a second-floor apartment on South Aberdeen. Fly, then 17, soon got into trouble. “He had no direction,” says Hardy. “Somehow he got drawn to things of the street. Next thing we knew he was into drugs.”Fly says he started with marijuana, liquor, and cigarettes, then moved to crack. His mother told him to stay away from his new friends, “but he was hardheaded and wouldn’t listen.”

In October 1981 Fly was charged with taking “indecent liberties” with a child, attempted rape, and aggravated kidnapping. “A lady two doors down said I had assaulted a little girl,” he says. “I didn’t do it. Somebody else did, a guy down another street. He was in a gangIwasn’t in no gang. I pleaded guilty because I was facing 6 to 30” years in prison. He got off with four years’ probation.

At the time of his arrest Fly had been working as a janitor and stock clerk at a grocery store. After he was sentenced he worked as a delivery driver until his company’s distribution routes were sold, and the next summer he worked for a south-side car wash. Other than his brief stint selling StreetWise legally, he hasn’t had a job since.

Fly went to prison for the first time in 1989, on a three-year sentence for delivering cocaine to an undercover officer in the gangway outside his family’s apartment. Released early in 1990, he moved in with his mother and Silas, who was then on disability. Fly too started getting disability, having been found to have “a form of mental retardation” while he was in prison. He had another operation on his legs at Cook County Hospital. “They took a bone out,” he says. “Istill have the scars.” He says he also earned his GED.

Family members say that during this time Fly stole a TV, telephones, money, a radio, curtains, and curtain rods from the house. “The neighbors had seen Kent do it,” says Hardy. “He wouldn’t fess up, but it got to where you didn’t feel you could put your purse down in your own homeyou always had to look out.” His mother says she tried to get him into drug counseling. “But he was crazy, and he wouldn’t do it.”

Fly first appeared in the South Loop in the early 90s, panhandling and selling StreetWise in the morning along Dearborn from Dearborn Station to the Dunkin’ Donuts at Jackson. Sometimes he went farther afield, trolling in front of the McDonald’s or the Walgreens on State. He says if he was lucky he could make $20 an hour. “He was superaggressive,” says Jerry Fluder, then a tactical-team sergeant in the First District, “and he’d get in people’s faces.”

At night Fly often stayed at thePacific Garden Mission on South State, which housed up to 600 “overnight guests,” about half of them homeless. The mission required guests to listen to dawn and late-night sermons, and Fly says he didn’t mind. “I didn’t like that shelter because I couldn’t sleep there. I’d wake up dizzy.” Yet when he was arrested for selling StreetWise illegally or for harassing passersby, he would list the shelter as his place of residence.

Fly often encountered the police on his rounds. “A lot of those who live on the street don’t want contact with us,” says Bill Ross, a veteran sergeant in the First District who now heads its CAPS program. “Kent Fly didn’t care.” Ross says that for a time Fly lived in a rag-filled box on Lower WackerFly denies itand Ross offered to get him help. “He said, ‘Get away from me.’ He wasn’t interested. Yet he’d ask for money from us. ‘A couple of bucks, officer. A couple of bucks,’ he’d say. And he didn’t care if you locked him up.”

The charges varied. Police records show, for example, that in December 1994 he sprayed tear gas into the eyes of a “pedestrian” and a “banker” at the First National Bank branch on Dearborn. In March 1995 he was hauled in for trying to sell the Chicago Jewish Star, a free bimonthly newspaper. That May he got picked up for stealing a StreetWise badge belonging to a vendor, and in June he was arrested for having crack paraphernalia stowed in his shoe. In April 1996 he was taken in for urinating in public, exposing himself, and blocking the street “in such an unreasonable manner as to alarm and disturb the peace.” Early on, court clerks knew who he was”the famous ‘Super Fly’ Kent” is scrawled on the file jacket of a case from 1994.

Meanwhile he’d become unwelcome at the Dunkin’ Donuts”The supervisor never liked me,” he saysand at the White Hen Pantry at Dearborn and Harrison. The convenience store’s manager, Robert Boone, says every day there’s an incident with a homeless person, many leading to arrests. “At first I tried to hire these people,” he says. “Well, one stole from me, the next was a drunk, and the third announced flat out, ‘I’m going to start dealing drugs, I’m going to steal from your store, and this isn’t going to work out.’ I have a three-strikes-and-you’re-out rule. After the third guy, I stopped hiring the homeless.”

Boone never considered hiring Fly. “It’s a nonstop hassle with this guy,” he says. “He’s a particular pain to women. I don’t know if you’ve ever seen him, but he’s just disgusting. Plus he can get very aggressive. He’ll talk back to you, cuss at you. When he gets how he gets I just walk him out of the store. He just doesn’t get the fact that he isn’t wanted.” Luis Montano, one of Boone’s shift managers, says that he sometimes confronted Fly and that Fly responded with racial slurs or shouted, “Go back to your own country.”

At SRO Chicago, a sports-themed grill just down the street from the White Hen, Fly got a marginally better reception. The owners, Dino and Tommy Bezanes, would have Fly arrested if he badgered their customers, but they also made deals with him. When the garbage collectors threw the garbage cans around, the brothers paid Fly $5 to line them up along the curb. “I remember one time this guy outside was pulling his pants down,” says Tommy. “We had Kent go over and tell him that that wasn’t acceptable behavior and that he’d better get moving.”

When the brothers sawFly getting into it with Boone or Montano, one of them would walk out and signal Fly to stop before he ended up in more trouble. “We were able to communicate with him nonverbally,” says Tommy Bezanes. “We had a detente, an understanding. We had a strange affection toward him, because we’d been through so much together. Sure, he was loud, obnoxious, and dirty, but to us and the beat cops he was just Kent.” He remembers Fly fleeing a beat officer after allegedly stealing something from the White Hen. “The cop was a young guy, but he couldn’t catch Kent,” he says. “Kent just jumped the rail of a parking lot and was gone.”

When Tommy Bezanes’s name comes up, Fly says warmly, “Yeah, Tommy. He looked out for me a lot. He’d give me $5, $10, $15 to get a room.”

In February 1995, Judge Janice McGaughey sentenced Fly to a year of conditional release on a battery charge; he was supposed to stay away from the complaining party, First National Bank, and to undergo alcohol treatment and psychological counseling. But Fly, accompanied by his mother, kept only one appointment with a social worker, who referred him to a hospital to “address health issues.” Jesse Reyes, director of the court’s social services department, says, “We had minimal contact with him. He simply wouldn’t come.”

Between February 1 and August 15, 1996, there were 14 court hearings involving the case, none of which Fly attended. McGaughey issued three separate warrants for his arrest, and he finally was picked up. She entered a guilty finding, and he spent 60 days in jail. (“I don’t remember him,” says Judge McGaughey, who saw up to 200 defendants daily.) “Trying to handle a case like thisthe toughest kind we haveis like handling without a bowl,” says Reyes. “There’s nothing to grab on to.”

In 1997 Fly suddenly vanished from the First District, and the shopkeepers and police wondered where he’d gone. He’d moved to the Near North Side, where, he says, “You can get more quick money.” His move soon showed up on his rap sheet, as he began being arrested in the 18th District. A couple of years ago Jerry Fluder transferred to the 18th. “Ihappened to be the watch commander one night, and they brought me a report of the arrests,” he says. “I saw Kent Fly’s name. ‘Ithought you disappeared,’ I said when I saw him. He said, ‘Nope, I just got out of the First District.'”

Last October, Lisa Lefler had Fly arrested againfor panhandling, bothering a customer, and refusing to leave her Shell station lot. This time she’d had enough, and the 18th District police decided to treat Fly as a chronic offender, requiring him to post bond and telling prosecutors to take his offenses more seriously. Lefler, accompanied by Jim Gelbort, a CAPS volunteer advocate, showed up twice in misdemeanor court. Then Fly demanded a jury trial, and the case was transferred to the courtroom of Marvin Luckman, at 13th and Michigan.

On the morning of January 18, Lefler was sitting on a spectator’s bench with Gelbort when she thought she heard Luckman’s clerk call Fly’s name. “Excuse me, should Igo up there?”she whispered to the sheriff’s deputy, who told her harshly to be quiet or she’d be thrown out of court. “This is her caseshe’s a witness,” Gelbort told the deputy, who ignored him. Lefler says, “He just continued to go off on me.”

When Fly was brought before the judge, Lefler rose and came forward. “Don’t stand there and make faces to this court,” the judge told her. Lefler had no idea what he was talking about. “What kind of face would a 37-year-old woman make in a courtroom?” she asks.

Through his public defender, Fly waived his right to a jury trial and pleaded guilty to criminal trespass, and Luckman handed him a 150-day sentence30 days less than he could have received. “I’m telling you now,” the judge said, “when you get out of jail you stay away from that gas station. If you don’t, I’ll give you the maximum.”

The public defender then said that Fly wanted the judge to know he’d finished a drug program during his time in jail.

Luckman contemplated Fly, then said, “I want to compliment you, sir. In Illinois we believe in rehabilitation as well as punishment. I hope you keep this up, so that I won’t ever have to see you again in this courtroom.” Luckman told Fly he had 30 days to withdraw his guilty plea, then, as Fly was being led off, added, “And stay away from that Shell station.”

Lefler walked out of the courtroom angry. “I didn’t mind having to go to court, because I want people like Kent Fly off the streets,” she said. “But when you’re treated like this it turns you off. I was totally disgusted. Kent Fly gets a nice thank-you for taking a drug class, though he’ll be right back on drugs. The judge treated me like a kindergartner. I was humiliated, treated like shit, with no thank-you.” Luckman says he doesn’t remember Lefler. The sheriff’s deputy says he was just doing his job.

Fly seemed about to prove Lefler wrong about him. He’d felt encouraged by his addiction counselor, Nancy Abram, and a few days before he pleaded guilty he said, “Miss Nancy and Ihave been talking about drugs, about changing my ways and my attitudeabout doing life right.” Abram had advised him to seek treatment at the Roseland office of the Human Resources Development Institute, which addresses drug addiction and mental-health problems on an outpatient basis, and Fly said he intended to go there as soon as he was released.

Jeremy Unruh, an assistant state’s attorney who has handled cases against Fly, calls the way vagrants like Fly continually move between the courts, jail, and the street “aggravated mopery.” He thinks the problem exists because of a change in public policy in the 1970s that forced mental hospitals to release their less-impaired patients into the community. “The institutions had to release all borderline people,” he says. “Kent would have been one of them. He doesn’t really belong in jail, but he doesn’t belong in the general public either.” Unruh thinks Fly should be examined thoroughly by a mental-health professional. “Apublic defender could have him undergo a mental-health exam,”he says. “But because he’s always brought in for an offense like disorderly conduct, his case never gets that far. It’s dismissed or he pleads guilty.”

Fly remembers having only one psychological exam in all his years passing through the courts. “I went to see a psychiatrist in the County Jail,” he says. “They wanted to put me in the psych ward, but they found I didn’t need it. That was a long time ago.”

“Look, Kent Fly isn’t crazy or slow,” says Lisa Lefler. “He understands. He knows how to play the game. So he finishes four weeks in jail. Big deal. Put him in a boot camp, make him clean bathrooms, give him some kind of community service. What they’re doing with him now isn’t helping him it’s only turning into a handicap.” Robert Boone, the White Hen manager, says, “He’s the pink elephant in the room. Society doesn’t want to look at him, nor do the courts. But someone has toit’s part of being a humane society. I think they need to get him into some type of program where he can put his time to good use and improve himself. Maybe jail is the answer, a place where he’s controlled. Or they should test him to see if he belongs on the street. If I was crazy, I’d want to be put in a mental institution.”

“Homelessness is only a symptom of a larger problem,” says Ervin McNeill, pastor of the Pacific Garden Mission, who was once briefly homeless himself. “The problem could be mental illness or the deception that being a vagabond frees you from the responsibility to love, work, and contribute to society. Many creatures of the streetand Iknow some have been out there 7, 15, or 20 yearshave been seduced by their desire to withdraw from society. It’s a tough cycle to break, but God gives you freedom of choice to do that.” He thinks that the Pacific Garden sermons Fly once heard are a bomb inside of him: “It will go off sometime and somewhere. Maybe it will go off too latemaybe when he’s standing in line waiting to enter hellbut it will go off.”

Police officers don’t believe they can do much to change the lives of disruptive vagrants such as Fly. “We arrest them for disorderly conduct or begging, and we lock them up,”says Gary Szparkowski, the lieutenant who now directs the tactical unit in the First District. “Then they’re gone. We don’t see them because they’re in the courts, and in time they’re back. It’s a revolving door, and there’s nothing much we can do about it.”

Judges don’t think they can do much either. “There are a couple of things that don’t happen when you put on a robeyour IQ doesn’t go up, and you don’t have ultimate power,” says Judge Luckman. “You have to do things strictly within the law. My concernmy obligationis to protect the citizens of the state. What can we do with him [Fly]? A judge is limited to whatever the penal statutes of the state say.”

No legal organization seems to have studied the issue recently. “This isn’t something that we’ve dealt with during my tenure,”says Pamela Wolf, chairman of the Chicago Bar Association’s criminal-law committee. The Cook County Court Watchers, a group founded in 1975 by the League of Women Voters that’s now under the umbrella of the Better Government Association, doesn’t even have enough volunteers to post observers in city courtrooms. “This is not something we’ve been able to look at,” says Wendy Sadler, chairman of the BGA’s court-activities committee.

According to the Chicago Department of Human Services, some 28,000 people signed in at the city’s overnight shelters last year. Many of those names are duplicates, yet it’s still safe to assume that thousands of homeless now live in the city. Of those, says Brooke Spellman, head of the city’s family support services, some 15 percent are categorized as “episodic,” or repeatedly without shelter; 5 percent are “chronic,” hard-core cases such as Fly. The city spends $15 million annually to provide overnight shelters and services for the homeless, including outreach teams that walk the streets, and it can make referrals to 4,000 subsidized apartments and rooms. Spellman says that the episodic and chronic homeless get 80 percent of service resources. “If we don’t solve those cases,” she says, “we will never end homelessness.” At a January retreat, a consortium of city agencies and provider organizations set a goal to rid the city of homelessness by 2010.

The consortium’s most promising venture is a pilot program set up by Thresholds, a psychiatric rehabilitation center, in conjunction with Cook County Jail. The project is offering extra assistance and counseling to 45 released offenders who have problems such as schizophrenia and bipolar disorder, most of whom are homeless. The program is expensive $450,000 a year but it has cut jail recidivism and rehospitalization rates of participants who’ve been involved for a year by more than 80 percent. “These are people who believe that nothing good is going to happen to them,” says Jerry Dincin, executive director of Thresholds. “The trick is to meet them on their own terms. Maybe they don’t want counseling. Maybe it’s a shelter or maybe a delousing. But they have to want some help.”

Some police, faced with mounting complaints from residents and merchants, are trying a different tactic. Last June and December the First District police invited local homeless people to a site in Grant Park, where they were offered jobs, housing, physical exams, flu shots, and drug rehabilitationall with no strings attached. More than 200 people responded. The 18th District police had their own “special services day” in August in Washington Square Park.

Fly didn’t make any of the gatherings. Occasionally he says he wants to better himselfhis life’s ambition is “a job in shipping and receiving” or to accept an outstretched hand, but the sentiment rarely lasts. Sometimes he acknowledges his dependence on drugs, sometimes he doesn’t. Sometimes he accepts that he’s responsible for the behavior that leads to his arrests, sometimes he won’t. “It’s not right to lock me up for nothing,” he said one day. “I think that’s a disgrace.” Then he paused. “It’s their fault,” he said, referring to the police and the merchants who lodge complaints against him. “I’m not in front of businesses, and they call the cops on me. They say I harass their customers, but I don’t. Sometimes I just stand there, and the cops tell me to leave. I just stand there, and Igo to jailfor no reason.”

His relatives say they’ve tried many times to get him to straighten up, all to no avail. “He just doesn’t think he has a problem,” says Pat Redmond. “He’s in denial. You can’t help somebody who doesn’t want to be helpedif you do, you put a jinx on yourself.”

Willie Silas died in 1995, and Henriettawho suffers from failing kidneys, high blood pressure, and asthmanow lives in a spare studio apartment in a church-run building in the New City neighborhood. “Kent won’t listen to anybody,” she says. “He wants to do things his way. He makes himself homeless.” When Kent called her one day this winter, she pleaded, “Come see your mama.” But he rarely goes. Redmond tells Henrietta when Fly ends up in jail, and Henrietta says she responds, “Lord Jesus, what did Kent do now?”

“It’s a decision he’s made to be on the streets,”says his half brother Clifton Silas, a sheet-metal worker who lives in the suburbs. “He has an attitude with us. I love my brother, but I can’t talk to him straight.” Bobbie Jean Hardy says, “This has been going on for years with Kent. There’s only one way out of here, and that’s death. That’s my greatest fear.”

Fly was released from jail on February 5, but he hasn’t yet gone to the drug-rehabilitation facility as he promised. “Miss Nancy set me up for that,” he says. “She told me to see this one person. But Ihaven’t gone there yet because I’ve been running the streets.”

Fly started training to get a new StreetWise license, then lost his training badge twice; he says he can’t afford the $20 replacement fee. On February 7 he was arrested for illegally selling a free publication and for impeding pedestrians. A week later he was nabbed for harassing customers exiting the 7-Eleven on North State. “We have people arrested every day for begging and harassing,” says Brian Kongnaewdee, the clerk who filed the complaint against Fly. “The only thing that changes are the faces.” In court on March 8, both charges against Fly were dismissed because neither witness showed up.

Fly was soon back panhandling and selling StreetWise in front of Pearl, and he kept turning up at the Chicago Avenue Shell station. “He gives you a smart-ass grin, as if to say, ‘Here I am again,'” says Lisa Lefler. Jerry Fluder ran into him crossing the street at Ninth and Wabash. He was wearing a three-quarter-length leather coat and carrying copies of StreetWise. Fluder, startled to see Fly outside his normal north-side territory, asked, “What you been up to?” Fly told him, “Doin’ my usual.” Fluder asked if he needed any help. Fly replied, “I do OK.”

In April, Fly pleaded guilty to trespassing at the Dominick’s on Division. He spent ten days in jail, where he celebrated his 38th birthday. “I told everybody it was my birthday, and a lot of people wished me well,” he says. “My sister was going to bake me a cake, but, you know, I was in jail.”

On a Friday in early May he was back on the street. A security guard shooed him away from the Bally’s on Orleans, so Fly hobbled over to the front of a building on Institute Place and sat down on a low wrought-iron fence. “StreetWise,” he called out to workers as they returned to the building after lunch.

A burly young man promised to give Fly something on his way out.

“I won’t be here then,” said Fly.

The man looked chastened and fished in his pockets. “I had lunch with my girlfriend, and she gave me nothing to take back to work,” he said. “How’s that for love? I got nothing for you.”

Fly shoved his hands in his pockets and stared at the ground.

A police cruiser pulled up, and the officer rolled down her window. “They’re complaining about you,” she said. “Move on.”

Fly rose from the fence and tottered back toward Bally’s.

Art accompanying story in printed newspaper (not available in this archive): photos/Robert Drea.