“Street Sweeping in the City that Works” by David Hagerty

A fresh breeze off the lake carried away the roar of cars and the decaying scents of the city. Yet before he’d passed the trinket shop, two police officers blocked his way….

Simmons lurched along the sidewalk of Rush Street, beside the gin joints and blues bars, around the broken bottles and vomit patches, past the Keep Our City Clean placards in the name of Mayor Richard J. Daley. In his good hand, Simmons carried the easel and sketchbook that enabled his trade while with the bad he gripped his crutch. He’d devised a half hitch wobble that offbalanced the two, but no one would call it graceful.

Along the way, he passed Sadie the sadist and Bobby the bouncer, who watched his progress but offered no greeting. They looked out on the wreckage from the previous night—the men sleeping in doorways, the whores smoking their first cigarettes—with casual indifference, as though it had no relationship to them or their trade, and awaited the evening crowd.

At Chicago Avenue, Simmons turned toward the city’s historic Water Tower, lone survivor of the great fire, where tourists coveted a memento. A fresh breeze off the lake carried away the roar of cars and the decaying scents of the city. Yet before he’d passed the trinket shop, two police officers blocked his way. Dean O’Malley and Josef Oleksy patrolled the red light district during daylight hours, rolling drunks and rescuing marks.

“Where you headed this fine day?” O’Malley said. He stared down at Simmons with a mixture of amusement and contempt.

“The usual spot,” Simmons said, and lifted his tablet like a wing.

“Not today,” said Oleksy, who played the heavy in this plot.

“It’s a great day to get your portrait painted,” said Simmons, and gestured to the sun rising above the silhouette of the skyscrapers.

“You mean parodied,” said O’Malley, and smiled cartoonishly.

“Same difference,” Simmons said.

“Not today,” said Oleksy.

“What’s so different about today?” Simmons said. “You seen me out plying my trade plenty of times before and never groused.”

The officers moved to either side of him, hooked their elbows through his spindly arms, and dragged him roughly toward a paddy-wagon. “You’ve got no need to manhandle me,” Simmons said, struggling. “It’s not like I can run off.” In his effort to regain his feet, Simmons dropped his easel but retained his crutch, his one constant companion. “Why you hassling me?” he said. “I’m just a guy making a living any way he can.”

“If you’d get a real job, we wouldn’t have to hassle you,” said O’Malley.

“Who’d hire me?” Simmons said.

The officers left that question unanswered.

At the station house, O’Malley banged out the arrest card on a Remington that chimed like a clock at the end of each line. He already knew Simmons’ full name and address but asked anyways, much as the detainee pretended to double check the facts while waiting to see the charges. When O’Malley filled in the blank with Muni Code 8-4-100, Simmons said, “What’s that?”

“What’s what?” said the cop without looking up.

“That code you’re laying on me.”


Simmons had been charged for that before but couldn’t recall seeing those numbers. “I’m an artist, not a vagrant.”

O’Malley huffed his dissent and yanked loose the card with violence, then led Simmons to a large holding cell, animated only by the buzzing of flies and fluorescents. Before placing him inside, the officer took his crutch but helped him to a bench seat. “You’ll get it back after your arraignment.”

“When’s that?”

“Monday morning,” O’Malley said and slammed the iron door so the clang resonated through the building.

The cell smelled of the usual urine and sweat, but also something sweet and herbal, like a cigarillo scented with perfume. Simmons glanced about him for the source but saw only more unfortunates like himself. A dozen men slumped on the concrete benches, but none he knew. He typed one as a pimp by his sateen suit and platform shoes. Another he pegged as a hophead from his bemused smile. A third he labelled a rumdum from his heavy eyes. Most, though, looked like average Joes. One had only a stump where his left hand should hang, another had a melted nub in place of an ear, a third had the cloudy eyes of the blind. They reminded him of Manet’s paintings of beggars and ragpickers, men no more damaged—nor likely more criminal—than himself.

He turned to the man with the stump and said, “Why’d you get pinched?”

The man shrugged his ignorance or indifference, Simmons couldn’t say.

“You?” Simmons said to the fire victim.

“They never tell.”

“What about you, blind man?”

The other startled like a pupil called on unexpectedly. “The officer claimed I was jaywalking, but I know I crossed at an intersection. I’ve been navigating these streets my entire life, and I felt the square of the curb with my cane….”

Simmons nodded to himself and studied the wall of bars separating them from their captors. It reminded him of a Skinner box, with them as the cat for conditioning, and holes on both ends so they could be observed.

“Fess up,” said the pimp to him. “What’s a lame like you do to get busted?”

“They wouldn’t say.”

“Come on now. You wouldn’t be asking us if you didn’t know yourself.”

Simmons nodded. “Muni Code 8-4-100.”

The pimp chuckled as though he too had not been caught in the same dragnet.

“What’s funny?” Simmons said.

Once the pimp had regained his composure, he eyed Simmons with judgement. “They’re accusing you with the ugly law.”

“The what?”

“The ugly law. It say the police can pick up anybody ‘diseased, maimed, mutilated, or deformed.’ Basically, anybody unsightly or disgusting.”

“Why do that?”

The hophead spoke. “To get us beggars off the street.”

“I’m not a beggar. I’m an artist. I studied at the Institute, memorized the Old Masters, won prizes.”

“That ain’t what people see,” said the pimp. “They see your claw,” he nodded to Simmons’ clutched hand, “your foot dragging behind you, your face twisting when you try to smile.”

He spoke the truth. For years, Simmons had tried to find work as a portrait painter, but once potential clients saw his birth defect, they sought other artists. They assumed one good hand was not good enough. No matter how skillful his portfolio, no one believed he could create beauty, as though some part of his being would inevitably seep into his canvas, contaminate his brush, defeat his dexterity.

“They should see my art,” Simmons said. “I can make anyone into a pinup. If a girl’s got a big nose, I accentuate her eyes. If she’s got a weak chin, I give her full lips. Thin hair becomes a strong profile.”

The pimp eyeballed him with renewed appreciation. “I bet you like that, don’t you. Staring at the girls, primping them.”

“I’m like Manet, finding beauty in the ugly. It’s my talent.”

“I don’t know about Manny, but the world don’t appreciate our talents. Take mine: introducing slow men to fast women. The squares never appreciate that, even when it’s them need introducing.”

Simmons shook his head. “That’s not what I do.”

The pimp smiled. “You sure? You sure those boys who pay to have their Dolly painted ain’t just tryin’ to get some lovin’? Read the Kinsey Report. Everybody needs somebody to love.”

Simmons waved away the suggestion like the smoke scent gathering in the airless room. “How do you know about the ugly law?”

The pimp smirked as he explained, “One of my customers got popped for it. Police told him he were too ugly to have a woman on his arm. Really, that’s just an excuse for rousting people who society don’t like.”

“But why pick up a schmo like me?”

“Ain’t you hear? Boss Daley told the civil service to sweep the streets of unsightly debris. He’s got the auto show rolling in—with six thousand people lining up to drop their money. He don’t want the people to pocket their greenbacks if they see some iniquity—like they’re not the ones give us most of our business!”

At the mention of the mayor’s name, the other inmates nodded their assent as though it were futile to resist the civic monarch widely known as “Boss” and “Hizzonor.” That little man had ruled the city for a decade through corruption and patronage, making Chicago into his personal property while dubbing it “the city that works.” Store owners complained they couldn’t get a loading zone or a business permit without first paying homage—but still they pledged to get out the vote for Daley come election time.

“That’s illegal!” Simmons said, more to himself than his audience.

The pimp smiled a knowing smile. “Not when they write the laws.”

Simmons sank into his bench as if his legs would not hold him upright. He stared at the barred cage that would be his home for the next three days and wondered what other indignities the city had in store for him. It didn’t take long for one to arrive.

Sgt. Wellinger rolled in a cart of tinned food trays and passed them through the meal slot connecting the cell to the outside world. When he lifted the bread off his sandwich, Simmons saw one thin slice of green baloney. He glanced to the single toilet, sitting in an open corner, then set aside the food. Instead, he bit into the mealy apple and chewed slowly, feeling his throat dry until he forced himself to swallow.

Quickly, the pimp sidled over to examine his tray. “Since you’re not fixing to eat that,” he said, lifting the sandwich. He smiled to reveal a glimmering jewel in one tooth.

Simmons nodded. He’d gone hungry before—during school, when he’d been classed with others like himself: the boys who were deaf, dumb, blind, and challenged, but not too challenged to understand the social order. They’d dubbed him Lefty and mocked his walk. Those limited only by their intellect would domineer over the others, stealing their food, their shoes, even Simmons’ crutch once, although he later found it in a trash bin a block away.

Still, his parents had preached self-sufficiency, scolded him not to accept handouts, be they from a church or a charity, so he’d learned to feed and clothe himself, tried to find some pride in a society bent on humbling him. Every day at his easel he had to prove himself before his subjects. He tried to hide his deformity, yet he could see their discomfort as they sat, watching his limp arm as he worked, their faces falling even as he urged them to smile. Yet once he’d finished and showed them their likeness, their expression turned again, from dread to delight.

His father claimed he lived like a hustler, but his hustle allowed him to scuffle by. Through pain and persistence, he’d secured a first-floor apartment in an SRO outside the city’s skid row, one with only two front steps and a walk-in shower. On a good day he could complete two images an hour, at a tenner each, earning him enough to survive the long chill of winter, when the city hibernated, and the sweat box of summer, when a cloud of humidity replaced the blanket of snow.

None of which helped him now, stuck in the cooler on a spring weekend when the tourists returned like sparrows. He’d counted on a flush Friday for the month’s rent. Instead, he could lose all he’d accumulated by missing out on his first good payday.

After stewing for what felt like hours but probably only amounted to minutes—time being immeasurable in the eternally dim, interior room of the jailhouse—Simmons forced himself to his feet and turned his back to the other men. From the sleeve of his bad arm he extracted a piece of graphite and began to draw on the gray canvas of the concrete wall. With a single stroke, he made an oval with a dent at the bottom. Then he plotted a bulbous nose, two sunken eyes, and a slick of hair off a high forehead. He finished with a Shriners fez, the tassel falling lazily to one side. In only a half dozen lines, he’d captured the round, jowly visage of da mayor by accentuating all his worst features.

“The man with the charcoal arm,” said the pimp, and applauded.

Still, Simmons stared at the image, calculating. The mayor had dictated policy for years, but never such a roundup. Why hadn’t the police just told him to lay off for the weekend? Hadn’t he always moved on when told to, even if it interrupted a portrait? Maybe, like Germany, they were finally coming for the deformed.

Simmons ignored them, consumed by the study of his situation. Without a hearing, he couldn’t even post bail much less beg for his recognizance….

Time passed as slowly as paint drying on a canvas. Meanwhile, the men traded war stories—including the blind man, who’d lost his sight in Korea, and the hophead, whose doc started his habit—and speculated on the contents of their next tray.

“Chipped beef on toast,” said the pimp. “Tough enough to break a chisel.”

“SOS we called it overseas,” said the blind vet. “Shit on a shingle.”

“More like save our stomachs,” said the hophead.

Simmons ignored them, consumed by the study of his situation. Without a hearing, he couldn’t even post bail much less beg for his recognizance. Too coincidental they’d rousted him on a Friday. Maybe the hophead spoke true and the city planned to sweep the streets.

Down the hall, officious typewriters covered up voices too distant to be distinct. Then the heavy steps of a flatfoot approached, accompanied by the softer soles of a civilian. When the two stopped outside the cell, Simmons looked into the evil eye of Sgt. Schumack.

“Who’s the vandal?” asked the sergeant, nodding at the portrait.

He goggled the men until his eyes rested on Simmons. “Before you’re sprung, that better be cleaned.”

“With what?” Simmons said.

The sergeant nodded to the only water in the cell—the toilet.

“I’ve got no rag,” Simmons said.

“Make one.”

As the turnkey turned to go, the second man, who wore a vest but no suit coat and a tie loose at the neck, stared at Simmons with curiosity. He sported a duck butt haircut and horn-rimmed cheaters that distinguished him as hip. From his breast pocket peeked a reporter’s notepad.

“You drew that?” he said to Simmons.

Glancing at the lawman, the inmate shrugged his acquiescence.

The civilian studied him for a time, as though in disbelief, then nodded more to himself than to his subject. “What’s your bit?”

“Just a guy getting by,” Simmons said.

“I mean why’d they pop you?”

Simmons shook his head, ashamed.

The reporter turned to the sergeant. “What kind of case did he catch?”

“Are you writing a book?”


“Vagrancy,” said the sergeant, then cast an eyeball on his prisoner. “Though we’ll be adding vandalism to that sheet if the walls aren’t mopped.”

The reporter cast another long look at the artwork before passing a card through the bars. “Once you slip this cage, call me,” he said. “I want to hear your tale, nightingale.”

After they’d stepped out of earshot, the other inmates questioned Simmons like jealous school girls.

“Who’s the slick dick?” said the pimp.

“Wally Deloitte, Daily News,” Simmons read off the card.

“What’s he want with a gimp?” said the pimp.

Simmons shrugged and turned away to study his artwork for clues.

That night, Simmons lay awake on his concrete bunk smelling the festering of idle men. Down the hall, the activity of the station house had quieted, but voices still murmured and typewriters still clanged, as the work of injustice never slept. Without a blanket or pillow, Simmons shivered against a draft. The jailhouse intended no comforts.

In his youth, before he gave up alcohol, Simmons had done several short stints there, back when shame drove him and the conviction that he’d never survive on his own. His Calvinist parents had taught him that a man’s life forecast his chances for salvation, and what salvation awaited a lame artist? That was before he’d discovered street art in a photo essay about Paris, where he dreamed of traveling, to study at the Académie and the Louvre.

Since he’d dried out, he’d developed a quiet confidence from his independence—until this latest pinch. Bad enough he’d miss a weekend, but what if they kept him longer as punishment for his impudence? He could lose his apartment and his spot on the square, where every go-getter competed for space.

As he pondered an indefinite lockup, Sgt. Schumack’s steps approached again. He stopped just opposite the inmate and stared at him through the bars, his face cut up into cubist angles. Again he appraised the image on the wall as though puzzled by its resemblance. “Before you get an inkling to turn stool pigeon, better think on your situation. You see how easy it is for us to cage a noisy bird. Next time, we might not give you a quick release.”

He strolled away on squeaking soles, leaving their echo as a reminder.

Across the cell, the pimp played a paradiddle with his ringed fingers. “What you think he wants with you?”

“Who?” Simmons said, although he already knew.

“The scandal monger.”


“You know.” He let the sentiment echo through the concrete cage without a reverb. “He writes the police beat. Always looking for tattletales.” He paused to let the significance sink in. “If you thinking of getting back at the fuzz for locking you up, think again. There is no justice for us.”

“I know.”

“Then why you scheming by moonlight?”


“Think how uncomfortable you’d be after a couple years of concrete bunks. Men like you don’t do well in the big house. Up there, there’s top dogs and underdogs, and you know which you’d be.”

He’d rendered it just another grey smear on the concrete…Yet the stink on his arm left a stark reminder of his error….

Before the breakfast tray of dry toast and wet eggs wheeled down the hall, Simmons had wiped clean his masterpiece using the damp sleeve of his shirt. It took a dozen trips—as he limped back and forth to the toilet without his brace—but he’d rendered it just another grey smear on the concrete.

Yet the stink on his arm left a stark reminder of his error. He could still smell it on Monday morning as he appeared before the judge to accept a sentence of time served.

By the time he touched pavement again, he’d dismissed the news man’s offer. He rode the El home, enjoying the view of the city even from the unsteady train, and limped up his front step to be greeted by Lenny, the lobby attendant, who asked with a smirk if he’d spent the weekend with a woman.

“A friend,” Simmons said and looked away.

“I thought you’d cut,” said Lenny. “Was wondering how much I could get for your girlie pictures.”

Simmons smiled and took back his key, then promised to pay his rent before week’s end, though he didn’t know how.

Later that day, as he sat in Water Tower plaza awaiting his first subject, he took in the smell of hot dogs roasting and savored his freedom. Then he watched a new Cadillac rush by and recalled his weekend in county—and the auto show that landed him there. The sergeant said he’d wind up back in the bucket for informing, but hadn’t that happened already? The last two days proved he could be rousted at any hour. If talking would get him payback, what would silence buy?

Inside the newsroom, typewriters clacked and clanged while people scurried between desks arranged in rows and columns, as though to create order out of anarchy. It reminded Simmons of nothing so much as the police station.

He presented Wally’s business card to the receptionist to prove his bonafides then stood by, feeling forlorn and out of place. There, too, people ignored Simmons—another wanting handouts. He half expected to be sent packing without a greeting, but the reporter offered him a friendly shake, which Simmons returned with a clasp of his bad hand, then followed him to his desk. By the time he’d crashed into a swivel chair, Simmons felt in a sweat with anticipation.

He foresaw the scrivener quizzing him about his rap sheet and his latest stint. He imagined a headline more humiliating than his incarceration. “Rejects Rousted.” Instead, the newsman asked about the portrait and his other work.

Before speaking, Simmons checked around them to be sure no one was snooping. “I can’t give you the poop on why I got locked up,” Simmons said, “but I can tell you what’s going on in this city. I see a lot, watching people outside, and I can tell you who’s coming and going. Could even draw them, if you want. No one notices me,” he gestured with his bad hand to explain.

The newsman smirked, derisively. “You ever draw cartoons?”

Simmons thought of the superheroes in comic books and shook his head. He disliked stories of people gifted with extraordinary powers.

“You should. You’d do good,” said the newsman. “That parody of Daley—best I’ve seen. And I’ve seen a lot.” He gestured to a wall of clippings behind his desk, with illustrations of local luminaries doing the dirty dealings of the city. “I write a column each day, the muck of the hog butchers. I could use an illustrator.”

Simmons had been scuffling for so long, he no longer dreamt of a John Square job. Where once he’d aspired to respectability, now he’d settle for invisibility. To be left to his ply his trade, free from the scorn of others, would be a blessing.

“I can’t,” Simmons said. “That’d draw more trouble.”

“So choose a handle,” said the reporter. “Nobody has to know your Christian name.”

Simmons studied the local artwork with admiration—simple line drawings that still depicted their subjects’ essence, then smiled at his chance to capture his captors with impunity.

“Lefty,” he said. “That about sums it up.”

In homage to Nelson Algren and The Man with the Golden Arm.

David Hagerty is the author of four novels, most recently The Tell Me You Are Cunning (Evolved Publishing, 2019). davidhagerty.net

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