Shadows of the Southside

Jamal "Jay" Roberts knew the rules of his neighborhood like the back of his hand. These rules were not written in books, of course, but engraved into cracked sidewalks and chain-link fences. Born and raised on Chicago's South Side, Jay was fifteen and already older than his years. He walked with the lean of someone who'd seen too much, but spoke with the passion of someone who dreamed of more. His mother, Miss Lorraine, worked double shifts at the nursing home on 79th just to make ends meet. His older brother, Darnell— who was once Jay's hero, now a ghost in the form of whispered warnings. "Don’t end up like Darnell." the neighbors would say, shaking their heads when the blue and red lights flickered down the block. Darnell had made his choices, and the streets had claimed him. That was the fate Jay was determined to escape. But escape wasn't easy when the streets held you in a chokehold. It's like running from a hungry lion—you can't slow down, can't look back, and every breath feels like it might be your last. Jay found solace at the Harold Washington Library downtown. While his friends chased fast money, he chased words. He read about cities where dreams weren’t deferred and where ambition didn’t come with a price tag. "Man, you always got your head in a book," his best friend Raheim teased one afternoon as they sat on the steps of an abandoned brownstone. Raheim–tall and brawny with a grin that masked hard truths, tossed a worn basketball between his hands. "Books ain’t gonna change nothin' 'round here." He shook his head in defeat. "Nah, but they show me there’s somethin' else out there," Jay replied, watching the sun cast shadows down the street. "You ever think about gettin' out, Heim?" Raheim's smile faded. "Ain’t nobody get out unless they carried out. You know that." But Jay refused to believe it. He had a plan—an acceptance letter from Northwestern, a partial scholarship, and enough money saved from tutoring kids at the community center to cover his first semester. It wasn’t everything, but it was enough to start. The problem was King, a self-proclaimed street entrepreneur with a short temper and long memory. Everybody knew King ran their block, and he had been watching Jay, eyeing him like a wolf sizing up prey. "Jay!" King called one evening, leaning against his black Charger. "I hear you smart. Real smart." Jay stiffened up. "I’m just tryna do me, King." King chuckled, gold teeth flashing. "Tryna do you don’t pay. But you run with me? You set. Ain’t gotta worry 'bout tuition, books, none of that." The offer dangled like a poisoned apple. Jay’s heart pounded. "I’m good. Thanks." King's smile dropped. "Ain’t nobody ever good in this city, Jay. You either eat, or you get ate." The next few weeks were tense. Jay avoided King’s corners, kept his head down, and worked extra hours tutoring. But the streets have ears, and word spread fast—Jay was leaving. To King, that was betrayal. One night, while walking home from the library, Jay spotted Raheim sprinting toward him, face slick with sweat. "Jay! They lookin' for you. King’s boys. They said you don’t get to walk away." Fear winded in Jay’s gut. He knew what that meant. Nobody said no to King without consequence. "I gotta bounce." Jay muttered, gripping his backpack tight. Raheim hesitated. "You got a place to go?" Jay nodded. "I got a cousin in Evanston. If I can make it to the Red Line, I'm good." But getting there meant crossing King’s territory. Jay cut through alleys and backyards, heart pounding with every step. The streets were alive—summer nights mixed with distant sirens and laughter from neighborhood sitters. He ducked behind dumpsters, avoiding familiar faces that might tip off his location. At 63rd, he saw them... two of King’s boys, Reggie and Tone, standing by the corner store, eyes sharp under the flickering streetlight. "Yo! There he go!" Tone shouted and Jay ran. He darted across Cottage Grove, barely missing a speeding car. Feet pounded behind him. He cut into Jackson Park, the moon casting ghostly shadows through the trees. The grass—wet and stuck beneath his sneakers. His mind raced. The Metra tracks. If he could hop the fence and follow the tracks north, he’d bypass the hot zones and hit the Red Line at Garfield. He sprinted, lungs burning. Behind him, Reggie's curses faded as Jay jumped the fence in one desperate leap, tearing his jeans but not stopping. He ran along the gravel, heart syncing with the rhythm of his shoes swifting the rusty rails. At Garfield, he paused only to catch his breath. The Red Line train screeched into the station. Jay jumped aboard just as the doors slid shut. Reggie and Tone burst onto the platform a second too late, fists pounding the glass as the train pulled away. Jay slumped into a seat, chest heaving, sweat dripping from his brow. But he was moving... moving toward freedom. The next morning, Jay stood on his cousin's porch in Evanston, staring at the email on his phone: Final confirmation of enrollment. Welcome to Northwestern University! He smiled—not just because he’d made it out but because he’d proven something. Escape wasn’t just for the lucky. It was for the determined, the dreamers, the ones who ran toward something greater, rather than away from fear. The South Side would always be part of him–its rhythms, its scars, its resilience. But it wouldn’t define him. Jamal "Jay" Roberts had escaped his fate. And now, he was free to shape his own. As he sat on the porch, the sun rising over quiet Evanston streets, Jay thought about the kids back home—the ones still stuck between survival and dreams. He promised himself he’d return one day, not just as proof that escape was possible, but as a guide. Maybe the streets wrote the first chapters of their lives, but Jay believed they could all pick up the pen and write their own endings. He was proof of that.