Pregnant Janitor Gave a Crippled Homeless Man $5. But then…

The morning sun barely peeked over the Chicago skyline as Emma jogged through the bustling underpass near Michigan Avenue, her sneakers pounding the concrete. Four months pregnant, she felt a quiet relief—no morning sickness, thank God, so she could still handle her job at the downtown coffee shop. But the exhaustion? That was another story. Dragging herself out of bed each morning was a battle, and she always ended up sprinting to make it on time. The underpass was a chaotic mix of commuters, street musicians, and the usual crowd of unhoused folks camped out near the exit. There was Tommy “One-Eye,” Mr. Johnson, and a handful of others, hands outstretched, asking for spare change.

Emma couldn’t just walk by. Her heart ached for them. Whenever she had a few bucks, she’d grab a hot coffee and a donut from Dunkin’ Donuts to share. They’d light up, thanking her with genuine warmth. The nearby flower vendors, though, weren’t impressed. They’d roll their eyes, muttering under their breath.

“Crazy girl,” one scoffed. “She’s pregnant, barely scraping by, and she’s feeding those hustlers? They’ll just blow it on booze.”

They didn’t get it. Emma knew what it was like to have nothing—no home, no family, no one waiting for you. She saw herself in those tired faces. Sure, some drank to numb the pain, but who could blame them? Standing in the chilly wind all day, watching people rush to their cozy lives while you’re invisible—it’d break anyone. Emma gave a quick wave to the group, then spotted someone new. A young guy, maybe in his early thirties, with messy curls and a crutch under one arm. He didn’t beg or call out, just stared into the distance, a worn baseball cap on the ground for coins. Something about him hit her hard. I’m complaining about my life, and this guy’s missing a leg, yet he’s still here, surviving.

Her emotions got the better of her. She darted to Dunkin’ Donuts, grabbed a warm cinnamon roll and a steaming coffee, and handed them over.

“Here, take this. From the heart. Enjoy,” she said softly.

The guy’s cheeks flushed, and he mumbled, “Thank you,” his eyes dropping to the ground, shy but grateful.

Not wanting to make him feel awkward, Emma flashed a smile and hurried off. But the encounter stirred up old wounds. Memories of her childhood flooded back—a mom who drank nonstop, a house filled with chaos and hunger. Emma could still smell the stale beer and cigarette smoke, see the dirty dishes piled high, and feel the sting of her mother’s hand when she dared ask for food. She’d scavenge scraps from the table, eating quickly before anyone noticed. At five, a kind neighbor, Miss Linda, couldn’t take it anymore and called Child Protective Services. Emma was taken to a foster home, crying for a mom who didn’t even notice she was gone.

Emma’s life in the foster group home wasn’t exactly a fairy tale. The Chicago foster group home was strict—meals were basic, rules were ironclad, and any slip-up meant extra chores. But at least no one hit her like her mom used to. Some kids got visits from aunts or cousins, bringing candy or cheap toys. Emma? She got one visit from Miss Linda, who handed her a small bag of Walgreens gummy bears. Her mom never showed, not once. That hurt clung to her like a shadow, and she swore she’d never abandon her own kid, no matter what.

School was her escape. Emma had a knack for numbers—math came easy, like breathing. She’d solve equations in her head while other kids fumbled with calculators. After aging out of foster care at 18, the state gave her a tiny studio apartment in a rundown building on 63rd Street in Englewood. The place was a mess—creaky floors, peeling paint, and a sagging couch that smelled like mildew. Still, it was hers. With her friend Sarah, Emma decided to take a chance and apply to college. No connections, no money, just grit. To her shock, she got into the University of Illinois at Chicago’s business program on a scholarship, thanks to her stellar grades.

Her dorm room was a step up, shared with two girls, Chloe and Mia, from cushy suburban families. They were all about frat parties and skipping lectures, while Emma buried herself in textbooks at the library. They’d tease her endlessly.

“Come on, fam!” Chloe laughed, tossing her hair. “It’s spring, the bars are packed, and you’re stuck studying? Live a little!”

“Nah, guys,” Emma shot back, adjusting her glasses. “Exams are coming, and I’m not flunking. No one’s got my back if I mess this up.”

Mia smirked. “Fine, but you’re letting us copy your notes, right? We’re out!”

Emma’s hard work paid off—she aced her first year, even finishing finals early with straight A’s. Chloe and Mia barely scraped by and were salty about it.

“Lucky nerd,” Mia muttered. “She’s not better than us, Chloe. Just got lucky.”

Jealous, they hatched a plan to mess with her. Summer break hit, and the dorms emptied out. Emma stayed behind—no family to visit, nowhere to go. She kept hitting the library, trying to stay busy. One day, Chloe and Mia showed up, all smiles.

“Yo, Emma!” Mia chirped. “We’re hitting a barbecue by Lake Michigan. Some seniors are coming—burgers, music, the works. Don’t tell us you’re studying on vacation!”

Emma hesitated. She wasn’t close with them, but the idea of a sunny day by the lake sounded amazing after months of stress. Plus, she was lonely. “Alright, I’m in,” she said, a grin creeping across her face. Why mope in her room when summer was calling?