During my four years of college, I didn’t work a single day. If I needed dinner, I called Lester. If I wanted a pack of cigarettes, I called Lester. Even the cash for our all-night gaming marathons at the local net cafe came straight out of his pocket. On graduation day, he threw a heavy arm around my shoulder, his eyes bloodshot from cheap whiskey, and said: “Bro, if you ever can’t make it out there, come find me. I’ve got you covered for life.” Ten years later. Under a highway overpass, on a bed of flattened cardboard, he was crouching in the shadows, chewing on a dry, stale crust of sliced bread. I knelt down and held out a business card. “Weekends off. Room and board included. Six-figure salary. You in?” He looked at the name on the card, and his hand shook so hard he dropped the bread. Can you guess the first thing he said to me? 1 October 2024. The air under the southside overpass in Chicago smelled sour. The stench of stale urine mixed with the sharp burn of cheap tobacco, right next to a pile of grease-stained sleeping bags bunched against the concrete. I stood there for a long time. Long enough that Toby, standing behind me, finally tugged at my sleeve. “Drew, are you sure this is the spot? Did we get the wrong address?” I didn’t look back. Because I had already seen him. He was crouching in the corner, leaning against a massive concrete pillar. His winter coat was so caked with grime you couldn’t tell its original color. His hair was matted, his beard scraggly, and he was clutching half a plastic bottle of water. If it weren’t for his eyes—eyes that still held a stubborn, fierce spark even in the gloom—I wouldn’t have recognized him. Lester. My roommate of four years. The most arrogant, unapologetic rich kid in our entire dorm building. The guy who had clapped me on the back and promised to cover me for life. And here he was, hiding in the shadow of an overpass. In that single second, my brain went haywire, rewinding like an old film reel, pulling me all the way back to September 2010. Freshman year. 2 September 2010. The northwest corner of the Chicago campus, Dorm Building Seven. I was hauling two cheap duffel bags up to the fourth floor, panting like a pack mule. The hallway was a zoo—students hauling storage bins, parents crying, luggage scraping against the linoleum. I was entirely on my own. My mom worked the line at a textile mill back home and couldn’t take a day off. She had slipped five hundred dollars into my hand, patted my head, and said, “Stretch it if you can, sweetie. If you run short, call me.” Five hundred dollars. For a whole semester. I figured if I tightened my belt and lived on air, I’d make it. Then I pushed open the door to Room 416. And realized my math was terribly off. The bed by the window was already claimed. A guy in a black Polo was commanding two professional movers as they unpacked. It wasn’t just a couple of suitcases. It looked like an entire department store. He had a 27-inch monitor, a top-of-the-line laptop, a wireless printer. A mini-fridge—an actual compressor unit, not some plastic USB novelty. And, I still remember this vividly, a premium Nespresso machine with a milk frother. This was 2010. Most kids in the dorms were still drinking instant coffee out of paper cups. I stood in the doorway, clutching my canvas duffel bags containing three faded T-shirts, two pairs of jeans, and a 24-pack of instant chicken ramen. Our eyes met. He was the first to speak. “You in 416 too? Top or bottom bunk?” “Bottom.” “Cool.” He stepped aside to give me room. “Make yourself at home.” I looked at his silk pillowcases, then at my bare mattress and cheap canvas bags. Right then, I realized God was testing my pride. Fortunately, I have one major redeeming quality. I have absolutely no shame. “Hey, man. Got any Coke in that fridge?” Those were the first words I said to him. We hadn’t even been in the same room for thirty seconds. He blinked, startled, and then he laughed. He reached into the fridge and tossed me a can. An ice-cold Pepsi. In the suffocating September heat, that first gulp froze my back teeth and sweetened my throat. I can still taste it if I close my eyes. And I still remember the way he smiled when he said: “I’m Lester. Looks like we’re roommates.” Roommates. He said it so casually. As if the word didn’t need four years of history to carry its weight, or ten years to collect on the debt. I just grunted, chugging the soda until it was gone. But in my head, I was thinking: “Looks like there are six more cans in that fridge.” 3 By the end of the first week, I had Lester’s story entirely figured out. His dad, Richard, was one of the top ten building material suppliers in Chicago. Concrete, steel, lumber—if a construction site needed it, his family sold it. How rich were they? Let’s put it this way. During freshman orientation, it rained cats and dogs for three straight days. The quad turned into a swamp. Our entire dorm was marching in the mud, our cheap sneakers practically dissolving. Lester made one phone call. Half an hour later, his family’s driver showed up with four brand-new pairs of weatherproof outdoor boots. Not just for Lester. One pair for every guy in our room. Our other roommates—Toby and “Big Benny”—were practically reduced to tears. Toby held his boots like they were holy relics. “Lester, you’re a lifesaver.” Benny went further, kissing the rubber. “Lester! From now on, you’re my second father!” Me? I took the boots, slipped them on, and said, “Wrong size. Half a size too big. Next time get a 10.5.” Lester stared at me for three seconds before letting out a loud laugh. “Drew, you seriously have no boundaries, do you?” I really didn’t. Especially when it came to food. The campus dining hall cost about six to ten dollars a meal. If I ate three meals a day, that was twenty dollars. Six hundred a month. Over two thousand a semester. I had exactly five hundred. Which meant that if I ate normally, I would starve to death by mid-October. But I didn’t starve. Because every day Lester went to the dining hall, he’d buy extra dishes. And I always happened to be standing right next to him. “Drew, I bought an extra double cheeseburger from the grill line. Take it.” “Drew, I can’t finish this plate of loaded potato skins. Do me a favor and clean them out.” “Drew, they have this buffalo chicken mac and cheese today. It’s too spicy for me. Finish it.” The first month, he thought it was a coincidence. The second month, he got suspicious. By the third month, he sat down at our usual table, looked across at me holding a single plate of plain French fries, fork poised, eyes gleaming, and sighed. He picked up a chicken tender, and before it could reach his mouth, my fork snatched it mid-air. “Hold on,” Lester said, putting down his fork. “Drew, did you even buy an entrée?” “Yeah.” “Where is it?” “The fries.” “…Fries are a side, not an entrée.” “Depends on how you define ‘entrée.’ Potatoes come from the earth, and things from the earth are—” “Shut up.” He fell silent for thirty seconds, then pushed his entire tray over to me. “From now on,” Lester said, “you eat mine.” “What about you?” “I’ll go buy another one.” A warm wave washed over me, but I couldn’t let it show. I calmly chewed on a tender and mumbled, “Get a larger portion next time.” From that day on, Lester’s meal card became my lifeline. His monthly allowance was ten thousand dollars. Ten thousand, in 2010. Meanwhile, my card balance never hit double digits. Was I a parasite? Yes. But Lester never said a word. Later, Toby asked him privately, “Don’t you think Drew is leeching off you too much?” Lester said something I still remember. “If he doesn’t leech off me, he doesn’t eat. It’s not like I can’t afford it.” He paused. “Besides, he’s just sponging a meal, not my soul.” The 2010 version of Lester was a guy who wore his heart on his sleeve. He had no idea what the dark side of the world looked like. He didn’t know that money runs out, people scatter, and some tables are set just to be cleared. But that was fine. I didn’t know either. I only cared about dinner. The dining hall was about to close. I pulled out my phone and texted him: “Where are you? Going to the dining hall? My card got deactivated again.” Lester replied instantly: “Deactivated? For the seventeenth time this semester?” I wrote back: “Cheap magnetic strips. You coming out?” “Yeah,” Lester replied, then added, “Drew, you’re going to owe me for the rest of your life.” I typed back: “Next time.” Next time for sure. I said those words over two hundred times in four years. 4 If freshman year was unorganized sponging, sophomore year was a systematic operation. I kept a schedule in my head. Monday to Friday, I knew his routine by heart. On Mondays he was in a good mood, so he’d go to the taco place—90% success rate. On Wednesdays he had late class, so he ordered delivery—perfect for waiting in the room to share the spoils. On Fridays he usually went out with his rich friends—hard to crash, but he usually brought back leftovers. Weekends were the gold standard. Every two weeks, he hosted. Not for me, but for his “inner circle”—rich kids from other majors, student government heads, pretty upperclassmen. The venues were never cheap: sushi, high-end Italian, steak houses, once even a private lounge. And I was always there. Once Lester scratched his head looking at the guest list: “I know I didn’t write your name down. How do you always know?” “Intuition.” “What kind of intuition?” “A spiritual connection. When you’re hungry, I get hungry.” “Spiritual connection? You’re a human tapeworm.” He complained, but he never kicked me out. Sometimes his wealthy friends couldn’t stand me. A guy named Henderson, whose dad owned a logistics firm, joked at the table: “Lester, is your shadow here on a monthly subscription or a free trial? He’s always sponging.” The table laughed. I didn’t. Lester didn’t either. He pushed the menu to me: “Drew, order whatever you want. Get the expensive stuff. My treat.” Then he turned to Henderson, voice quiet but clear: “He’s my brother. What he eats is on my tab, not yours.” That night, I ordered a hundred-and-fifty-dollar dry-aged Tomahawk steak. After eating, I let out a satisfied belch. Lester stared at my shameless face, grinding his teeth: “Drew, could you at least “pretend” to feel bad?” For his birthday, everyone brought gifts. Henderson gave him a silver Zippo, Toby saved up for a month to buy a bottle of decent whiskey, Benny got him a pair of Jordans. When it was my turn, everyone watched. I pulled a plain white envelope from my pocket. Lester opened it. A sheet of printer paper with one line: “I.O.U. Drew owes Lester $4,300. Due date: Never.” Signed and fingerprinted. The room went quiet. Then Lester laughed—a genuine, deep belly laugh. “Drew! You are the most shameless bastard I have ever met.” “Thank you.” “But you’re also the most entertaining.” He paused. “I’m keeping this. If you ever strike it rich…” “Unlikely.” “Let me finish. If you ever strike it rich, you’re buying me dinner.” He folded the paper and slipped it into his wallet. By senior year, I noticed it was still there. Creased and faded, but tucked inside his expensive leather wallet, right next to his credit cards. Anyway, I’m rambling. The night we graduated, we drank too much. He threw his arm around my neck, slurring his words: “Drew… you’re probably never going to amount to much, are you?” “Yep.” “That’s fine. It’s okay. You’ve got me.” “Yep.” “When I take over my dad’s firm, you’ll be my assistant. I’ll pay you ten grand a month.” “Deal.” “Eight grand.” “Deal.” “Five grand.” “…What’s your game here?” “Testing your bottom line.” “Free,” I said. “Huh?” “Just feed me.” He laughed again, then passed out on the table. Looking at him, I remembered what my mom told me before I left for college. “Drew, don’t take things from people without paying them back. Remember what you owe, because sooner or later, the bill comes due.” She was a simple woman, but that stuck with me. Remember what you owe. The bill always comes. I kept track. I just didn’t expect the bill to be paid ten years later, under an overpass. During my junior year, something happened. My mom was hospitalized. Uterine fibroids. It wasn’t life-threatening, but she needed surgery. Between the procedure and the recovery, it was going to cost about twenty thousand dollars. When I got the call, I was in the library. My mom’s voice was soft, carrying that tentative tone of someone terrified of being a burden. “It’s nothing serious, sweetie. Just a small operation. Don’t worry. The factory insurance covers some of it, but… we’re still a bit short.” “How short?” “Twelve thousand.” I hung up and stood in the hallway for a long time. That month, I had sixty-three dollars on my student ID card. My bank account had four hundred and ten. Combined, it wasn’t even a drop in the bucket. When I got back to the dorm, I didn’t say a word. I just climbed onto my bunk and stared at the ceiling. Lester was playing a video game. Mid-match, he glanced up at me. “Drew, not eating dinner?” “Not hungry.” “You? Not hungry?” He probably thought the sky was falling, but he didn’t press. For the next week, I worked myself into the ground. The campus work-study jobs were already taken, so I looked off-campus. Passing out flyers for twenty bucks an hour. Unloading trucks for fifty a shift. Washing dishes in a greasy kitchen for seventy or eighty bucks a night. Classes during the day, labor at night, crashing into bed at dawn. Everyone in the room noticed. Toby was the first to speak up. “Drew, is everything okay? You’ve lost like ten pounds.” “Just dieting.” “You’re already a twig, man. Any more and you’ll disappear.” I didn’t answer. Lester didn’t ask me directly. His method was different. He watched. One night I got back at one in the morning. The dorm was pitch black. I quietly climbed up to my bunk, exhausted. And found a paper bag next to my pillow.
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