On a snowy Wednesday, two days before their final move-out date, a group of people huddled over a desk in the lobby of the apartment building at 7500 South Shore Drive in Chicago.They were picking up checks and turning in keys to representatives from Friedman Communities, the foreclosed building’s court-appointed manager. A judge earlier this week ordered the squalid South Shore building vacated by Dec. 12, calling it a fire trap. Nearby, residents rolled out dollies loaded with boxes and trash bags through the front door.Most of the people who were living there have moved out by now. Some made arrangements with friends and family. Others got help from the city or local nonprofits and found new places to live.But Darren Hightower, 41, was one of a handful of people with no long-term plan.He picked up his first $2,500 check — he’ll receive a second in the same amount Friday — and headed to his third-floor apartment in an elevator that had been broken for months. The property manager had one of the building’s two elevators fixed just in time for moving week. A resident carries a lamp on Wednesday as she prepares to move out before a court-ordered deadline.Esther Yoon-Ji Kang/WBEZ Hightower remembered the first time he toured the one-bedroom unit.“It was decent,” he said. “You got the beach down the street. It was affordable. I [had] a five-minute commute to work at the time.”He had high hopes for the place back then. He set up his printing equipment, mounted his TV and assembled a microwave stand that he loved for the kitchen.For Hightower, the building now holds memories of a difficult time in his life, but is also a reminder of how he advocated for himself and his neighbors.‘We spoke up for ourselves’In the summer of 2023, just four weeks after he moved into the sprawling apartment complex, Hightower’s life began to unravel. A workplace injury required surgery on both of his wrists. He lost hours at work and a number of side gigs. A massive leak in his ceiling sent water pouring down and damaged his TV and couch. Rodents and insects infested the building and eventually his unit. There was a stretch of 45 days where Hightower went without gas. And then there were the broken elevators.The property manager at the time — Strength in Management, whom many residents blame for the building’s rapid decline — was mostly unresponsive. Strength in Management CEO Corey Oliver previously declined WBEZ’s request to respond to specific criticism from residents.Around the same time, several migrants moved into the building as part of a state rental assistance program for asylum seekers. Some squatters also moved in. Building upkeep was basically nonexistent. MacArthur Benton carries a dolly back into the building after helping one of his neighbors move out.Esther Yoon-Ji Kang/WBEZ One day in 2024, in the lobby, Hightower ran into a wheelchair-bound neighbor, who asked for a slice of bread.“Most people ask you for money, so I'm like, ‘What's wrong?’ ” he remembers asking the neighbor. “He told me, ‘I've been stuck in this lobby for two days because the elevator broke down.’ That hurt me. I wanted to carry him upstairs so bad, but I'm dealing with the surgeries and everything.”Hightower was so affected by the incident that he called the Metropolitan Tenants Organization hotline. With the help of a young organizer, Jonah Karsh, he started knocking on doors in his free time.The tenants union gained some steam, but as time wore on, Hightower’s neighbors grew discouraged that they weren’t seeing quick results. The union’s numbers dwindled until at one point, it was just Hightower and Karsh texting back and forth.And then, on the night of Sept. 30, as Hightower sat in the emergency room at Advocate Trinity Hospital with a swollen throat, a swarm of federal agents kicked down doors and zip-tied the residents at the South Shore building, ultimately arresting dozens of migrants and a handful of U.S. citizens.Hightower came home from the hospital at 3 a.m. to a ransacked building, but after things had quieted down.“My anxiety probably would have freaked me out,” he said. “I really felt blessed to not have even had to go through [the raid].”There was a media frenzy in the days that followed. Then, just as swiftly as they arrived, the cameras were gone. But Hightower and his neighbors began organizing again.With help from another group, Southside Together, they held news conferences decrying the lack of help from the new court-appointed property manager, Friedman Communities, which did not respond to multiple requests for comment.They also demanded more resources from the city and the state. They even filed a motion to push back the move-out date, albeit unsuccessfully.Still, Hightower said, the fight has been worth it.“Even if we didn’t get the outcome we wanted, it was worth it because we spoke up for ourselves,” he said on Wednesday, as he threw items into bins and made calls about apartments. Darren Hightower calling about available apartments two days before the move-out date. A judge-appointed property manager was ordered to help residents relocate, but tenants say that “help” was merely a check and a list of phone numbers.Esther Yoon-Ji Kang/WBEZ ‘Should I just go, start somewhere new?’For Hightower, the apartment search has been particularly difficult. Since he found out about the Friday deadline two weeks ago, he has applied for several apartments but has not heard back.There aren’t many units in his price range, and he’s unable to afford even many studio apartments. His reduced paycheck and a recent bankruptcy have made things even harder. He was driving around viewing units as late as Thursday.Hightower does have family nearby, a younger sister who lives on the South Side. But he says, she “has a full home… she has four kids, she has a man, and she has a mother-in-law that she helps take care of. I love the fact that she still tells me, ‘Hey, I’m here,’ but I’m like, ‘I’m your big brother, I got this.’ ”This weekend, he plans to crash at a hotel or maybe on a friend's couch. After that, he’s not sure.He moved in 2020 from the small city of Camden, N.J., to Chicago. But the big city, he said, “has had its way with me” over the past five years.“I’m thinking about, should I just take these checks, pack up my [stuff] and … just go, start somewhere new?” he asked. “But also in my head, it’s like, ‘You ain't no f------ quitter,' you know? So it's like, I'm battling myself.”On Wednesday, a squatter he calls “Unc” came knocking a few times on Hightower’s door. Hightower greeted him cheerfully each time, giving Unc food, a sweater, a roll of toilet paper, and a can of beer.Later that day, Hightower rented a van to deliver his bed that he sold to someone online, and he put a few more things in storage on Thursday. He plans to break down his cherished microwave stand to take with him on Friday, along with some clothes and shoes.As for the rest of his belongings, he said he’ll have to leave them all behind. Darren Hightower entering his apartment for one of the last times. For Hightower, the South Shore building holds difficult memories but also reminds him of how he advocated for himself and his neighbors.Esther Yoon-Ji Kang/WBEZ ...read more read less