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Residents of raided South Shore apartment building still face eviction after judge denies pleas for more time

December 8, 2025 by Chicago Tribune

Despite a last-minute plea for more time, eviction looms for the remaining residents of the troubled South Shore apartment building raided by immigration agents earlier this year.

Two weeks ago, residents of 7500 South Shore Drive were blindsided by a court order mandating that the decrepit complex be vacated by Dec. 12. Maintaining the order has left them scrambling to find housing in bitterly cold weather, so residents — as part of the recently formed 7500 South Shore Tenants Union — filed an emergency motion requesting more time for and assistance with relocation.

But a Cook County judge denied those requests Monday, according to the union’s legal representation and community organizers who have been helping residents chart a path forward.

In the wake of the denial, Sam Barth with the Law Center for Better Housing, which is representing the union, has advised remaining residents to prepare to be out by Friday, he told the Tribune Monday afternoon. Barth said he was concerned the deadline would be met safely.

“The tenants reached out to us because they’re in a really desperate situation,” he said.

In the late-night hours of Sept. 30, agents dressed for combat rappelled from helicopters onto the roof of 7500 South Shore Drive. They broke through windows and stormed inside, where they crashed through doors and placed residents in zip ties and on buses or in the back of box trucks. Many Venezuelan migrants lived in the building and were taken in the raid.

Resident Isaiah Bray attends a 7500 South Shore Tenants Union press conference in front of his apartment building in Chicago on Dec. 2, 2025. Bray has lived in the apartment building for nine years. (Eileen T. Meslar/Chicago Tribune)
Resident Isaiah Bray attends a 7500 South Shore Tenants Union news conference in front of the apartment building in Chicago on Dec. 2, 2025. Bray has lived in the apartment building for nine years. (Eileen T. Meslar/Chicago Tribune)

Officials said at the time that the operation, which has since become one of the most infamous moments in President Donald Trump’s Operation Midway Blitz, was meant to target Tren de Aragua gang members. In the nearly two months since, the Department of Homeland Security has provided no evidence to back that allegation and has offered little information about the 37 people who were arrested that night.

Meanwhile, the militarized operation distressed a complex already in crisis, as deteriorating living conditions plagued the building long before the arrival of agents.

Two months later, the Circuit Court of Cook County granted an order mandating those with valid leases to vacate by Dec. 5 and all the occupants to leave by Dec. 12.

As the deadline approached, the South Shore Tenants Union on Dec. 3 filed an emergency motion requesting that the court extend the building’s vacate date by two months. The motion also asked that the city and the building’s management firm, Friedman Communities, create a relocation plan and provide relocation services to union members, including $7,500 in paid assistance.

Friedman was recently appointed manager of the apartment building after a prolonged legal dispute between lender Wells Fargo and Trinity Flood, the Wisconsin-based owner of the property.

A day after union members made their eleventh-hour plea, Mayor Brandon Johnson wrote to Friedman co-CEO David Friedman. He requested that the Dec. 12 move-out date be postponed and that each household receive a $7,500 lump-sum payment to cover relocation and temporary housing costs.

“(Residents’) living conditions have been unsafe for far too long, and they now face the imminent threat of homelessness,” Johnson wrote. “The City has stretched its emergency, housing, and public health resources to stabilize this situation, but without immediate action from you, these families will suffer significant and avoidable harm.”

Housing organizer Jonah Karsh called Monday’s denial disappointing and concerning.

“While we grant the building is extremely dangerous, we are equally concerned about the possibility people won’t have anywhere to go on Friday,” he said.

Karsh said organizers are shifting their focus to helping marshal as much assistance for residents “as humanly possible.”

“We’re gonna try to get everything we can in the absence of more time,” he said. “But we’re concerned that even then, it’s not enough.”

tkenny@chicagotribune.com

Filed Under: Bears

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