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To understand that horrific Chicago apartment raid, go back in time—to Texas

October 16, 2025
in Law & Defense
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To understand that horrific Chicago apartment raid, go back in time—to Texas
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Months before hundreds of federal immigration agents raided a rundown apartment complex in Chicago—some even rappelling onto the roof from Blackhawk helicopters in the early hours of September 30—local law enforcement had repeatedly visited the building to try to remove some immigrants living there, according to a longtime tenant.

The immigrants, many from Venezuela, had fallen behind on rent, and the landlord, a real estate investor from Wisconsin, wanted them gone. During multiple visits, officers from the Cook County Sheriff’s Office locked some of the people out of their units, says Cassandra Murray, 55, a US citizen who lived on the building’s fourth floor for about a decade.

The place was in dire need of renovations—mold, mice, broken elevators, and a putrid stench were common—but despite the barely habitable conditions, some of the evicted families returned soon after the deputies left. “I felt sorry for them, especially the women with children, because I could tell these people had nowhere to go,” Murray told me.

The raid at 7500 S. South Shore Drive became a flashpoint in the Trump administration’s militarized effort to detain and deport immigrants. Nearly 300 federal officers from Border Patrol, the FBI, and other agencies arrested 37 people, forcibly separating children from their parents and pulling residents into vans outside. Afterward, Illinois Gov. J.B. Pritzker, who criticized the operation, urged state agencies to investigate whether agents had used excessive force against kids in the building or infringed on people’s rights

But the story of the raid is not only a story about aggressive agents; it is also a story about the struggles asylum seekers face while seeking safe and affordable housing. Some of the Venezuelans at 7500 S. South Shore were reportedly in the building without a lease; others had moved in with temporary rental assistance from a state program, but that funding ended and city-run shelters for immigrants had closed. “They were all just looking for somewhere to stay,” says Murray.

To understand the raid, you need to rewind to 2022, when Texas’ Republican Gov. Greg Abbott began busing migrants to so-called sanctuary cities, including Chicago, to protest the Biden administration’s immigration policies. At the height of Abbott’s political stunt, 12 to 15 busloads of immigrants were arriving in Chicago every day—about 28,000 people by late 2023, and 50,000 by late 2024. Many slept on the floors of police stations or at O’Hare airport, waiting for space in shelters.

Resettling the new arrivals was a financial strain: In November 2023, Chicago’s City Council allocated $150 million and the state chipped in another $160 million, on top of the $176 million that had already been given by the city, state, and federal governments. The funding would go toward an intake center and winterized tent shelters that could hold 2,000 migrants for up to six months at a time.

But these were temporary solutions: By late 2024, as border crossings from Mexico plummeted, the city prepared to close the shelters in January 2025. Instead, Chicago announced a new “unified” shelter system that would house migrants together with non-migrants experiencing homelessness. “This will help to ensure that we have a single and equitable shelter system for anyone,” Mayor Brandon Johnson said at the time.

“That building was fucked up before the raid,” says a tenant organizer. “Now you’ve got this horrific thing that happened.”

There were downsides: Migrants who had been in the United States for longer than 30 days were no longer eligible for placement in a shelter. And there wouldn’t be enough beds for everyone. “Could this lead to people on the street?” Johnson added. “I don’t want to see anyone lose, right? But the harsh reality is that we can do what we can afford. We’ve been stretched to the limits.”

In 2022, the state had also created a program to help transition immigrants from shelters to apartments; the Asylum Seeker Emergency Rental Assistance Program (ASERAP) provided up to six months of rental assistance. But this, too, was temporary. In 2023, six months of rental assistance was reduced to three months, sparking concerns that people might be forced back onto the streets if their immigration cases stalled and they didn’t have work permits yet. Three months “is such a short amount of time,” Charlotte Long, then a housing specialist connecting migrants with apartments, told Block Club Chicago.

By mid-2024, ASERAP, which also relied on federal funding, was no longer taking applications. The Illinois Department of Human Services told me that the program assisted more than 6,600 households from 2022 to mid-2024. The state did not track what happened to immigrants after they were placed in apartments and their financial assistance ran out. But some were clearly struggling.

In 2024, Injustice Watch reported that Illinois officials had placed recent Venezuelan arrivals in an apartment in Woodlawn that city officials had taken to court over unsafe conditions, such as rats and flooding. Others wound up in the South Shore neighborhood—the “eviction capital” of Chicago, as organizer Dixon Romeo, from the group Southside Together, put it to me.

In fact, WBEZ reported that asylum seekers receiving state rental assistance were more likely to end up in the 60649 zip code, which includes South Shore, than anywhere else in the city.

Broken and boarded up windows at 7500 S. South Shore Drive. Federal agents raided the building during the early morning hours of September 30. Residents were awaken by flash-bang grenades and helicopters.Joshua Lott/The Washington Post/Getty

The apartment complex at 7500 S. South Shore was in disarray long before federal agents tore it apart. For years, tenants’ maintenance requests were ignored by management. In 2024, Jonah Karsh of the Metropolitan Tenants Organization started helping residents demand improvements, including having their gas turned on so they could cook. But it was an uphill battle. City lawyers eventually sued the owner’s companies for a long list of code violations, noting in court documents that fire extinguishers were missing and “all stairways are filthy with strong smell of urine.”

“It’s difficult to walk through without swallowing a gnat,” reporters for WBEZ and the Chicago Sun-Times wrote after they visited the site. “It’s dimly lit inside and completely dark in some corners. A stray cat roams the second floor, likely hunting the mice or cockroaches that residents say infest the building…Elevators are out of order and filled with garbage…Water pours through the ceiling of one unit, pooling below.”

“That building was fucked up before the raid,” says Romeo, the organizer at Southside Together, who has canvassed tenants there. “City, state, county, federal government—everybody has a role in why that building looks like it does. Now you’ve got this horrific thing that happened and there’s a lot of light on the situation,” he adds, “but there are buildings like that in every city in America, whether they’re raided by ICE or not. There are housing issues here.”

According to news reports, one resident saw someone he believed to be a worker from the building photographing units “where the Venezuelans lived.”

The 130-unit complex is owned by Trinity Flood, the Wisconsin real estate investor, who purchased it in 2020, along with two other distressed South Side buildings. After the sale, she sued the previous owners, alleging they’d overcharged her and hadn’t informed her about all the renovation needs, or that the apartment required 24-hour security, which Flood claimed would cost $15,000 a month. (The suit was settled in 2023, according to The Real Deal, a real estate news outlet that examined the property’s history of code violations.) The building had failed the past 14 annual inspections, per city records, and in April Wells Fargo sued to foreclose on the building. Both the bank and the city have requested that a court-appointed receiver be put in charge of the complex, but litigation is ongoing.

Murray, the fourth-floor tenant, says conditions took a turn for the worse after Flood assigned a firm called Strength in Management to manage the building in 2024. The new company did not hire security for the building prior to the raid, even though the front doors didn’t lock. (Neither Flood nor Strength in Management responded to my requests for comment.) “The building was wide open, like we lived in a barn,” says Murray. Anyone could walk in.

As a result, the unhoused population grew, driven in part by immigrants, including some whose rental assistance had run out. Murray estimates there were more squatters in the building than paying tenants. (Some had stopped paying rent in protest of the abysmal conditions.) Strength in Management filed 25 eviction cases in 2024, more than in the prior four years combined; sheriff’s deputies came around multiple times this year, Murray told me, but the squatters kept coming back, or new ones would arrive. “I remember hearing on the news about how the shelters shut down for them,” she adds. (The Sheriff’s Office declined to comment.)

In August, a city attorney told a lawyer for Wells Fargo that Strength in Management had been unable to “re-assert control over the building” after it was overrun by “armed occupants.” The Department of Homeland Security, too, claimed its agents targeted the building because it was “known to be frequented” by members and associates of the Tren de Aragua gang; prior to the raid, a 25-year-old resident of the building was charged with murdering someone in the neighborhood. (DHS has since admitted that only 8 of the 37 people arrested in the raid had a criminal record, and only one was a verified Tren de Aragua member.)

Murray says her immigrant neighbors weren’t causing trouble, and she never saw any gang activity or other behavior that scared her: “Even though the building was open the way it was, nobody ever bothered nobody—the building was quiet.” When some immigrants first moved in two or three years ago, she says, she felt frustrated that not all of them were taking their trash out, but they were receptive to her complaints and ultimately proved to be friendly neighbors: It was the Venezuelans who put up lights in the dark hallways, she says—not management—and they swept and mopped the floors and cleaned the stains off the stairs.  

Personal items strew about an apartment hallway.
Debris and personal items belonging to Venezuelan immigrants were strewn in a hallway.Jim Vondruska/Reuters/Redux

In the early hours of September 30, while residents were asleep in their beds, hundreds of federal agents stormed the apartment. Rodrick Johnson, a US citizen, told Block Club Chicago that he heard “people dropping on the roof” before FBI agents busted through his door. Officers handcuffed occupants with zip ties, then led them outside to vans, where they sat for hours wondering whether they would be arrested.

It’s unclear who tipped off the feds for the raid. Chicago officials said they didn’t have advance notice about it or collaborate on the operation.

Days earlier, according to WBEZ and the Sun-Times, one resident saw someone he believed to be a worker from the building photographing the units “where the Venezuelans lived.” After the raid, reporters found a map crumpled up in the entryway of the apartment that labeled each unit as either “vacant,” “tenant,” or “firearms.”

The units designated as “vacant” had been raided—tape was left over their doors, labeled with the letters “PC,” according to a video I was shown of one hallway and a photo from WBEZ. Most units designated as “tenant” appeared to have been left alone, leading to questions: How did federal officers know about the building’s layout and occupancy? Karsh, of the Metropolitan Tenants Organization, notes that the landlord or property management would have likely possessed that information. Had federal immigration agents, he wondered, been deployed as an extralegal eviction force?

After the raid, a small moving crew told Block Club Chicago that they were clearing out the now-empty units, but they didn’t say who hired them. “Doors were boarded up,” the outlet added. “In one room, there were zip ties and blood stains on the floor next to baby shoes.”

As journalists came by, seeking more information, property management informed tenants that it would finally lock the front door and hire armed security. Murray, who just moved out, is frustrated about the timing. “Now they have security because they don’t want them to see the real truth,” she says. “But we have been asking for security for years and couldn’t get it.”



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