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What a Chicago immigration raid says about Trumpism
October 27, 2025
AT 7500 South Shore Drive, an apartment complex in Chicago, the front gate and door are wide open. Walk inside and you find an almost abandoned building. Though a few apartments have sturdy gates and double bolts, most lack doors and are closed by plywood. A few are open to the world. Inside one a bunch of balloons and a bouquet of roses suggest a recent celebration. A pushchair sits in one corner. A copy of the New Testament, in Spanish, lies on the floor. There is no sign of the occupants. Most likely they are in an immigration detention centre somewhere.
Back on September 6th President Donald Trump posted a picture on his Truth Social page referencing “Apocalypse Now”, a war film, with the caption “Chicago about to find out why it’s called the Department of WAR.” On September 30th a raid on 7500 South Shore Drive showed he meant it. At around 1am, at least 300 masked federal agents, mostly from border patrol, some rappelling from helicopters, others using breaching ladders, stormed into the building. They threw flashbang grenades into the corridors, smashed in doors and then marched everyone, including children, into the street in their pyjamas. Some 37 Venezuelan immigrants were taken away.
One of the residents who remains is Alicia Brooks, a 33-year-old American citizen. By her account, when the raid started, she heard a helicopter right outside her window on the fifth floor. “I started to get my key, and I was grabbed,” she says. “I was zip-tied in front of me and escorted outside the building.” Dozens of men in military-style uniforms carrying assault rifles evacuated the complex “like it was on fire”, she says. They lined up the inhabitants outside, zip-tying the hands of the adults, and put them on buses.
By law, to question somebody, immigration officers must have reason to think they could be an illegal immigrant. To arrest somebody, they need probable cause. Ms Brooks, who is black, with an American accent, says she repeatedly asked officers why she was being arrested, and pointed out her citizenship. Nobody asked her any questions. When she continued to object to her arrest, an officer knocked her to the ground, removed the zip-ties and replaced them with handcuffs, locked as tightly as they would go. By the time she was released, together with several other citizens, she says the sun was coming up.
According to the Department of Homeland Security (DHS), the raid was ordered to target members of “Tren de Aragua”, a loose Venezuelan crime group that Mr Trump says is a state-backed terrorist organisation at war with the United States. At the scene Greg Bovino, the chief patrol officer at the border agency, said that overwhelming force was needed because “we know there’s weapons” and because gang members had taken over the building, where they were trafficking in sex and drugs. He said this to NewsNation, a news channel which was invited along for the raid.
DHS has so far produced no evidence to support their allegations. Though the building had many Venezuelan migrants living there, remaining residents say the idea that they were gang members is ludicrous. Ms Brooks says that in some ways the Venezuelans could be bad tenants—leaving rubbish outside their doors and playing loud music. But, she adds, they also fixed up broken lights in the buildings’ corridors. Another resident says that the Venezuelans were mostly quiet and decent people.
What is clear is that the building was troubled even before it was the site of an airborne assault. Last October Wells Fargo, a bank, filed in Cook County court to put the building into foreclosure, alleging that the owner was behind on mortgage payments. A receiver was appointed last month. Court filings claim the building had problems with crime. City inspectors visited in April and found multiple code violations, such as lifts not working. One window was blown out even before the raid, and it is unclear whether anyone was actively managing the 100 or so units. Some of them appear to have housed squatters. None of that amounts to a gang takeover. But many Chicagoans are wondering who tipped off DHS.
South Shore, which is about nine miles south of the Chicago Loop, was 92% black and 96% native-born according to Census Data gathered from 2019 to 2023. The neighbourhood is not rich, but neither is it among Chicago’s roughest: the survey data showed around 16% of households had incomes higher than $100,000. From 2022 to 2024 though some 50,000 asylum seekers came to Chicago, mostly bussed to the city by the state of Texas. As they settled in, they drifted to parts of the city with cheap housing. For immigrants with no credit history, little cash and at best informal employment, even buildings as badly maintained as the one at South Shore Drive can be a lifeline. But the flood of impoverished new arrivals created tension with other residents.
What happens now? For DHS, the raid seemed to achieve its goal. Not long after, the agency published a short video of the raid, with Hollywood-style visuals of young Hispanic men being led away in cuffs. As with much of “Operation Midway Blitz”, as the immigration crackdown in Chicago is officially called, the production of video content seems to be a priority. On September 25th border-patrol boats made a show of prowling the Chicago River downtown, perhaps looking for migrants on an architecture cruise. Professional videographers have been spotted filming Kristi Noem, the homeland- security secretary, at an immigration facility in Broadview, a western suburb of the city.
Since the operation launched in early September, over a thousand immigrants have been detained. Yet the president promised domination—tricky to achieve in a metropolis of 9m people. The videos give a sense that feds are everywhere. “We are here, Chicago, and we are not going anywhere,” said Mr Bovino on September 27th. On October 5th the administration confirmed the National Guard had been called out to the city. A day later Illinois sued Mr Trump, seeking to block the deployment. If judges allow it, there will be plenty more opportunities to create video content. ■
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