The raid on South Shore Drive was one of the largest episodes in the new immigration campaign launched by Donald Trump’s administration across America’s biggest cities. The nighttime operation—conducted with helicopters, flash grenades, and dozens of armed agents—was presented as a strike against a Venezuelan criminal group. But no evidence was provided, and among those detained were U.S. citizens.
For Trump, the raid served as a vivid demonstration of how he intends to “restore order” in cities where federal authority has long clashed with local governments.
On Chicago’s South Side, at 7500 South Shore Drive, the gates of a residential complex stand wide open. Inside lies a nearly empty, dilapidated building. A few apartments remain locked behind heavy bars and padlocks, but most are boarded up or missing doors altogether. In one room: a bunch of balloons, a bouquet of roses, a baby stroller, and a Spanish-language New Testament. Signs of life remain—but the people are gone. They were likely taken to one of the migrant detention centers.
On September 6, Donald Trump posted on his Truth Social network a still from Apocalypse Now captioned: “Chicago Is About to Find Out Why It’s Called the Department of War.” By September 30, his meaning was clear. Around 1 a.m., the building on South Shore Drive came under assault: more than 300 federal agents, mostly from the Border Patrol, stormed inside. Some rappelled from helicopters; others climbed in on ladders. Flash grenades echoed through the corridors as doors were smashed open with battering rams. All residents, including children, were forced out into the street—many still in pajamas. Thirty-seven Venezuelan migrants were detained.
Homeland Security
Among those who remained in the building was 33-year-old American citizen Alisha Brooks. She recalls that it all began when a helicopter hovered right outside her window. “I was reaching for my keys when they grabbed me,” she says. “They put plastic zip ties on my wrists and led me out of the building.” According to her, the armed men acted “like in a fire drill”—lining everyone up along the street, binding the adults, and loading them onto buses.
By law, immigration officers may question only those for whom there are reasonable grounds to suspect unlawful presence. Arrests require a separate legal basis. Brooks, an African American with a distinct Chicago accent, says she repeatedly told the officers that she was a U.S. citizen and asked why she was being detained. She received no answer. When she began to protest, one of the agents threw her to the ground, removed the plastic ties, and replaced them with metal handcuffs, tightening them painfully. She was released only at dawn—along with several other American citizens.
The Department of Homeland Security said the operation targeted the Venezuelan criminal group “Tren de Aragua,” which Trump had declared “a terrorist organization waging war against the United States.” Border Patrol chief Greg Bovino explained on site that the use of force was necessary “because we know there are weapons there,” claiming the building had been taken over by gang members involved in human and drug trafficking. He made the remarks to NewsNation, which had been granted advance access to film the raid.
But the agency provided no evidence to support those claims. Residents and neighbors find the story of a “building takeover” implausible. Brooks says the Venezuelans who did live there “weren’t the tidiest neighbors”—they left trash by their doors and played loud music—but they also fixed lights in the hallway. Other tenants describe them as peaceful and friendly.
The building itself had long been in decline. As early as October last year, Wells Fargo filed a foreclosure lawsuit over unpaid debts. In September, the court appointed an external administrator. Case documents mention broken elevators, shattered windows, unsanitary conditions, and incidents of crime. Some apartments were apparently occupied by homeless people. All this points to neglect but offers no evidence of “gang activity.” Meanwhile, residents wonder who alerted the authorities to the building.
The South Shore neighborhood lies about nine miles south of downtown Chicago. According to census data from 2019–2023, 92% of its residents are African American and 96% are U.S.-born. It is neither impoverished nor affluent: around 16% of households earn more than $100,000 a year. Between 2022 and 2024, roughly 50,000 asylum seekers arrived in Chicago, most of them sent from Texas. They could only find housing where rents were low. For people without credit histories, savings, or steady jobs, even semi-derelict buildings offered a rare chance at shelter. Yet the influx of migrants has heightened tensions between newcomers and longtime residents.
For the Department of Homeland Security, the operation was presented as a clear success. Almost immediately after the raid, the agency released a short video montage of arrests edited like an action movie. As in other episodes of “Operation Midway Blitz”—a campaign to tighten immigration control in Chicago—particular emphasis was placed on video production. On September 25, patrol boats staged a conspicuous sweep along the Chicago River, as if searching for migrants on tourist vessels. In the suburb of Broadview, professional videographers filmed Homeland Security Secretary Kristi Noem at an immigration facility.
Since the campaign’s launch in early September, more than a thousand people have been detained. Trump promised “total suppression”—an unlikely goal for a metropolis of nine million. Yet the videos convey an image of federal omnipresence. “We’re here, Chicago, and we’re not going anywhere,” Bovino declared on September 27. On October 5, authorities confirmed the deployment of the National Guard to the city. The very next day, the state of Illinois filed a lawsuit seeking to block the decision. Unless the courts intervene, the administration will have no shortage of opportunities for new dramatic footage.