Chicago raid targeted squatters, not gangs, court records show

Newly revealed arrest records show that a high-profile immigration raid on a South Shore Chicago apartment building last year that became a symbol of President Trump’s harsh immigration tactics actually targeted squatters, not Venezuelan gang members.

The court documents were first reported by ProPublica.

Quickly after the September 30, 2025 raid, the Department of Homeland Security published a dramatic video of the operation, showing agents with their guns drawn, some repelling out of a Black Hawk helicopter onto the roof, and leading people away with their hands zip-tied.

On multiple occasions, the Trump Administration has said the building was frequented by Tren de Aragua members, a Venezuelan gang.

But, arrest records for two of the men show the government’s stated reason for the raid was to take out squatters, and not gang members. The documents were included in a motion filed in an ongoing case challenging warrantless arrests in Chicago.  

In the documents DHS stated “this operation was based on intelligence that there were illegal aliens unlawfully occupying apartments in the building.” There is no mention of criminal gangs or Tren de Aragua.

“This is the most brazen unconstitutional use of force in an operation that I’ve seen in my entire career,” he said. “They have no legal authority to be addressing purported squatters, that is not within the purview of the federal government.”

Fleming represents the two men — a Venezuelan man and a Mexican man both in the country illegally — in the ongoing litigation that claims the federal government continues to violate the 2022 Castañon Nava settlement agreement which limits Immigration and Customs Enforcement’s ability to arrest people without warrants or probable cause.

Thirty five other undocumented immigrants were also arrested with no connection to the gang. Some had a criminal record.

According to the arrest records, “the entry and subsequent search of the premise was facilitated as a result of the building’s owner/manager’s verbal and written consent.” The search, the record states, consisted of apartments “that were not legally rented or leased at the time.”

Fleming, with the National Immigrant Justice Center, said the latest developments show the federal government lies when conducting these operations.

“Any time the administration speaks about what is the basis of their enforcement,” Fleming said, “the public at this point should treat those statements with deep skepticism.” He added that whether it’s the fatal shootings by immigration agents of Renee Good and Alex Pretti in Minneapolis or the killing of Silverio Villegas in Chicago “once the facts come out, it becomes very clear that the administration is not being honest with the public.”