Chicago ICE Raid Targeted Squatters, Not Gang Members, Records Show

Court records reveal a discrepancy between the Trump Administration's public statements and the actual justification for the immigration operation.

Published on Feb. 6, 2026

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A recently surfaced trove of court records has revealed that a September 2025 immigration raid in Chicago, initially presented as a crackdown on the Venezuelan gang Tren de Aragua, primarily targeted alleged squatters. The raid, complete with dramatic video footage of agents descending from a Black Hawk helicopter, was touted by the Department of Homeland Security (DHS) as a victory against a dangerous criminal element. However, arrest records for two individuals detained during the operation explicitly state the government's focus was on individuals unlawfully occupying apartments - a matter typically outside the purview of federal immigration enforcement.

Why it matters

The revelations about the true nature of the raid raise serious questions about transparency and the potential for politically motivated enforcement. The case is part of ongoing litigation challenging warrantless arrests by Immigration and Customs Enforcement (ICE) in Chicago, further fueling concerns about federal overreach and the blurring of lines between immigration enforcement and local issues.

The details

The court documents detailing the raid were included as evidence in the case challenging the 2022 Castañon Nava settlement agreement, which limits ICE's ability to make arrests without proper warrants or probable cause. When questioned about the court records, DHS spokesperson Tricia McLaughlin did not address the discrepancy directly, instead citing the arrest of two individuals allegedly linked to a foreign terrorist organization and Tren de Aragua, citing unspecified 'limitations' on providing further information.

  • The September 2025 immigration raid took place in Chicago.
  • The 2022 Castañon Nava settlement agreement, which limits ICE's ability to make arrests without proper warrants or probable cause, is the focus of ongoing litigation.

The players

Mark Fleming

Associate director of federal litigation at the National Immigrant Justice Center, who described the situation as a 'brazen unconstitutional employ of force' and emphasized that addressing squatters falls outside the federal government's authority.

Tricia McLaughlin

A DHS spokesperson who did not directly address the discrepancy between the administration's public statements and the arrest records, instead citing the arrest of two individuals allegedly linked to a foreign terrorist organization and Tren de Aragua.

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What they’re saying

“We must not let individuals continue to damage private property in San Francisco.”

— Robert Jenkins, San Francisco resident (San Francisco Chronicle)

“Fifty years is such an accomplishment in San Francisco, especially with the way the city has changed over the years.”

— Gordon Edgar, grocery employee (Instagram)

What’s next

The judge in the case will decide on Tuesday whether or not to allow Walker Reed Quinn out on bail.

The takeaway

This case highlights growing concerns in the community about repeat offenders released on bail, raising questions about bail reform, public safety on SF streets, and if any special laws to govern autonomous vehicles in residential and commercial areas.