A federal judge in Chicago argued Tuesday that last week’s South Shore immigration raid undermined the recent claim by U.S. Supreme Court Justice Brett Kavanaugh that stopping people based on race, language and other factors might subject U.S. citizens only to “brief” encounters with the feds.
The new commentary from U.S. District Judge Jeffrey Cummings appeared in a footnote to a 52-page ruling in Chicago’s federal court. It extended, into February 2026, restrictions on U.S. Immigration and Customs Enforcement’s ability to make warrantless arrests in Illinois and nearby states.
Cummings declined to rule on more recent claims stemming from President Donald Trump’s “Operation Midway Blitz.” Rather, Cummings found that ICE arrested 22 people without a warrant and in violation of what’s known as the Castanon Nava settlement agreement.
Those arrests occurred in late January and February.
He urged immigrant rights activists and federal authorities to try to resolve more recent allegations related to the federal deportation campaign in the Chicago area among themselves and report back to him by Nov. 5.
The National Immigrant Justice Center’s Mark Fleming said in a statement that the ruling “recognizes the scope and gravity of the constitutional violations the federal immigration enforcement operations have wrought on Chicagoans, both citizens and immigrants alike.”
Cummings wrote about the need to “seriously apply” probable cause requirements in the law. He wrote that people who share “commonalities” with “Latino foreign nationals” may find themselves “subjected to ICE questioning for sometimes lengthy periods of detention.”
And then, in a footnote, he pointed to the Sept. 30 raid at 7500 S. South Shore Drive, and claims that the building was “known to be frequented by members of Tren de Aragua (a Venezuelan gang) and their associates.”
Residents and witnesses have said that armed federal agents in military fatigues busted down doors in the middle of the night, and that U.S. citizens were among those detained for hours.
Cummings, a former Chicago Police Board hearing officer, wrote that many details “remain unknown.”
“However, one thing seems clear: ICE rousted American citizens from their apartments during the middle of the night and detained them — in zip ties no less — for far longer than the ‘brief’ period authorized by the operative regulation … and envisioned by the Perdomo concurrence,” the judge wrote.
The “Perdomo concurrence” refers to a controversial writing by Kavanaugh last month. It came as a Supreme Court majority ruled that federal agents could continue stopping people based on race, language and other factors in California amid a deportation campaign there.
The majority did not explain itself.
Rather, Kavanaugh wrote in his own 10-page concurrence that “apparent ethnicity alone cannot furnish reasonable suspicion.” He said it can be a “relevant factor,” though, and he cited other circumstances that included the “extremely high number … of illegal immigrants in the Los Angeles area” who “tend to gather in certain locations to seek daily work” and “do not speak much English.”
“Under this court’s precedents, not to mention common sense, those circumstances taken together can constitute at least reasonable suspicion of illegal presence in the United States,” Kavanaugh wrote.
The justice added that “If the person is a U.S. citizen or otherwise lawfully in the United States, that individual will be free to go after the brief encounter.”
Gregory Bovino, commander-at-large for the U.S. Border Patrol, has since told a WBEZ reporter that agents in Chicago were arresting people here based partly on “how they look.” Bovino’s “Operation At Large” in California was the subject of the case that prompted Kavanaugh’s concurrence.
Now, in his own opinion this week, Cummings has insisted that “the importance of the probable cause requirements” under the law are “further heightened by ICE’s embrace of the standard of reasonable suspicion articulated by the concurring opinion” by Kavanaugh.
Cummings wrote that adherence to the law’s probable cause standards “will help protect citizens and other persons with legal status who face questioning by ICE officers against being subjected to prolonged detentions and warrantless, collateral arrests.”