In the latest judicial blow to President Donald Trump’s push to detain and deport undocumented immigrants en masse, a judge ruled Wednesday hundreds of people arrested in an Illinois immigration operation must be released.
The detained people must be granted bond by the end of next week, the judge ruled, but big questions remain about how the process will play out – including locating those arrested, some of whom have been moved across the country, plaintiffs say.
Here’s what we know – and what we don’t know about what happens next.
US District Judge Jeffrey Cummings, who was nominated by former US President Joe Biden in 2023, sided with attorneys from the National Immigrant Justice Center and the ACLU, who filed a lawsuit alleging federal agents violated a 2022 settlement agreement over warrantless arrests in the Chicago area.
Last month, Cummings ruled agents violated the previously agreed upon consent decree.
Under the decree, if ICE seeks to make a warrantless arrest, it must meet conditions like establishing probable cause that someone is in the country illegally, assessing their community ties and whether they could be a flight risk.
The plaintiffs alleged more than 3,000 people were arrested between June and October in “Operation Midway Blitz,” the federal government’s immigration crackdown in Chicago and surrounding areas.
The settlement remains in effect until February 2, 2026, and says if someone is arrested in a way “that violates the settlement in the Chicago Area of Responsibility—which includes in Illinois, Indiana, Wisconsin, Kansas, Kentucky, and Missouri— they may be able to seek individual remedies—including immediate release from detention.”
Who will be released and when?
Of the 3,000 people arrested between June and October, 615 – one-fifth – are not subject to mandatory detention and don’t have final orders of removal, the ruling says. Those who remain detained out of that group, as long as they don’t pose a high public safety risk, must be granted bond by noon on November 21, according to the ruling.
But two challenges will remain: locating people and figuring out who and how their bond will get paid.
“What’s challenging is at this point, they’ve moved these people all over the country,” Fleming told CNN on Thursday. “Let’s say we were able to post bond for a lot of these people and we were working on it with families, with other organizations … I’m not certain that the government is going to bring them back to Chicago and so they will drop them in the middle of nowhere where they’ve detained them.”
The organization believes at least 1,100 of the 3,000 arrested individuals have voluntarily left the country, saying they “gave up” fighting their cases, Fleming said during a news conference Wednesday.
“They are people who disproportionately had no interaction with the immigration or criminal justice system,” Fleming told CNN. “Who’ve lived in the community for years, have families, have businesses, you name it, who were stopped in the community, whether driving to work, picking up kids at school.”
Government attorneys have requested a stay of Cummings’ order until next Friday, according to Fleming; the legal pause could prevent the government from deporting or detaining someone until the court decides next steps.
But immigration officials seem undeterred in their mission.
“If (Pritzker is) pleased that he thinks operations are being ratcheted down, well, just the opposite is going to occur,” Gregory Bovino, the top Border Patrol official leading Operation Midway Blitz, told Fox News on Thursday.
“We’re ratcheting operations up in Chicago,” he said.
In response to the ruling, Department of Homeland Security spokesperson Tricia McLaughlin said the decision is putting the lives of Americans at risk.
“At every turn, activist judges, sanctuary politicians, and violent rioters have actively tried to prevent our law enforcement officers from arresting and removing the worst of the worst,” McLaughlin said in a statement to CNN Wednesday. “Now an ACTIVIST JUDGE is putting the lives of Americans directly at risk by ordering 615 illegal aliens be released into the community.”
CNN has reached out to DHS for comment on whether it plans to appeal Cummings’ order.
Meanwhile, Bovino left Chicago Thursday morning with his CBP agents and will head next to Charlotte, North Carolina, according to a source familiar with the planning.
DHS declined to comment on his exact whereabouts, with McLaughlin saying Bovino “has multiple bounties on his head from Latin Kings and other cartels.” Bovino told Fox News later that day he was in West Virginia.
Bovino and other federal agents have faced scrutiny, including from a federal judge, for alleged heavy-handed tactics and violent use of force against people getting arrested and protesters.
“All of this, all of the tactics of Bovino, all of the tactics of (Immigration and Customs Enforcement) have been unlawful in the vast, vast majority of arrests,” Fleming said Wednesday.
ICE will continue to carry out immigration enforcement operations in Chicago, McLaughlin previously told CNN, while other immigration legal challenges move through the courts.
State advocates have alleged “inhumane” conditions at a federal immigration facility in a Chicago suburb, where protesters have been demonstrating for weeks, with some leading to arrests. Those protesters and news outlets are at the center of another legal battle as they claim federal agents violated their First Amendment rights by repeatedly using tear gas and other weapons on them.
The state of Illinois and Chicago have also sued the Trump administration over its move to deploy National Guard troops to Chicago amid protests against the federal government’s immigration enforcement campaign.
CNN’s Whitney Wild, Dianne Gallagher and Priscilla Alvarez contributed to this report.
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