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In Chicago, ICE Raids Reveal Trump’s Turning Point on Discretion

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October 25, 2025
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A photo shows a man with a medium skin tone and a olive green t-shirt holding his phone up toward a group law enforcement agents, who are standing in uniform on the other side of yellow police tape.
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12:00 p.m. EDT

10.25.2025

ICE’s crackdown in Chicago reflects a deeper reshaping of the immigration system toward a singular focus: removing people with little or no review.

A photo shows a man with a medium skin tone and a olive green t-shirt holding his phone up toward a group law enforcement agents, who are standing in uniform on the other side of yellow police tape.

Residents of Chicago’s Brighton Park neighborhood confronted U.S. Border Patrol and other law enforcement in early October.
Octavio Jones/AFP via Getty Images

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In Chicago this week, Immigration and Customs Enforcement agents allegedly pointed a gun at a state representative and his staff on the city’s North Side. The next day, raids in the heavily Latino neighborhood of Little Village, in the city, and Cicero, a western suburb, led to arrests of two American citizens — staffers of a city alderman. One local leader called the raids a “brutal escalation” of the Trump administration’s ongoing immigration enforcement.

Nearly two months into ICE’s campaign in Chicago, disruptive, chaotic scenes like this are hardly surprising anymore. In recent weeks, agents have rappelled into an apartment building from a Black Hawk helicopter, fired pepper balls at peaceful protesters, and allegedly zip-tied the hands of children. ICE and the Department of Homeland Security have not commented in some of these instances, or they have said the officers’ actions were justified.

This spectacle of enforcement isn’t merely incidental. Part of the rationale for the administration’s intense posture has always been to terrify people into self-deportation, ProPublica noted in a report this week. The Chicago effort has included cinematic promotional videos of the aggressive, militarized campaign. An AFP fact check found that at least one White House video promoting the Chicago operation included footage from earlier enforcement across the country.

Meanwhile, in communities across Chicago, people are creating their own kind of commotion to slow down ICE. The sounds of whistles have periodically blanketed neighborhoods, as people monitor enforcement activity and alert others that agents are in the area. Those efforts have come alongside rapid response protests and court battles over whether agents have used excessive force on demonstrators.

Beneath all the commotion, though, the work of hardening the immigration system has been methodical. According to ICE, federal officers made more than 1,000 arrests over roughly the first month of the operation, sweeping up both new arrivals and long-time Chicagoans. Calls to Chicago-area legal assistance hotlines by families of people arrested by immigration authorities have “skyrocketed”. Many of those detained have been transferred to facilities in Louisiana and Texas, far from their families and lawyers, and without hope for release while their immigration case is pending.

According to immigration lawyers, these outcomes reflect a deeper reshaping of the machinery of detention and deportation away from discretion and toward a singular focus: getting people out of the country as rapidly as possible, by any means necessary.

Historically, ICE agents at a local field office could consider the individual circumstances of a case — for example, whether an immigrant was a nursing mother or had serious medical conditions — in deciding whether to make them a priority for arrest.

“That discretion has totally evaporated,” said Sarah Cockrum, the supervising attorney at Beyond Legal Aid, a Chicago legal services organization representing people in immigration court. Now, Cockrum said, “there are children with cancer who are in detention — just really awful things.”

In fact, not only were agents previously allowed to consider such factors — under a memo issued at the beginning of the Biden Administration, they were required to consider all facts and circumstances in making arrest decisions. The memo stated that the “overriding question” in deciding whether to make an arrest was whether a noncitizen presented a public safety risk.

The Trump administration reversed that framework entirely just days after the president took office, essentially redefining discretion as the authority to detain and deport more quickly, rather than to weigh the individual facts of a person’s life.

Once ICE makes an arrest, the next place where officials have traditionally had some discretion is in the judicial branch. Days before DHS announced its operation in Chicago, however, the Board of Immigration Appeals ruled that immigration judges lack the authority to grant bond to anyone who entered the U.S. without authorization.

It’s not the only way the administration has sought to limit the power of judges. Since early summer, government lawyers in Chicago’s immigration court, and around the country, have increasingly asked judges to dismiss immigration cases, only for federal officers to arrest the immigrant after their hearing. In many cases, the government sought to deport the immigrant through expedited removal, a rapid process that happens without judicial review and had previously been used largely for people apprehended near the border who had been in the U.S. only a short time. In August, a federal judge paused the administration’s efforts to expand the use of expedited removal.

“One thing we’re seeing is a big push to remove people from the immigration court system so that they don’t get a chance to fight their case in court,” Cockrum said.

With fewer avenues for ICE officers or immigration judges to allow someone to remain in the U.S. or out of detention, immigrant-rights advocates have turned to the federal courts. Earlier this month, a federal judge ruled that ICE had violated a 2022 court-ordered agreement that limits ICE’s ability to make warrantless arrests in six midwestern states, including Illinois.

As ICE allegedly breaches existing legal protections and the administration looks for ways to write other protections out of existence, communities across the region are feeling the impact. In Niles, next to Chicago, 16-year-old Ofelia Torres, who is battling a rare and aggressive form of cancer, took to social media to plead for her father Reuben Torres Maldonado’s release. She described him as the “main parent who watches my brother while I stayed at the hospital.” Torres Maldonado is also the family’s primary breadwinner, the Chicago Tribune reported. He was arrested last weekend in a home improvement store parking lot.

Cockrum said that in the past, someone like Torres Maldonado — a father to a sick child, who had lived more than half his life in America, with only minor traffic offenses on his record — would have been exactly the type of person likely to be deprioritized for enforcement. If arrested, he likely would have been granted bond while his case proceeded.

Instead, a statement from administration officials dismissed legal efforts to free him as “nothing more than a desperate Hail Mary attempt to keep a criminal illegal alien in our country.” In the statement, officials said that he backed into a government vehicle while attempting to flee.

On Thursday, a federal judge postponed any ruling on his release.





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