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Trump’s bad week in court

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Published on October 10, 2025

Trump’s bad week in court

Thousands of demonstrators gather at Ida B. Wells Drive and Michigan Avenue following an anti-Trump protest that was held in response to Trump’s threats to send federal troops into Chicago despite no requests from local or state leaders on Sept. 6, 2025. Photo by Ash Lane for The TRiiBE®

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The TRiiBE is working in collaboration with indie investigative newsroom Unraveled Press and alt-weekly Chicago Reader to bring you confirmed sightings of U.S. Immigration and Customs Enforcement (ICE) and other federal agents in the Chicago area.

Thursday wasn’t a great day in Chicago’s federal courthouse for President Donald Trump’s administration. In two separate major decisions, District Judges Sara Ellis and April Perry issued temporary restraining orders respectively aiming to rein in federal immigration agents’ violent behavior and prevent the mobilization of National Guard troops in Illinois.

Friday was another busy day for the Trump administration in the federal court. Among the cases we had our eyes on included a hearing for a man accused of placing a $10,000 murder hit on Border Patrol Chief Gregory Bovino, and a separate but ultimately cancelled preliminary hearing for two individuals facing assault charges for allegedly blocking in and ramming vehicles operated by Border Patrol agents in Chicago’s Brighton Park neighborhood last Saturday.

Here’s a look at where things stand in Chicago’s federal courthouse.

Illinois, Chicago win temporary restraining order against National Guard federalization and deployment 

District Judge April Perry, a Joe Biden appointee, granted Illinois and Chicago a temporary restraining order that bars the Trump administration’s deployment of National Guard troops against state and city officials’ wills. Perry delivered an oral version of the order from the bench on Thursday afternoon, entering a written version of the order about an hour later.

As written, the order states “defendants, their officers, agents, assigns entered, and all persons acting in concert with them, are temporarily enjoined from ordering the federalization and deployment of the National Guard of the United States within Illinois.”

Her ruling comes four days after Illinois Governor JB Pritzker announced he had learned 400 Texas National Guard members were being ordered to “Illinois, Oregon, and other locations within the United States,” three days after Illinois and Chicago filed a lawsuit against Trump and the Department of Homeland Security (DHS) to block that National Guard deployment, and two days after the Chicago Sun-Times reported that Texas guard troops had arrived at a military training center in the Chicago suburbs.  

Perry made her decision Thursday after hearing oral arguments by attorneys representing Illinois and Chicago, as well the Trump administration and DHS. The judge had questions for both sets of attorneys, but was especially skeptical of the arguments presented by U.S. Deputy Assistant Attorney General Eric Hamilton.

Hamilton bemoaned “the sustained violence these last few weeks,” and argued to the court that Trump considered Illinois to be in danger of rebellion. He cited protests at the suburban Broadview ICE facility and alleged attacks on federal immigration agents acting in the Chicago area since the start of September, which he said was impacting the federal agents’ ability to enforce the law.

Masked federal agents coming out of the Broadview ICE facility after launching tear gas and shooting chemical irritants at demonstrators on Sept. 19, 2025. Photo by Ash Lane for The TRiiBE®
Demonstration outside Broadview ICE facility just outside of Chicago on Sept. 19, 2025. Photo by Ash Lane for The TRiiBE®

Perry, however, said she saw “no credible evidence there is a danger of rebellion in the state of Illinois,” noting that federal agents were still carrying out Trump’s mass deportation campaign despite protests and confrontations with locals. 

“Deportations are up. Arrests are up… the federal laws are being executed,” Perry said.

Perry also found that the Trump administration’s perception of events in Chicago was “simply unreliable,” and that federal agents’ behavior was itself to blame for the escalation of civil unrest. 

She noted incidents of agents deploying chemical weapons against peaceful protestors, Chicago communities and members of the press, and found that bringing National Guard into the situation would “add fuel to the fire the defendants themselves have started.”  

At a press conference following Perry’s ruling, Illinois Attorney General Kwame Raoul thanked the Illinois legal team for their efforts, calling them “heroes” who stood up for state sovereignty and helped determine whether the president has “unfettered authority to militarize our cities.” 

“Our constitution, our rule of law… has to be respected by everybody to the extent that we continue to be the United States that our founding fathers thought we would be,” Raoul said.

However, Raoul mostly sidestepped questions on how officials could ensure the Trump administration, and the National Guard already sent to Illinois, comply with the restraining order.

“It is up to the defendants to make certain they abide by the judge’s order,” Raoul said.

Judge Perry’s order clarifies that it expires in two weeks, and that the parties must meet again on Oct. 22 to determine if the order must be extended an additional two weeks. 

The Trump administration filed an appeal of the order to the 7th Circuit U.S. Court of Appeals on Thursday evening.

Journalists, protestors win restraining order to rein in federal agents’ violent behavior

District Judge Sara Ellis, a Barack Obama appointee, formally entered an order Thursday aiming to protect press and members of the public from abuse at the hands of ICE agents and other federal officers involved with immigration enforcement.

The order, among other elements, bars federal agents in the northern Illinois court district from “dispersing, arresting, threatening to arrest, threatening or using physical force against any person whom they should reasonably know is a journalist” without probable cause to believe they have committed a crime. The northern Illinois court district includes Chicago and the surrounding suburbs.

Protestors, elected officials and media retreated once federal agents hurled tear gas at the crowd outside the Broadview ICE facility on Sept. 19, 2025. Photo by Ash Lane for The TRiiBE.
Tear gas was deployed by federal agents at the ICE facility in Broadview on Sept. 26, 2025. Photo by Seed Lynn for The TRiiBE®

The order also bars agents, with some exceptions, from issuing a dispersal order requiring any person to leave a public space they are lawfully on, and from using riot weapons on “members of the press, protestors, or religious practitioners” who are not threatening the agents’ safety. 

Perhaps most significantly, Ellis’ order also compels often-masked federal agents to wear “visible identification” if they are not in uniform or working undercover. Ellis notes in the order that this identification can consist of a “unique recognizable alphanumeric identifier sequence.” 

The order is part of a class action lawsuit filed Monday against Trump, Homeland Security Secretary Kristi Noem, multiple federal agencies and “unnamed federal officer defendants.” Federal agents have spent a month shooting pepper balls, tear gas, rubber bullets and flashbangs into protestor crowds, Chicago communities and press alike. Agents have also arrested at least one Chicago journalist, Unraveled Press co-founder Steve Held, and have been caught on camera shooting reporters and clergy in the head and groin with pepper balls.

“We would like [federal agents] to hesitate before shooting priests and journalists,” an attorney for the journalists and protestors told Ellis at one point in court proceedings that resulted in the order.

Ellis set another court hearing for Oct. 23 to determine if her temporary order could be converted into a longer-term preliminary injunction.

Less than 24 hours after Ellis entered her order, masked federal agents arrested another Chicago journalist, longtime WGN producer Debbie Brockman.

Judge orders Broadview ICE fence to come down

District Judge LaShonda Hunt, a Joe Biden appointee, issued another temporary restraining order Thursday evening that requires DHS to remove a fence it erected late last month in front of the Broadview ICE facility. 

Broadview sued DHS and Kristi Noem to remove the fence last Friday, claiming it was a public safety hazard and noting in their complaint that federal agents had refused to remove it voluntarily.

The street in front of the Broadview ICE facility in Broadview fenced off on Sept 23, 2025. Photo credit Matthew Kaplan

Hunt granted the village’s motion for an order to remove the fence, and directed both Broadview and DHS to respond to her order by 2:00 p.m. Friday afternoon. 

Felony case against neurodivergent man to be dismissed

Federal prosecutors moved Thursday to dismiss a felony assault case against Paul Ivery, a 26-year-old Black man and Oak Park resident whom federal agents arrested during a protest at the Broadview ICE facility on Sept. 27. Ivery reportedly has an intellectual disability, and according to a Homeland Security Investigations affidavit attached to his felony complaint, he agreed to waive his Miranda rights while in federal custody. 

The dismissal marks the fourth time this week that U.S. attorneys have tossed their cases against people arrested at the Sept. 27 protest. U.S. Magistrate Judge Gabriel Fuentes agreed at separate hearings Wednesday to toss the cases of Ray Collins and Jocelyne Robledo, a couple who together faced felony charges for allegedly assaulting federal officers at the protest while legally carrying pistols, and Luci Mazur, who faced a misdemeanor charge for allegedly resisting/impeding a federal agent.

U.S. attorneys are still pursuing an assault charge against Dana Briggs, a 70-year-old veteran who, according to a relevant affidavit, fell down in front of Border Patrol agents at the Sept. 27 protest. However, court filings show the government is only pursuing a misdemeanor against Briggs, rather than a felony charge. 

New developments today, Oct. 10

U.S. Magistrate Judge Gabriel Fuentes officially dismissed Ivery’s case during a 10:00 a.m. hearing Friday. His friends and neighbors attended the hearing and applauded the judge’s move. 

Ivery and his family left the courthouse without speaking to the press. Scott Sakiyama, a spokesperson for the family, described how they felt about his ordeal. 

“It was really scary,” Sakiyama said. “If the case had gone forward, it probably would have lasted for months. And so, it’s just such a relief to have it over now.” 

Sakiyama said he didn’t know whether Ivery would return to the Broadview ICE facility to protest. He urged any other potential protestors to be aware of the danger posed by federal agents — regardless of Judge Ellis’ temporary restraining order meant to rein them in. 

“It’s not safe. What your rights are don’t matter the way the ICE officers are acting right now,” Sakiyama said. “I’m hopeful that the TRO that was just entered will make that more safe but I’m not optimistic.” 

Briggs also faced his arraignment hearing on Friday morning. Briggs entered a plea of not guilty to his misdemeanor assault charge, and the government agreed to formally dismiss its felony complaint against him. 

Fuentes set the start of Briggs’ jury trial for Dec. 8, saying the court wouldn’t delay trial over a possible lack of jurors — should the current government shutdown last that long. 

“We’ll have to cross that bridge when we get to it,” the judge said. 

Fuentes also ordered the government to turn over alleged video evidence supporting affidavits against Briggs and Luci Mazur, another Sept. 27 protest arrestee whose case the government dismissed Thursday.   

Also Friday morning, a detention hearing was held for a man named Juan Espinoza Martinez, who faces accusations he placed a $10,000 murder hit on Border Patrol Chief Gregory Bovino. Bovino has become a face of the Trump administration’s mass deportation campaign in Chicago, particularly regarding the activation of militarized Border Patrol agents. 

DHS, whose credibility has now been called into question by press, elected officials, and federal judges, announced Espinoza Martinez’s arrest on Oct. 6. 

U.S. Marshals led Espinoza Martinez into the courtroom Friday in an orange prison jumper. The hearing only lasted about 10 minutes; just enough time for Magistrate Judge Maria Valdez to set a preliminary hearing in his case for next Wednesday, Oct. 15, and to declare that Espinoza Martinez would remain in federal custody in the meantime. 

A preliminary hearing scheduled Friday for Marimar Martinez and Anthony Ian Santos Ruiz, two individuals facing felony assault charges for allegedly blocking in and ramming vehicles operated by Border Patrol agents in Chicago’s Brighton Park neighborhood on Saturday, was abruptly cancelled before it convened. Magistrate Judge Heather McShain filed a court entry indicating the hearing had been stricken because a grand jury had returned an indictment against the pair. 

Martinez’s shooting led to a standoff between Chicago locals and militarized federal agents on Saturday afternoon. The confrontation ended when federal agents deployed tear gas onto the street and sped off in a long convoy amid the resulting chaos. The gas affected protestors, press, community members on adjacent streets, and even Chicago Police officers who had placed themselves between the feds and the crowd.

U.S. Magistrate Judge Heather McShain ordered both Martinez and Santos Ruiz released on Monday, per relevant court filings. Chicago Tribune journalist Jason Meisner also reported that Martinez’s attorney Chris Parente questioned the government’s narrative, and argued to McShain that the armed federal agents were the real danger. The attorney reportedly claimed they had been driving through local communities in an SUV marked with an Uber logo.

“What I do know is, it was Ms. Martinez who has seven holes in her body from five shots from this agent, who fired within seconds of getting out of this vehicle,” Meisner reported Parente telling the court.

According to WBEZ, body-camera video of a Border Patrol agent involved in the shooting says “Do something, bitch,” before pulling over and shooting Martinez.

40th and Kedzie in Chicago, where locals are facing down militarized federal agents in Brighton Park neighborhood on Oct. 4, 2025. Photo by Dave Byrnes/Unraveled Press

Martinez’s shooting also led to a standoff between Chicago locals and militarized federal agents on Saturday afternoon. The confrontation ended when federal agents deployed tear gas onto the street and sped off in a long convoy amid the resulting chaos. The gas affected protestors, press, community members on adjacent streets, and even Chicago Police officers who had placed themselves between the feds and the crowd.

U.S. Magistrate Judge Heather McShain ordered both Martinez and Santos Ruiz released on Monday, per relevant court filings. Chicago Tribune journalist Jason Meisner also reported that Martinez’s attorney Chris Parente questioned the government’s narrative, and argued to McShain that the armed federal agents were the real danger. The attorney reportedly claimed they had been driving through local communities in an SUV marked with an Uber logo.

“What I do know is, it was Ms. Martinez who has seven holes in her body from five shots from this agent, who fired within seconds of getting out of this vehicle,” Meisner reported Parente telling the court.


According to WBEZ, body-camera video of a Border Patrol agent involved in the shooting says “Do something, bitch,” before pulling over and shooting Martinez.