A still frame photo shows Border Patrol chief Gregory Bovino toss what appears to be a canister of tear gas at protesters in Chicago on Oct. 23, 2025.
An anti-immigration enforcement protester holds a sign outside the federal courthouse in Chicago on Oct. 28. The chants of demonstrators on the street could be heard on the 14th floor of the courthouse where Border Patrol chief Gregory Bovino testified.

CHICAGO – A federal judge in Chicago had a clear message to the Trump administration: She will enforce her court orders limiting the type of force agents can use in the city.

U.S. District Court Judge Sara L. Ellis on Oct. 28 ordered Homeland Security officials to turn over all use of force reports and related body camera footage that the agency has in connection with the Chicago-area crackdown. She also cited an Oct. 25 incident in a North Side neighborhood in which she said trick-or-treaters were "tear-gassed on their way to celebrate Halloween."

Additionally, she warned that she better not receive any complaints on Halloween night of tear gas being used near children: "Know that it is a day when people are going to be out minding their own business."

She also ordered agents to provide information on anyone arrested in connection with protesting immigration enforcement and to have the Border Patrol's top leader in the area deliver daily reports in person at the courthouse as well as begin using a body camera.

Ellis – who issued orders limiting the kinds of tactics immigration enforcement agents can use amid the White House’s crackdown in Illinois – hauled the administration’s top enforcement official Customs and Border Patrol Commander at-Large Gregory Bovino into court to ensure he understood the limits she had put upon him and his agents.

The judge questioned Bovino, President Donald Trump’s face of the Operation Midway Blitz, in response to court filings contending he and his agents have violated orders she gave limiting how agents use chemical weapons and physical force.

Ellis issued a temporary restraining order in connection with a lawsuit brought by journalists, clergy and protesters that agents were using force unnecessarily. Ellis' orders compel agents to give warnings before using chemical agents such as pepper spray and limit using physical force to instances where agents face immediate harm.

Since Ellis first issued the restraining order on Oct. 9, lawyers for the journalists have filed multiple notices that federal agents have violated Ellis' orders. Most recently, lawyers for the journalists, clergy and protesters filed notice that Bovino violated her orders in tear-gassing protesters in a raid on a Chicago Mexican neighborhood.

"I’m not afraid to enforce this TRO," Ellis told lawyers for the Department of Homeland Security about 90 minutes after Bovino took the stand. "I have serious questions about whether it’s being followed so under my inherent power to enforce the TRO, this is what I’m requiring."

Lawyers for Homeland Security objected to Ellis' new orders but the judge said she would not change them and would issue them in writing shortly. Ellis denied a request from the attorneys for civilians to bar agents’ use of tear gas altogether.

At the end of his testimony, Bovino told Ellis, "we will abide by the TRO and all the accoutrements contained therein."

The hearing at the Dirksen federal courthouse in Chicago comes as the U.S. Supreme Court weighs whether to let the White House deploy the military to the city. The Trump administration says troops are needed to carry out an immigration enforcement crackdown aimed at the "worst of the worst" criminal immigrants.

Local Democratic officials view the blitz as a power grab by the Republican White House and have taken issue with federal agents using chemical weapons on residential streets during enforcement raids.

On Oct. 27, Homeland Security Assistant Secretary for Public Affairs said over "3,000 illegal aliens, including rapists, murderers, and gang members" have been arrested in connection with the blitz. USA TODAY has not been able to independently verify the criminal background or immigration status of detainees.

Homeland Security officials did not immediately respond to further request for comment on Ellis' new orders.

Who is Gregory Bovino, the man behind Trump's Midway Blitz?

Border Patrol chief Bovino arrived in Chicago as part of Operation Midway Blitz on Sept. 16, he announced on X, and he quickly became the face of the operation.

He made waves in the city after he and heavily armed agents were seen aboard boats on the Chicago River. Bovino also drew criticism from locals after telling a local radio reporter that immigration agents were arresting people at least partly based on "how they look." Most notably he participated in a high-profile raid that saw agents rappelling from Black Hawk helicopters to storm a South Side apartment building.

The longtime Border Patrol veteran boasts of his agents’ successes often on social media. About an hour before appearing in court, he posted on X a picture of a man with a bloodied face arrested in connection with the blitz.

"Another drug dealer and Latin King gang member dethroned!" Bovino wrote. "This is a prime example of how our enforcement operations are out here arresting criminal illegal aliens who threaten our American way of life.

Bovino appeared in court wearing his green Border Patrol uniform. He speaks with a distinct Carolina accent.

An agency spokesperson previously said of Bovino that "DHS can think of nobody better to correct Judge Ellis’ deep misconceptions about its mission, and we thank him for his service."

The Homeland Security official is also connected to another case playing out in federal court in Chicago. Prosecutors say Juan Espinoza Martinez, a 37-year-old Chicago man, is accused of offering $10,000 for Bovino’s killing. Espinoza Martinez’s attorney says he is innocent. The case is set to go to trial in January.

Judge questions use of tear gas near trick-or-treaters

In court, Ellis went through the temporary restraining order line by line, stopping in places where attorneys for civilians had filed notices claiming the order had been violated. She spoke at length about an Oct. 25 incident in a North Side neighborhood in which she said trick-or-treaters were "tear-gassed on their way to celebrate Halloween."

"These kids, as you can imagine, their sense of safety was shattered," Ellis told Bovino, "and it’s going to take a long time for that to come back, if ever. Not only was their sense of safety shattered but it’s connected to something that should have been a really happy day … that is one of the reasons why I’m having you in today, to ensure as you go about enforcing the law, that it’s done in a manner that is objectively reasonable and consistent with your obligations."

Bovino declined to speak about specific instances where his agents were reported using chemical agents without giving warnings or were reported using force unnecessarily.

"Each situation is dependent on the situation and I'd like to know more about these various activities before saying things one way or another," Bovino said.

Ellis warned that according to sworn declarations, agents pointed guns at Chicagoans who had gone out to protest immigration enforcement. According to the declarations, the experience left people afraid to protest again.

"Under the First Amendment we cannot have people be afraid," Ellis said. "They don’t have to like what you’re doing and it’s OK, that’s what democracy is. They can say they don’t like what you’re doing, they don’t have to like how you’re enforcing the law, they can say they want you to leave Chicago – that’s OK, and they can’t get tear-gassed for it."

Ellis ordered Bovino to begin making daily reports to her on Oct. 29, to have a working body camera by Oct. 31 and for any new use of force reports to be turned over to her.

Bovino, who was reported violating the restraining order in deploying two canisters of tear gas on Oct. 23, could have easily disproven the allegations, Ellis said, if he had been wearing a body camera.

"I’m not going to tie these agents’ hands because I’m not out there and in the end it’s not my job," she said. "But I am going to expect that they know their responsibility when it comes to use of force and if they’re using tear gas, they better be able to back that up."

(This story has been updated to add new information.)

This article originally appeared on USA TODAY: Chicago judge scolds Trump enforcer after kids 'tear-gassed' on way to Halloween party.

Reporting by Michael Loria, USA TODAY / USA TODAY

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