President Donald Trump's immigration crackdown pushes forward in Chicago despite continued pushback on the ground and in court.

Operation Midway Blitz started Sept. 8, with the Department of Homeland Security saying it would target "the worst of the worst," among people who are in the country illegally. They say they have arrested more than 1,500 people, though USA TODAY has not been able to independently verify their count. Federal immigration officials have followed people in their cars, rappelled from helicopters in an apartment building raid and clashed with protesters at a facility in the suburbs.

Trump had deployed the National Guard to assist immigration agents, but it was challenged in court along with other DHS efforts. What's the latest on those cases? Here is what to know:

Are National Guard troops deployed in Chicago?

The U.S. Supreme Court is currently weighing whether to allow Trump to deploy troops to Chicago or not.

Trump moved to deploy hundreds of Illinois and Texas National Guard troops to the Chicago region as part of his blitz campaign in the beginning of October. His lawyers argued agents are unable to enforce federal law without the help of the military and that the push back agents are experiencing in Chicago amounts to a potential "rebellion."

However, in response to a lawsuit from the Illinois Attorney General's Office, U.S. District Judge April M. Perry barred the White House from deploying troops. Perry questioned whether the Homeland Security allegations White House lawyers cited in their arguments were "tethered to reality."

Trump's lawyers appealed Perry's decision but the U.S. Court of Appeals for the Seventh Circuit upheld Perry's decision in a unanimous decision. But Trump’s lawyers appealed again and the case is now before the Supreme Court. It’s unclear when they could rule.

Trump administration lawyers have agreed to let Perry’s order barring the National Guard deployments remain in place until the Supreme Court rules. Legal experts say the White House’s offer indicates they believe the high court will rule in their favor, according to reporting by the Chicago Sun-Times.

DHS agents sued over use of chemical weapons

A group of journalists, clergy and protesters also filed a lawsuit against Homeland Security agents over their use of chemical weapons on people in the Chicago area. In an Oct. 9 court hearing, Deputy Assistant Attorney General Eric Hamilton said federal agents had deployed $100,000 of non-lethal weapons to stop "rioters" from hindering immigration enforcement.

U.S. District Judge Sara L. Ellis issued an order limiting agents’ use of chemical weapons in the Chicago area and compelling them to wear identification.

Ellis amended her order a week later on Oct. 16 to ensure agents wear body-worn cameras after she was concerned that immigration agents were not following her orders. She also ordered top Homeland Security officials into court to testify.

Customs and Border Protection Deputy Incident Cmdr. Kyle Harvick and Deputy Immigration and Customs Enforcement Field Office Director Shawn Byers both told the judge on Oct. 20 that agents were following her orders to issue warnings before using chemical weapons.

Locals being teargassed say they have not heard any warnings being used. Harvick and Byers’ testimony comes after Perry found in a separate case that Homeland Security’s account of events in the city was not reliable.

Harvick also justified federal agents shooting a local pastor with a pepper ball. A clip of the incident shows the Rev. David Black standing among a group of protesters before he’s shot directly in the head by an agent posted on a rooftop building.

"What’s not being shown is he was given multiple commands to move," Harvick said.

Byers said 75 people have been arrested in the Chicago area in connection with attempting to block immigration enforcement.

Up next in the case, Ellis is allowing Customs and Border Protection Commander at-Large Chief Gregory Bovino to be deposed in connection with how he has directed his agents. Bovino is the face of the blitz. Among actions he’s participated in are the raids on Little Village and a Sept. 30 raid on a South Side apartment building that saw agents rappelling from Black Hawk helicopters.

Cases against protesters not going the Trump administration's way

People throughout the Chicago region have filled the streets to protest Trump's immigration crackdown. Homeland Security's detainee processing facility in the suburb of Broadview in particular has become a hotbed of protests, and on Sept. 29 Attorney General promised "violence against federal officers will not be tolerated."

"The DOJ is deploying agents to protect ICE facilities, arrest violent agitators on the spot, and bring the strongest federal charges possible," Bondi said on X. "The rule of law will prevail."

So far, the cases have not gone the Trump administration's way.

On Sept. 29, the U.S. Attorney's Office announced charges against five people in connection with protests outside the immigration enforcement processing facility. Charges against four of the people have been dropped and charges against Dana Briggs, a 70-year-old Vietnam-era veteran, have been downgraded to misdemeanor charges.

Charges against Ray Collins, 31, and Jocelyne Robledo, 30, were dropped after the grand jury declined to return an indictment, a rarity in the federal system. Federal officials initially touted the couple's arrest as an example of the kind of violence agents were facing. Both were found to be carrying guns when they were arrested. However, they were found to be carrying the guns lawfully.

Chicago man accused of putting a hit on top Border Patrol official

Juan Espinoza Martinez, a native of Mexico, is accused of offering $10,000 for the killing of Bovino, the face of the Trump administration's crackdown on the Chicago area.

In a news release, Homeland Security shared screenshots of Snapchat messages the 37-year-old is suspected of sending that offered $2,000 for information on Bovino and "10k if u take him down."

Espinoza Martinez's attorney says his client is innocent.

A jury trial in the case is set to begin the week of Jan. 20.

Woman shot by Border Patrol faces charges

Miramar Martinez and Anthony Ian Santos Ruiz face charges for assaulting federal officers in connection with an incident dating back to Oct. 4. According to federal court filings, the pair were following Border Patrol in their cars and crashed into agents' vehicles in the Southwest Side neighborhood of Brighton Park.

Prosecutors say an agent fired five shots at Martinez in self-defense at the scene of the accident. At her Oct. 15 arraignment, bandages for her wounds could be seen sticking out from the orange jumpsuit Martinez wore to court.

Martinez’s attorneys say federal agents attacked their client: “We don't think this is a complicated case,” said attorney Christopher Parente in an Oct. 15 hearing. “It's a car accident where one of the drivers gets out and shoots the other driver.”

A jury trial in the case is set to begin Feb. 2.

Alderperson detained by federal agents files lawsuit

Ald. Jessie Fuentes, a Chicago City Council member, filed a lawsuit against federal agents after they briefly detained her at a hospital in her jurisdiction. Fuentes was asking agents whether they had a judicial warrant to arrest a suspect the agents were pursuing at the facility.

The agents handcuffed her, led her outside and threatened to arrest her if she returned to the hospital, according to a copy of the lawsuit shared with USA TODAY.

Fuentes filed a Federal Tort Claims Act lawsuit in response to the incident for $100,000 in damages.

Pursuing charges against federal officers can be extremely difficult, according to legal experts. But a Federal Tort Claims Act lawsuit, which holds the U.S. government accountable rather than the individual officer, is seen as a potentially viable way to hold officers accountable.

Immigration agents face scrutiny for warrantless arrests

Another case playing out in federal court in Chicago has to do with whether immigration agents have warrants for the people they arrest in the region.

A 2022 lawsuit settlement agreement in the Northern District of Illinois limits how ICE agents can make arrests without warrants and during traffic stops.

In response to immigration enforcement under the Trump administration, plaintiffs in the case have filed notices that immigration agents have violated the settlement agreement.

A federal judge has already found that at least 22 people were arrested by immigration agents in violation of the agreement, court filings show. The judge allowed for the people to be released and ordered the officers who made the arrests to be retrained, according to Mark Fleming, an attorney involved in the case for the National Immigrant Justice Center.

Fleming said plaintiffs in the case plan to continue to notify the court of further potential violations of the agreement.

Kinsey Crowley is the Trump Connect reporter for the USA TODAY Network. Reach her at kcrowley@gannett.com. Follow her on X and TikTok @kinseycrowley or Bluesky at @kinseycrowley.bsky.social.

This article originally appeared on USA TODAY: What's happening with the troops in Chicago? What to know on legal cases against 'blitz'

Reporting by Kinsey Crowley and Michael Loria, USA TODAY NETWORK / USA TODAY

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