The nation has been given a split screen view of Chicago.

On one side, President Donald Trump declares the city a war-torn “hellhole” requiring deployment of National Guard troops to help enforce his administration’s aggressive immigration enforcement efforts as the Department of Homeland Security posts propaganda videos on social media.

Appeals court denies Trump administration request to halt judge’s ruling on National Guard pending appeal

On the other, more than a million people, largely tourists from around the world, are gathering across the city and at Grant Park to urge on runners in the Chicago Marathon after tens of thousands had converged in Wrigleyville to cheer on the Cubs.

“This is JB Pritzker reporting from war torn Chicago,” the state’s Democratic governor said Thursday in a mock field report for “Jimmy Kimmel Live!” wearing body armor while walking along a quiet sidewalk on the riverfront’s Wacker Drive.

“As you can see, there’s utter mayhem and chaos on the ground. It’s quite disturbing,” he said. “The Milwaukee Brewers have come in to attack our Chicago Cubs. We’ve seen people being forced to eat hot dogs with ketchup on them and our deep dish pizza, well, has gone shallow. So it’s a challenge to survive here in the city of Chicago, but there’s no hellscape that I’d rather be in.”

Pritzker’s “report” came as U.S. District Judge April Perry on Thursday handed the governor, along with other Illinois Democrats and administration opponents, a major victory by issuing a temporary restraining order that blocked the president’s federalized Illinois and Texas National Guard troops from duty to assist with immigrant enforcement activities.

Pritzker knows that Chicago’s issues are more than binary pictures. And while the governor has placed his faith in the judiciary, there are questions whether a stream of recent federal court defeats for the Trump administration will only prompt a more serious reaction from Trump, using the powers of the presidency at his disposal and his willingness to go after those who he perceives as his political enemies.

Trump did not have a good week in federal court in Chicago.

In addition to the National Guard ruling, U.S. District Judge LaShonda Hunt on Thursday ordered the removal of a fence erected outside the U.S. Immigration and Customs Enforcement facility’s Broadview detention facility for violating the west suburb’s right to access its own land.

Also Thursday, U.S. District Judge Sara Ellis issued a temporary restraining order preventing federal agents from using pepper-spray bullets, tear gas and other weapons associated with riot control against journalists and protesters who don’t pose a serious threat. Ellis also banned federal agents from using physical force or arrest against journalists unless they are crime suspects.

And on Tuesday, U.S. District Judge Jeffrey Cummings extended until February a consent decree that limits ICE agents’ authority to make warrantless arrests and requires them to disclose monthly any warrantless arrests they make. Cummings also found that the agency had violated the consent decree earlier this year.

“You want me to express joy? Look, I am pleased, if that doesn’t come across my face and my words. I am very pleased,” Pritzker told reporters Friday of Perry’s National Guard ruling.

“We’ve always said that we have to rely on the judiciary to be the check and balance on what the president and the Congress are trying to do or sometimes failing to do,” he said. “So we’re going to take them to court. We think we’re going to get the right results, because we know that it’s unconstitutional for him to attack our states and our cities the way that he has.”

But the victory may only be temporary. The Trump administration has already appealed Perry’s ruling to the 7th U.S. Circuit Court of Appeals. And as Perry was hearing arguments in the case, the 9th U.S. Circuit Court of Appeals appeared to be favoring Trump and presidential “deference” in a challenge to a similar ruling by a federal judge in Oregon who blocked the president’s federalization of the California and Oregon National Guard for deployment in Portland.

As Perry did in her ruling, Judge Karin Immergut found conditions on the ground at protests of ICE facilities did not constitute a “rebellion” or were as dire and in need of a federal response as portrayed by administration lawyers. Immergut said the federalization issue was “untethered to the facts.”

But during a simultaneous hearing of the 9th Circuit Court of Appeals, Trump-appointed Judge Ryan Nelson questioned whether the judiciary can put conditions on presidential National Guard deployments.

“I am sort of trying to figure out how a district court of any nature is supposed to get in and question whether the president’s assessment of executing the laws is right or wrong,” Nelson said.

If the 7th Circuit in Chicago and 5th Circuit based in San Francisco reached opposite conclusions, it would provide the legal grist for the conservative-dominated U.S. Supreme Court to decide — a prospect viewed as providing Democrats an unfavorable outcome.

“This thing could be in the Supreme Court in a couple of weeks. So it is a victory, certainly, but it’s just the first step, and what could be a long road of appeals,” said Pat Brady, a former federal prosecutor and state GOP chairman who has not supported Trump.

“The courts tend to give deference to the president on national security issues and that’s what the appellate court looks like looks like it’s doing” in the Oregon case, Brady said.

Even if the lower court rulings stand, Trump also has the ability to invoke the two-century-old Insurrection Act to make military deployments on domestic soil that go far beyond the protection of federal assets and agents that were part of his original federalization of the National Guard.

“I’d do it if it was necessary. So far it hasn’t been necessary, but we have an Insurrection Act for a reason,” Trump told reporters Tuesday. “If I had to enact it, I’d do that. If people were being killed and courts were holding us up, or governors or mayors were holding us up, sure, I’d do that.”

The Insurrection Act allows a president to deploy the military to “suppress rebellion” or “insurrection” when enforcing federal law becomes “impracticable.” It is an exception to the federal Posse Comitatus Act, which prohibits the use of U.S. military assets from taking part in law enforcement actions on domestic soil.

Past Supreme Court rulings have given the president broad discretionary powers to decide if conditions have been met to invoke the Insurrection Act. But the nation’s highest court has left the door open for judicial review to determine if a president invoked the law “in bad faith” or in going beyond “a permitted range of honest judgment.” And the actions of the military, once invoked, are also subject to judicial review.

Invocation of the Insurrection Act would almost surely be contested in court by Pritzker and Attorney General Kwame Raoul, leading to another series of court battles.

“I think the governor and Kwame are doing this for all the right reasons,” said veteran Democratic political consultant Pete Giangreco. “So the question becomes, where, at what point, does the Illinois attorney general and the Illinois governor run out of legal cards? I think we’re rapidly getting to that place.”

With Pritzker a high-profile Trump critic as he seeks a third term as governor and also considers a potential 2028 bid for the White House, there are also questions how far a president who has vowed revenge against his political enemies will go.

Trump previously floated a suggestion that Pritzker and Chicago Mayor Brandon Johnson be “jailed,” something largely viewed as fanciful political rhetoric.

But the state could face consequences regarding attempts to cut federal grants and funds beyond the Trump administration’s recent move to freeze $2.1 billion in previously approved transit funding, largely dedicated to the effort to extend the CTA’s Red Line to the Far South Side, out of concerns over “race-based contracting” for the project.

“Trump is always going to double down. He is always going to try to win the fight,” Giangreco said. “He either backs down or he doubles down. And he’s been much more into the double down way lately.”

Brady said “pretty much everything Trump’s been doing recently as president, from the tariffs on, are all pushing the limits of what his authority is and that’s been a conservative strain of thought forever, that the executive needs to be stronger.”

“This is going to be a battle and there’s going to be consequences,” he said. “I think there’s big risk, but I understand exactly why they’re doing it as Democrats: You can’t sit back.”

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(Chicago Tribune’s Olivia Olander contributed.)

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