Trump Admin’s Laziness Is Messing Up Its Effort to Deploy the National Guard to Portland

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Oct 27, 2025

A Baffling Legal Blunder

For some inscrutable reason, the Trump Justice Department appealed only one of two temporary restraining orders blocking it from sending National Guard troops into Oregon.

The first temporary restraining order (TRO), handed down by U.S. District Judge Karin Immergut, a Trump appointee, blocked the Oregon Guard from deploying. The second, which she was forced to issue to stop the administration from circumventing her first order by sending the California Guard to Portland, blocked all Guards from any state and D.C.

The Trump administration only appealed the first order, which a Trumpy 9th Circuit panel agreeably paused last week. The DOJ then directed Immergut to dissolve her second TRO, claiming that since it was premised on the same reasoning as the first, the two are linked. They instructed her to do so immediately, at least as far as it was still preventing the Oregon Guard from deploying. She did not obey.

At a Friday hearing on the matter, Immergut grilled the administration on a new issue that colors the debate: Oregon and Portland had submitted a letter to the 9th Circuit, showing that the administration had lied about the number of Federal Protection Service officers who were redeployed to Portland due to increasing unrest at anti-ICE protests.

Immergut asked the DOJ’s Jacob Moshe Roth if it wasn’t “premature” for her to dissolve her second TRO while the appellate panel is still deciding whether the factual error justifies reversing its order. She added that the numerical discrepancy was a “material difference” in what the administration had initially presented to the court.

She also mused over the difference in the number of Guards the administration wanted to call up from Oregon and then from the other states, saying that the facts of the second TRO were “different” and “arguably part of a different analysis.”

In short: The Trump administration has seen its appellate court victory delayed for days, hamstrung in its effort to flood Portland with armed troops, all due to its own baffling legal blunder. And Immergut — who has become a punching bag from an administration livid that its own appointee won’t dutifully perform her role of judicial stooge — refuses to clean up the DOJ’s mistake for it.

–Kate Riga (Josh Kovensky contributed reporting)

Bovino in Court Tomorrow

CBP commander and federal lib-owner Greg Bovino will have his day in court tomorrow. There, he’s expected to answer questions from a Chicago federal judge over why his actions and those of his subordinates over the past week did not violate her court order mandating that federal law enforcement not use tear gas against peaceful protestors and that they wear identification.

Attorneys in the case described an episode in the residential Chicago neighborhood of Old Irving Park that, per their telling, violated both. Officers were chasing someone they were trying to arrest and entered a quiet street that was preparing to hold a Halloween Parade. One bystander was purportedly tackled to the ground; as they left, officers allegedly deployed tear gas. In another episode, people in the neighborhood of Lakeview started to protest after federal agents arrested a person in a resident’s front yard. As officers drove away in an SUV, one allegedly threw a tear gas canister out of the car.

The allegations all describe behavior that’s in flagrant violation of the order, which allows officers to use gas and other riot control measures only if there’s a clear threat. The judge in the case has already emphasized that she’s unhappy that some of her orders are not taking effect, saying earlier this month that she doesn’t live in a “cave” and is aware when it is being violated.

But it does demonstrate that while Bovino is a leader of the operation, in some ways he’s a figurehead: the allegations of order-flouting in Chicago go far beyond him.

— Josh Kovensky

Jeffries Met With Illinois Dems to Discuss Redistricting

Illinois could be one step closer to approving a revised congressional map.

House Minority Leader Hakeem Jeffries (D-NY) met with Illinois Democrats on Monday to discuss the possibility of approving a redistricting proposal as a way to offset Trump’s power grab in red states across the country.

Jeffries reportedly met with the Illinois Legislative Black Caucus to discuss approving a new map, according to Punchbowl News. As it stands now, Illinois has 17 House seats, 14 of which are Democrat, and three are held by Republicans. A revised map would likely flip one Republican seat in an effort to counter Trump’s nationwide gerrymandering battle as he pressures red states with Republican-controlled state legislatures to help him hold onto power in Congress.

Although these plans are still up in the air, Illinois Gov. JB Pritzker has publicly said that redistricting — to blunt the impact of redrawn maps in Texas, Missouri and North Carolina — is a possibility. “None of us want to do it. None of us want to go through a redistricting process. But if we’re forced to, it’s something we’ll consider doing,” Pritzker told NPR.

Democratic counter efforts are currently underway in California, where there is a redistricting proposal on the ballot. And in Virginia, Democrats are considering approving a revised congressional map, which could flip three Republican seats.

— Khaya Himmelman