Dugan's defense says new precedent makes conviction 'invalid'

A reversal would be another embarrassment for Trump's DOJ — and a blow to its attacks on an independent judiciary.

Then-Judge Hannah Dugan (Photo by Scott Olson/Getty Images)

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MILWAUKEE, Wisc. — A federal judge on Wednesday sharply questioned the basis of the conviction of former Milwaukee County Judge Hannah Dugan, repeatedly pressing the government about the theory of the case in light of new precedent.

During roughly 45 minutes of oral argument, U.S. District Judge Lynn Adelman did little to reveal how he would rule, but he grappled with a core issue underlying the guilty verdict.

An ‘invalid theory’

Late last year, a jury delivered a surprising mixed verdict in Dugan’s case.

Despite acquitting Dugan of a misdemeanor count of concealing an undocumented immigrant from federal agents, the jury convicted her of a felony count of obstructing a pending proceeding — namely, the immigrant’s arrest. The substance of the charges were similar, and most of the facts of the case were undisputed.

Prosecutors accused then-Judge Dugan of trying to prevent immigration authorities from arresting Eduardo Flores-Ruiz, a criminal defendant who had been facing domestic violence charges in her courtroom in April 2025.

Federal agents did not have a judicial warrant for Flores-Ruiz’s arrest, only an administrative warrant internal to the agency.

Dugan’s attorney Steven Biskupic noted that the government’s case hinged upon blurring the distinction: “They said that the type of warrant did not matter.”

Since Dugan’s conviction, the Fourth Circuit disagreed with that legal position in U.S. v. Hernandez, a case reversing the obstruction conviction of an immigrant who escaped from his own arrest. The court found that the existence of an ICE warrant did not create a “proceeding” within the meaning of the statute.

Biskupic said that the development means that “the only appellate court in the country to address the issue” found that the government’s case hinges upon “an invalid theory.”

If one accepts the government’s argument, Biskupic said: “Then, everything ICE does is a proceeding and subject to a felony five years.”

‘A really long operation’

When questioning the government, Judge Adelman kept returning to a theme: the breadth of the government’s definition of a “proceeding.”

“Wouldn’t you agree that the way you’re defining ‘proceeding’ is a really long operation?” Adelman asked Assistant U.S. Attorney Richard Frohling.

Shortly into oral arguments, Adelman drew an analogy about how to describe the proceedings taking place in his courthouse.

“Are we 10 minutes into it or a couple of years into it?” he asked.

Frohling noted that it’s been a little more than a year since Dugan’s arrest in April 2025, but he reiterated the government’s view that a proceeding might not be time-limited.

Judge Adelman pressed, “A proceeding could be a couple of years?”

The prosecutor replied, “It could be a couple of minutes. It could be a couple of years. It depends on the context.”

Judge Adelman is not bound by the Fourth Circuit’s precedent, and prosecutors called the Hernandez case an “outlier.” The government, however, previously cited the lower court’s decision in the same case when it supported their position.

“It wasn’t an outlier when [prosecutors] thought it [supported] their theory,” Biskupic noted.

Wisconsin falls within the Seventh Circuit’s jurisdiction, where an existing precedent in the Senffner case states that “proceeding” should be defined “rather broadly.” But that case did not squarely address immigration arrests.

Biskupic said of Senffner: “It’s not as broad as the law enforcement exception.”

A reversal of Dugan’s conviction could deliver a major blow to the Trump Justice Department, voiding one of its rare victories in a high-profile case — and removing an arrow from the quiver of federal prosecutors targeting judges who seek to keep their courthouses safe from immigration enforcement.

During Dugan’s trial, a jury heard evidence about how Donald Trump’s controversial policy sparked anger, fear and confusion in the Milwaukee County Circuit Court System. The chief judge of the circuit opposed the policy as chilling access to justice for crime victims who happen to be immigrants.

All Rise News covered Dugan’s trial from in its entirety late last year: Catch up on reporting of closing arguments and the verdict here.