Former Milwaukee County Circuit Judge Hannah Dugan was supposed to learn her fate on Wednesday. Instead, she left a federal courtroom in Milwaukee with her sentencing postponed indefinitely, and her felony obstruction conviction hanging by a legal thread that neither side could tie off.
U.S. District Judge Lynn Adelman halted the proceedings to weigh whether to throw out the jury verdict against Dugan, 67, who was convicted of helping an illegal immigrant evade federal immigration officers inside her own courthouse. Adelman heard arguments from both sides but did not rule from the bench and gave no indication of when he might decide.
The case, the first time a Wisconsin state judge went to trial on charges of obstructing immigration agents, became a flashpoint in the broader fight over courthouses as safe havens for illegal immigrants. And now, more than a year after the events that led to Dugan's arrest, the conviction itself is in doubt.
The facts of April 18, 2025, are not in dispute. Immigration officers went to the Milwaukee County courthouse after learning that Eduardo Flores-Ruiz had re-entered the country illegally and was scheduled to appear before Dugan for a hearing in a state battery case.
When the officers arrived, Dugan confronted them outside her courtroom. She told them their administrative warrant was not sufficient grounds to arrest Flores-Ruiz and directed them to the chief judge's office.
After the agents left, Dugan led Flores-Ruiz and his attorney out through a private jury door.
The maneuver failed. Agents spotted Flores-Ruiz in the corridor, followed him outside, and arrested him after a foot chase. Flores-Ruiz was deported in November. A week after the courthouse incident, FBI agents arrested Dugan in the same building and led her out in handcuffs.
The Trump administration and its allies branded Dugan an "activist judge." Republican state lawmakers threatened impeachment. A jury convicted her of felony obstruction on December 19, though it acquitted her of a misdemeanor charge of concealing an individual to prevent arrest. Two weeks after the conviction, Dugan resigned from the bench, ending a nine-year judicial career.
The pattern of judges intervening to shield illegal immigrants from federal enforcement has become a recurring problem. Dugan's case was supposed to draw a line.
Dugan's attorney, Steven Biskupic, built his argument on a ruling from the 4th U.S. Circuit Court of Appeals. That court, in April, overturned a Virginia immigration case that both the judge and prosecutors had cited during Dugan's trial.
The Virginia case involved an immigrant who was in the country illegally and was detained by ICE before escaping. The appeals court found that ICE's enforcement action did not constitute a "pending proceeding" as required under the federal obstruction law. Without a "pending proceeding," the obstruction charge could not stand.
Biskupic told the court that the same logic applied to Dugan. There was no "pending proceeding" against Flores-Ruiz in Dugan's courtroom, only an administrative warrant for his arrest. If the warrant alone doesn't qualify, the conviction collapses.
"Our primary argument is this was an invalid theory of conviction."
That was Biskupic's summary of the defense position. If the underlying legal theory is wrong, the jury's verdict doesn't matter.
Acting U.S. Attorney Richard Frohling, representing the Eastern District of Wisconsin, urged Adelman to leave the conviction in place. Frohling argued that the Virginia case involved different facts and that other cases supported the government's theory.
He went further, contending that the 4th Circuit was simply wrong to overturn the Virginia ruling.
"The court should stick with its ruling."
Adelman pressed Frohling on what constitutes a "proceeding" under the law and how long one lasts. Frohling's answer was revealing in its vagueness.
"It could be a couple minutes, it could be a couple years. It all depends on the context."
That kind of elastic definition is exactly the sort of thing defense attorneys love to exploit, and exactly the kind of ambiguity that makes federal obstruction law a contested instrument in immigration enforcement.
The broader question of how federal judges handle politically charged cases is never far from the surface in proceedings like this one.
Dugan faces up to five years in prison if the conviction stands. Federal sentencing guidelines generally call for probation for defendants with no criminal history who are convicted of nonviolent crimes, which would likely apply to Dugan. But the symbolic weight of the case far exceeds whatever sentence she might receive.
This was the Trump administration's marquee prosecution of a state judge who physically intervened to help an illegal immigrant escape federal custody. The case was meant to send a signal: courthouses are not sanctuary zones, and judges who obstruct immigration enforcement will face consequences.
If Adelman overturns the conviction on a legal technicality, that ICE enforcement actions don't qualify as "pending proceedings" under the obstruction statute, the signal reverses. Every state judge in the country who sympathizes with illegal immigrants facing deportation gets a roadmap for interference. Confront the agents, question their paperwork, shuffle the defendant out a back door, and if it goes sideways, argue that no "proceeding" was obstructed.
Wisconsin's judiciary already tilts in a direction that should concern conservatives. Liberals locked down a 5-2 majority on the state Supreme Court in recent elections, and the political environment that produced Dugan's conduct on the bench hasn't changed.
Dugan was present for Wednesday's arguments but did not speak. She and attorneys for both sides left the courtroom without commenting to reporters.
The silence is fitting. The case now rests entirely with Adelman, who gave no timeline for his decision. Meanwhile, Flores-Ruiz, the illegal immigrant whose battery case brought him to Dugan's courtroom in the first place, was deported months ago. The man Dugan tried to shield from federal officers is gone. The legal wreckage she created is not.
The 4th Circuit's Virginia ruling, which Biskupic is leaning on, applies in a different federal jurisdiction. Whether Adelman feels bound by it, persuaded by it, or free to ignore it is an open question. Frohling pointed to other cases that he said support the conviction, though the specifics of those cases were not detailed in Wednesday's arguments.
The broader fight over courthouse enforcement continues to play out in jurisdictions across the country. Wisconsin's liberal judicial majority ensures the state's courts will remain a battleground for years.
Strip away the legal jargon and the appellate maneuvering, and the facts are plain. A sitting judge confronted federal officers, questioned their authority, sent them away on a pretext, and then personally escorted the man they were looking for out a back door. The man ran. The agents chased him. The judge knew exactly what she was doing.
Whether the federal obstruction statute's language about "pending proceedings" perfectly maps onto every ICE enforcement action is a legitimate legal question. But the conduct itself, a judge using her position and her courthouse access to help an illegal immigrant flee from lawful federal officers, is the kind of behavior that erodes public trust in the judiciary and makes a mockery of the rule of law.
A jury of twelve citizens heard the evidence and convicted her. Dugan's defense team now wants a single federal judge to erase that verdict based on an appeals court ruling from another circuit involving different facts. Prosecutors say the cases aren't comparable. The law, as Frohling noted, depends on context.
Here is the context that matters most: a judge helped an illegal immigrant who had re-entered the country unlawfully, a man facing a battery charge, slip past federal officers. She did it deliberately, using the private corridors of her courthouse. And when it all came to light, the FBI arrested her in handcuffs.
If that doesn't qualify as obstruction, then the word has lost its meaning, and courthouses across America just became the safest place in the country for anyone trying to dodge a federal warrant.