Federal judge pauses sentencing to weigh argument in Wisconsin judge's immigration case conviction

MILWAUKEE (AP) — A federal judge on Wednesday considered whether to throw out a jury's guilty verdict against former Wisconsin Judge Hannah Dugan, who was convicted of felony obstruction for helping an immigrant evade federal officers.

The case was an early test of how the courts would respond to President Donald Trump’s sweeping immigration crackdown.

Dugan had been scheduled to be sentenced on Wednesday, but U.S. District Judge Lynn Adelman postponed the proceedings indefinitely to instead hear arguments about whether to overturn her conviction.

Adelman did not rule from the bench and did not indicate when he might issue a decision. Dugan and attorneys for both sides left the courtroom without commenting to reporters.

Former judge's attorney points to a Virginia case

Dugan’s attorney Steven Biskupic argued that her conviction was invalid and should be overturned. He said that was necessary because a federal appeals court in April overturned a key Virginia immigration case that the judge and prosecutors had cited in the Dugan case.

Biskupic argued that based on the 4th U.S. Circuit Court of Appeals overturning that ruling, Dugan was improperly convicted, procedurally, under a certain federal law.

“Our primary argument is this was an invalid theory of conviction," Biskupic said.

In the Virginia case, an immigrant who was in the country illegally was detained by U.S. Immigration and Customs Enforcement agents and later escaped. He was recaptured and indicted on a charge of obstructing a pending immigration proceeding.

The federal appeals court found that the ICE action did not constitute a “pending proceeding,” as is required under the federal obstruction law.

Dugan’s attorneys argue that she should not have been charged because there was no “pending proceeding” against the immigrant in her courtroom being sought by ICE agents, only a warrant filed for his arrest. The filing of a warrant does not constitute a “proceeding” under the law, Biskupic argued.

Prosecutors countered that the facts in the Virginia case are different and don’t apply to Dugan's. They also argued that other cases support Dugan's conviction.

“The court should stick with its ruling,” said Richard Frohling, acting U.S. attorney for the eastern district of Wisconsin.

In response to a question from the judge, he contended that the appeals court was wrong to overturn the Virginia case. The judge also quizzed Frohling on what constitutes a proceeding under the law and how long it lasts.

“It could be a couple minutes, it could be a couple years," Frohling said. "It all depends on the context.”

Dugan's sentencing was postponed so the court can hear new arguments

Dugan, 67, faces up to five years in prison after a jury convicted her on Dec. 19. But it is unlikely that Dugan would be sentenced to prison. Federal sentencing guidelines generally call for probation for defendants like her who have no criminal history and are convicted of a nonviolent crime.

She resigned from her position as a Milwaukee County circuit judge two weeks after her conviction amid threats of impeachment from Republican state lawmakers. She had been a judge for nine years.

Dugan was present for Wednesday's arguments but did not speak.

The Trump administration brought the case against Dugan as the president pressed ahead with his sweeping immigration crackdown. Trump’s administration and his allies branded Dugan as an activist judge, while Dugan’s attorneys said she was being unfairly targeted and argued, unsuccessfully, that she was immune from being charged because she was a judge.

Dugan’s case marked the first time that a state judge in Wisconsin went to trial on charges of obstructing immigration agents. She was acquitted of concealing an individual to prevent arrest, a misdemeanor.

Dugan helped an immigrant wanted by ICE agents

On April 18, 2025, immigration officers went to the Milwaukee County courthouse after learning Eduardo Flores-Ruiz had reentered the country illegally and was scheduled to appear before Dugan for a hearing in a state battery case.

Dugan confronted agents outside her courtroom and directed them to the chief judge’s office because she told them their administrative warrant wasn’t sufficient grounds to arrest Flores-Ruiz.

After the agents left, she led Flores-Ruiz and his attorney out a private jury door. Agents spotted Flores-Ruiz in the corridor, followed him outside and arrested him after a foot chase. A week later, FBI agents arrested Dugan in the courthouse, leading her outside in handcuffs.

Flores-Ruiz was deported in November.