A federal judge has refused to throw out the obstruction of justice conviction of Hannah Dugan, the former Milwaukee County Circuit Court judge who spirited a man out of her courtroom through a private jury door to help him evade immigration officers waiting to detain him. U.S. District Judge Lynn Adelman ruled Tuesday that Dugan's conviction will stand, rejecting her attorneys' argument that the ICE operation at the courthouse did not qualify as a "pending proceeding" under federal obstruction law.
Dugan, 67, faces up to five years in prison. Adelman has not yet set a sentencing date.
The case became a flashpoint early in President Donald Trump's push to enforce immigration law, testing whether a sitting state judge could use the authority of her bench to shield an illegal immigrant from federal agents, and whether the legal system would hold her accountable for it. The answer, for now, is yes.
On April 18, 2025, immigration officers went to the Milwaukee County courthouse after learning that Eduardo Flores-Ruiz had reentered the country illegally and was scheduled to appear before Dugan for a hearing in a state battery case. The Associated Press reported that Dugan confronted the agents outside her courtroom and directed them to the chief judge's office, telling them their administrative warrant was not sufficient grounds to arrest Flores-Ruiz.
After the agents left, Dugan led Flores-Ruiz and his attorney out through a private jury door.
The escape was short-lived. Agents spotted Flores-Ruiz in a corridor, followed him outside, and arrested him after a foot chase. One week later, FBI agents arrested Dugan herself inside the same courthouse and led her out in handcuffs.
The image of a sitting judge, someone sworn to uphold the law, being walked out of a courthouse in restraints for obstructing federal officers captured a tension that has played out in courtrooms across the country. Judges in New York and elsewhere have clashed with immigration enforcement over courthouse operations, but Dugan's case went further: she didn't issue a ruling or file a motion. She physically moved a defendant out a back door.
Dugan's defense team built its challenge around a federal appeals court ruling in a Virginia immigration case. That ruling found that the ICE action in the Virginia matter did not constitute a "pending proceeding" as required under the federal obstruction statute. Dugan's attorneys argued the same logic applied here: there was no "pending proceeding" against Flores-Ruiz in her courtroom, only a warrant filed for his arrest.
They had also argued, unsuccessfully, that Dugan was immune from prosecution because she was acting as a judge.
Prosecutors pushed back hard, arguing the Virginia case involved different facts and did not control Dugan's situation. They pointed to other cases they said supported the conviction. Adelman agreed with the government.
In his ruling, Adelman wrote that the attempted arrest of Flores-Ruiz counted as a "pending proceeding" in part because it was a planned and targeted operation, not an arrest resulting from a random encounter. He drew a distinction between ICE and other law enforcement agencies:
"Defendant argues that ICE was acting as a law enforcement agency here. But this ignores the fact that, unlike, say, the FBI, ICE can issue its own warrants and adjudicate and effectuate a removal, as it did with Flores-Ruiz, without the involvement of a court. This makes a difference."
That reasoning matters. Adelman's ruling treats ICE's administrative removal process as a proceeding in its own right, a legal framework that could strengthen future obstruction cases against anyone who interferes with immigration enforcement operations.
Dugan's legal team was blunt in response, calling the decision wrong. The broader fight over how federal courts handle challenges to Trump-era immigration enforcement continues to produce significant rulings across the federal judiciary.
A jury convicted Dugan on Dec. 19 of obstruction of justice. She was acquitted on a separate misdemeanor charge of concealing an individual to prevent arrest. Two weeks after her conviction, she resigned from the Milwaukee County Circuit Court. She had served as a judge for nine years.
Republican state lawmakers had threatened impeachment following the guilty verdict. Dugan's supporters said she was unfairly targeted. Her attorneys echoed that claim. Trump allies, meanwhile, described Dugan as an activist judge, a characterization the case record does little to rebut.
Adelman had postponed Dugan's sentencing on June 3 to weigh whether the conviction should be overturned. His Tuesday ruling closes that door. He did not immediately schedule a new sentencing date. Dugan faces up to five years in prison, though she is described as unlikely to receive time behind bars.
That potential leniency is worth noting. A nine-year veteran of the bench used her position to physically obstruct federal officers carrying out a lawful operation, and the system may still treat her more gently than it treats many defendants who pass through courtrooms like hers. The broader question of how the federal judiciary handles politically charged cases, from controversial judicial conduct to high-profile appeals, remains far from settled.
Eduardo Flores-Ruiz, the man Dugan tried to help escape, was deported in November. He had reentered the country illegally and was in the courthouse on a battery charge when ICE came for him. The system caught up with him despite Dugan's intervention, it just took longer than it should have.
The Trump administration brought the case against Dugan as it pressed forward with immigration enforcement. The prosecution sent a clear message: no one, not even a judge, sits above the law when it comes to obstructing federal officers. The conviction's survival on post-trial review reinforces that message.
Across the federal bench, fights over immigration enforcement, executive authority, and judicial power continue to shape the legal landscape. Major rulings from the Fifth Circuit and other appellate courts have shown that the judiciary is not a monolith, and that outcomes depend heavily on which judges hear which cases.
Dugan's case is simpler than most. She saw federal agents coming for a man in her courtroom. She told them their warrant wasn't good enough. She sent them away and then walked the man out a back door. A jury called it obstruction. A federal judge agreed.
When the person obstructing justice is the one wearing the robe, the system has a bigger problem than one bad case. It has a trust problem, and no ruling can fix that.