A jury found a Wisconsin judge accused of helping a Mexican immigrant dodge federal authorities guilty of obstruction on December 18, marking a victory for Donald Trump as he continues his sweeping authoritarian crackdown on the judiciary across the country.
Federal prosecutors charged Milwaukee County Circuit Judge Hannah Dugan with obstruction, a felony, and concealing an individual to prevent arrest, a misdemeanor, in April. The jury acquitted her on the concealment count, but she still faces up to five years in prison on the obstruction count.
The jury returned the verdicts after deliberating for six hours. Dugan and her attorneys left the courtroom, ducked into a side conference room, and closed the door without speaking to reporters.
The jury’s findings have drawn sharp criticism because the case itself was built on an unprecedented use of federal obstruction law against a sitting state judge — a step legal scholars said had never been taken in a prior president’s administration.
The charges were filed only after Donald Trump intensified his efforts to punish local judicial resistance to immigration arrests, creating an atmosphere in which routine courthouse decisions were recast as criminal acts.
Throughout the trial, witnesses acknowledged that courthouse policy on handling immigration agents was unsettled, that agents could have arrested the defendant at multiple points, and that the prosecution relied heavily on interpreting split-second decisions as intentional obstruction rather than procedural confusion.
Those factors have fueled claims that the outcome reflects political pressure more than impartial justice.
The verdict brings an end to a case that unfolded under rare scrutiny, but understanding how the trial reached this point requires looking back at the rapid sequence of testimony that defined each day in court.
Over four days, prosecutors and the defense built competing narratives from the same set of encounters inside the Milwaukee County Courthouse, turning routine procedures into pivotal evidence and elevating split-second decisions into questions of intent and authority.
What emerged was a tightly compressed trial that shifted in tone from hour to hour — from procedural disagreements to sharply contested interpretations of a judge’s role during a federal arrest attempt. Witnesses, audio recordings, and courthouse movements all carried outsized weight as each side pushed jurors toward a broader meaning of the case.
The following is a day-by-day account of those arguments and how the courtroom dynamic shaped the path to the final decision.
MONDAY, DECEMBER 15 – DAY 1
Prosecutors played audio recordings on December 15 as they tried to show jurors that a Wisconsin judge knew what was at stake earlier this year when she directed an immigrant to a private door while federal agents were in the courthouse to arrest the man.
“I’ll get the heat,” Milwaukee County Circuit Judge Hannah Dugan told her court reporter as they discussed who would assist Eduardo Flores-Ruiz, according to courtroom audio.
Federal prosecutors charged Dugan with obstruction and concealment in April, an extraordinary consequence of President Donald Trump’s immigration crackdown. According to an FBI affidavit, a team of six federal agents and officers traveled to the Milwaukee County courthouse on April 18 to arrest Flores-Ruiz, 31, for being in the country illegally.
Flores-Ruiz was facing state battery charges and was scheduled to appear at a hearing in front of Dugan that morning. The team planned to arrest him when he came out of the hearing.
According to the affidavit, Dugan learned the agents and officers were in the hallway waiting for Flores-Ruiz. She left the courtroom and told them to consult with the chief judge. After several agents left to see the chief judge, she led Flores-Ruiz out of her courtroom through a private back door.
The private door led Flores-Ruiz back to the public hallway. Agents followed him outside and eventually arrested him after a foot chase. He was deported months later.
Courthouse video shows Dugan directing members of the arrest team toward the chief judge’s office and she hasn’t disputed that she led Flores-Ruiz out of the courtroom. The case hinges on whether she was intentionally trying to prevent his arrest.
Prosecutors opened her trial on December 15 in federal court in Milwaukee by working to show that the judge told the agents to see the chief judge to create an opening for Flores-Ruiz to escape.
FBI Special Agent Erin Lucker testified that while agents were in the chief judge’s office, Dugan moved Flores-Ruiz’s case to the top of her docket, scheduled another hearing for him and told him he could appear via Zoom before directing him out through the back door. All this was done within minutes, Lucker said.
Prosecutors played audio from her courtroom in which Dugan and her court reporter discussed who should lead Flores-Ruiz out of the courtroom. After the reporter offered to help him, Dugan said that she’d do it.
“I’ll get the heat,” Dugan said.
The arrest team “did not expect a judge, sworn to uphold the law, would divide their arrest team and impede their efforts to do their jobs,” Assistant U.S. Attorney Keith Alexander told jurors.
Defense attorney Steven Biskupic countered that the judge had no intention of obstructing agents. He said during his opening statements that Dugan was following a draft courthouse policy that called for court personnel to refer immigration agents looking to make an arrest in the courthouse to supervisors.
Dugan didn’t obstruct the team, Biskupic said, pointing out that two agents who didn’t go to the chief judge’s office could have arrested Flores-Ruiz as soon as he stepped into the public corridor but instead followed him outside before trying to apprehend him.
“Now, after the fact, everyone wants to blame Judge Dugan,” Biskupic told the jury.
The government’s case is expected to run through December 18, with roughly two dozen witnesses expected to testify. The maximum sentence for the more serious charge, obstruction, is five years in prison, though federal judges have much discretion to go lower.
Ahead of the trial, U.S. District Judge Lynn Adelman declined to dismiss the charges, saying there was no firmly established immunity for Dugan.
Democrats say Trump is looking to make an example of Dugan to blunt judicial opposition to immigration arrests. Dugan told police she and her family found threatening flyers at their homes this spring. The administration has branded her an activist judge.
Republican U.S. Rep. Tom Tiffany, a fierce Trump loyalist running for Wisconsin governor next year, urged authorities to “lock her up” in a recent tweet.
TUESDAY, DECEMBER 16 – DAY 2
A colleague of the Milwaukee judge accused of helping a Mexican immigrant evade arrest testified on December 16 that she was shocked by her fellow judge’s behavior.
“Judges shouldn’t help defendants evade arrest,” Milwaukee County Circuit Judge Kristela Cervera testified at Hannah Dugan’s trial.
The testimony on the second day of trial came after officers involved in the arrest told the jury that Dugan’s behavior on April 18 made it more dangerous for them to do their jobs.
Dugan is on trial on charges of obstruction and concealment in connection with the incident. The maximum sentence for obstruction, the more serious charge, is five years in prison, though federal judges have much discretion to go lower.
The highly unusual charges against a sitting judge are an extraordinary consequence of President Donald Trump’s immigration crackdown. Dugan’s supporters say Trump is looking to make an example of her to blunt judicial opposition to immigration arrests.
Eduardo Flores-Ruiz was scheduled to appear before Dugan on the morning of April 18 on state battery charges. Prosecutors allege that after Dugan learned that federal officers were in the hallway waiting to arrest him, she cleared a path for him to escape by directing the officers to the chief judge’s office and then leading Eduardo-Flores out of her courtroom through a private door.
Cervera testified that she was irritated that Dugan used her as backup during the incident, making her come out of her courtroom into the hallway while still wearing her robe.
Dugan proceeded to angrily confront two officers waiting to arrest Flores-Ruiz, telling them repeatedly that they needed a judicial warrant before sending them to the chief judge’s chambers, Cervera testified. She escorted the officers to the chambers while Dugan returned to her courtroom, she said.
Dugan approached her three days later and said she was “in the doghouse” with the chief judge, saying something to the effect that the chief was upset with her because she had “tried to help that guy,” Cervera testified.
When she learned that Dugan had led Flores-Ruiz out the private door, “I was shocked,” Cervera testified.
FBI agent Phillip Jackling testified on December 16 that he was concerned that his team was divided when Dugan directed agents to speak with the chief judge.
Dugan appeared angry when she approached him in the hallway outside her courtroom, he said. Another member of the arrest team, Customs and Border Protection Supervisory Officer Joseph Zuraw, said Dugan jerked her thumb over her shoulder and told him to “get out” before directing him to the chief judge’s chambers.
Four of the arrest team’s six members were in the chief judge’s chambers or a hallway leading to the chambers when Flores-Ruiz left the courtroom, the agents testified. Zuraw said he remembered thinking: “This is a bad spot we’re in right now. It’s a bad spot because we don’t’ have a decent number of officers to safely make an arrest.”
The team followed him outside the courthouse and had to chase him down through traffic when they could have safely arrested him in the building, they testified.
Dugan’s defense team has suggested that agents could have arrested Flores-Ruiz at any point in the hallway and Dugan shouldn’t be blamed for their decision to wait until he was outside.
Defense attorney Steven Biskupic said in opening statements that the judge had no intention of obstructing agents. He said that Dugan was just following a draft courthouse policy that called for court personnel to refer immigration agents looking to make an arrest in the courthouse to supervisors.
The U.S. Department of Homeland Security announced in November that Flores-Ruiz had been deported.
WEDNESDAY, DECEMBER 17 – DAY 3
A Wisconsin judge accused of helping a Mexican immigrant evade federal authorities is set to present her case as her trial on obstruction and concealment charges winds down.
Prosecutors rested their case against Milwaukee County Circuit Judge Hannah Dugan on December 17 after three days of testimony. Dugan’s defense attorneys said they planned to call four witnesses starting on December 18. It wasn’t clear whether Dugan would take the stand. Closing arguments could begin as early as the afternoon of December 18.
The highly unusual charges against a sitting judge are an extraordinary consequence of President Donald Trump’s immigration crackdown. Dugan’s supporters say Trump is looking to make an example of her to blunt judicial opposition to immigration arrests.
Prosecutors have tried to show that Dugan intentionally interfered with members of a federal immigration task force’s efforts to arrest 31-year-old Eduardo Flores-Ruiz at the Milwaukee County Courthouse.
Members of the task force testified that they learned Flores-Ruiz was in the country illegally after he was arrested in Milwaukee on state battery charges. He was scheduled to appear for a hearing in front of Dugan on April 18. Six agents and officers staked out Dugan’s courtroom that morning, ready to arrest him when he emerged from the hearing.
They testified that Dugan and another judge, Kristela Cervera, stepped into the hallway wearing their robes. Dugan angrily told four members of the team to report to the chief judge’s office.
As Cervera led them to the office, Dugan went back to her courtroom and led Flores-Ruiz out a private door into the hallway. Prosecutors produced transcripts of audio recordings from microphones in her courtroom that show Dugan told her court reporter that she’d take “the heat” for showing Flores-Ruiz out the private door.
Two agents Dugan missed during her confrontations with the team followed Flores-Ruiz outside and a foot chase through traffic ensued before he was finally arrested. Members of the team testified that Dugan divided them and forced them out of position, leaving them too short-handed to make a safe arrest in the hallway.
Cervera, for her part, testified that she was uncomfortable backing up Dugan during her confrontations with the arrest team. She said she was shocked when she heard Dugan led Flores-Ruiz out a private door, adding that judges shouldn’t help defendants evade arrest. Cervera also testified that Dugan told her three days after the incident that Dugan was “in the doghouse” with the chief judge, Carl Ashley, because she “tried to help that guy.”
Dugan’s attorneys have countered during cross-examinations that Dugan didn’t intend to obstruct the arrest team and was trying to follow a draft courthouse policy from Ashley that called for court employees to refer immigration agents looking to make an arrest in the courthouse to supervisors.
They’ve also argued that the arrest team could have apprehended Flores-Ruiz at any point after he emerged from the courtroom and Dugan shouldn’t be blamed for their decision to wait until he got outside.
THURSDAY, DECEMBER 18 – DAY 4
Prosecutors on December 18 tried to convince a jury that a Wisconsin judge put her personal beliefs above the law and helped a Mexican immigrant evade federal authorities seeking to arrest him in the courthouse.
Milwaukee County Circuit Judge Hannah Dugan did not take the stand in her own defense as she faces obstruction and concealment charges. The case was expected to head to the jury late on December 18 following closing arguments.
“You don’t have to agree with immigration enforcement policy to see this was wrong,” Assistant U.S. Attorney Kelly Brown Watzka told the jury in closing arguments. “You just have to agree the law applies equally to everyone.”
The highly unusual charges against a sitting judge are an extraordinary consequence of President Donald Trump’s immigration crackdown. Dugan’s supporters say Trump is looking to make an example of her to blunt judicial opposition to immigration arrests.
Prosecutors have tried to show that Dugan intentionally interfered with members of a federal immigration task force’s efforts to arrest 31-year-old Eduardo Flores-Ruiz at the Milwaukee County Courthouse.
Brown Watzka told the jury that Dugan provided Flores-Ruiz with an escape route.
“A judge does not have absolute authority to do whatever she wants whenever she puts on her robe,” Brown Watzka said. “The defendant is not on trial for her views on immigration policy. She is on trial because she made a series of deliberate decisions to step outside the law in order to help an individual evade federal arrest.”
Brown Watzka pointed out that Dugan had a whispered discussion with her court reporter about which of them should guide Flores-Ruiz out the private door and down a back staircase out of the arrest team’s sight.
Flores-Ruiz ultimately did not take the stairs and instead went through the private door into the public hallway, but Brown Watzka said that means nothing.
“The only thing that matters is the defendant’s intent,” she said. “The stairs discussion proves beyond a reasonable doubt that the defendant intended to prevent the arrest.”
Dugan’s attorneys called four witnesses on December 18, including a public defender who took photographs of the arrest team in the hallway and two judges who testified that a draft policy about how to handle immigration arrests was in flux in the weeks before Flores-Ruiz’s arrest.
Former Milwaukee mayor and Democratic congressman Tom Barrett testified that he’s known Dugan since high school and described her as “extremely honest.”
Officers who came to arrest Flores-Ruiz on April 18 testified that they learned he was in the country illegally after he was arrested in Milwaukee on state battery charges. They testified that Dugan and another judge, Kristela Cervera, stepped into the hallway wearing their robes. Dugan angrily told four members of the team to report to the chief judge’s office, the officers testified.
As Cervera led them to the office, Dugan returned to her courtroom and led Flores-Ruiz out a private door into the hallway. Prosecutors produced transcripts of audio recordings from microphones in her courtroom that show Dugan told her court reporter that she’d take “the heat” for showing Flores-Ruiz out the private door.
Two agents Dugan missed during her confrontations with the team followed Flores-Ruiz outside, and a foot chase through traffic ensued before he was finally arrested. Members of the team testified that Dugan divided them and forced them out of position, leaving them too short-handed to make a safe arrest in the hallway.
Dugan’s attorneys argued that the arrest team could have apprehended Flores-Ruiz at any point after he emerged from the courtroom and Dugan shouldn’t be blamed for their decision to wait until he got outside.
The case is a “shot across the bow” to state judges everywhere meant to intimidate them, said Howard Schweber, a political scientist and affiliate faculty of the University of Wisconsin Law School.
“It is unthinkable that this prosecution would have been brought in a prior administration,” Schweber said. “This is truly extraordinary, I would even say unprecedented certainly in my adult lifetime. I have never seen anything like it. And professionally its quite shocking.”
Dugan’s team filed a motion late on December 17 asking U.S. District Judge Lynn Adelman, who is presiding over the case, to find Dugan not guilty without asking jurors to deliberate. Adelman did not immediately rule December 18 on the motion, which is common after prosecutors present their case.
