Fellow Wisconsin judge ‘shocked’ by Hannah Dugan’s response to immigration officers

A colleague of the Milwaukee judge accused of helping a Mexican immigrant evade federal arrest testified Tuesday that she was shocked by her fellow judge’s behavior during an incident that has drawn national attention amid heightened tensions over immigration enforcement.

“Judges shouldn’t help defendants evade arrest,” Milwaukee County Circuit Judge Kristela Cervera told the jury during the second day of Hannah Dugan’s trial on charges of obstruction and concealment.

Federal prosecutors allege that Dugan helped Eduardo Flores-Ruiz escape immigration agents on April 18 when he appeared before her on state battery charges. If convicted, Dugan faces up to five years in prison on the more serious obstruction charge, though federal sentencing guidelines give judges considerable discretion.

Cervera testified that she became irritated when Dugan pulled her away from her courtroom duties during the incident. According to her testimony, Dugan confronted two officers waiting to arrest Flores-Ruiz, repeatedly insisting they needed a judicial warrant before directing them to the chief judge’s chambers. While Cervera escorted the officers, Dugan returned to her courtroom.

The prosecution built its case around testimony from law enforcement officers who claimed Dugan’s actions endangered their safety and complicated what should have been a routine arrest. FBI agent Phillip Jackling expressed concern that his team became divided when Dugan directed agents away from her courtroom.

Customs and Border Protection Supervisory Officer Joseph Zuraw testified that Dugan appeared angry, jerked her thumb over her shoulder, and told him to “get out” before sending him to the chief judge’s office.

“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,” Zuraw recalled thinking when he realized that four of the six team members were away from the courtroom area when Flores-Ruiz exited.

According to testimony, after Dugan led Flores-Ruiz out through a private door, the agents had to pursue him through traffic outside the courthouse rather than making a controlled arrest inside the building.

The case has become a flashpoint in the ongoing national debate over immigration enforcement. Dugan’s supporters argue that the prosecution represents an attempt by the Trump administration to intimidate judges who might resist aggressive immigration enforcement tactics in courthouses, which some legal experts have criticized as potentially deterring immigrants from participating in the justice system.

Cervera further testified that three days after the incident, Dugan approached her saying she was “in the doghouse” with the chief judge for having “tried to help that guy.” Learning that Dugan had led Flores-Ruiz out through a private door left Cervera “shocked,” she told the court.

Defense attorney Steven Biskupic has maintained that Dugan had no intention of obstructing agents. In opening statements, he argued that the judge was simply following a draft courthouse policy directing court personnel to refer immigration agents to supervisors. The defense has also suggested that agents could have arrested Flores-Ruiz at any point in the hallway and shouldn’t blame Dugan for their decision to wait until he was outside.

The U.S. Department of Homeland Security confirmed in November that Flores-Ruiz has since been deported to Mexico.

The unusual prosecution of a sitting judge has drawn significant attention from legal observers and immigration advocates. Court proceedings like this raise important questions about the boundaries between judicial independence and law enforcement operations, particularly in cases involving federal immigration enforcement in state and local court facilities.

The trial continues as both sides present their evidence in a case that highlights the complex intersection of immigration enforcement, judicial authority, and courthouse security protocols in an increasingly polarized political climate.