Wisconsin judge pleads not guilty to helping a man evade federal immigration agents

Supporters of judge Hannah Dugan protest outside the United States Federal Building and Courthouse in Milwaukee, Wis., on April 15, 2025. (Todd Richmond / AP Photo)

MILWAUKEE — A Wisconsin judge pleaded not guilty Thursday to charges accusing her of helping a man who is illegally in the country evade U.S. immigration authorities seeking to arrest him in her courthouse.

Milwaukee County Circuit Judge Hannah Dugan entered the plea during a brief arraignment in federal court. Magistrate Judge Stephen Dries scheduled a trial to begin July 21. Dugan’s lead attorney, Steven Biskupic, told the judge that he expects the trial to last a week.

Dugan, her lawyers and prosecutors left the hearing without speaking to reporters.

The accusations against Dugan

She is charged with concealing an individual to prevent arrest and obstruction. Prosecutors say she escorted Eduardo Flores-Ruiz and his lawyer out of her courtroom through a back door on April 18 after learning that U.S. Immigration and Customs Enforcement agents were in the courthouse seeking to arrest him for being in the country illegally. She could face up to six years in prison if convicted on both counts.

Her attorneys say she’s innocent. They filed a motion Wednesday to dismiss the case, saying she was acting in her official capacity as a judge and therefore is immune to prosecution. They also maintain that the federal government violated Wisconsin’s sovereignty by disrupting a state courtroom and prosecuting a state judge.

A public backlash

Dugan’s arrest has inflamed tensions between Trump administration and Democrats over the president’s sweeping immigration crackdown.

Dozens of demonstrators gathered outside the courthouse ahead of Thursday’s hearing, with some holding signs that read, “Only Fascists Arrest Judges -- Drop the Charges,” “Department of Justice Over-Reach” and “Keep Your Hands Off Our Judges!!” The crowd chanted “Due process rights,” “Hands off our freedom,” and “Si se puede” -- Spanish for “Yes, we can” -- which is a rallying cry for immigrant rights advocates.

One man stood alone across the street holding a Trump flag.

Nancy Camden, from suburban Mequon north of Milwaukee, was among the protesters calling for the case to be dismissed. She said she believes ICE shouldn’t have tried to arrest Flores-Ruiz inside the courthouse and the Department of Justice “overreached” in charging Dugan.

“How they handled this and made a big show of arresting her and putting her in handcuffs, all of that was intimidation,” Camden said. “And I’m not going to be intimidated. I’m fighting back.”

Esther Cabrera, an organizer with the Milwaukee Alliance Against Racist and Political Repression, said the charges against Dugan amount to “state-funded repression.”

“If we are going to go after judges, if we’re going to go after mayors, we have to understand that they can come after anybody,” she said. “And that’s kind of why we wanted to make a presence out here today is to say that you can’t come after everyone and it stops here.”

The case background

According to court documents, Flores-Ruiz illegally reentered the U.S. after being deported in 2013. Online court records show he was charged with three counts of misdemeanor domestic abuse in Milwaukee County in March, and he was in Dugan’s courtroom on April 18 for a hearing in that case.

According to an FBI affidavit, Dugan was alerted to the agents’ presence by her clerk, who was informed by an attorney that the agents appeared to be in the hallway. Dugan was visibly angry and called the situation “absurd” before leaving the bench and retreating to her chambers, the affidavit contends. She and another judge later approached members of the arrest team in the courthouse with what witnesses described as a “confrontational, angry demeanor.”

After a back-and-forth with the agents over the warrant for Flores-Ruiz, Dugan demanded they speak with the chief judge and led them from the courtroom, according to the affidavit.

After she returned to the courtroom, witnesses heard her say something to the effect of “wait, come with me” before ushering Flores-Ruiz and his attorney out through a door typically used only by deputies, jurors, court staff and in-custody defendants, the affidavit alleges. Flores-Ruiz was free on a signature bond in the abuse case, according to online state court records. Federal agents ultimately detained him outside the courthouse after a foot chase.

The state Supreme Court suspended Dugan last week, saying the move was necessary to preserve public confidence in the judiciary. She was freed after her arrest.

How the case might play out

John Vaudreuil, a former federal prosecutor in Wisconsin who isn’t involved in Dugan’s or Flores-Ruiz’s cases, said the Trump administration seems to want to make an example out of Dugan. U.S. Attorney General Pam Bondi or Deputy Attorney General Todd Blanche, rather than the U.S. attorney in Milwaukee, are likely making the decisions on how to proceed, making it less likely prosecutors will reduce the charges against Dugan in a deal, he said.

Her attorneys will likely try to push for a jury trial, Vaudreuil predicted, because they know that “people feel very strongly about the way the president and administration is conducting immigration policy.”

Dugan is represented by some of Wisconsin’s most accomplished lawyers. Biskupic was a federal prosecutor for 20 years and served seven years as U.S. attorney in Milwaukee. Paul Clement, meanwhile, is a former U.S. solicitor general who has argued more than 100 cases in front of the U.S. Supreme Court. Both were appointed to jobs by former Republican President George W. Bush.

By Todd Richmond

Associated Press reporters Scott Bauer in Madison, Wisconsin, and Laura Bargfeld contributed to this report.