On an April morning, behind the neoclassical facade of the Milwaukee County Courthouse, a typically bustling day of misdemeanor cases was just beginning in Judge Hannah C. Dugan’s sixth-floor courtroom.
But what would unfold in a matter of minutes was anything but typical.
Eduardo Flores-Ruiz, a defendant at the courthouse facing domestic battery charges, left Judge Dugan’s courtroom through a side door after his hearing was adjourned — at the judge’s urging, witnesses said. He was then chased on foot by federal agents, who arrested him for immigration violations.
The episode prompted the Trump administration to take an unusual step: charging Judge Dugan with obstructing a proceeding of a federal agency and concealing an individual to prevent his discovery and arrest. The Department of Justice said that she had directed Mr. Flores-Ruiz, an undocumented immigrant from Mexico, and his lawyer to exit through the side door in hopes that he would evade arrest.
Her trial is set to begin at a federal courthouse in Milwaukee on Monday and is expected to last a week. Judge Dugan, who has maintained her innocence, faces up to six years in prison if convicted and an uncertain future legal career.
The case has become an object of public fascination in Wisconsin, particularly as a national political debate over illegal immigration has raged in the background. To some, the case is a symbol of the Trump administration’s intolerance for any signs of resistance. To others, it is an example of a judge failing to adhere to a central tenet of impartiality.
“Many of the facts here aren’t going to be in dispute,” said Steven Wright, a law professor at the University of Wisconsin. “What the prosecution has to prove is that she acted with some type of bad motive, that she intended to prevent the federal officers from fulfilling their duties.”
Federal agents said that Judge Dugan was “visibly upset and had a confrontational, angry demeanor” and that she had called the situation “absurd” when she learned that agents were in the courthouse to arrest Mr. Flores-Ruiz. Immigration agents did not typically make arrests in the courthouse at the time, and judges, prosecutors and public defenders generally oppose the practice because it can undermine confidence in state and local courts.
The jury, chosen on Thursday from a pool of residents from 12 counties in Wisconsin, includes nine men and five women. Two jurors are alternates and will be dismissed before deliberations begin.
U.S. District Judge Lynn Adelman, who was appointed by former President Bill Clinton, will preside over the trial.
At least nine federal law enforcement officials are expected to testify, including officials from the Federal Bureau of Investigation, Immigration and Customs Enforcement, the Drug Enforcement Administration and Customs and Border Protection.
Other potential witnesses include several other Milwaukee County judges, including Chief Judge Carl Ashley, and Tom Barrett, a Democrat and former longtime mayor of Milwaukee, who is a friend of Judge Dugan.
In interviews, some people in the Milwaukee area said they believed Judge Dugan, who is widely known in progressive circles in Milwaukee, had been trying to interfere with immigration agents because of her own policy beliefs.
“I feel like she kind of just went beyond her duties, and she felt like she was above the law,” said Natasha Lindow, 40, a resident of the Milwaukee suburb of Greenfield, who described herself as politically conservative. “In that moment, she assisted the guy, and in my opinion, I think she has to now see what her peers think.”
Others defended Judge Dugan’s actions, saying they believed the Trump administration had gone too far with what appeared to be a political prosecution.
“It really feels like they went after this judge who was just trying to protect immigrants,” said Sangita Nayak, 50, an elementary school teacher in Milwaukee. “It kind of describes the character of the current situation that we’re in, where it feels like anything could happen for folks who are the most vulnerable in our community.”
Since Judge Dugan’s arrest, protesters have frequently gathered in downtown Milwaukee to show their support for her, including during jury selection last week. Demonstrations are expected to continue in downtown Milwaukee throughout the trial.
After a string of defeats in high-profile prosecutions, the Trump administration has signaled that it views the Dugan case as an opportunity to send a message.
Pam Bondi, the attorney general, said earlier this year that the case demonstrates that there are consequences for judges who interfere with immigration policy.
“Some of these judges think they’re above the law. They are not,” she said. “We will come after you and prosecute you. We will find you.”
Judge Dugan was elected by a wide margin in 2016, beating an incumbent appointee of Scott Walker, the Republican former governor of Wisconsin. She ran unopposed for re-election in 2022, and her current term expires in 2028.
A 1987 graduate of the University of Wisconsin Law School, Judge Dugan carved out a legal career with a focus on representing people who were low-income or members of marginalized groups. As a young lawyer, she took a job at Legal Action of Wisconsin, a group that provides free legal services, where she specialized in housing, public benefits and Social Security cases.
She later worked as the executive director for Catholic Charities of Southeastern Wisconsin and as a lawyer for Legal Aid. In 1995, she represented people who panhandled on downtown sidewalks, arguing that banning them from doing so was unconstitutional.
Judge Dugan, 66, has been on administrative leave since April but has continued to collect her $174,000 salary. She was temporarily removed from the bench by the Wisconsin Supreme Court while the case against her worked its way through the court.
In June, Mr. Flores-Ruiz agreed to plead guilty to entering the United States illegally after being removed from the country in 2013. He was deported to Mexico in November.
Julie Bosman is the Chicago bureau chief for The Times, writing and reporting stories from around the Midwest.
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