Dugan seeks leniency before ICE obstruction sentence

Prosecutors and defense attorneys for Hannah Dugan are painting contrasting pictures of the former Milwaukee County circuit judge as she nears sentencing on a conviction of obstructing federal immigration agents.

Dugan is expected to speak — her first public statement since she was arrested more than a year ago — when U.S. District Judge Lynn Adelman sentences her at the federal courthouse in downtown Milwaukee on July 8.

The case thrust the 67-year-old Milwaukee native to the forefront of a clash between local judges and the Trump administration over immigration enforcement.

In their sentencing memo, prosecutors wrote that Dugan violated her judicial oath because she personally disagreed with immigration enforcement and put law enforcement and the public at risk.

“Judges are entrusted with tremendous discretion, but there is a line they cannot cross,” Executive Assistant U.S. Attorney Richard Frohling wrote. “The defendant crossed that line.”

Her defense team wrote that Dugan is an exemplary public servant whose life has been shattered by the prosecution for a quick decision she made during a chaotic time at the Milwaukee County courthouse.

Submitting nearly 20 letters of support from diverse sources, Dugan’s team said she “has been punished enough.”

Sentencing guidelines call for prison time

Under the federal sentencing guidelines, the presentence report calls for 15 to 21 months behind bars. The maximum sentence is five years in prison.

Adelman is not bound by the guidelines. A liberal judge, Adelman has a reputation for sentencing below the guideline range, but not always.

Prosecutors noted that the average sentence for obstruction cases is 16 months, but didn’t recommend a sentence, saying, “This was a serious offense, and it warrants a correspondingly serious sentence.”

Dugan’s team wrote that the case was overcharged. They suggested she be sentenced to time served. She spent part of a day in federal custody.

“She was handcuffed and shackled during her arrest, photographed publicly by plan, and intentionally shamed from coast to coast by the leadership of the U.S. Department of Justice and FBI. There is no need for further deterrence, either specifically or generally,” the defense wrote.

Regardless of the sentence, the defense said it will appeal the case to the 7th Circuit Court of Appeals.

Legal career serving the underprivileged

Before becoming a judge, Dugan spent her legal career serving poor and otherwise disadvantaged clients, her attorney said.

“A deeply religious Catholic, she has followed the Gospel message of serving others less fortunate,” the team wrote.

Former longtime Milwaukee County District Attorney E. Michael McCann wrote of Dugan, “To her, the statement of Christ ‘that whatever you do for these the least of mine, you do for me’ was a motivating factor. … She is thoughtful, careful, generous, respectful of citizens rich and poor.”

Dugan worked at Legal Action of Wisconsin and Legal Aid Society of Wisconsin for nearly 20 years. She was elected judge in 2016. She resigned earlier this year, after the trial.

Joe Wall, a Milwaukee County judge and former federal prosecutor, praised Dugan’s service and said the way she was arrested was unnecessary. Dugan was frisked and handcuffed behind her back during her arrest at the courthouse, then remained handcuffed and shackled at her ankles during an appearance before a judge.

“It was meant to humiliate her in the eyes of her colleagues and the general public,” Wall wrote.

First case of its kind to go to trial

On April 18, 2025, ICE agents came to Dugan’s courtroom to arrest Eduardo Flores-Ruiz, who had illegally re-entered the U.S. and was set to appear in her courtroom on battery charges.

Dugan and another judge questioned the agents and directed them to the office of the chief judge.

Dugan returned to her courtroom, called Flores-Ruiz’s case, and then led him and his lawyer into a hallway reserved for staff and jurors.

Flores-Ruiz and his attorney emerged in the public corridor. Agents followed. Flores-Ruiz was arrested outside after a short foot chase.

A jury found Dugan guilty of obstructing a federal immigration proceeding, a felony, and not guilty of a misdemeanor charge of concealing a fugitive whom ICE agents were seeking to arrest.

“The nine-year judicial career of Judge Dugan [and almost 40-year legal career] came to an end because of approximately five minutes of immediate reactions to learning that an ICE enforcement action was to take place on the sixth floor near her courtroom,” the defense wrote.

Putting herself above the law

Prosecutors acknowledged Dugan’s community roles but said her “privileged upbringing” meant she knew better than to break the law.

“The defendant’s refusal to acknowledge the wrongfulness of her conduct raises legitimate concerns about respect for the law and suggests a continuing belief that her personal disagreement with federal immigration law justified her obstruction of lawful government functions,” Frohling wrote.

He said Dugan did a disservice to several constituents, including the victims of Flores-Ruiz, who were left bewildered in court the day of the incident.

“She placed the interests of a criminal defendant above the rights of his victims, used her colleague to unwittingly facilitate the crime, and placed law enforcement agents and members of the public in danger by undermining an arrest plan, resulting in a foot chase through moving traffic outside of the courthouse.”

The defense said the case has had ripple effects across Dugan’s life. She had to move out of her home and has a security detail because of threats made against her, their memo says.

“Whether deserved or not, the ongoing residual effect was to force Hannah Dugan into life as a recluse.”