Prosecutors say former Milwaukee County Judge Hannah Dugan committed a “serious offense” that deserves a “serious sentence.”
Her attorneys, however, say the 67-year-old has already been punished enough after being arrested, resigning from her judgeship and facing threats as the high-profile case played out. They asked a federal judge to sentence Dugan to “time served” — which means she would not receive any additional punishment.
In December, a jury found Dugan guilty of impeding or obstructing an official proceeding. The felony conviction stems from an incident on April 18, 2025. That’s when Dugan led a man through a side door of her Milwaukee County courtroom after federal agents showed up at the courthouse to arrest him for being in the country illegally.
Understanding Wisconsin, Together.
WPR’s “Wisconsin Today” newsletter keeps you connected to the state you love without feeling overwhelmed. No paywall. No agenda. No corporate filter.
Now, Dugan’s case is set for sentencing on July 8 before U.S. District Judge Lynn Adelman. Dugan will speak during that hearing, her attorneys wrote in a memo submitted Wednesday. That will mark her first time addressing the court directly in the case, since Dugan did not take the stand during her four-day trial in Milwaukee.
In a memo filed Wednesday, prosecutors told Adelman that Dugan’s sentence should reflect the “serious nature of her conduct.” Under federal law, her conviction carries a maximum penalty of five years in prison.
In their recently-filed memo, prosecutors did not recommend exactly what Dugan’s sentence should be, although they did suggest that, based on federal guidelines outlined in a pre-sentencing report, 15 to 21 months in prison would be “reasonable.”
Dugan’s defense team disputed that conclusion. They pointed to Dugan’s lack of a criminal history, and said there was no possibility of her repeating the offense for which she was convicted.
“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,” defense attorneys wrote. “There is no need for further deterrence, either specifically or generally.”
Defense attorneys highlighted Dugan’s history of public service, which included roles with the Legal Aid Society of Wisconsin, Catholic Charities of Milwaukee and the City of Milwaukee Ethics Board. Dugan also served on the Wisconsin Judicial Commission — a body that investigates misconduct allegations against judges — from 2000 to 2006.
The defense also submitted letters from Dugan’s seven siblings, and from prominent figures including E. Michael McCann, a Democrat who spent four decades as Milwaukee County District Attorney. McCann told the court Dugan has been profoundly influenced by her Catholic faith.
“Some lawyers perform such work simply because it provides a living,” McCann wrote. “I know Hannah Dugan and she was an attorney who assisted poor people because they were in need and required help. She was free of disdain for their often limited economic situations.”
Prosecutors, however, contended that Dugan’s civic involvement does not excuse her actions on April 18. Rather they said, it’s clear that she knew what she was doing was wrong.
“Unlike many defendants who appear before this Court, the defendant has led a privileged life,” prosecutors wrote. “Her background suggests that she had no reason to involve herself in criminally obstructive conduct.”
They argued her offense was especially egregiously because she abused her power as a judge in order to obstruct federal officers. And they suggested she had been motivated by her personal feelings about immigration enforcement.
“Public officials must understand that they cannot substitute personal viewpoints for legal duty,” they wrote.
On April 18 of last year, a team of six federal agents entered the courthouse with an immigration-related warrant for the arrest Eduardo Flores-Ruiz.
Flores-Ruiz had been scheduled to appear in Dugan’s courtroom that day on domestic battery charges.
But, after those agents arrived and informed court officials of their arrest plans, Dugan directed Flores-Ruiz through a side door of her courtroom and said that his hearing would be rescheduled. Agents chased Flores-Ruiz down on foot and arrested him just outside the courthouse. He was later deported to Mexico.
By “intentionally thwarting” the agents’ plans, Dugan’s actions on that day put others in danger, prosecutors argued.
“What was planned as a low-key, safe arrest involving six law enforcement officers in a public area within the courthouse turned into a foot chase outside of the courthouse by a portion of the team through moving traffic,” the U.S. attorney’s office wrote.
Dugan’s attorneys have repeatedly argued that her case was wrongly decided. So far, their attempts to overturn her conviction have been unsuccessful, but they could continue that process by filing an appeal after her sentencing.
How likely is prison time for Hannah Dugan?
In their recent filing, prosecutors pointed to federal sentencing data and said that the average sentence was 16 months in prison for people with little to no criminal histories who committed similar obstruction-related charges.
But John Gross, a criminal defense attorney who teaches at the University of Wisconsin Law School, argues it’s misleading to compare Dugan’s circumstances to those other cases.
“This is really an unprecedented case where you’re prosecuting a judge, and the only other similar case to this was a deferred prosecution agreement,” Gross said.
During the first Trump administration, federal prosecutors brought criminal charges against Massachusetts-based District Court Judge Shelly Joseph after she was accused of leading a man through a back door of the courthouse so that he could avoid immigration authorities. In 2022, after Democratic President Joe Biden took office, federal prosecutors agreed to dismiss the charges against Joseph as part of a plea deal that involved Joseph referring herself to the Massachusetts Commission on Judicial Conduct.
Dugan’s attorneys have argued — so far unsuccessfully — that on that fateful day last April, Dugan was merely exercising the authority a local judge has to run her own courtroom. They also attempted to argue — unsuccessfully — that immigration enforcement lacked the legal authority to carry out the type of arrest they had planned within the Milwaukee County courthouse.
“This is an instance where there were real questions about the legality of her conduct,” Gross said. “She’s going to appeal this and we could see an appellate court decide that she did have some level of judicial immunity, even though that wasn’t an argument that was adopted by the trial court.”
In their memo, prosecutors contended that a serious sentence is needed because Dugan’s actions undermined trust in the judicial system.
“The public must know that there are consequences for those who abuse their trust,” they wrote. “No one is above the law, particularly those entrusted with administering it.”
Nonetheless, Gross said it would be hard to conclude that Dugan needs to be incarcerated because she’s a danger to the public.
“What sense does it make to send Judge Dugan to jail?” he said, “I would be very surprised if the judge found that it was necessary and appropriate to sentence her to some period of incarceration.”
Wisconsin Public Radio, © Copyright 2026, Board of Regents of the University of Wisconsin System and Wisconsin Educational Communications Board.
