A criminal trial in Milwaukee is turning court staff into witnesses in a first-of-its kind case testing the limits over how much a state judge must help—or can hinder—Trump officials seeking to deport migrants.
On Monday, Assistant US Attorney Keith S. Alexander told the jury that Milwaukee County trial judge Hannah Dugan obstructed a federal immigration proceeding and concealed a US Immigration and Customs Enforcement target in April. That action—escorting him out a side door from her courtroom away from awaiting federal officials—is enough to put a judge behind bars, they say.
“‘I’ll do it, I’ll get the heat.’ That’s what the defendant Hannah Dugan said when she was using her role as a judge to help a man accused of battery in her courtroom avoid a lawful federal arrest,” Alexander said to the jury inside the Eastern District of Wisconsin courthouse.
The trial is a rare glimpse into the processes and staff that keep local courts moving, but also the struggle of state officials accommodating aggressive immigration enforcement under the Trump administration.
Pretrial motions indicate the government is pushing to keep the issue of intent away from national politics, instead focused narrowly on what happened April 18 when Eduardo Flores-Ruiz appeared in Dugan’s courtroom and was ushered away from authorities who later caught him outside the Milwaukee County courthouse. Dugan was arrested one week later.
‘Above the Law’
Dugan’s legal team is led by former US Attorney for the Eastern District of Wisconsin Steven M. Biskupic, a high-profile conservative appointed by George W. Bush. He said shifting federal immigration policy caused widespread confusion among state jurists seeking guidance on ICE arrests in their courts.
“Judges in all cases try to balance the interest of the parties. They’re not here to just serve ICE, they’re not here to serve one side of or the other—they’re here to balance,” said Biskupic at the end of a 20-minute opening statement in Judge Lynn Adelman’s courtroom.
Alexander said the evidence was clear that Dugan altered the way she normally runs her courtroom so Flores-Ruiz, a migrant who had been previously deported, couldn’t again be sent back to Mexico.
“The judicial robe the defendant wore that day did not put her above the law,” Alexander said.
The prosecutors showed video evidence of Dugan speaking with ICE officers in a public hallway who came to the courthouse to apprehend Flores-Ruiz.
The prosecution says that minutes after Dugan confronted officers in her hallway she quickly canceled the defendant’s case. Captured on audio, the jurors heard how she spoke with her court staff, suggesting the defendant could go “down the stairs” away from the agents. When her staffer expressed concern she could get in trouble, Dugan said, “I’ll do it. I’ll get the heat,” and escorted him and his lawyer through a side door normally used by jurors that led to a hallway.
That hallway could have led Flores-Ruiz down stairs and away from the arresting officers. Instead, Alexander said, his inexperienced public defender led him back into the public hallway.
“An arrest that was supposed to happen in the public hallway in a courthouse turned into a footchase,” Alexander said.
‘Anger, Confusion and Paranoia’
The prosecution said they could call more than two dozen witnesses, including the staff in and around the massive Milwaukee County Courthouse.
At least one judge, and court staff and lawyers practicing in Dugan’s courtroom will be called, Alexander said, and they all will say Dugan’s actions were not routine.
“She has strong views about immigration enforcement. For none of that is she on trial,” he said. “She’s on trial today because those strongly held views motivated her to make a decision to cross the line.”
Those views came from the “anger, confusion and paranoia” judges in Milwaukee were facing in the light of arrests in their courthouse, Biskupic said.
Judges had urged court leaders to draft guidance after migrants had been arrested before hearings, with one arrest tacking place in the gallery of a courtroom. Jurors were shown how Dugan herself emailed colleagues discussing how attendance at her hearings was down because of the fear of ICE arrests.
In light of these concerns the courthouse issued draft guidance, requiring ICE officers to check in with the chief judge prior to arrests. Biskupic said Dugan was only following correct policy to ensure the courthouse was orderly.
“We’re in uncharted waters. You show up at a hearing, you’re sitting in the gallery, can ICE just come up and arrest you?” Biskupic said. “Little did she know it was her head that was going to be at risk with these policies.”
The case is U.S. v. Dugan, E.D. Wis., No. 2:25-cr-00089, trial 12/15/25.
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