Judge Listens to Arguments As Dugan Case is Reopened

Milwaukee Federal Courthouse. Photo by Mariiana Tzotcheva

In December, a jury was empaneled, a trial was held and former Milwaukee County Circuit Court Judge Hannah Dugan was convicted of one count of obstruction of a federal proceeding.

The proceeding in question was an immigration enforcement operation carried out by federal agents seeking to arrest an immigrant appearing in Dugan’s courtroom on April 18, 2025 — or was it?

That’s the question that has brought Dugan’s trial back to the federal courtroom where the verdict against her was decided just over five months ago. Recently, the 4th U.S. Circuit Court of Appeals overturned a decision in United States v. Hernandez, altering the case law also at the center of the case that resulted in Dugan’s conviction. That conviction now hinges on the court’s interpretation of the word “proceeding” as written in the federal statute under which Dugan was convicted.

On that day in April, when Dugan spoke to U.S. Immigration and Customs Enforcement (ICE) agents in the hallways of the Milwaukee courthouse and sent their target, Eduardo Flores-Ruiz, out a side door of her courtroom, the federal government argued that a pending immigration proceeding was occurring. Dugan’s attorneys argue it was merely a law enforcement operation, not a pending proceeding; therefore, Dugan could not be convicted of obstructing a pending proceeding.

“This was an invalid theory of conviction,” attorney Steven Biskupic, a former U.S. attorney representing Dugan, said during oral arguments for a motion hearing Wednesday before U.S. District Judge Lynn Adelman.

The defense is asking the court to reconsider Dugan’s conviction in light of the new legal interpretation advanced in the U.S. v. Hernandez decision in the 4th U.S. Circuit. That decision declared a distinction between a pending proceeding and a law enforcement action. The actions taken by federal agents on the day in question affecting Dugan were “quintessential” law enforcement actions, not actions contained within a larger proceeding, and to argue otherwise would be to expand the scope of a proceeding to everything ICE does, Biskupic contended.

In the Hernandez case, the federal government accepted the decision of the 4th U.S. Circuit and did not challenge dismissal of the case — “the same federal government that says Hernandez was wrongly decided,” Biskupic said.

The U.S. Attorney’s Office for the Eastern District of Wisconsin sees it differently. The 4th U.S. Circuit “wrongly decided” the case, and decisions in appellate courts going back to 1966 support a broad interpretation of “pending proceeding,” Executive Assistant U.S. Attorney Richard G. Frohling argued Wednesday. The case law was “properly applied” the first time around, he said. A pending proceeding, he said, covers all acts, from issuing a warrant to arresting an individual and so on. When Flores-Ruiz was arrested, there was an active civil immigration proceeding that was separate from the law enforcement consideration of potential criminal charges against Flores-Ruiz for being in the country illegally, he argued.

The hearing Wednesday was initially scheduled as a sentencing hearing. It was changed to a motion hearing after the defense pushed for acquittal under the new case law. If Dugan’s conviction stands, she could be sentenced to a fine or imprisonment for up to five years, or both.

Regardless of Adelman’s decision on the motion, Dugan will still be able to appeal the case to the 7th Circuit Court of Appeals, where her attorneys could advance the same arguments in support of acquittal.