A federal judge has denied a request by former Milwaukee judge Hannah Dugan to either overturn her December conviction for obstructing an immigration proceeding. In a 32-page decision filed Tuesday, U.S. District Judge Lynn Adelman disagreed with Dugan’s attorneys that a recent appeals court decision that immigration enforcement actions are not “proceedings” means  her conviction should be overturned. 

In early 2025, Dugan was in court when she learned of that plain-clothes immigration agents were in the hall outside her courtroom, waiting to arrest Eduardo Flores-Ruiz, who was appearing for a routine hearing, for being in the country illegally. How to handle immigration enforcement had been a top concern among local judges, following a string of arrests by federal agents in and around the Milwaukee County Courthouse. Neither the county sheriff nor the Milwaukee Police Department participate in immigration enforcement and detention. 

Dugan confronted the agents in her judge’s robes, and directed them to check in with the chief judge. When most of the arrest team went to the office, Dugan went back into her courtroom and called Flores-Ruiz, set a new court date, and then led  him and his attorney out of the courtroom through a non-public hallway. Flores-Ruiz rode down in an elevator with one of the federal agents and was arrested outside after a brief foot pursuit. Dugan was later charged with obstructing agents and concealing Flores-Ruiz from them.

The appeals court decision centered around United States v. Hernandez, involving a man who’d been charged with obstruction after escaping immigration custody. In that case, the defendant argued that executing his removal order was not part of the proceeding, which ended once the final removal order was issued. When Dugan went to trial, the Hernandez case was still on appeal. Adelman instructed Dugan’s jury that “‘pending proceeding’ simply means any process taking place in the manner and form prescribed for conducting business by or before a department or government agency, including all steps and stages in such an action from its inception to its conclusion.” Federal agents testified that there are a number of steps in an immigration proceeding, beginning before an arrest and continuing through removal.

When Adelman approved the jury instructions, which were recommended by prosecutors, he relied on United States v. Hernandez. Adelman said that the instructions proposed by the defense team defined “proceeding” too narrowly. “In the present case, the government alleged that defendant obstructed an arrest (step eight),” Adelman wrote in his decision denying Dugan acquittal or a re-trial. Adelman also wrote that motions for reconsideration serve the limited function of correcting errors of law or fact, or to present newly discovered evidence. “Motions for reconsideration are not to be granted lightly,” Adelman wrote. 

Dugan’s attorneys argued that Adelman originally relied on the Hernandez case in deciding that “proceeding” was broad enough to include obstructing immigration agents from executing an administrative warrant. Now that an appeals court reversed the decision in Hernandez and ruled that  immigration enforcement is not a “pending proceeding” as presented to Dugan’s jury, they said Adelman should reconsider his own decision and grant an acquittal. 

Prosecutors countered that the Hernandez ruling “is neither binding nor persuasive, and thus fails to satisfy the ‘heavy burden required for consideration,’” according to Adelman’s summary of the arguments. 

“The problem for the defense is that this case did not involve some random encounter on the street,” Adelman wrote. “It was a targeted operation, conducted pursuant to agency procedures, including the issuance of an arrest warrant for a specific person.” Adelman also wrote that classifying immigration enforcement as “mere police activity” is inappropriate, as “the FBI, ICE can issue its own warrants and adjudicate and effectuate a removal…without the involvement of a court.”

For those reasons, Adelman ruled that the burden for reconsideration in Dugan’s case had not been met. A new court date for Dugan’s sentencing or other proceedings was not yet available Tuesday in online court records.