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.

As former Milwaukee Judge Hannah Dugan approaches sentencing after being convicted of obstructing federal agents during an immigration arrest last year, attorneys on both sides of the case are battling over whether new precedents around federal statutes should apply to the former Milwaukee County Circuit Court judge. 

The FBI arrested Dugan last year on charges she helped a man who was making a routine appearance in her court evade immigration officers who were waiting for him in the public hallway outside the courtroom. 

Court staff initially noticed the agents and informed Dugan, who approached them and told the agents to go check in with the chief judge. 

While the agents waited to talk to Chief Judge Carl Ashley, Dugan went back to her courtroom and quickly called 30-year-old Mexican-born Eduardo Flores Ruiz and his attorney, set a date for them to come back, and then allowed them to exit the courtroom through a non-public hallway, at the end of which was a door back into the hallway where the agents waited. After going out that door, Flores-Ruiz and his attorney unknowingly rode the elevator down with one of the undercover agents. Flores Ruiz was arrested outside after a brief foot pursuit. 

Dugan was charged with obstructing federal agents and concealing Flores Ruiz. After a trial in December, a federal jury found Dugan guilty of felony obstruction but not guilty of misdemeanor concealment. Dugan’s attorneys highlighted the split verdict and moved for U.S. District Judge Lynn Adelman to overturn the conviction. 

In April, Urban Milwaukee reported, Dugan’s legal team filed a motion arguing that a recent U.S. Circuit Court of Appeals decision changed the precedent governing the legal interpretation of the federal statute under which Dugan was convicted. The decision, in United States v. Hernandez, held that immigration proceedings do not include deportation operations, relevant since Dugan, who resigned shortly after her trial, was convicted of obstructing an immigration “proceeding.” 

Federal prosecutors have countered that the appeals court decision “is neither binding nor persuasive, and it does nothing to call into question this Court’s reasoning.” They argue that the jury instructions crafted by prosecutors and provided to the jury by Judge Adelman over instructions crafted by the defense team were sound. Adelman had previously denied a request from Dugan’s legal team for acquittal and a new trial.

Dugan faces up to five years in prison and $350,000 in fines. Her sentencing is scheduled for June 3.