Former Milwaukee judge loses last-chance appeal of ICE obstruction conviction

MILWAUKEE (CN) — A federal judge upheld former Milwaukee County Circuit Court Judge Hannah Dugan's felony obstruction conviction on reconsideration Tuesday.

A jury convicted Dugan of obstructing U.S. Immigration and Customs Enforcement officers but acquitted on the lesser charge of concealing an individual set for deportation following a weeklong trial just before Christmas. She faced up to five years in jail for the felony.

Dugan swiftly appealed the verdict, asking U.S. District Judge Lynn Adelman to order a new trial based in part on her repeated claim of immunity for acts done within her purview as a judge controlling her courtroom.

Adelman, a Bill Clinton appointee, denied the motion but noted that a decision in the pending appeal in United States v. Hernandez could cause him to later reverse course. The appeal was decided in April, prompting Dugan to ask the court again to reconsider her conviction.

The court held oral arguments Wednesday on the motion, where defense attorney Steven Biskupic argued the Fourth Circuit's narrowed definition of "pending proceeding" should be applied to Dugan's case.

"Right now there are, what, 10 million people estimated to be here illegally," Biskupic said. "That's 10 million potential proceedings. That cannot be. This [hearing] is a proceeding, but walking through the metal detector this morning was not a proceeding."

Federal prosecutors relied heavily on an expansive definition of "pending proceeding" throughout Dugan's trial which encompasses the obstruction of an ICE administrative arrest warrant, such as the one at issue in Dugan's case.

The Fourth Circuit reversed course on the subject, ruling in Hernandez that executing an ICE administrative warrant is pure police action falling under the exception of the felony obstruction law.

Assistant U.S. Attorney Richard Frohling argued that the proceeding here began in March 2024 when immigration officers identified Eduardo Flores-Ruiz — the subject of the warrant that Dugan obstructed — as a target for removal and ended when he was deported last summer.

Adelman took issue with this timeline: "So the proceeding was six months long? That's your view? Isn't there a sort of instinctive sense that it's a pretty long time for a proceeding?"

"Well, how long have we been in this proceeding?" Frohling said, gesturing with his hands to the grand courtroom.

"That's the question — have we been in this proceeding for 20 minutes or for over a year?" Adelman said in rebuttal.

Frohling conceded to Adelman's critique, later noting the government's view that Hernandez was wrongly decided and should not be controlling in this case.

Dugan's looming sentencing was postponed to hear reconsideration arguments.