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.

U.S. District Judge Lynn Adelman found the case at the center of Dugan’s appeal is not similar enough to the present case to meet the heavy burden of reconsideration.

“The problem for the defense is that this case did not involve some random encounter on the street,” the Bill Clinton appointee reasoned in his 32-page order. “It was a targeted operation, conducted pursuant to agency procedures, including the issuance of an arrest warrant for a specific person.”

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 the judge 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 initially 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.

Adelman said in Tuesday’s ruling that Dugan oversimplified the order, and downplayed the differences between this case and the facts of Hernandez.

Particularly, in the latter case, a different government agency had already ordered Dennis Zeledon Hernandez’s removal when ICE issued a warrant and took him into custody. A few days before his scheduled removal, he escaped.

His escape was obstruction of the proceedings against him, but because ICE issued the warrant for removal after an immigration court had already decided he was to be removed, the warrant was not part of the proceeding and considered “pure enforcement action.”

Here, Dugan obstructed a part of ICE’s investigation into whether Flores-Ruiz had violated federal law by returning to the United States without permission, according to Adelman.

The obstructive conduct in the present case occurred before a final removal order was issued — a period fully covered by the law under which Dugan was convicted, supported by a larger body of more relevant case law than that found in the novel decision in Hernandez.

“Reading Hernandez more broadly — to exclude all ICE enforcement and removal operations, regardless of the stage, from [the obstruction law] — cannot be reconciled with the plain language of the statute or the existing case law,” Adelman said. “Perhaps the Seventh Circuit will pare back its obstruction case law based on the authorities defendant cites, but it is not for this court to anticipate such a change.”

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.

While *Hernandez *is the first case to directly address ICE removal actions under the federal obstruction statute, other courts have addressed the scope and its applicability to various agency actions.

Adelman noted several cases which explore the limitations of the obstruction statute, all of which read together make it impossible to exclude all enforcement actions or investigations.

The parties could not be immediately reached for comment. Dugan’s sentencing has not yet been rescheduled.

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