Milwaukee judge appeals ICE obstruction conviction as sentencing looms

MILWAUKEE (CN) — Armed with new precedent, former Milwaukee County Circuit Court Judge Hannah Dugan took another crack this week at overturning her conviction for obstructing federal immigration enforcement.

In an incident last April that drew nationwide attention, Dugan helped a man evade immigration agents by sending them to an office — then ushering the man down a private hallway. A jury in December convicted her of felony obstruction. They acquitted her of a lesser charge of concealing an individual facing deportation.

In January, Dugan filed a post-trial motion in January asking U.S. District Judge Lynn Adelman, a Bill Clinton appointee, to overturn her conviction or order a new trial. Adelman denied her motion, setting sentencing for June.

Dugan took another big swing on Wednesday, filing a motion to reconsider. The motion relies on a recent opinion out of the Fourth Circuit, which Dugan says invalidates the very premise on which she was convicted.

"This court repeatedly relied upon a district court decision that has now been reversed," Dugan says in the 9-page motion. "The factual and legal record in this case cannot be squared with the Fourth Circuit holding."

To break it down: Dugan says that to convict her, Adelman, government prosecutors and ultimately the jury relied on a definition of "pending proceeding" that included the execution of an ICE arrest warrant. Under that definition, which comes from United States v. Hernandez, Dugan was determined to have obstructed a pending proceeding.

Jury instructions included this definition, which led them to convict Dugan even if she didn't know at the time who exactly was named on the warrant — an issue of much debate during jury deliberations.

In his order denying Dugan's January motion for acquittal, Adelman said he found the Hernandez ruling was persuasive but noted that an appeal in Hernandez's case could upend precedent.

That's exactly what happened. Considering Hernandez, a Fourth Circuit panel in April determined that ICE efforts to apprehend a migrant are not inherently a proceeding, reversing a lower court ruling.

That case involves Dennis Hernandez, who was taken into ICE custody soon after a Department of Homeland Security warrant for removal was issued in 2023. He escaped soon after, according to court documents, then was recaptured.

The government charged Hernandez with obstructing an immigration proceeding using the same statute under which Dugan was convicted. On appeal, he argued that there was no pending proceeding when he escaped.

The Fourth Circuit agreed. By the time ICE recaptured Hernandez — thus carrying out an immigration court's judgment — "the hearing before the immigration court had concluded," U.S. Circuit Chief Judge Roger Gregory, a Bill Clinton appointee, wrote in a 17-page opinion. Therefore, Hernandez "was no longer 'awaiting decision' from the immigration judge."

Dugan says the ruling narrows the definition of pending proceedings, clarifying that enforcement proceedings are not included in the obstruction law under which both she and Hernandez were charged.

Prosecutors argued Dugan had committed obstruction because officers were trying to execute an administrative warrant that was just one step in overall removal proceedings. But "regardless of ICE's broader powers, the execution of a removal warrant is 'mere police' activity that has long been excluded from the definition of a proceeding," Dugan argues, citing the Fourth Circuit opinion from April 16.

Even so, the Fourth Circuit's consideration was a matter of first impression — meaning no other circuit has yet looked into the nuances of the issue. As such, it offer limited guidance for how to read the obstruction statute.

In her motion, Dugan flips that logic on its head, arguing the lack of comparable rulings show how novel and unsettled the issue is. The stakes are high for the former judge: If ultimately sentenced, she could face up to five years in prison.