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A federal judge postponed the sentencing of now-former Milwaukee County Judge Hannah Dugan and set the stage for oral arguments on her motion for a judgment of acquittal or a new trial.
Typically, such post-trial motions are extremely difficult to win because federal judges are reluctant to disturb a jury’s verdict in a criminal case.
In a Substack Live, former U.S. Attorney Harry Litman and I explain why the legal landscape has changed, and a federal judge appears to be taking Dugan’s latest motion seriously.
The critical jury instructions
First, here’s a refresher on a case that could have substantial ramifications for the Trump administration’s attacks on the judiciary.
In April 2025, then-Judge Dugan was arrested on charges of concealing an undocumented immigrant in her courtroom, Eduardo Flores-Ruiz, from federal authorities and obstructing his arrest. The jury’s mixed verdict surprised many legal observers: The panel cleared Dugan of the misdemeanor concealment charge and convicted her of felony obstruction.
As jurors later clarified in an interview with the Milwaukee Journal-Sentinel, the seeming disconnect came down to U.S. District Judge Lynn Adelman’s instructions. There was no direct evidence that Dugan knew specifically that ICE agents had come to arrest Flores-Ruiz, and jurors asked the judge for guidance about whether Dugan needed to know the identity of the individual ICE wanted to arrest.
On the concealment count, Adelman’s instructions made clear that Dugan needed to know that ICE wanted to arrest Flores-Ruiz. On the obstruction count, Adelman told jurors that Dugan needed “sufficient knowledge” about the nature of the immigration proceedings at issue.
The mixed verdict shortly followed those instructions, which have been central to Dugan’s attempts to overturn her conviction.
Judge Adelman crafted his instructions on the obstruction charge partly based on an out-of-district precedent that he said he found “persuasive”: U.S. v. Hernandez. Following her conviction, that precedent was overturned.
‘A case of first impression’
Almost a year after Dugan’s arrest, the Fourth Circuit overturned the case of Dennis Zeledon Hernandez, a noncitizen who escaped from ICE custody and was charged with obstructing his own immigration proceedings.
The federal appellate court found that immigration enforcement does not constitute “pending proceedings.”
For Dugan’s defense, the finding is explosive.
Although Fourth Circuit precedent is not binding on the Eastern District of Wisconsin, it was said to be a “case of first impression,” meaning that no other appellate court had addressed the question. What’s more, the Hernandez precedent overturns the specific lower court ruling that Adelman found “persuasive.”
Adelman appears to agree that Dugan’s argument is substantial.
After initially denying Dugan’s post-trial motions on written briefings alone, Adelman has scheduled oral arguments to decide whether to reconsider his ruling. The ramifications here could be enormous. Dugan resigned her judgeship in the wake of her conviction, and accepting the Fourth Circuit’s reasoning could result in a judgment of acquittal.
As Harry Litman and I discuss, interpreting the statute (18 U.S.C. 1505) to rule out prosecutions for obstructing immigration arrests would disarm the Trump administration’s attempts to threaten judges with felony prosecution for protecting the integrity of their courthouses.
It would also turn a rare victory in a high-profile Trump Justice Department case into another embarrassing defeat.
Oral arguments on the matter are scheduled for Weds., June 3 at 10 a.m. Central Time.
Watch the analysis in full in the video at the top of this newsletter, and read Dugan’s legal brief in full here.
