Fourteen months ago, Hannah Dugan was handing down rulings from the bench in Milwaukee County. On July 8, she sits on the other side of a federal courtroom, waiting for U.S. District Judge Lynn Adelman to decide whether her felony conviction for shielding a defendant from immigration agents ends in prison time.
The Justice Department isn't hedging. In a sentencing memorandum reported by Law&Crime, prosecutors argue that "a serious sentence is necessary to reaffirm a foundational principle of our criminal justice system: no one is above the law, particularly those entrusted with administering it." Dugan's lawyers want the opposite: a sentence of time served, on the grounds that public humiliation, a security detail, and a shattered career already amount to punishment enough.
What Happened Inside the Milwaukee County Courthouse
The case begins on April 18, 2025, when a team of ICE, FBI, DEA and Customs and Border Protection officers showed up at the Milwaukee County Courthouse to execute an arrest warrant for Eduardo Flores-Ruiz, a Mexican national who'd been deported once before, reentered the country illegally, and was due in Dugan's courtroom on domestic battery charges. Per the Justice Department's own charging announcement, Dugan left the bench, confronted the agents waiting in the hallway, insisted — incorrectly — that they needed a judicial rather than an administrative warrant, and sent them down the hall to the chief judge's office. With the agents out of sight, she skipped Flores-Ruiz's scheduled hearing and walked him and his attorney out through a restricted jury door instead of the courtroom's public exit. Agents spotted him in the corridor moments later and caught him after a short foot chase outside the building.
Flores-Ruiz was deported that November, CNN's coverage of the verdict noted.
A Split Verdict, a Resignation, and a Long Legal Fight
A federal jury took six hours to reach its verdict on December 18, 2025, convicting Dugan of one felony count of obstructing a federal proceeding while acquitting her of a related misdemeanor charge of concealing a person from arrest, according to the Wisconsin Examiner. Her lead attorney, Steve Biskupic, told reporters afterward that he couldn't reconcile how a jury could split its verdict on two charges built from nearly identical elements, WTMJ reported. Dugan resigned her seat on the circuit court on January 3, as Republican state lawmakers pushed toward impeachment.
Her attorneys have tried twice to undo the conviction — and lost twice. Adelman first rejected a bid for acquittal or a new trial in early April. Then, after a Fourth Circuit panel ruled in an unrelated Virginia case that an ICE arrest doesn't automatically count as a "pending proceeding" under the same obstruction statute, Dugan's team asked Adelman to reconsider — a request detailed by Courthouse News Service. That fight pushed her original June 3 sentencing date off the calendar entirely, replaced instead with oral arguments. Adelman sided with the government again on June 16, writing that Flores-Ruiz's case involved "a targeted operation, conducted pursuant to agency procedures," not a random street encounter — clearing the way for the July 8 date. Dugan intends to appeal to the 7th U.S. Circuit Court of Appeals no matter what sentence she receives.
The Math Behind the Sentencing Fight
A presentence report pegs Dugan's guideline range at 15 to 21 months, with a statutory ceiling of five years, and prosecutors note — without formally recommending a number — that obstruction defendants with clean records typically draw sentences averaging around 16 months, based on the Milwaukee Journal Sentinel's review of the dueling memos, republished by the Chippewa Herald. Dugan's team counters that the guideline calculation is inflated and that a realistic range runs from zero to six months — roughly matching the single day she spent in federal custody after her arrest. Adelman isn't bound by any of these figures; he's known for sentencing below guideline ranges, though not in every case, the same reporting notes.
Two Portraits of the Same Woman
Dugan's sentencing memo leans on nearly forty years in the law and nine years on the bench, framing the courthouse incident as roughly five minutes of bad judgment at the end of an otherwise unblemished career. Her filing describes life since the arrest as a kind of forced seclusion — moving out of her home, taking on a security detail, giving up public appearances — and includes close to twenty letters of support, among them one from longtime former Milwaukee County District Attorney E. Michael McCann.
Prosecutors read the same biography differently. Her decades of legal training, they argue, mean she understood exactly what she was doing and chose to do it anyway — and her continued insistence that her actions were lawful, rather than any expression of regret, is itself an aggravating factor for the court to weigh.
A Case the Administration Has Repeatedly Framed as a Warning
Dugan's prosecution has become a recurring talking point for an administration eager to signal that judicial resistance to immigration enforcement carries consequences. Attorney General Pam Bondi used the phrase "no one is above the law" both when Dugan was first arrested in April 2025 and again after her December conviction, according to a reporter's contemporaneous post documenting Bondi's reaction to the verdict.
What Comes Next
Dugan is expected to address the court herself on July 8 — the first time she has spoken publicly about the case since her arrest, having declined to testify during her four-day trial. Whatever sentence Adelman hands down, it's unlikely to be the final chapter: Dugan's appeal to the 7th Circuit is already teed up, and legal observers say the case's underlying legal question — what counts as a "pending proceeding" under the obstruction statute — could eventually reach the U.S. Supreme Court.
