Former Wisconsin Judge Avoids Jail After Helping Mexican Man Evade ICE

ICE agents walked into the Milwaukee County Courthouse on April 18, 2025. They had a warrant. They knew where to find Eduardo Flores-Ruiz. He was in courtroom duty, waiting for his hearing, a Mexican citizen who had illegally reentered the United States.

What happened next turned a routine enforcement operation into a federal case that would end with a judge being sentenced by a judge.

Hannah Dugan, 67, a Milwaukee County circuit court judge, saw the agents coming. She told them to wait in the chief judge's office down the hall. Then she directed Flores-Ruiz and his attorney out the back door of her courtroom.

The agents did not find him inside. They caught up with him outside the courthouse. But the damage was done. The act of helping a defendant slip out the back to avoid federal immigration authorities landed Dugan in the middle of a legal showdown that cost her her career and nearly her freedom.

She will not go to prison. But she is no longer a judge.

On July 8, 2026, US District Judge Lynn Adelman fined Dugan $5,000 for felony obstruction of federal agents. No prison time. The decision surprised both sides of the debate.

Prosecutors had pushed for incarceration. Immigration hardliners had called for a strong message. Immigration advocates had called the charges an overreach. Adelman split the difference in a way that left almost no one fully satisfied.

In court, Dugan addressed the judge before sentencing. Cameras are not allowed in federal courtrooms, but reporters transcribed her statement. "For nine years, I have strived to administer justice fairly, uphold our laws, Constitution and decorum of the court and safety the public deserves," she said. "I did that with the same intentions on April 18, 2025."

She described the moment ICE agents arrived as a situation "previously unseen in the state courts." Her actions, she said, were not done with "any malicious intent." She said she was "just a public servant who was trying to do my job."

Adelman acknowledged the collateral consequences Dugan had already faced. She was suspended from the bench after her arrest, resigned in January 2026 under threat of impeachment by Wisconsin Republicans, and lost a career she had held for nearly a decade. Her pension was preserved, but her reputation was not.

"This amounts to significant punishment, regardless of what I do today," Adelman said at sentencing.

The Man at The Center of It All

Eduardo Flores-Ruiz was the reason ICE came to the courthouse that day. He had illegally reentered the United States after a prior deportation. His case was on Dugan's docket. When the agents arrived, she made a split-second decision that would define the rest of her career.

Flores-Ruiz was arrested outside the courthouse. He later pleaded guilty to illegal reentry and was deported in November 2025. He has not commented publicly on the case.

A jury found Dugan guilty of felony obstruction in December 2025 but acquitted her of a separate misdemeanor charge that accused her of helping Flores-Ruiz evade arrest. The split verdict reflected the ambiguity at the heart of the case: did she obstruct justice, or was she trying to maintain control of her courtroom?

The legal fight is not over

Dugan's defense attorney, Jason Luczak, said outside the courthouse after sentencing that the "collateral consequences" his client faced were severe. He announced plans to appeal the fine to the US Court of Appeals for the Seventh Circuit.

"We think the appellate process will play out, and we will be successful," Luczak said.

The appeal will likely center on the definition of "proceedings" under federal obstruction law. A separate ruling from the Fourth Circuit Court of Appeals in Virginia, issued in a different immigration case, found that obstructing an ICE arrest warrant did not count as interfering with a federal proceeding. Dugan's team argued that precedent should apply to her case. Adelman disagreed.

For now, the $5,000 fine stands. Dugan walks free. But the irony is hard to miss: a judge who spent years sentencing others was herself sentenced. She asked for mercy. She got it from a fellow judge.

The question of whether she deserved it depends entirely on which side of the courtroom you were sitting on.