Obstruction in a Robe is still Obstruction

On December 18, 2025, a Milwaukee County jury did something refreshingly old-fashioned: it applied the law. The result? Circuit Judge Hannah Dugan—yes, that Judge Dugan—was convicted of felony obstruction of justice for allegedly helping a Mexican immigrant slip past federal ICE agents who were waiting outside her courtroom like extras in a very unamused episode of Law & Order.

According to the record, this wasn’t some abstract act of resistance or a clerical misunderstanding. In April, prosecutors say Dugan physically escorted the man out a side exit and pointed federal agents in the wrong direction. Not a ruling. Not an opinion. A hallway maneuver.

The jury acquitted her of a misdemeanor count of concealing a person from arrest, but let’s not kid ourselves—that’s like being cleared of jaywalking after getting nailed for grand theft auto. The felony obstruction conviction is the one that matters. It carries up to five years in prison and, under Wisconsin law, effectively hands in her judicial resignation for her.

Even The New York Times—not exactly ICE’s biggest fan—acknowledged the obvious: convicted felons don’t get to keep wearing the robe.

Cue the predictable outrage. Supporters are framing Dugan as a martyr to conscience, a brave jurist standing athwart an unjust immigration system. That’s a compelling story—until you remember she wasn’t running a protest. She was running a courtroom. Judges don’t get to freelance immigration policy between hearings.

This wasn’t a ruling from the bench. It was a logistical assist.

And no, this isn’t unprecedented. In 2019, Massachusetts Judge Shelley M. Richmond Joseph pulled a similar stunt and was charged with obstruction. But that case fizzled—charges dropped, resignation tendered, awkward silence all around. Dugan didn’t get that graceful exit. Her case went to a jury. And the jury wasn’t interested in vibes, intentions, or virtue signaling.

Here’s the part that seems to confuse people: judicial independence means freedom from political pressure—not freedom from the law itself. A judge is not a resistance fighter. The courtroom is not a sanctuary city. And a side door is not a legal argument.

You don’t get to obstruct federal agents and then hide behind the bench like it’s a moral force field.

From a Valley Viewpoint, this case isn’t really about immigration. It’s about arrogance. About what happens when someone in power decides that their beliefs outrank the system they swore to uphold. And about a justice system that, for once, didn’t blink just because the defendant wore a robe.

Lesson learned: the law doesn’t care how righteous you feel—especially when you’re pointing people toward the exit.

Published by Ed Kowalski

Ed Kowalski is a Pleasant Valley resident, media voice, and policy-focused professional whose work sits at the intersection of law, public policy, and community life. Ed has spent his career working in senior leadership roles across human resources, compliance, and operations, helping organizations navigate complex legal and regulatory environments. His work has focused on accountability, risk management, workforce issues, and translating policy and law into practical outcomes that affect people’s jobs, livelihoods, and communities. Ed is also a familiar voice in the Hudson Valley media landscape. He most recently served as the morning host of Hudson Valley This Morning on WKIP and is currently a frequent contributor to Hudson Valley Focus with Tom Sipos on Pamal Broadcasting. In addition, Ed is the creator of The Valley Viewpoint, a commentary and narrative platform focused on law, justice, government accountability, and the real-world impact of public policy. Across broadcast and written media, Ed’s work emphasizes transparency, access to justice, institutional integrity, and public trust. Ed is a graduate of Xavier High School, Fordham University, and Georgetown University, holding a Certificate in Business Leadership from Georgetown. His Jesuit education shaped his belief that ideas carry obligations—and that leadership requires both discipline and moral clarity. He lives in Pleasant Valley.

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