Tensions Erupt as Judge Arrested for Allegedly Aiding Immigration Evasion in Milwaukee
On a fiery Saturday in Milwaukee, the streets outside the FBI office echoed with chants of “Immigrants are here to stay!” as protesters rallied behind a local judge caught in the crosshairs of an escalating immigration clash. Their signs, defiantly reading "Liberty and Justice for All," symbolized the broader resistance brewing across the country.
At the center of the storm? Milwaukee County Circuit Judge Hannah Dugan, arrested by FBI agents for allegedly helping a man evade immigration authorities right inside her own courthouse. Her case has quickly become a symbol of the mounting tension between state and local officials and the Trump administration’s aggressive immigration enforcement.
Here’s what’s unfolding:
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The Arrest:
Early Friday morning, Judge Dugan was taken into custody on courthouse grounds, a moment that stunned many in Wisconsin’s legal circles. She was later brought before a federal judge in Milwaukee and released, facing charges of concealing an individual to prevent his discovery and arrest and obstructing or impeding a proceeding. -
The Incident:
According to an FBI affidavit, Judge Dugan was reportedly furious after learning that U.S. Immigration and Customs Enforcement (ICE) agents were lurking around the courthouse, waiting to arrest a man named Eduardo Flores-Ruiz. Witnesses say she called the situation “absurd,” left the bench in anger, and ultimately helped Flores-Ruiz and his attorney slip out a jury door — a route typically reserved for jurors and in-custody defendants, not free civilians. -
The Fallout:
Flores-Ruiz, who has a troubling history of domestic violence charges, didn’t get far. Federal agents chased him down outside the courthouse and arrested him after a brief foot pursuit. Court records reveal that he had been deported back in 2013 but reentered the U.S. unlawfully.
The Bigger Picture: A Brewing Battle Over Immigration and Judicial Independence
Judge Dugan’s dramatic arrest isn’t just about one man slipping through a courthouse door — it’s about two branches of government clashing head-on.
President Trump’s administration has long accused state and local officials of undermining federal immigration priorities, and this case provided yet another flashpoint. U.S. Attorney General Pam Bondi didn’t mince words: “The rule of law is very simple. It doesn't matter what line of work you're in. If you break the law, we will follow the facts and we will prosecute you,” she declared in a video posted on X (formerly Twitter).
The White House doubled down, emphasizing that no one is above the law — an ironic rallying cry considering critics, both Democratic and Republican, have pointed out Trump's own legal troubles.
Democrats Fight Back
Meanwhile, Wisconsin Democrats came out swinging in defense of judicial independence:
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State Rep. Ryan Clancy fired up the crowd during Saturday’s protest, declaring, "Functioning democracies do not lock up judges."
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Governor Tony Evers issued a sharp statement accusing Trump’s team of using "dangerous rhetoric" to attack the judiciary.
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Senator Tammy Baldwin warned that arresting a sitting judge could “threaten the separation of powers between the executive and judicial branches.”
In short: this isn’t just legal drama — it’s a full-blown constitutional showdown.
A Judge’s Background: Who is Hannah Dugan?
Before her arrest made national headlines, Judge Hannah Dugan had built a reputation for fighting for justice. She was elected to the county court in 2016 and had served in probate and civil divisions. Her roots trace back to the Legal Aid Society and Legal Action Wisconsin, organizations dedicated to helping the underserved.
Dugan is a proud University of Wisconsin-Madison alumna, earning her Bachelor of Arts in 1981 and her law degree in 1987. Friends and colleagues say her commitment to due process and civil rights runs deep.
Emilio De Torre, head of Milwaukee Turners (a progressive group where Dugan once served on the board), spoke passionately at Friday’s earlier protest:
"She was certainly trying to make sure that due process is not disrupted and that the sanctity of the courts is upheld."
Inside the Courthouse Drama
According to the affidavit, tensions boiled over when Dugan was tipped off by her clerk about ICE agents waiting in the courthouse hallway. After confronting the agents with what witnesses described as a “confrontational, angry demeanor,” Dugan tried to redirect them to the chief judge's office.
But then came the pivotal moment: after leading ICE agents away, she returned to her courtroom, gestured to Flores-Ruiz and his lawyer, and ushered them through a non-public jury door — a move almost unheard of for non-custodial defendants and their counsel.
Meanwhile, a sign remained posted on Dugan’s courtroom door Friday that seemed to hint at her deep concern:
"If any attorney or court official knows or believes that a person feels unsafe coming to courtroom 615, notify the clerk and request a Zoom appearance."
The Man at the Center: Eduardo Flores-Ruiz
Flores-Ruiz, just 30 years old, wasn’t exactly a poster child for immigration reform. He had been facing misdemeanor domestic battery charges, accused of attacking a roommate and two women during a fight sparked by — of all things — loud music.
If convicted, Flores-Ruiz could land up to nine months in prison and face a $10,000 fine for each count. However, what made his case even more problematic was his history: deported once in 2013, he had illegally reentered the U.S., and a federal judge had just ruled a day before the courthouse incident that he should remain in custody pending trial.
His public defender, Alexander Kostal, has so far declined to comment.
Not a First: Echoes from Massachusetts
This isn’t the first time a judge has faced legal peril for allegedly helping someone dodge ICE. Remember Shelley Joseph, the Massachusetts judge charged under Trump’s first term for letting a man sneak out the back of a courthouse?
That case triggered outrage among legal scholars, many calling it politically motivated. Ultimately, the charges against Judge Joseph were dropped under the Biden administration, once she agreed to submit to state-level judicial discipline instead.
The Department of Justice’s Warning Shot
In January, the DOJ made it clear: they were actively investigating state and local officials who might be obstructing federal immigration operations. They even flagged potential charges like conspiracy and harboring illegal immigrants — sending a chilling message to public servants nationwide.
Judge Dugan’s arrest seems to be the latest, most dramatic chapter in that campaign.
Bottom Line?
What’s happening in Milwaukee right now is much bigger than Judge Hannah Dugan or Eduardo Flores-Ruiz.
It’s about the collision of federal power and local resistance, the fragility of judicial independence, and the fear that courtrooms — the heart of American democracy — might no longer be neutral ground.
As this case unfolds, one thing’s for sure: the whole country will be watching.
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