People gather to sing and show support for Judge Hannah Dugan ahead of her federal trial. (Photo by Isiah Holmes/Wisconsin Examiner)

A federal jury will begin hearing the case against Milwaukee County Circuit Court Judge Hannah Dugan, 66, on Monday in a lawsuit that has drawn national attention, weighing how far the Trump administration can go in squashing resistance to its nationwide crackdown on immigrants. 

The case revolves around events in  April, when Eduardo Flores-Ruiz, a 30-year-old Mexican immigrant who had  been charged with battery, appeared in Dugan’s courtroom. Federal agents also arrived at the courtroom that day, seeking Flores-Ruiz, whom they said entered the country illegally over a decade ago. 

Dugan confronted  the federal agents as they waited outside her courtroom. Later, she led Flores-Ruiz  and his attorney out of her courtroom through a side door which led  into the same hallway where the federal agents were waiting. Flores-Ruiz was followed into the elevator and outside by the agents, who chased and then arrested him. 

Days later, Dugan was arrested and handcuffed by FBI agents and charged with obstruction and concealing an individual. FBI Director Kash Patel posted photographs of Dugan in handcuffs and celebrated her arrest, writing on X, “No one is above the law.” 

In early April, prior to Flores-Ruiz, ICE arrested two other people at the Milwaukee County Courthouse. Officials expressed concerns that the arrests were causing defendants, witnesses and victims to avoid coming to court or cooperating with law enforcement. 

Milwaukee County Executive David Crowley objected to what he characterized as intimidation tactics in enforcing its immigration crackdown and wielding the power of the state against  “anyone who opposes these policies.” In a statement, Crowley said, “we have an obligation to administer our courts in a safe, efficient manner that delivers due process for anyone.” 

Christine Neumann-Ortiz, executive director of the immigrant rights group Voces de la Frontera, said that the Trump officials  “basically want to be unleashed to do whatever they want to commit these raids in courtrooms across the country.” Milwaukee-area Democratic Sens. Chris Larson and Tim Carpenter and Reps. Christine Sinicki, Darrin Madison, Supreme Moore Omokunde, Angelito Tenorio, and Sequanna Taylor issued a joint statement calling the county courthouse “a sanctuary for justice and peace where the accused come forward willingly in a fair an unbiased process”, and warned that “arresting people out of a courtroom will lead to a breakdown of civil society.” 

At the end of April, the Wisconsin Supreme Court suspended Dugan with pay. Her case catalyzed protests outside the Milwaukee FBI Office, and was repeatedly mentioned at the summer’s No Kings protests. In July, Republican lawmakers introduced a bill to withhold pay for suspended judges. 

“In these rare circumstances, these judges’ actions and alleged misconduct rose to such a level that suspension was warranted,” the bill’s authors, Sen. Cory Tomczyk (R-Mosinee), Assembly Majority Leader Tyler August (R-Walworth) and Rep. Shae Sortwell (R-Two Rivers) wrote in a memo.  “Simply put, Wisconsin taxpayers must be protected from the misconduct and/or commission of a crime by rogue judges.”

If convicted, Dugan, who has pleaded not guilty, faces six years in prison. Her legal team initially attempted to have the case thrown out,  t arguing that Dugan is covered by  judicial immunity. That argument was rejected by U.S. Magistrate Judge Nancy Joseph of the Eastern District of Wisconsin, who wrote that judges have civil immunity for official actions, but not criminal immunity, and that the case should go forward.

“As she said after her unnecessary arrest, Judge Dugan asserts her innocence and looks forward to being vindicated in court,” Dugan’s defense attorneys said in a statement.

On Thursday night, a crowd gathered outside the federal courthouse to support Dugan. 

Therese Heeg, 66, told the Wisconsin Examiner that she felt a responsibility to attend the rally to “protect our democracy for my children, my grandchildren, my son-in-law who’s unable to live in the U.S. because he’s from Africa, my best friend’s children who are Hispanic who are afraid for their lives, even though they’re citizens.” Heeg said she’s worried about immigration enforcement coming to the city to take people away. “Every single day there’s more and more atrocities happening right here,” said Heeg. “We are trapping people in camps…I used to wonder what it was like to live under the Nazis, and now I know, I’m living it. It’s shocking, it’s hard to comprehend at the same time that it’s happening every single day. 

Jury selection on Thursday was  closed off from the public and media by U.S. District Judge Lynn Adelman, who is hearing the case. Adelman was responding to concerns from both the prosecution and defense that public questioning would taint the jury. An audio feed allowing media to listen to the jury selection process was restored following a legal   challenge by the Milwaukee Journal Sentinel.

Sister Barbara Pfarr, who is among the leaders of the faith-based social justice group MICAH, said that the national attention on Dugan’s case shows that the judge struck a nerve by standing up to the  Trump administration. Pfarr was disturbed by the effort to restrict press access during jury selection, and wondered whether anything similar would happen during the trial. “That’s the other big reason that I’m here, we’ve lost our democracy.”

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Federal agents patrol the halls of immigration court in New York City in October. While arrests at federal immigration courts have received widespread attention, U.S. Immigration and Customs Enforcement have also arrested individuals at state courthouses, prompting some Democratic states to impose restrictions. (Photo by Michael M. Santiago/Getty Images)

A day after President Donald Trump took office, U.S. Immigration and Customs Enforcement issued a new directive to its agents: Arrests at courthouses, restricted under the Biden administration, were again permissible.

In Connecticut, a group of observers who keep watch on ICE activity in and around Stamford Superior Court have since witnessed a series of arrests. In one high-profile case in August, federal agents pursued two men into a bathroom.

“Is it an activity you want to be interfering with, people fulfilling their duty when they’re called to court and going to court? For me, it’s insanity,” said David Michel, a Democratic former state representative in Connecticut who helps observe courthouse activity.

Fueled by the Stamford uproar, Connecticut lawmakers last week approved restrictions on civil arrests and mask-wearing by federal law enforcement at state courthouses. And on Monday, a federal judge tossed a lawsuit brought by the U.S. Department of Justice that had sought to block similar restrictions in New York.

They are the latest examples of a growing number of Democratic states, and some judges, pushing back against ICE arrests in and around state courthouses. State lawmakers and other officials worry the raids risk keeping people from testifying in criminal trials, fighting evictions or seeking restraining orders against domestic abusers.

The courthouse arrests mark an intensifying clash between the Trump administration and Democratic states that pits federal authority against state sovereignty. Sitting at the core of the fight are questions about how much power states have to control what happens in their own courts and the physical grounds they sit on.

In Illinois, lawmakers approved a ban on civil immigration arrests at courthouses in October. In Rhode Island, lawmakers plan to again push for a ban after an earlier measure didn’t advance in March. Connecticut lawmakers were codifying limits imposed by the state Supreme Court chief justice in September. Democratic Gov. Ned Lamont is expected to sign the bill.

States that are clamping down on ICE continue to allow the agency to make criminal arrests, as opposed to noncriminal civil arrests. Many people arrested and subsequently deported are taken on noncriminal, administrative warrants. As of Sept. 21, 71.5% of ICE detainees had no criminal convictions, according to the Transactional Records Access Clearinghouse, a data research organization.

Some states, such as New York, already have limits on immigration enforcement in courthouses that date back to the first Trump administration, when ICE agents also engaged in courthouse arrests. New York’s Protect Our Courts Act, in place since 2020, prohibits civil arrests of people at state and local courthouses without a judicial warrant. The law also applies to people traveling to and from court, extending protections beyond courthouse grounds.

“One of the cornerstones of our democracy is open access to the courts. When that access is denied or chilled, all of us are made less safe and less free,” said Oren Sellstrom, litigation director at Lawyers for Civil Rights, a Boston-based group that works to provide legal support to immigrants, people of color and low-income individuals.

But in addition to challenging the New York law, the Justice Department is prosecuting a Wisconsin state judge, alleging she illegally helped a migrant avoid ICE agents.

“We aren’t some medieval kingdom; there are no legal sanctuaries where you can hide and avoid the consequences for breaking the law,” U.S. Department of Homeland Security Assistant Secretary for Public Affairs Tricia McLaughlin said in a statement to Stateline. “Nothing in the constitution prohibits arresting a lawbreaker where you find them.”

Some Republican lawmakers oppose efforts to limit ICE arrests in and near courthouses, arguing state officials should stay out of the way of federal law enforcement. The Ohio Senate in June passed a bill that would prohibit public officials from interfering in immigration arrests or prohibiting cooperation with ICE; the move came after judges in Franklin County, which includes Columbus, imposed restrictions on civil arrests in courthouses.

“The United States is a nation of immigrants, but we are also a nation of law and order. To have a civilized society, laws must be respected, this includes immigration laws,” Ohio Republican state Sen. Kristina Roegner, the bill’s sponsor, said in a news release at the time.

Roegner didn’t respond to Stateline’s interview request. The legislation remains in a House committee.

Knowing where a target will be

Courthouses offer an attractive location for ICE to make immigration arrests, according to both ICE and advocates for migrants.

Court records and hearing schedules often indicate who is expected in the building on any given day. Administrative warrants don’t allow ICE to enter private homes without permission, but the same protections don’t apply in public areas, such as courthouses. And many people have a strong incentive to show up for court, knowing that warrants can potentially be issued for their arrest if they don’t.

“So in some respects, it’s easy pickings,” said Steven Brown, executive director of the ACLU of Rhode Island.

In June, ICE arrested Pablo Grave de la Cruz at Rhode Island Traffic Tribunal in Cranston. A 36-year-old Rhode Island resident, he had come from Guatemala illegally as a teenager.

“They pulled up on him like he was a murderer or a rapist,” friend Brittany Donohue told the Rhode Island Current, which chronicled de la Cruz’s case. “He was leaving traffic court.”

An immigration judge has since granted de la Cruz permission to self-deport.

McLaughlin, the Homeland Security assistant secretary, said in her statement that allowing law enforcement to make arrests “of criminal illegal aliens in courthouses is common sense” — conserving law enforcement resources because officers know where a target will be. The department said the practice is safer for officers and the community, noting that individuals have gone through courthouse security.

Still, ICE’s directive on courthouse arrests sets some limits on the agency’s activity.

Agents “should, to the extent practicable” conduct civil immigration arrests in non-public areas of the courthouse and avoid public entrances. Actions should be taken “discreetly” to minimize disruption to court proceedings, and agents should generally avoid areas wholly dedicated to non-criminal proceedings, such as family court, the directive says.

Crucially, the directive says ICE can conduct civil immigration arrests “where such action is not precluded by laws imposed by the jurisdiction.” In other words, the agency’s guidance directs agents to respect state and local bans on noncriminal arrests.

Trump administration court actions

But the Trump administration has also gone to court to try to overcome state-level restrictions.

The Justice Department sued in June over New York’s Protect Our Courts Act, arguing that it “purposefully shields dangerous aliens” from lawful detention. The department says the law violates the U.S. Constitution’s supremacy clause, under which federal law supersedes state law.

New York Democratic Attorney General Letitia James argued the state law doesn’t conflict with federal law and sought the lawsuit’s dismissal.

U.S. District Court Judge Mae D’Agostino, an appointee of President Barack Obama, on Monday granted James’ motion. The judge wrote that the “entire purpose” of the lawsuit was to allow the federal government to commandeer New York’s resources — such as court schedules and court security screening measures — to aid immigration enforcement, even though states cannot generally be required to help the federal government enforce federal law.

“Compelling New York to allow federal immigration authorities to reap the benefits of the work of state employees is no different than permitting the federal government to commandeer state officials directly in furtherance of federal objectives,” the judge wrote.

The Justice Department didn’t immediately respond to a request for comment.

The department is also prosecuting Wisconsin Judge Hannah Dugan, who prosecutors allege helped a person living in the country illegally avoid ICE agents in April inside a Milwaukee courthouse by letting him exit a courtroom through a side door. (Agents apprehended the individual near the courthouse.) A federal grand jury indicted Dugan on a count of concealing an individual and a count of obstructing a proceeding.

In court documents, Dugan’s lawyers have called the prosecution “virtually unprecedented and entirely unconstitutional.”

Dugan has pleaded not guilty, and a trial is set for December.

Lawmakers seek ‘order’ in courthouses

Rhode Island Democratic state Sen. Meghan Kallman is championing legislation that would generally ban civil arrests at courthouses. The measure received a hearing, but a legislative committee recommended further study.

Kallman hopes the bill will go further next year. The sense of urgency has intensified, she said, and more people now understand the consequences of what is happening.

“In order to create a system of law that is functioning and that encourages trust, we have to make those [courthouse] spaces safe,” she said.

Back in Connecticut, Democratic state Rep. Steven Stafstrom said his day job as a commercial litigator brings him into courthouses across the state weekly. Based on his conversations with court staff, other lawyers and senior administration within the judicial branch, he said “there’s a genuine fear, not just for safety, but for disruptions of orderly court processes in our courthouses.”

Some Connecticut Republicans have questioned whether a law that only pertains to civil arrests would prove effective. State Rep. Craig Fishbein, the ranking Republican on the House Judiciary Committee, noted during floor debate that entering the United States without permission is a criminal offense — a misdemeanor for first-time offenders and a felony for repeat offenders. Because of that, he suggested the measure wouldn’t stop many courthouse arrests.

“The advocates think they’re getting no arrests in courthouses, but they’ve been sold a bill of goods,” he said.

Stafstrom, who chairs the Judiciary Committee, said in response that he believed the legislation protects many people who are in the country illegally because that crime is often not prosecuted.

“All we’re asking is for ICE to recognize the need for order in our courthouses,” Stafstrom said.

Stateline reporter Jonathan Shorman can be reached at jshorman@stateline.org.