Protesters chant after arrest of judge accused of helping man evade immigration authorities

MILWAUKEE (AP) — Protesters chanted and marched Saturday outside the FBI after agents arrested a Milwaukee judge accused of helping a man evade immigration authorities. The case has escalated a clash between the Trump administration and local authorities over the Republican president’s sweeping immigration crackdown.

Milwaukee County Circuit Court Judge Hannah Dugan is accused of escorting the man and his lawyer out of her courtroom through the jury door last week after learning that immigration authorities were seeking his arrest. The man was taken into custody outside the courthouse after agents chased him on foot.

President Donald Trump's administration has accused state and local officials of interfering with his immigration enforcement priorities. The arrest also comes amid a growing battle between the administration and the federal judiciary over the president’s executive actions over deportations and other matters.

On Saturday, protesters chanted “Immigrants are here to stay” and held up signs saying, “Liberty and Justice for All” outside the FBI's Milwaukee division.

“The judiciary acts as a check to unchecked executive power. And functioning democracies do not lock up judges,” Democratic state Rep. Ryan Clancy told the crowd before it marched around the area.

Dugan was taken into custody by the FBI on Friday morning on the courthouse grounds, according to U.S. Marshals Service spokesperson Brady McCarron. She appeared briefly in federal court in Milwaukee later Friday before being released from custody. She faces charges of “concealing an individual to prevent his discovery and arrest” and obstructing or impeding a proceeding.

“Judge Dugan wholeheartedly regrets and protests her arrest. It was not made in the interest of public safety," her attorney, Craig Mastantuono, said during the hearing. He declined to comment to an Associated Press reporter following her court appearance.

Democratic Wisconsin Gov. Tony Evers, in a statement on the arrest, accused the Trump administration of repeatedly using “dangerous rhetoric to attack and attempt to undermine our judiciary at every level.”

“I will continue to put my faith in our justice system as this situation plays out in the court of law," he said.

Court papers suggest Dugan was alerted to the presence of U.S. Immigration and Customs Enforcement agents in the courthouse by her clerk, who was informed by an attorney that they appeared to be in the hallway.

The FBI affidavit describes Dugan as “visibly angry” over the arrival of immigration agents in the courthouse and says that she pronounced the situation “absurd” before leaving the bench and retreating to her chambers. It says she and another judge later approached members of the arrest team inside the courthouse, displaying what witnesses described as a “confrontational, angry demeanor.”

After a back-and-forth with officers over the warrant for the man, Eduardo Flores-Ruiz, she demanded that the arrest team speak with the chief judge and led them away from the courtroom, the affidavit says.

After directing the arrest team to the chief judge's office, investigators say, Dugan returned to the courtroom and was heard saying words to the effect of “wait, come with me” before ushering Flores-Ruiz and his lawyer through a jury door into a non-public area of the courthouse. The action was unusual, the affidavit says, because “only deputies, juries, court staff, and in-custody defendants being escorted by deputies used the back jury door. Defense attorneys and defendants who were not in custody never used the jury door.”

A sign that remained posted on Dugan’s courtroom door Friday advised that if any attorney or other court official “knows or believes that a person feels unsafe coming to the courthouse to courtroom 615,” they should notify the clerk and request an appearance via Zoom.

Flores-Ruiz, 30, was in Dugan’s court for a hearing after being charged with three counts of misdemeanor domestic battery. Confronted by a roommate for playing loud music on March 12, Flores-Ruiz allegedly fought with him in the kitchen and struck a woman who tried to break them up, according to the police affidavit in the case.

Another woman who tried to break up the fight and called police allegedly got elbowed in the arm by Flores-Ruiz.

Flores-Ruiz faces up to nine months in prison and a $10,000 fine on each count if convicted. His public defender, Alexander Kostal, did not immediately return a phone message Friday seeking comment.

A federal judge, the same one Dugan would appear before a day later, had ordered Thursday that Flores-Ruiz remain jailed pending trial. Flores-Ruiz had been in the U.S. since reentering the country after he was deported in 2013, according to court documents.

Attorney General Pam Bondi said victims were sitting in the courtroom with state prosecutors when the judge helped him escape immigration arrest.

“The rule of law is very simple," she said in a video posted on X. "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.”

White House officials echoed the sentiment of no one being above the law.

Sen. Tammy Baldwin, a Democrat who represents Wisconsin, called the arrest of a sitting judge a “gravely serious and drastic move” that “threatens to breach” the separation of power between the executive and judicial branches.

Emilio De Torre, executive director of Milwaukee Turners, said during an earlier protest Friday afternoon outside the federal courthouse that Dugan was a former board member for the local civic group who “was certainly trying to make sure that due process is not disrupted and that the sanctity of the courts is upheld.”

“Sending armed FBI and ICE agents into buildings like this will intimidate individuals showing up to court to pay fines, to deal with whatever court proceedings they may have,” De Torre added.

The case is similar to one brought during the first Trump administration against a Massachusetts judge, who was accused of helping a man sneak out a back door of a courthouse to evade a waiting immigration enforcement agent.

That prosecution sparked outrage from many in the legal community, who slammed the case as politically motivated. Prosecutors dropped the case against Newton District Judge Shelley Joseph in 2022 under the Democratic Biden administration after she agreed to refer herself to a state agency that investigates allegations of misconduct by members of the bench.

The Justice Department had previously signaled that it was going to crack down on local officials who thwart federal immigration efforts.

The department in January ordered prosecutors to investigate for potential criminal charges any state and local officials who obstruct or impede federal functions. As potential avenues for prosecution, a memo cited a conspiracy offense as well as a law prohibiting the harboring of people in the country illegally.

Dugan was elected in 2016 to the county court Branch 31. She also has served in the court’s probate and civil divisions, according to her judicial candidate biography.

Before being elected to public office, Dugan practiced at Legal Action of Wisconsin and the Legal Aid Society. She graduated from the University of Wisconsin-Madison in 1981 with a bachelor of arts degree and earned her Juris Doctorate in 1987 from the school.

Richer reported from Washington. Associated Press reporters Eric Tucker in Washington, Corey Williams in Detroit and Hallie Golden in Seattle contributed.

A sign is posted on the doors of Judge Hannah Dugan courtroom Friday, April 25, 2025, in Milwaukee. (AP Photo/Andy Manis)

FILE - FBI director Kash Patel arrives on the South Lawn of the White House before President Donald Trump and first lady Melania Trump participate in the White House Easter Egg Roll, April 21, 2025, in Washington. (AP Photo/Alex Brandon, File)

A sign is posted on the doors of Judge Hannah Dugan courtroom Friday, April 25, 2025, in Milwaukee. (AP Photo/Andy Manis)

Traffic passes the Federal courthouse in Milwaukee on Friday, April 25, 2025. (AP Photo/Devi Shastri)

FILE - FBI director Kash Patel arrives on the South Lawn of the White House before President Donald Trump and first lady Melania Trump participate in the White House Easter Egg Roll, April 21, 2025, in Washington. (AP Photo/Alex Brandon, File)

Rep. Christine Sinicki, D-Milwaukee, addresses the media outside of the federal courthouse Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested. (AP Photo/Andy Manis)

Traffic passes the Federal courthouse in Milwaukee on Friday, April 25, 2025. (AP Photo/Devi Shastri)

Rep. Christine Sinicki, D-Milwaukee, addresses the media outside of the federal courthouse Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested. (AP Photo/Andy Manis)

Milwaukee Mayor Cavalier Johnson addresses the media Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested on courthouse grounds. (AP Photo/Andy Manis)

Milwaukee Mayor Cavalier Johnson addresses the media Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested on courthouse grounds. (AP Photo/Andy Manis)

Milwaukee Mayor Cavalier Johnson addresses the media Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested on courthouse grounds. (AP Photo/Andy Manis)

Milwaukee Mayor Cavalier Johnson addresses the media Friday, April 25, 2025, in Milwaukee after county Judge Hannah Dugan was arrested on courthouse grounds. (AP Photo/Andy Manis)

This 2016 photo shows Judge Hannah Dugan in Milwaukee. (Lee Matz/Milwaukee Independent via AP)

This 2016 photo shows Judge Hannah Dugan in Milwaukee. (Lee Matz/Milwaukee Independent via AP)

FBI director Kash Patel arrives on the South Lawn of the White House before President Donald Trump and first lady Melania Trump participate in the White House Easter Egg Roll Monday, April 21, 2025, in Washington. (AP Photo/Alex Brandon)

FBI director Kash Patel arrives on the South Lawn of the White House before President Donald Trump and first lady Melania Trump participate in the White House Easter Egg Roll Monday, April 21, 2025, in Washington. (AP Photo/Alex Brandon)

U.S. President Donald Trump wants to own Greenland. He has repeatedly said the United States must take control of the strategically located and mineral-rich island, which is a semiautonomous region that's part of NATO ally Denmark.

Officials from Denmark, Greenland and the United States met Thursday in Washington and will meet again next week to discuss a renewed push by the White House, which is considering a range of options, including using military force, to acquire the island.

Trump said Friday he is going to do “something on Greenland, whether they like it or not.”

If it's not done “the easy way, we're going to do it the hard way," he said without elaborating what that could entail. In an interview Thursday, he told The New York Times that he wants to own Greenland because “ownership gives you things and elements that you can’t get from just signing a document.”

Danish Prime Minister Mette Frederiksen has warned that an American takeover of Greenland would mark the end of NATO, and Greenlanders say they don't want to become part of the U.S.

This is a look at some of the ways the U.S. could take control of Greenland and the potential challenges.

Trump and his officials have indicated they want to control Greenland to enhance American security and explore business and mining deals. But Imran Bayoumi, an associate director at the Atlantic Council’s Scowcroft Center for Strategy and Security, said the sudden focus on Greenland is also the result of decades of neglect by several U.S. presidents towards Washington's position in the Arctic.

The current fixation is partly down to “the realization we need to increase our presence in the Arctic, and we don’t yet have the right strategy or vision to do so,” he said.

If the U.S. took control of Greenland by force, it would plunge NATO into a crisis, possibly an existential one.

While Greenland is the largest island in the world, it has a population of around 57,000 and doesn't have its own military. Defense is provided by Denmark, whose military is dwarfed by that of the U.S.

It's unclear how the remaining members of NATO would respond if the U.S. decided to forcibly take control of the island or if they would come to Denmark's aid.

“If the United States chooses to attack another NATO country militarily, then everything stops,” Frederiksen has said.

Trump said he needs control of the island to guarantee American security, citing the threat from Russian and Chinese ships in the region, but “it's not true” said Lin Mortensgaard, an expert on the international politics of the Arctic at the Danish Institute for International Studies, or DIIS.

While there are probably Russian submarines — as there are across the Arctic region — there are no surface vessels, Mortensgaard said. China has research vessels in the Central Arctic Ocean, and while the Chinese and Russian militaries have done joint military exercises in the Arctic, they have taken place closer to Alaska, she said.

Bayoumi, of the Atlantic Council, said he doubted Trump would take control of Greenland by force because it’s unpopular with both Democratic and Republican lawmakers, and would likely “fundamentally alter” U.S. relationships with allies worldwide.

The U.S. already has access to Greenland under a 1951 defense agreement, and Denmark and Greenland would be “quite happy” to accommodate a beefed up American military presence, Mortensgaard said.

For that reason, “blowing up the NATO alliance” for something Trump has already, doesn’t make sense, said Ulrik Pram Gad, an expert on Greenland at DIIS.

U.S. Secretary of State Marco Rubio told a select group of U.S. lawmakers this week that it was the Republican administration’s intention to eventually purchase Greenland, as opposed to using military force. Danish and Greenlandic officials have previously said the island isn't for sale.

It's not clear how much buying the island could cost, or if the U.S. would be buying it from Denmark or Greenland.

Washington also could boost its military presence in Greenland “through cooperation and diplomacy,” without taking it over, Bayoumi said.

One option could be for the U.S. to get a veto over security decisions made by the Greenlandic government, as it has in islands in the Pacific Ocean, Gad said.

Palau, Micronesia and the Marshall Islands have a Compact of Free Association, or COFA, with the U.S.

That would give Washington the right to operate military bases and make decisions about the islands’ security in exchange for U.S. security guarantees and around $7 billion of yearly economic assistance, according to the Congressional Research Service.

It's not clear how much that would improve upon Washington's current security strategy. The U.S. already operates the remote Pituffik Space Base in northwestern Greenland, and can bring as many troops as it wants under existing agreements.

Greenlandic politician Aaja Chemnitz told The Associated Press that Greenlanders want more rights, including independence, but don't want to become part of the U.S.

Gad suggested influence operations to persuade Greenlanders to join the U.S. would likely fail. He said that is because the community on the island is small and the language is “inaccessible.”

Danish Foreign Minister Lars Løkke Rasmussen summoned the top U.S. official in Denmark in August to complain that “foreign actors” were seeking to influence the country’s future. Danish media reported that at least three people with connections to Trump carried out covert influence operations in Greenland.

Even if the U.S. managed to take control of Greenland, it would likely come with a large bill, Gad said. That’s because Greenlanders currently have Danish citizenship and access to the Danish welfare system, including free health care and schooling.

To match that, “Trump would have to build a welfare state for Greenlanders that he doesn’t want for his own citizens,” Gad said.

Since 1945, the American military presence in Greenland has decreased from thousands of soldiers over 17 bases and installations to 200 at the remote Pituffik Space Base in the northwest of the island, Rasmussen said last year. The base supports missile warning, missile defense and space surveillance operations for the U.S. and NATO.

U.S. Vice President J.D. Vance told Fox News on Thursday that Denmark has neglected its missile defense obligations in Greenland, but Mortensgaard said that it makes “little sense to criticize Denmark,” because the main reason why the U.S. operates the Pituffik base in the north of the island is to provide early detection of missiles.

The best outcome for Denmark would be to update the defense agreement, which allows the U.S. to have a military presence on the island and have Trump sign it with a “gold-plated signature,” Gad said.

But he suggested that's unlikely because Greenland is “handy” to the U.S president.

When Trump wants to change the news agenda — including distracting from domestic political problems — “he can just say the word ‘Greenland' and this starts all over again," Gad said.

CORRECT THE ORDER OF SPEAKERS, FILE - Denmark's Prime Minister Mette Frederiksen, right, and Greenland's Prime Minister Jens-Frederik Nielsen, left, speak on April 27, 2025, in Marienborg, Denmark. (Mads Claus Rasmussen/Ritzau Scanpix via AP, File)

FILE - Danish military forces participate in an exercise with hundreds of troops from several European NATO members in the Arctic Ocean in Nuuk, Greenland, Sept. 15, 2025. (AP Photo/Ebrahim Noroozi, File)

President Donald Trump listens as he was speaking with reporters while in flight on Air Force One, Sunday, Jan. 4, 2026, as returning to Joint Base Andrews, Md. (AP Photo/Alex Brandon)

Danish Prime Minister Mette Frederiksen arrives for a meeting of the Coalition of the Willing at the Elysee Palace in Paris, France, Tuesday, Jan.6, 2026. (Yoan Valat, Pool photo via AP)

FILE - A plane carrying Donald Trump Jr. lands in Nuuk, Greenland, Jan. 7, 2025. (Emil Stach/Ritzau Scanpix via AP, file)