Wisconsin judge pleads not guilty to helping a man evade federal immigration agents

MILWAUKEE (AP) — A Wisconsin judge pleaded not guilty Thursday to charges accusing her of helping a man who is illegally in the country evade U.S. immigration authorities seeking to arrest him in her courthouse.

Milwaukee County Circuit Judge Hannah Dugan entered the plea during a brief arraignment in federal court. Magistrate Judge Stephen Dries scheduled a trial to begin July 21. Dugan’s lead attorney, Steven Biskupic, told the judge that he expects the trial to last a week.

Dugan, her lawyers and prosecutors left the hearing without speaking to reporters.

She is charged with concealing an individual to prevent arrest and obstruction. Prosecutors say she escorted Eduardo Flores-Ruiz and his lawyer out of her courtroom through a back door on April 18 after learning that U.S. Immigration and Customs Enforcement agents were in the courthouse seeking to arrest him for being in the country illegally. She could face up to six years in prison if convicted on both counts.

Her attorneys say she’s innocent. They filed a motion Wednesday to dismiss the case, saying she was acting in her official capacity as a judge and therefore is immune to prosecution. They also maintain that the federal government violated Wisconsin’s sovereignty by disrupting a state courtroom and prosecuting a state judge.

Dugan's arrest has inflamed tensions between Trump administration and Democrats over the president’s sweeping immigration crackdown.

Dozens of demonstrators gathered outside the courthouse ahead of Thursday's hearing, with some holding signs that read, “Only Fascists Arrest Judges -- Drop the Charges,” “Department of Justice Over-Reach” and “Keep Your Hands Off Our Judges!!” The crowd chanted “Due process rights,” “Hands off our freedom,” and “Si se puede” — Spanish for “Yes, we can” — which is a rallying cry for immigrant rights advocates.

One man stood alone across the street holding a Trump flag.

Nancy Camden, from suburban Mequon north of Milwaukee, was among the protesters calling for the case to be dismissed. She said she believes ICE shouldn't have tried to arrest Flores-Ruiz inside the courthouse and the Department of Justice “overreached” in charging Dugan.

“How they handled this and made a big show of arresting her and putting her in handcuffs, all of that was intimidation,” Camden said. “And I’m not going to be intimidated. I’m fighting back.”

Esther Cabrera, an organizer with the Milwaukee Alliance Against Racist and Political Repression, said the charges against Dugan amount to “state-funded repression.”

“If we are going to go after judges, if we’re going to go after mayors, we have to understand that they can come after anybody,” she said. “And that’s kind of why we wanted to make a presence out here today is to say that you can’t come after everyone and it stops here.”

According to court documents, Flores-Ruiz illegally reentered the U.S. after being deported in 2013. Online court records show he was charged with three counts of misdemeanor domestic abuse in Milwaukee County in March, and he was in Dugan’s courtroom on April 18 for a hearing in that case.

According to an FBI affidavit, Dugan was alerted to the agents’ presence by her clerk, who was informed by an attorney that the agents appeared to be in the hallway. Dugan was visibly angry and called the situation “absurd” before leaving the bench and retreating to her chambers, the affidavit contends. She and another judge later approached members of the arrest team in the courthouse with what witnesses described as a “confrontational, angry demeanor.”

After a back-and-forth with the agents over the warrant for Flores-Ruiz, Dugan demanded they speak with the chief judge and led them from the courtroom, according to the affidavit.

After she returned to the courtroom, witnesses heard her say something to the effect of “wait, come with me” before ushering Flores-Ruiz and his attorney out through a door typically used only by deputies, jurors, court staff and in-custody defendants, the affidavit alleges. Flores-Ruiz was free on a signature bond in the abuse case, according to online state court records. Federal agents ultimately detained him outside the courthouse after a foot chase.

The state Supreme Court suspended Dugan last week, saying the move was necessary to preserve public confidence in the judiciary. She was freed after her arrest.

John Vaudreuil, a former federal prosecutor in Wisconsin who isn’t involved in Dugan’s or Flores-Ruiz’s cases, said the Trump administration seems to want to make an example out of Dugan. U.S. Attorney General Pam Bondi or Deputy Attorney General Todd Blanche, rather than the U.S. attorney in Milwaukee, are likely making the decisions on how to proceed, making it less likely prosecutors will reduce the charges against Dugan in a deal, he said.

Her attorneys will likely try to push for a jury trial, Vaudreuil predicted, because they know that “people feel very strongly about the way the president and administration is conducting immigration policy.”

Dugan is represented by some of Wisconsin's most accomplished lawyers. Biskupic was a federal prosecutor for 20 years and served seven years as U.S. attorney in Milwaukee. Paul Clement, meanwhile, is a former U.S. solicitor general who has argued more than 100 cases in front of the U.S. Supreme Court. Both were appointed to jobs by former Republican President George W. Bush.

Associated Press reporters Scott Bauer in Madison, Wisconsin, and Laura Bargfeld contributed to this report.

Protesters gather outside of federal courthouse as Milwaukee County Circuit Judge Hannah Dugan appeared for a hearing, Thursday, May 15, 2025 in Milwaukee. (AP Photo/Andy Manis)

Milwaukee County Circuit Judge Hannah Dugan leaves the federal courthouse after a hearing Thursday, May 15, 2025, in Milwaukee. (AP Photo/Andy Manis)

Supporters of Judge Hannah Dugan protest outside the United States Federal Building and Courthouse in Milwaukee, Wis. on Thursday, April 15, 2025 ahead of Dugan's arraignment on charges that she helped a man in the country illegally evade arrest by immigration authorities. (AP Photo/Todd Richmond)

Supporters of Judge Hannah Dugan protest outside the United States Federal Building and Courthouse in Milwaukee, Wis. on Thursday, April 15, 2025 ahead of Dugan's arraignment on charges that she helped a man in the country illegally evade arrest by immigration authorities. (AP Photo/Todd Richmond)

Supporters of Judge Hannah Dugan protest outside the United States Federal Building and Courthouse in Milwaukee, Wis. on Thursday, April 15, 2025 ahead of Dugan's arraignment on charges that she helped a man in the country illegally evade arrest by immigration authorities. (AP Photo/Todd Richmond)

FILE - Judge Hannah Dugan poses for a photo in Milwaukee in 2016. (Lee Matz/Milwaukee Independent via AP, File)

A tense calm hangs over Venezuela after the U.S. military operation that deposed President Nicolás Maduro, who was brought to New York to face criminal charges.

President Donald Trump said the U.S. would “run” the South American country and tap its vast oil reserves to sell to other nations.

Maduro and his wife landed late Saturday afternoon at a small airport in New York. The couple face U.S. charges of participating in a narco-terrorism conspiracy.

The dramatic action capped an intensive Trump administration pressure campaign on Venezuela’s autocratic leader and months of secret planning, resulting in the most assertive American action to achieve regime change since the 2003 invasion of Iraq. Legal experts raised questions about the lawfulness of the operation, which was done without congressional approval. Venezuela’s vice president, Delcy Rodriguez, meanwhile, demanded that the United States free Maduro and called him the country’s rightful leader as her nation’s high court named her interim president.

Here's the latest:

Associated Press video on Sunday shows a banner now on display in Iran’s capital warning the United States and Israel that their soldiers could be killed if they take action in the country.

Trump’s recent comment that the U.S. “will come to their rescue” if Iran kills peaceful protesters has taken on a new meaning after the U.S. capture of Venezuelan President Nicolás Maduro, a longtime ally of Tehran.

Iran’s Foreign Ministry has condemned the “illegal U.S. attack against Venezuela.” U.S. Defense Secretary Pete Hegseth has said adversaries of the U.S. should note that “America can project our will anywhere, anytime.”

From California to Missouri and Texas, protestors are planning demonstrations Sunday and through the week against President Donald Trump’s military operation and capture of Maduro, which one protest description called “the illegal, unconstitutional invasion of Venezuela.”

Dozens appear to be organized by chapters of Indivisible, a left-leaning group, and many take umbrage with Trump’s plans to take control of Venezuela’s oil industry and ask American companies to revitalize it.

U.S. Sen. Chuck Grassley, a Republican from Iowa who serves as Senate president pro tempore, posted on X Saturday that Maduro is a narco-terrorist and his drug trafficking resulted in the deaths of too many Americans. He likened the Trump operation to then-President George Bush’s decision in 1989 to capture Panamanian dictator Manuel Noriega following his indictment for drug trafficking.

Illinois Gov. JB Pritzker, a Democrat and one of President Donald Trump’s most outspoken critics, posted that U.S. military action in Venezuela is unconstitutional and is putting troops in harm’s way with no long-term strategy. “The American people deserve a President focused on making their lives more affordable,” Pritzker wrote.

U.S. Sen. Tammy Baldwin, a Democrat from Wisconsin, posted a statement on X calling the strikes illegal and criticizing Trump for taking action without congressional approval. “The President does not have the unilateral authority to invade foreign countries, oust their governments, and seize their resources,” she wrote.

France’s foreign minister says the departure of President Nicolás Maduro “is good news for the Venezuelans” and called for a peaceful and democratic transition of power.

Jean-Noël Barrot said “Maduro was an unscrupulous dictator who confiscated Venezuelans’ freedom and stole their elections.”

“Then, yes, we pointed out that the method used infringes the principles of international law,” Barrot said about the U.S. military operation on France 2 national television.

Chuck Schumer, the Democratic Senate leader, called Maduro “a horrible, horrible person” but added, “You don’t treat lawlessness with other lawlessness. And that’s what’s happened.”

“We have learned through the years that, when America tries to regime change and nation-building in this way, the American people pay the price in both blood and results,” Schumer told ABC’s “This Week.”

Homeland Security Secretary Kristi Noem says President Donald Trump’s conversations with Venezuelan Vice President Delcy Rodriguez now are ”very matter-of-fact and very clear: You can lead or you can get out of the way, because we’re not going to allow you to continue to subvert American influence and our need to have a free country like Venezuela to work with rather than to have dictators in place who perpetuate crimes and drug trafficking.”

Noem tells “Fox News Sunday” that the United States wants a leader in Venezuela who will be “a partner that understands that we’re going to protect America” when it comes to stopping drug trafficking and “terrorists from coming into our country.”

She says that “we’re looking for a leader that will stand up beside us and embrace those freedoms and liberties for the Venezuelan people but also ensure that they’re not perpetuating crimes around the globe like they’ve had in the past.”

Secretary of State Marco Rubio appeared to back off Trump’s assertions that the U.S. was running Venezuela, insisting instead that Washington will use control of the South American country’s oil industry to force policy changes and, “We expect that it’s going to lead to results here.”

“We’re hopeful, hopeful, that it does positive results for the people for Venezuela,” Rubio told ABC’s “This Week.” “But, ultimately, most importantly, in the national interest of the United States.”

Asked about Trump suggesting that Rubio would be among the U.S. officials helping to run Venezuela, Rubio offered no details but said, “I’m obviously very intricately involved in the policy” going forward.

He said of Venezuela’s interim leader: “We don’t believe this regime in place is legitimate” because the country never held free and fair elections.

Venezuela’s capital Caracas was unusually quiet Sunday with few vehicles moving around. Convenience stores, gas stations and other businesses were mostly closed.

The presence of police and members of the military across the city was notable for its smaller size compared with an average day and even more so with the days when people protested against Maduro’s government in previous years.

Meanwhile, soldiers attempted to clear an area of an air base that had been on fire along with at least three passenger buses following Saturday’s U.S. attack.

The Brooklyn jail holding Nicolás Maduro is a facility so troubled that some judges have refused to send people there even as it has housed such famous inmates as music stars R. Kelly and Sean “Diddy” Combs.

Opened in the early 1990s, the Metropolitan Detention Center, or MDC Brooklyn, currently houses about 1,300 inmates.

It’s the routine landing spot for people awaiting trial in federal courts in Manhattan and Brooklyn, holding alleged gangsters and drug traffickers alongside some people accused of white collar crimes.

Maduro is not the first president of a country to be locked up there.

Juan Orlando Hernández, the former president of Honduras, was imprisoned at MDC Brooklyn while he was on trial for trafficking hundreds of tons of cocaine into the U.S. Hernández was pardoned and freed by President Donald Trump in December.

▶ Read more about MDC Brooklyn

Residents look at a damaged apartment complex that neighbors say was hit during U.S. strikes to capture Venezuelan President Nicolás Maduro, in Catia La Mar, Venezuela, Sunday, Jan. 4, 2026. (AP Photo/Matias Delacroix)

A soldier stands atop an armored vehicle driving toward Caracas, Venezuela, Sunday, Jan. 4, 2026. (AP Photo/Matias Delacroix)

Shoppers line up at a supermarket in Caracas, Venezuela, Sunday, Jan. 4, 2026. (AP Photo/Ariana Cubillos)