The arrest of a Wisconsin judge.

I’m Isaac Saul, and this is Tangle: an independent, nonpartisan, subscriber-supported politics newsletter that summarizes the best arguments from across the political spectrum on the news of the day — then “my take.”

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• Yes, Biden really did make a mess of immigration
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Quick hits.

1. Secretary of State Marco Rubio said the United States would make a decision this week about whether to continue its attempts to broker a peace deal between Russia and Ukraine. The remarks follow President Donald Trump’s meeting with Ukrainian President Volodymyr Zelensky during Pope Francis’s funeral and Trump’s public criticism of a Russian drone attack on Kyiv on Thursday. (The latest) Separately, Russian President Vladimir Putin announced a three-day ceasefire in Ukraine starting on May 8 to mark the commemoration of the end of World War II. (The announcement)
2. 11 people were killed, and at least 20 were injured, after a man drove a vehicle into a crowd at a street festival in Vancouver, British Columbia. Vancouver police said they have arrested a suspect and do not believe it was an act of terrorism. (The incident) 
3. The Trump administration restored potentially thousands of student visa registrations that it had attempted to cancel, following a series of legal challenges to the elimination of visas from a federal database used to track foreign students. (The decision) Separately, the Trump administration deported two mothers in the country illegally with their children, some of whom are U.S. citizens, aged two, four, and seven. (The removals)
4. Former Rep. George Santos (R-NY) was sentenced to seven years and three months in prison after pleading guilty to wire fraud and aggravated identity theft. (The sentence)
5. Rep. Gerry Connolly (D-VA) announced he will resign as ranking member of the House Oversight Committee and will not seek reelection in 2026 due to ongoing health challenges from cancer. (The announcement)

Today's topic.

The arrest of a Wisconsin judge. On Friday, the Federal Bureau of Investigation (FBI) arrested Milwaukee County Circuit Judge Hannah Dugan for allegedly helping an unauthorized migrant evade arrest. Dugan was charged with “obstructing or impeding a proceeding before a department or agency of the United States” and “concealing an individual to prevent his discovery and arrest,” as stated in a criminal complaint signed by Milwaukee FBI agents and unsealed on Friday.

According to the complaint, Eduardo Flores-Ruiz was charged in Milwaukee, Wisconsin, with battery and domestic abuse on March 18 for an incident that allegedly occurred on March 12. Then, agents from the Department of Homeland Security and Milwaukee’s Immigration and Customs Enforcement, Enforcement and Removal Operations (ICE ERO) identified Flores-Ruiz as a Mexican national who had entered the United States illegally after having been deported in 2013. ICE ERO issued a warrant for Flores-Ruiz’s arrest on April 17. 

Judge Dugan presided over Flores-Ruiz’s criminal hearing on April 18, after which FBI, ICE, and Drug Enforcement Agency (DEA) agents planned to arrest Flores-Ruiz in a public hallway outside the courtroom. According to the complaint, Judge Dugan “appeared visibly angry” when informed of ICE’s presence, then allegedly attempted to expedite Flores-Ruiz’s hearing before directing him to exit through a jury door to avoid arrest. DEA and FBI agents pursued Flores-Ruiz outside the courthouse and apprehended him.

On Friday, FBI agents arrested Dugan on obstruction of justice charges. “We believe Judge Dugan intentionally misdirected federal agents away from the subject to be arrested in her courthouse, Eduardo Flores Ruiz, allowing the subject — an illegal alien — to evade arrest,” FBI Director Kash Patel said in a post on X on Friday. 

Many Republicans immediately supported Dugan’s arrest and criticized her behavior. “I think some of these judges think they are beyond and above the law and they are not,” Attorney General Pam Bondi told Fox News. “We're sending a very strong message today.” In Wisconsin, state Republicans signaled that they may seek to remove Judge Dugan from office.

Conversely, many Democrats spoke out against Dugan’s arrest. “It is remarkable that the Administration would dare to start arresting state court judges," Rep. Jamie Raskin (D-MD) said. "It's a whole new descent into government chaos.” Rep. Mark Pocan (D-WI) called the judge’s arrest “stuff I expect from Third World countries.”

Details of the case resemble a similar occurrence during Trump’s first term when Massachusetts Judge Shelley Joseph was criminally charged with impeding a federal immigration arrest of a defendant in her courtroom in 2018. Federal prosecutors agreed to drop Joseph’s case in 2022, but state judicial disciplinary authorities accused her of engaging in willful misconduct in December 2024.

Today, we’ll break down what the left and right are saying about Dugan’s arrest. Then, my take.

What the left is saying.

• The left is critical of Dugan’s arrest, with many arguing the Trump administration is trying to intimidate judges.
• Some say this story is a predictable outcome of ICE’s courtroom-arrest policy.
• Others suggest the arrest introduces more uncertainty into the relationship between the executive and the judiciary. 

In The Atlantic, Adam Serwer said the Trump administration is sending a clear message to the judiciary.

“Bondi might have easily stuck to the specifics of Dugan’s case, insisting that her behavior was particularly egregious, and that Dugan’s indictment was about her individual conduct and not the judiciary as a whole. Indeed, in 2019, that’s precisely what the Donald Trump-appointed U.S. attorney Andrew Lelling did in a similar case, when a Massachusetts judge, Shelley Joseph, was indicted for allegedly helping an undocumented immigrant escape,” Serwer wrote. “But Bondi chose to do the opposite, implying that Dugan’s indictment was an attempt to intimidate the judiciary itself. The ‘message’ is that judges who anger the administration will be prosecuted at Trump’s whim.”

“One need not approve of Dugan’s alleged conduct here to understand that the Trump administration is attempting to intimidate judges into doing its bidding. After all, there are other ways to sanction judges: Although the federal case against Joseph was dismissed, she has been charged by the Massachusetts Commission on Judicial Conduct, a process that avoids executive encroachments on judicial authority,” Serwer said. “Allowing the Wisconsin Judicial Commission to evaluate whether Dugan’s behavior crossed a line, however, would not yield the political result that Trump and Bondi are seeking.”

In Slate, Douglas Keith argued that Dugan’s arrest “puts us all at risk.”

“The move is an escalation in the conflict between the Trump administration and local authorities over immigration policies. It also undermines the ability of judiciaries to effectively carry out their duties,” Keith wrote. “ICE’s own policy changes—which dramatically increased the frequency of immigration arrests in courthouses—set federal law enforcement on a collision course with state courts. These policy changes were made despite ample evidence and clear calls from judges, prosecutors, and others that immigration enforcement in state courthouses makes communities less safe.”

“These arrests resulted in chaos in courthouses across the country. Chase scenes played out in courthouse hallways. People who were scheduled to appear before a judge disappeared immediately before their hearing. One incident in New York City was so violent that witnesses thought the person ICE arrested had been kidnapped,” Keith said. “If the government has any interest in keeping communities safe, it can heed the calls of those judges, prosecutors, and court administrators who have said clearly: Keep immigration enforcement out of courts and let judges do their jobs.”

In New York Magazine, Cristian Farias wrote “Dugan’s arrest has nothing to do with public safety.”

“A close reading of the 13-page affidavit supporting the criminal complaint, which notes that Dugan ‘became visibly angry’ when she learned of ICE’s presence at the courthouse last week — a turn of events she called ‘absurd’ — reveals the true import of this circus: None of it made anyone any safer,” Farias said. “As a matter of basic federalism, which Republicans and conservatives have long embraced, armed federal agents from ICE, the FBI, and the Drug Enforcement Administration shouldn’t be roaming around a state courthouse looking for people who are there for other reasons.”

“These kinds of tactics hamper the court system in other ways: victims and witnesses with immigrant backgrounds become fearful and unwilling to come to court when their presence and participation is essential in cases that have nothing to do with criminal law,” Farias wrote. “The chilling effect on future court operations will be unavoidable. Coupled with the Trump Justice Department’s stated policy of going after state and local officials who don’t fall in line with the administration’s immigration crackdown, Dugan’s arrest may just be the tip of the spear in our new federalism.”

What the right is saying.

• Many on the right support Dugan’s arrest, saying she is credibly accused of aiding Flores-Ruiz’s attempt to evade ICE. 
• Some say that Dugan is the latest judge to try to subvert the law for political ends.
• Others suggest that Democrats’ claims of a constitutional crisis are overwrought.

In The Washington Examiner, Byron York asked “will Judge Dugan become the next hero of the resistance?”

“Based on the facts laid out in the affidavit, prosecutors charged Dugan with ‘obstructing or impeding a proceeding before a department or agency of the United States’ and ‘concealing an individual to prevent his discovery and arrest,’ both felonies. Meanwhile, Flores-Ruiz is in ICE custody,” York wrote. “And now the politics begins. According to a Milwaukee Journal-Sentinel account, ‘As word of Dugan’s arrest spread, about two dozen protesters linked arms in front of the courthouse, chanting ‘No justice, no peace. Let the judge be released.’ Some waved American flags. One protester held a sign that read ‘Only Fascists Arrest Judges.’”

“Here’s the thing. We know who the villain is, but who are Democrats going to make the hero in this story? The answer, of course, seems to be Dugan — but remember, all this was done on behalf of Eduardo Flores-Ruiz,” York said. “It’s similar to the problem Democrats face in the Kilmar Abrego Garcia case. With that, Democrats have argued that even if Abrego Garcia is a gang member, which they still deny, the case is really about due process and everyone’s rights in America… But people might still ask: Why should a judge of all people obstruct federal agents and the enforcement of immigration law when the facts in the case seem so clear-cut?”

In The American Spectator, David Catron wrote about Dugan’s “arrogant offense."

“Sen. Dick Durbin denounced Dugan’s arrest in an overwrought statement: ‘The Trump Administration continues to test the limits of our Constitution … When immigration enforcement officials interfere with our criminal justice system, it undermines public safety,’” Catron said. “Durbin is a little confused. It was Judge Dugan who ‘interfered in our criminal justice system’ by personally conducting Flores-Ruiz out of her courtroom through an exit outside of which she knew no federal agents would be waiting.”

“This kind of lawlessness is not, of course, restricted to Wisconsin. On the same day Judge Dugan was taken into custody, the DOJ arrested a former Doña Ana County judge in New Mexico. Jose Luis Cano and his wife Nancy Ann Cano were charged with ‘evidence tampering related to the federal investigation and prosecution against Cristhian Ortega-Lopez,’” Catron wrote. “This makes two judges arrested and two judges who, for all intents and purposes, refuse to adhere to their oaths of office. All four, and many more, see themselves as part of ‘the resistance.’ But what are they resisting? It isn’t just President Trump or even the will of the people. It’s the rule of law.”

In Fox News, Jonathan Turley said “out-of-control judges, not FBI, appear to have crossed 'red line.’”

“As soon as the news of the arrest was reported, Democrats declared another constitutional crisis. [Sen. Amy] Klobuchar added that the arrest ‘is a drastic move threatening the rule of law’ and a ‘grave step and undermines our system of checks and balances,’” Turley wrote. That is a curious claim unless Klobuchar believes that the officers are lying. If not, Klobuchar is suggesting that a judge should not be held accountable for actively shielding a wanted person and facilitating their evasion of law enforcement… This judge is accused of conduct that has resulted in charges for other citizens. The judicial robe is not some form of invisibility cloak that allows judges to engage in alleged criminal acts.”

“I am perplexed by Democrats rushing to denounce the arrest of Dugan before we know whether these allegations are supported. If she escorted the suspect to a non-public door to facilitate his escape, that conduct is a shocking abandonment of judicial ethics,” Turley said. “I have often criticized the reckless rhetoric directed against judges, including those who have ruled against the Trump administration. We need to maintain our civility and respect as we work through these often difficult questions. However, that works both ways. Judges have to reinforce respect for the judiciary in their own conduct.”

My take.

Reminder: "My take" is a section where I give myself space to share my own personal opinion. If you have feedback, criticism or compliments, don't unsubscribe. Write in by replying to this email, or leave a comment.

• At first, the headline of a judge’s arrest worried me.
• After reading the facts, I see sufficient reason to warrant Judge Dugan’s arrest.
• The Trump administration still could have pursued a less confrontational path, and I feel unsure about what happens now.

When news of this story first broke, I found out through a (deleted, then re-posted) tweet by FBI Director Kash Patel. Like a lot of people, my initial response was pretty reactionary. I posted that “Republicans who don't oppose this are signing up for a future Democratic president to use the FBI to arrest judges. I hope you're all ready for that.”

Not long after, I went on the Tangle Sunday podcast with Ari, our managing editor, and Kmele Foster of The Fifth Column, and we discussed the limited details we had about the arrest at the time. All three of us agreed that we felt like some kind of Rubicon had been crossed — Trump was arresting the judges now, was the general tenor. In a lot of ways, it’s still hard to shake that feeling. Trump, his attorney general, the head of the FBI, and conservative influencers have been threatening “rogue judges” for weeks, calling to impeach judges who rule against them and promising to fight back against the judiciary. And on Friday, they arrested a county judge in Wisconsin, in her own courtroom.

Then the criminal complaint came out, and as I read through the details provided in the affidavit I started to feel that the case against Judge Dugan was... credible. The basic story seems to be that Judge Dugan was upset law enforcement officers were trying to arrest someone near her courtroom, so she intentionally allowed Eduardo Flores-Ruiz, the defendant in a criminal case in her court, to exit through a “jury door” that is not typically (or, by some accounts, ever) used for defendants, which resulted in FBI and DEA agents chasing the defendant on foot to apprehend him.

A few things about the criminal complaint stand out: First, FBI and DEA agents regularly make arrests in public spaces at courthouses. In fact they prefer it, because they know where defendants are, that they are not armed, and that they have limited ways to evade arrest. In this case, the government says that when the defendant got outside, he tried to make a run for it, which both validates this method of arrest and makes Judge Dugan’s alleged actions quite dangerous. 

Second, the detailed account provided by FBI agent Lindsay Schloemer seems to be corroborated by several witnesses, including plainclothes agents, lawyers in the courtroom, a courtroom deputy, and a Victim Witness Specialist. In other words, Schloemer’s retelling is not just the preferred narrative of law enforcement officers. Lastly, and somewhat tangentially, the number of people involved in arresting a single person for deportation is remarkable (at least several FBI agents, several DEA agents, several CBP agents, and several “deportation officers”). 

After reading through the whole document, I felt that there were at least open questions about Dugan’s actions that warranted her arrest. I’ve been pretty compelled by the “nobody is above the law” principle, which is why I said the DOJ was right to criminally charge President Trump and why they’d also be right to pursue charges against Bill Clinton for alleged rape or George W. Bush for torture and illegal wire-tapping. Wouldn’t we have a better country if the powerful feared accountability? And why would that ethos apply to presidents but not a county judge?

This isn’t even new territory. Almost the same thing happened in 2018, an event that seven years later isn’t seen as a sea change in American history but instead has been all but forgotten.

Having said all that, there are still reasons to be concerned about Dugan’s arrest. 

Judges have discretion over their courtrooms, so Judge Dugan was well within her legal authority to tell ICE agents to wait in a public area outside and to ask a chief judge to determine where they can and can’t make arrests. Rather than sneaking him out some back door, it seems like the judge basically got him out of the building faster, on a route that still had him take public hallways entirely in view of the agents there to arrest him. Indeed, paragraph 33 of the complaint says that explicitly: 

…after leaving the Chief Judge’s vestibule and returning to the public hallway, DEA Agent A reported that Flores-Ruiz and his attorney were in the public hallway. DEA Agent B also observed Flores-Ruiz and his attorney in the hallway near Courtroom 615… At approximately 8:50 a.m., DEA Agent A alerted other members of the arrest team that DEA Agent A was on the elevator with Flores-Ruiz.

So… Flores-Ruiz exited the courtroom into a public hallway where he could be legally arrested, at Judge Dugan’s discretion, and was then accompanied by a DEA agent in an elevator as he exited the courthouse. All of this, to be clear, is in the FBI’s criminal complaint, before even hearing the judge’s defense. This kind of undermines the idea that Dugan attempted some big secret escape that was thwarted by law enforcement. 

Furthermore, this practice of courtroom arrests, while safer for law enforcement, has a very obvious negative effect: It reduces the likelihood of defendants and witnesses showing up to court, since they know it is a place they could get scooped up by immigration authorities. This worsens a problem Trump and many conservatives have articulated, that migrants here illegally don’t show up to court hearings.

All of this leaves me feeling pretty conflicted. On the one hand, my initial reaction still feels valid. The context of what the Trump administration is doing is relevant. It’s arresting a judge at a time when it is threatening the judiciary, pushing executive power to the limits, and testing the reach of court orders. That all makes me feel pretty squeamish. It’s also fair to wonder if these allegations are worth charging a judge with two felony offenses instead of referring her for judicial review, as eventually happened with the Massachusetts judge from 2018. 

On the other hand, if you simply asked me, “after reading the charging complaint, do you think Judge Dugan’s conduct justifies her arrest?” my answer would be… yes. That’s not to say that she is definitely guilty — her defense and statements from other witnesses could fully exonerate her (which is the point of due process), but it did seem like she was angry at the situation and tried to help Flores-Ruiz avoid law enforcement. To my point above, being a judge should not prevent law enforcement from investigating you for wrongdoing. 

Lastly, some political sentiment is obviously at play. For example, imagine for a moment if Judge Dugan were someone who denied the results of the 2020 election, and the defendant in question had been charged with trying to access ballot machines to help prove election fraud. Would people on the left be upset to see Dugan arrested on suspicion of helping that person avoid arrest? I doubt it.  

Ultimately, first impressions are a powerful thing — and I have trouble shaking the feeling that the Trump administration is intentionally escalating its tension with the judiciary, which is a game of chicken that has no good ending. But I think the only wise thing to do is reserve judgment on Dugan’s guilt or innocence by waiting for more information to come out, and waiting to see whether this prosecution gets pursued in earnest — or at all.

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Your questions, answered.

Q: In the [Sunday, April 20] podcast, Ari threw out a common line “we are an overmedicated society” — curious what specific examples he is referring to besides ADHD meds.

— Jeff from Henderson, Nevada

Ari Weitzman, Managing Editor: I’m glad you asked. For those who didn’t listen to last week’s Sunday podcast, Isaac brought up a New York Times article suggesting that we’ve focused too much on the benefits of ADHD medication and under-estimated the long-term side effects. That brought me to share one of my personal beliefs that I’ve kept in the back of my mind: We’re generally over-reliant on medication as a solution to our health problems in the United States.

Before I get into the numbers, I want to say first that I know a lot of people use genuinely transformational medications that weren’t available in years and decades past. I’ve also benefited from medical interventions for all kinds of ailments from broken bones, asthma attacks, ligament tears, and even a tumor on my small intestine — so I’m not anti-medicine or anti-science. However, at a population level, it’s hard to believe that all the routine medication we prescribe is truly necessary in every situation.

Let me start here: 65% of U.S. adults have taken prescription medication in the past year. Not only that, but 89% of U.S. adults age 65 and older have taken prescription medication in the past year, and about 40% take five or more prescription medications (triple the rate from twenty years ago). 

We take more antidepressants than our peer nations; based on CDC data from 2015–2018, 13% of U.S. adults had taken an antidepressant in the last month (at the time of the survey), compared to 7% of Europeans in 2015. We also take more painkillers; the opioid use rate in the United States is 26 times higher than it is in Japan. Then, there’s the grandaddy of them all: weight-loss drugs. One in eight U.S. adults has taken Ozempic or another GLP-1 drug in the past year, and about 6% are currently prescribed one. In total, North Americans comprise 76% of the global market for GLP-1 drugs.

These numbers tell me that we turn to medication very quickly to solve our problems instead of exploring other methods of health care.

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Under the radar.

A New York Times investigation into the plane and helicopter crash near Reagan National Airport in January found that the pilot of the Army helicopter did not heed a suggestion from her co-pilot to make a left turn in the moments preceding the accident. Chief Warrant Officer 2 Andrew Loyd Eaves, who served as the instructor on the flight, reportedly told Captain Rebecca Lobach that air traffic control wanted her to turn the helicopter to avoid a collision threat with the commercial airplane, but Lobach did not adjust the aircraft’s course. The finding adds to a series of issues with the helicopter that potentially led to the accident, including a flight path above its mandated altitude and the breakdown of radio communications between the helicopter’s crew and air traffic controllers. Investigators are working to determine whether other factors may have contributed to the crash. The New York Times has the story.

Numbers.

• 2016. The year Milwaukee County Circuit Judge Hannah Dugan was elected to the bench. 
• 2028. The year Dugan’s current term ends. 
• 6. The maximum number of years Dugan could be sentenced to serve in prison if convicted. 
• 2013. The year that Eduardo Flores-Ruiz was first deported from the United States after illegally crossing the border. 
• 12. The approximate number of years that Flores-Ruiz has been living in the United States since entering the country a second time after his first deportation. 
• 98%. The percentage of Americans who say it is important that federal judges are impartial in deciding cases, according to an April 2025 Pew Research poll.
• 54%. The percentage of Americans who say they are confident that judges are impartial in deciding cases. 
• 54% and 55%. The percentage of Republicans and Democrats, respectively, who say they are confident that judges are impartial in deciding cases. 

The extras.

• One year ago today we had just released an interview between Isaac and former Rep. Ken Buck (R-CO).
• The most clicked link in Thursday’s newsletter was our YouTube video exploring Elon Musk’s claims that noncitizens are receiving Social Security benefits and voting.
• Nothing to do with politics: The best cities to start a new business in are all particularly sunny.
• Thursday’s survey: 2,637 readers answered our survey on the tariffs on China with 38% saying President Trump should impose tariffs at or below the previous rate. “Tariffs should be targeted with a specific plan and goal in mind. A blanket tariff is just a form of sales tax,” one respondent said. 

Have a nice day.

A trail camera in Queensland, Australia, captured a red deer and a red fox joining each other  for a moonlit stroll. The wildlife enthusiast who posted the video said it was a rare sight, and that the two animals appeared to be intentionally walking together. “I’ve had many trail cameras in this area, and I’ve captured hundreds of fox interactions with other foxes and animals, but I’ve never seen two different species just walking together like this,” he said. Sunny Skyz has the story (and video).

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