On Monday Dec. 15, the federal criminal trial starts for Judge Hannah Dugan. Dugan is a Milwaukee County Circuit Court judge who’s accused of helping an undocumented immigrant slip out of her courtroom to try and evade ICE agents. To find out more about Dugan’s jury trial — and what it says about politics today —Lake Effect's Joy Powers spoke with WUWM reporter Maayan Silver.
Joy Powers: First, what is Dugan charged with?
Maayan Silver: Dugan is facing two counts: obstruction — a felony — and concealing an individual to prevent an arrest — a misdemeanor. She was indicted by a grand jury and entered not guilty pleas in May. Dugan’s jury trial starts [Dec. 15], and she could face up to six years in prison if convicted.
But as the Milwaukee Journal Sentinel notes: “[if convicted] first-time nonviolent offenders typically get shorter sentences or probation.” For the time being, she has been suspended with pay by the Wisconsin Supreme Court.
As you have noted, Dugan says she’s innocent. Before we dive into the legal aspects of this trial, can you explain its political implications?
It’s an unusual case: A judge accused of helping a defendant evade ICE. There is a Massachusetts judge who was charged federally for a similar action during President Trump’s first term. When Biden won in 2020, his justice department dismissed those charges and the judge had to face a disciplinary board instead.
Laurie Levenson is a former federal prosecutor and current law professor at Loyola Law School. Here’s some context from her for why these prosecutions are so rare:
"Until recently, until this administration, courthouses were by-and-large off-limits to what federal authorities wanted to do, certainly for immigration enforcement," says Levenson. "And there was this general understanding and respect that ICE could do their arrests. They could go people's homes, they could take them off the streets. But the courthouses should not be disrupted for lots of reasons, because you don't want people not to come to their court proceedings, and because the courthouses have to deal with a range of issues, whether it be criminal actions or others, so there was this understanding that the feds would not interfere with the operation of courthouses."
"Now, of course, all that has gone out the window with the current administration and Department of Justice," she continues. "[The Trump administration has] been extremely aggressive in how they've tried to do their immigration enforcement.
I’d imagine that has made Judge Dugan a hero to some, and a pariah to others.
Yes. People on the left describe this case a symbol of bullying and authoritarianism. And the fact that she was arrested at the Milwaukee County Courthouse in May, on the job, in such a public way, also showed this administration wants to make an example of her. There are likely to be protests this week.
On the right, Trump and his top officials have gone after Dugan publicly. FBI director Kash Patel posted a photo on the social media site X of Dugan in handcuffs, with the caption: “No one is above the law.” He then deleted it and posted another message commending FBI agents after Dugan appeared in court.
Attorney General Pam Bondi also commented about the case on Fox News. And President Donald Trump re-posted commentary about the case on Truth Social.
The Department of Homeland Security called Dugan an “activist judge” on X.
So, can you break down the issues that this case has tapped into?
Yes, first are the wide-spread concerns over the Trump administration’s immigration enforcement efforts, or support for them, as we have discussed.
But Dugan’s trial is also coming at a time of unprecedented litigation by and against the Trump administration. And there’s been some pushback against Trump. Grand juries in DC, Chicago and elsewhere are refusing to indict people protesting ICE. The man charged with throwing his sandwich at a federal agent was acquitted last month . Federal lawsuits are being dismissed or not charged against Trump adversaries former FBI director James Comey and New York Attorney General Leticia James.
Here’s what politics professor Barry Burden had to say about it. He’s with UW-Madison.
"Well, I do think there are two dimensions going on in this drama simultaneously," says Burden. "One is the debate about immigration and the ICE raids under the Trump administration, and this particular person who's now been deported from the U.S., and was at issue in what happened in the courtroom."
Burden says the second dimension is about the battle between the Trump administration and the courts. "There have been a record number of federal lawsuits filed against actions of the Trump administration on everything from immigration actions to how they're treating universities and law firms and other businesses, to cuts to the federal government, actions overseas. Just a tremendous amount of activity, and the Trump administration has been rebuffed in a lot of those cases. Their actions have been stopped, overturned, or at least put on hold. And it connects to the gripes, frankly, that Donald Trump has about the court system. He thinks that liberal judges — judges are acting against him in a biased way."
"So there are sort of two trains running here simultaneously," says Burden, "And I think it all coming together in one case, has just made what is kind of a small event in the city of Milwaukee turn into a national story."
Also, there’s a discussion here from a legal perspective about what is the role and purview of state court judges and federal immigration enforcement.
Can you explain that?
Immigration enforcement is solely the responsibility of the federal government. States do not have the power to enforce federal immigration law, even though there have been a lot of attempts by the current administration to enlist the support of local law enforcement for federal purposes. Also, state court judges have significant autonomy over how they want to control their courtrooms.
I talked to John Gross about this. He’s director of the Public Defender Project at UW Law School.
Gross gives a hypothetical situation: law enforcement wants to arrest someone and asks the court to hold the defendant’s case until the afternoon. Gross explains what the judge could decide.
"'I'm not holding up this court's calendar,'" says Gross, speaking as a hypothetical judge. "'I'm not making the attorney stay here 'til the afternoon to call this case. They have to be on trial with another judge, so I need to call the case now. Sorry, law enforcement.' Now, am I concealing? Am I acting in a corrupt way? I'm certainly making it so that law enforcement is not going to be able to arrest this individual today, but I'm entitled to do that as a judicial officer, running my calendar."
Looking at April 18 when ICE agents came to Dugan’s courtroom — what do prosecutors say happened?
According to court papers, ICE agents wanted to arrest Eduardo Flores-Ruiz, an undocumented immigrant, for being in the U.S. unlawfully. They determined he’d be appearing before Judge Dugan at the county courthouse on April 18, on misdemeanor charges of domestic assault.
Before court started, ICE agents went to the hallway outside of Dugan’s courtroom and told Dugan’s clerk that they wanted to arrest Flores-Ruiz. Prosecutors claim that once Dugan found out that ICE was there to arrest the man, she became “visibly upset.”
According to the complaint, she went to talk to the agents. They showed her an administrative warrant for the man’s arrest. Judge Dugan allegedly told them that they needed a judicial warrant. A judicial warrant is one that’s reviewed and approved by a judge.
She also allegedly told them to go to the chief judge’s office to figure out the proper way to do this. Allegedly, the agents agreed to wait until Flores-Ruiz’s court hearing was done to arrest him in the public hallway of the courthouse. But prosecutors say that Dugan didn’t call Flores-Ruiz’s case. The Milwaukee Journal Sentinel reports it was rescheduled due to logistical problems, including the lack of a court interpreter, and Dugan set his case for a Zoom hearing.
Dugan then allegedly ushered Flores-Ruiz and his attorney out of her courtroom through a back door for jurors. Court papers describe that Flores-Ruiz and his attorney did, ultimately, end up in the public hallway, though a bit further from where agents had been sitting. Still, ICE agents saw him, and one got on an elevator with him and his attorney. They chased him outside and eventually caught him and arrested him. In one filing, prosecutors allege they have evidence of Dugan saying she would “take the heat” for her actions.
There is much more to it, obviously. And there's video surveillance of much of this from courthouse cameras, though without sound. The parties are also debating the admissibility of audio recordings of Dugan inside her courtroom.
So what does the prosecution have to prove?
Well, the burden of proof is on prosecutors. They have to convince 12 jurors to unanimously agree that Dugan committed the two crimes beyond a reasonable doubt. One of the legal experts I talked to, Laurie Levenson, says that might be difficult, because the charges have to do with Dugan’s intent.
"Really, all this case is about is what was going on in the judge's head," says Levenson. "Whether she was trying to conceal someone, whether she was trying to impede and obstruct a proceeding, or whether she was trying to do what she thought was her job: run her courtroom, deal with her cases, and try to keep from having the Department of Homeland Security interfere with that with an action that she didn't have advance notice of, or really a clear direction of how she was supposed to deal with it."
Both the former prosecutors and the defense attorneys I’ve spoken with agree that what Dugan was thinking as the events unfolded on April 18th is key to the case.
Do you have any insights on what the defense is going to argue?
The defense has been pretty tight-lipped. What we do know is that they filed a motion in November that describes the Milwaukee County Courthouse policy on ICE arrests as in flux. It says that Chief Judge Carl Ashley was working on a policy which would dictate where in the courthouse that ICE could safely arrest people. There were some draft policies and some emails between Dugan and others that they’re going to try and introduce.
John Gross, from the Public Defender Project (not directly involved in this case) says this:
"I would expect the defense to introduce some of those memos that were going back and forth. Some of the wording in those memos might have influenced Judge Dugan’s understanding of what was going on, or might be relevant to her mental state, right? Like, if the memo, if the chief judge sent a memo saying, ‘Don't interfere with ICE agents making arrests in the hallways.’ Okay, well, she's been given instructions not to do that. Does she now have a corrupt intent?"
"But if the memo is equivocal in some way, and it's a memo saying from the chief judge, ‘I'm engaged in ongoing discussions about how this can be done in a way that satisfies all the parties, and I understand concerns about the chilling effect that immigration enforcement could have in the courthouse. However, I know you all have legitimate concern.’ But you know, whatever it says in there is going to be relevant to show what Judge Dugan was thinking based on those memos."
Gross explains that what is going to be in dispute is what her intent was. Dugan can only be convicted if a jury finds she was doing what she did with a “corrupt intent” or a corrupt purpose.
It’s a jury trial. What are the possible outcomes?
So, a jury — all 12 people — would have to unanimously agree to either convict or acquit Dugan. One way Dugan could be acquitted is if the jury doesn’t think the government has proven its case.
Another way is through jury nullification. Defense lawyers are not allowed to argue for this in federal court. But it can still happen, according to Josh Blackman. He’s a law professor at South Texas College of Law in Houston.
"Nullification goes down a different path," says Blackman. "Nullification says, ‘OK, let's assume she did it. Let's assume she had the right state of mind, the right intent. But this prosecution is unjust, right? The government's wrong for bringing this case. Or the law itself is unjust. We should not prohibit judges in the state court from helping these aliens, right?’ Nullification would be saying to the prosecutor, 'We don't care what the law says. We're going to get rid of your case because we think it's wrong.'"
If all the jurors can’t agree, there could be a mistrial. That means the case could be tried again. But experts say the government would likely look at how many people were holding out from a guilty verdict, and that could make a difference as to whether the case would get charged again.
