Judge Hannah Dugan leaves court in her federal trial, where she was convicted of a felony for obstructing immigration officers. (Photo by Isiah Holmes/Wisconsin Examiner)

According to the Eastern District of Wisconsin’s Interim U.S. Attorney Brad Schimel, freshly appointed to his position by President Donald Trump, the federal trial of Milwaukee Judge Hannah Dugan had nothing to do with politics. “There’s not a political aspect to it,” Schimel told reporters after Dugan’s felony conviction on charges she obstructed U.S. immigration agents as they tried to make an arrest inside the Milwaukee courthouse. “We weren’t trying to make an example out of anyone,” Schimel said. “This was necessary to hold Judge Dugan accountable because of the actions she took.”

Schimel didn’t say whether Dugan’s very public arrest and perp walk through the courthouse was also necessary, along with the social media posts by Trump’s FBI director Kash Patel and Attorney General Pam Bondi, crowing about the arrest and sharing photos of Dugan in handcuffs. 

There is no doubt that the Dugan case was highly political from the start. 

As a coalition of democracy and civic organizations in Wisconsin declared in a statement after the verdict, Dugan’s prosecution threatens the integrity of our justice system and “sends a troubling message about the consequences faced by judges who act to protect due process in their courtrooms.”

But Schimel is right about one thing: Dugan’s trial this week was mainly about “a single day — a single bad day — in a public courthouse.”

That narrow focus helped the prosecution win a conviction in a confusing mixed verdict. The jury found Dugan not guilty of a misdemeanor offense for concealing Eduardo Flores-Ruiz, the defendant she led out a side door while immigration agents waited near the main door of her courtroom to arrest him. At the same time, the jury found Dugan guilty of the more serious charge of obstructing the agents in their effort to make the arrest. The two charges are based on some of the same elements, and Dugan’s defense attorneys are now asking that her conviction be overturned on that basis.

An observer watching the trial from afar with no inside knowledge of the defense strategy might wonder why Dugan’s defense team didn’t enter a guilty plea on the misdemeanor charge and then strongly contest the felony obstruction charge as an outrageous overreach in a heavily politicized prosecution. That might have led to a more favorable mixed verdict, in which the jury found that Dugan was probably guilty of something, but that it did not rise to the level of a felony with a potential penalty of five years in prison.

I’m no expert, but daily reports from the trial this week gave me the strong impression that things weren’t going well for Dugan as long as witnesses and lawyers focused on a blow-by-blow account of the events of April 18. Witness testimony described an agitated Dugan, whose colleague, Judge Kristela Cervera, testified — damagingly —  that she was uncomfortable with how Dugan managed the federal agents she was outraged to find hanging around outside her courtroom. 

It’s not surprising that the jury agreed with the prosecution that Dugan was not cooperative and that she wanted to get Flores-Ruiz out of her courtroom in a way that made an end-run around the unprecedented meddling of federal immigration enforcement inside the courthouse. Like other judges and courthouse staff, she was upset about the disruption caused by ICE agents stalking people who showed up to court.

But, as Dean Strang, a law professor at Loyola University Chicago School of Law and a long-time Wisconsin criminal defense lawyer, told me in April just before he joined the defense team and stopped talking about the case to the press, “Whatever you think of the actual conduct the complaint alleges, there is a real question about whether there’s even arguably any federal crime here.” 

The government’s behavior was “extraordinarily atypical” for a nonviolent, non-drug charge involving someone who is not a flight risk, Strang added.

The handcuffs, the public arrest at Dugan’s workplace, the media circus — none of it was normal, or justified. When Bondi and Patel began posting pictures of Dugan in handcuffs on social media to brag about it, “what is it they are trying to do?” Strang asked. His conclusion: “Humiliate and terrify, not just her but every other judge in the country.”

The Wisconsin Democracy Campaign, Voces de la Frontera, and Common Cause-Wisconsin agree with that assessment, writing in their statement reacting to the conviction that Dugan’s felony conviction threatens the integrity of our justice system as a whole, and undermines the functioning of the courts by scaring away defendants, witnesses and plaintiffs who are afraid they might be arrested if they show up to participate in legal proceedings.

But that big picture perspective was not a major feature of the defense’s closing arguments, which relied heavily on raising reasonable doubt about Dugan’s intentions and her actions during a stressful and chaotic day.

That’s frustrating because, contrary to Schimel’s assertions, the big picture, not the events of “a single bad day” is what was actually at stake in this case.

One of the most distressing aspects of the Dugan trial was the prosecution’s through-the-looking-glass invocation of the rule of law and the integrity of the courts.

The federal agents called to the stand, the prosecutors in the courtroom, and Schimel, in his summary of the case, made a big point about the “safety” of law enforcement officers. 

Repeatedly, we heard that immigration agents prefer to make arrests inside courthouses because they provide a “safe” environment in which to operate. 

In his comments on the verdict, Schimel emphasized that Dugan jeopardized the safety of federal officers by causing them to arrest Flores-Ruiz on the street instead of inside the courthouse: “The defendant’s actions provided an opportunity for a wanted subject to flee outside of that secure courthouse environment,” Schimel said.

This upside-down view of safety has become a regular MAGA talking point, with Republicans claiming that when citizens demand that masked agents identify themselves or make videos of ICE dragging people out of their cars, they are jeopardizing the safety of law enforcement officers — as opposed to trying to protect their neighbors’ safety in the face of violent attacks by anonymous thugs. 

Churches, day care centers and peaceful suburban neighborhoods are also “safe” environments for armed, masked federal agents. But their activities there are making our communities less safe. 

Assistant U.S. Attorney Kelly Brown Watzka, delivering the prosecution’s closing argument, told the jury it must draw a line against judges interfering with law enforcement, or else “there is only chaos,” and that “chaos is what the rule of law is intended to prevent.”

But chaos is what we have now, with federal agents terrorizing communities, dragging people out of courthouses and private residences, deporting them without due process and punishing those who stand in their way in an attempt to defend civil society.

The real questions raised by Dugan’s case are whether we believe the “safety” of the agents making those dubious arrests matters more than the safety of our communities, and whether we want the courts to be able to regulate the conduct in their own courthouses as a check on the government’s exercise of raw power.

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Milwaukee County Circuit Judge Hannah Dugan leaves the Milwaukee Federal Courthouse on May 15, 2025. Judge Dugan appeared in federal court to answer charges that she helped Eduardo Flores-Ruiz, an undocumented immigrant, elude federal arrest while he was making an appearance in her courtroom on April 18. (Photo by Scott Olson/Getty Images)

Updated at 9:14 p.m. Thursday, Dec. 18

After six hours of deliberation, a federal jury found Milwaukee County Circuit Court Judge Hannah Dugan guilty of felony obstruction but not guilty of misdemeanor concealing a person from federal immigration law enforcement. The high-profile federal trial stemmed from Dugan’s interaction with federal agents who came to her courtroom to arrest a man who was appearing before her on April 18.

“You don’t have to agree with immigration enforcement policy to see this was wrong. You just have to agree the law applies equally to everyone,” Assistant U.S. Attorney Kelly Brown Watzka told the jury in closing arguments.

Dugan’s case gained national attention, with her defense attorneys saying in closing arguments that the federal government was trying to make an example of the 66-year-old judge in an effort to “crush” those who try to stand up to federal power. Defense attorney Jason Luczak asked the jury to consider whether they were willing to accept the level of government overreach he and other attorneys argued was exemplified in the case. 

Dugan invoked her Fifth Amendment rights and didn’t testify during the trial. 

During their deliberations, the jurors asked multiple questions of the judge. Among them was whether Dugan needed to know exactly who immigration officers had come to the courthouse to arrest. The question went to the obstruction charge Dugan faced, and U.S. District Judge Lynn Adelman decided that in fact Dugan would need to have known the federal agent’s target in order for the obstruction charge to apply. Prosecutors argued vehemently against Adelman’s decision.

Jurors also asked to see the policies of Immigration and Customs Enforcement (ICE) in regards to serving warrants. 

Later, after another jury question, Adelman advised jurors that Dugan needed to have “sufficient knowledge” of a “pending proceeding,” as defined in statute, in order to obstruct that proceeding. 

Closing arguments

Prosecutors made their closing arguments in the federal trial Thursday, asking jurors to consider what happens when judges decide which laws they want to follow based on their own personal beliefs. Dugan was accused of interfering with federal agents as they tried to make an immigration arrest outside her courtroom, and with helping their target to evade arrest. Jurors, Assistant U.S. Attorney Kelly Brown Watzka said in her closing argument, must draw a line, without which “there is only chaos,” and that “chaos is what the rule of law is intended to prevent. 

Calling immigration enforcement a “polarizing issue” nationwide, prosecutors said that Dugan was not on trial for her personal beliefs, but because she “stepped outside of the law.” As they flashed slides and footage to the jury, the prosecution heavily featured statements from Milwaukee County Circuit Court Judge Kristela Cervera, who accompanied Dugan into the hallway at the courthouse to confront the agents. Cervera testified against Dugan saying, “judges shouldn’t be helping defendants evade arrest,” a quote prosecutors highlighted to the jury. 

Dugan knew that the agents had a warrant, prosecutors argued, yet concealed Eduardo Flores-Ruiz, the immigrant they were there to arrest. Dugan’s obstruction of the agents was completed the moment she led Flores-Ruiz and his attorney, Mercedes de la Rosa, to a non-public door to exit her courtroom, the prosecution asserted. Flores-Ruiz exited into the same hallway where agents were waiting for him, and they arrested him shortly afterwards outside the courthouse. But “it simply does not matter what happened next,” prosecutors said. 

Although de la Rosa, whom prosecutors described as “naive and inexperienced,” took the door to the public hallway where agents were waiting, they told the jury Dugan intended for Flores-Ruiz and his attorney to use a staircase to exit on the fifth floor. To buttress their argument, prosecutors played courtroom audio that captured Dugan talking with court reporter Joan Butz and saying “down the stairs” as well as Dugan saying, “I’ll do it…I’ll take the heat,” and Butz responding, “I’d rather get in trouble.” 

Prosecutors argued that had Flores-Ruiz taken the stairs instead of going out into the hallway, that the agents “would have never found” the Mexican-born man, who was in the country without legal authorization. Repeatedly, prosecutors said that no one should ever “second guess” the decisions of ICE agents and law enforcement. 

Dugan was described as “stern” and “angrily pointing” in the hallway, rounding up nearly the entire arrest team and telling them to go to the chief judge’s office. Cervera led the agents to the office, testifying that she felt “abandoned” by Dugan and  “roped into” Dugan’s plan. “No one is above the law,” the prosecution stressed.

Attorney Jason Luczak, delivering the closing  for Dugan’s defense, tried to poke holes in the prosecution’s narrative. “This is a very important case; this is a very unprecedented trial,” Luczak said. “Make no mistake…the government is trying to make an example” out of Dugan, he said. He added that the jury had the power to check what he described as “overreach” by the federal government. 

Luczak stressed that prior to the second Trump administration, ICE arrests had never occurred at the Milwaukee County Courthouse. When the arrests began in late March, individuals had been reportedly arrested in elevators and before attending family court, actions which should have been reported up the agency’s chain of command but weren’t, he said. “They’re not even following their own policies,” Luczak said. “This caused concerns, legitimate concerns, among the judges.” 

The jury was asked to consider whether they really believe that Dugan would put her career at risk for Flores-Ruiz. “This case is riddled with doubts,” said Luczak, stressing that the jury could only convict if they find Dugan guilty beyond a reasonable doubt. “There are consequences on rubber-stamping what the government wants you to rubber-stamp,” he said.

Jurors were reminded of the many emails sent by various judges asking for a policy, sharing stories of having people detained during court, and the slew of questions they had about how the county courthouse could respond. Chief Judge Carl Ashley had released a statement saying that ICE presence at the courthouse discouraged participation in the justice process and eroded trust in the courts’ integrity. 

Luczak also cast doubt on Cervera’s testimony. Jurors were played mute security camera video and asked to decide whether they believe Cervera that Dugan told the agents three times that they needed a judicial warrant, something that didn’t appear to happen in the video. “Judge Cervera is wrong,” said Luczak. “I don’t know if she’s lying, but I could think of some reasons why.” Cervera, the attorney argued, was trying to save herself by throwing Dugan under the bus. “You’re either a friend or an enemy of the government,” he said, asking the jury to consider why prosecutors relied on her statements so heavily. 

When Dugan spoke with the agents, Luczak said, “she’s not being confrontational, she’s being a judge.” He also highlighted that agents contradicted themselves in testimony and in the interviews they gave to FBI agents after the incident. Luczak pointed out that the agents never ran down the hallway to the elevators, as they’d implied. The audio evidence provided by prosecutors had also been taken from multiple microphones and put into one file, and was not audible in many areas, Luczak told the jury, adding, “I don’t think you can see this as very good evidence at all.” 

“If you don’t trust the evidence that the government is putting forward, it’s just another reasonable doubt,” Luczak said. Dugan never concealed Flores-Ruiz from the agents, who never entered her court to keep eyes on him, he said, adding that she never told de la Rosa to take the stairs. Luczak highlighted that prosecutors showed the jury video of the hall, with the filmer going down the stairs and not into the hallway, the opposite of what actually occurred. He called the government’s downplaying of concerns around ICE “tone deaf,” and questioned why Cervera herself texted her sister to warn her about sweeping arrests coming to the courthouse if she, too, didn’t have concerns.

“Justice is not what the government is seeking today,” Luczak. “They’re just wrong.” He told the jury to rely on Dugan’s emails to determine her state of mind, including one where she wrote: “We are in some uncharted waters with some very serious and even potential tragic community interests at risk in the balance.” 

The jury was given instructions by Adelman, and began deliberations shortly after 2 p.m. At around 3:45 p.m., the jury sent out a question to the judge. Interim U.S. Attorney for the Eastern District of Wisconsin Brad Schimel, who lost a bid for the Wisconsin Supreme Court earlier this year, made an appearance in the gallery as Adelman read the question from jurors about whether they were allowed to see ICE policies, which were included among the exhibits. 

Defense calls former Mayor Barrett as character witness

As witness testimony in the trial against Dugan concluded Thursday morning, Milwaukee County judges and public defenders spoke about the confusion and questions they faced when Immigration and Customs Enforcement (ICE) began arresting people at the county courthouse. Former Milwaukee Mayor Tom Barrett was also called to the stand as a character witness, testifying that he’s  known Dugan for over 50 years since they were in high school together. 

Milwaukee County Circuit Court Judges Katie Kegel and Laura Gramling-Perez testified for the defense about emails local judges sent each other, asking for guidance and sharing stories about having people “snatched” out of their courtrooms and seeing ICE agents sitting in cars outside the court. 

One judge chimed in on the chain, “does this mean that Milwaukee County is cooperating with ICE?” Milwaukee County does not cooperate with ICE detainer requests in the jail. The Milwaukee Police Department also has its own policies limiting cooperation with ICE.

Judges air concerns about courthouse arrests

In one of her emails, Gramling-Perez strongly urged the creation of a policy on courthouse arrests by ICE. Under such a policy, she testified, ICE agents would be required to check in with the chief judge before conducting any enforcement. When the arrest team arrived the morning of April 18, they checked in with security who notified their supervisors at the Milwaukee County Sheriff’s Office. Security initially believed the agents would need to be escorted by the sheriff’s office, but a sergeant told them that wouldn’t be necessary. 

Gramling-Perez reviewed emails on the stand that said “the historic protocols are now shifting quickly,” and explaining  that although state and local law enforcement have conducted arrests around the court in the past, those activities were always guided by clear policies or practices which were respected by law enforcement. “The ICE detentions are a different animal,” one email stated.

Prosecutors repeatedly attempted to get Gramling-Perez to say that ICE arrests were allowed in public hallways, per the “key takeaways” that she outlined in her email to Dugan and other judges. Gramling-Perez, however, didn’t budge. When prosecutors showed her images of documents they claimed were part of her presentation, she said she’d never seen them before. When they pressed her to say that ICE arrests could happen in public hallways, she countered that her emailed explanations were not all inclusive, that she is not an expert on the matter, but that even public hallway arrests have their limits. 

Gramling-Perez testified that although discussion of a policy had begun, no policy had yet been established by the chief judge. 

Attorney Maura Gingerich, a public defender, was also called to the stand as a defense witness. Gingerich testified wearing a black suit with a black mask she said she wore for health reasons — attire similar to what she wore on April 18, when security cameras captured her photographing the plain-clothes ICE, FBI, DEA, and Border Patrol task force members in the courthouse hallway. Gingerich testified that she took photographs of the agents to send to her supervisor, so that the chief judge would be notified that the agents had returned and could offer guidance. 

“I think that it was very stressful to see what I thought were a number of law enforcement on the sixth floor without uniform,” Gingerich testified, noting she had already gone to another courtroom when Dugan approached the agents. One of the prosecutors  suggested  Gingerich followed the agents to another courtroom and was cooperating with Dugan,  saying, “I know what you guys were trying to do,” but Gingrich denied that characterization. Gingrich said she never saw Dugan that morning. 

Barrett calls Dugan ‘extremely honest’; Dugan invokes the Fifth Amendment

Former Milwaukee Mayor Tom Barrett testified as a character witness for Dugan, saying he has known her and the Dugan family for half a century. They first met when they attended the same high school.

Barrett described Dugan as very active in the community, an enthusiastic participant in community organizations and in  her church. “I think that she is extremely honest and I know that she will tell you exactly how she feels,” Barrett testified, adding that he feels that Dugan is a good person. 

The defense rested its case ahead of a lunch break. Dugan invoked her Fifth Amendment rights not to testify. Defense attorney Steven Biskupic noted on the record that he objected  to draft instructions the judge gave the jury, after Adleman chose jury instructions crafted by the prosecution instead of the defense.

Dugan faces up to five years in prison and a $350,000 fine for the felony conviction, but as a nonviolent offender with a record of service to her community is unlikely to be sentenced to time behind bars. Her sentencing hearing has not yet been scheduled.

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Milwaukee County Circuit Judge Hannah Dugan leaves the Milwaukee Federal Courthouse. Judge Dugan is on trial on charges that she helped Eduardo Flores-Ruiz, an undocumented immigrant, elude federal arrest while he was making an appearance in her courtroom on April 18. (Photo by Scott Olson/Getty Images)

Milwaukee County Chief Judge Carl Ashley took the stand on the third day of the high profile trial of  Judge Hannah Dugan, who is accused of obstructing federal immigration agents and hiding the man they came to the Milwaukee County Courthouse to arrest. 

Ashley was asked about an email he wrote on April 4 to his fellow judges, following a string of courthouse arrests by immigration officers. The chief judge, like many of his colleagues, was disturbed by the arrests, and feared that they would disrupt the courthouse’s business and erode the public’s trust that the courthouse was a safe place. 

Ashley wrote that ICE arrests could likely be prohibited inside courtrooms but that “I’m not sure we have the authority to intervene with what happens in the public hallway.”

As the judges were discussing a plan for responding to the ICE presence at the courthouse, Ashley offered a training presentation — which Dugan was unable to attend  — that highlighted in part that immigration enforcement could happen in the public hallways, but not against certain groups of people such as victims of crimes. 

While questioning Ashley, prosecutors showed the jury an email Dugan sent in response to the training which said that “optimally” a policy guiding how court staff should respond to the presence of immigration officers would be desirable. Less than an hour later, Ashley attached a draft policy to an email, and sent it off to Dugan and other judges. Ashley testified that he wanted as much feedback on the policy as possible, including from the sheriff’s office, the district attorney and other “system partners.” He also reached out to Immigration and Customs Enforcement (ICE) to get their input, agreeing with prosecutors who said Ashley “wanted to get it right.” 

Although the policy had been drafted, it had not been officially instituted. The policy was non-binding on April 18 when agents arrived outside Dugan’s courtroom, and did not explicitly state that ICE could not make arrests in the public hallway, Ashley acknowledged on the stand. 

Part of the draft  policy advised court staff to contact their immediate supervisors about the presence of ICE, and said Ashley should be among those notified. Dugan’s defense attorneys argued in prior days of testimony that Dugan was following the draft policy when she went into the hallway outside her courtroom to confirm that the plain-clothes agents there had a non-judicial, administrative warrant and to tell them to go check in with the chief judge. The draft policy stated that all court staff were expected to comply with its guidance, and advised staff that administrative  warrants do not compel staff to comply with requests from ICE agents. 

Ashley testified that he was at home when the agents were sent to his office by Dugan. He recalled getting a call from Brian Barkow, chief deputy of the Milwaukee County Sheriff’s Office, advising him that ICE was in the building to arrest someone. After calling the deputy administrator, Ashley confirmed that agents were there. However, Ashley did not direct them to be brought to his office, the chief judge testified. Texts Ashley sent to Dugan telling her to call him went unanswered. She later replied that she had left the court to attend Good Friday church services. 

“I was concerned about what might’ve happened,” said Ashley, who then sent out another email notifying the judges about the ICE activity at the courthouse. He mentioned in the email that “all the agent’s actions were consistent with the draft policy.” 

Judges, courthouse staff upset by ICE presence

Prosecutors have accused Dugan of having “strongly held views” about ICE arrests at the courthouse. Wednesday’s testimony demonstrated that judges and courthouse staff were struggling with the arrival of ICE at the courthouse and trying to formulate a response.

On April 6, in the wake of the first arrests, Ashley issued a press release stating that ICE operating around the courthouse “can deter individuals, particularly immigrants and marginalized communities, from attending court hearings, seeking legal assistance, or reporting crimes,” and that “this undermines the fundamental right to access the courts and seek legal remedies.” This could lead to a lack of trust in the judicial system which could foster “a reluctance to engage with law enforcement, legal representation, and the courts, ultimately hindering the administration of justice.” 

Ashley read the press release on the stand, his voice booming through the federal courtroom. It stated  that “allowing ICE agents to operate within courthouse complexes has the potential to significantly damage the integrity of the court system,” and that “it undermines the principles of justice, fairness, and equality before the law, and ultimately jeopardizes the rights of individuals seeking to navigate the legal process. Courts remain safe havens for all individuals, free from the threats of immigration enforcement.”

The chief judge confirmed on the stand that he continued to hold these beliefs. During cross examination, defense attorneys showed a version of the draft policy, highlighting that it was based on a policy created by San Francisco, California. Ashley testified to editing the draft policy by removing a sentence stating that ICE agents are allowed to arrest people in the public areas of a courthouse, which appeared in the original policy from California. 

Melissa Buss, a Milwaukee County assistant district attorney who was assigned to Dugan’s court, testified Wednesday that she saw Dugan motion to attorney Mercedes de la Rosa — who was representing Flores-Ruiz — to “come here” as she stood by the jury door leading to the non-public hallway. Buss said it was unusual that Dugan appeared to be “directing” de la Rosa, and that the judge seemed “frustrated” whereas de la Rosa seemed “frazzled or confused.” Buss said that she wasn’t aware that Dugan had called Flores-Ruiz’s case early, despite audio recordings showing that Dugan spoke into a microphone and called the man’s case loudly, and set a date for him to re-appear via Zoom. 

Clerk calls ICE agent ‘fascist’

Prosecutors also called Alan Freed Jr., a deputy clerk in Dugan’s court. Freed recalled hearing from public defenders that ICE was in the hallways, saying that he was “upset and a little outraged.” Freed walked back into the courtroom to tell Dugan that there were “ICE guys in the hallway,” which was captured on courtroom audio. Freed also said that Dugan told him not to call the chief judge. Later, when Freed checked back in the hall, he saw agents walking towards the chief judge’s office after being directed there by Dugan. As one of the agents walked past Freed testified that he called the agent a “fascist.” 

Freed was grilled by prosecutors about who said what in the audio recordings, but he testified that he couldn’t recall some of the events of April 18. He’d sat through thousands of cases, including many in Dugan’s court, and had never seen a similar chain of events play out. Freed said it is not unusual for cases to be called off the record as Flores-Ruiz’s was, echoing Buss who said judges can call cases at random and that this was not unusual as prosecutors argued. 

Hasty exit out a side door

De la Rosa also testified that she was concerned about the news that ICE was in the building when she arrived at the courthouse. She’d only been a public defender in Milwaukee since March 2025, not long before ICE began arresting people inside the building. When Flores-Ruiz arrived, she was nervous to get him in and out of the building as quickly as possible to avoid contact with ICE. She asked for the pretrial hearing to be called off the record, and described herself as visibly anxious and even “obnoxious.” 

After Dugan was finished calling her case, de la Rosa recalled Dugan motioning for her and Flores-Ruiz to come by the jury door. She’d had judges lead her and clients out of side doors before, but only in particular circumstances, such as to avoid emotional victims, she said. “I kind of remember being scared or freaked out,” she testified, adding that she was stressed about the agents, and was bouncing back and forth between two languages to translate what was happening to Flores-Ruiz. “My brain was spinning,” she said. When the jury door opened into the hallway, de la Rosa testified, Dugan took a couple of steps in and directed her and her client straight down the hall towards the door that led to the public hallway. 

De la Rosa testified that she was never directed to go to the staircase in that hall, which led to a different floor, and didn’t even know that it existed. Her case had been called before attorney Walter Piel, who arrived early to court with his client. “I was a little frustrated that I wasn’t called first,” Piel testified, but added that he didn’t think that was unusual. When de la Rosa got outside, after unknowingly riding the elevator down with a plain-clothes ICE agent, she heard someone call Flores-Ruiz’s name. Flores-Ruiz ran, and agents arrested him down the street after a brief foot pursuit. 

The young defense attorney recalled being grilled about the incident by the FBI multiple times in interviews which stretched four to six hours in total. De la Rosa testified Wednesday that when Dugan allowed her to use the non-public hallway, she interpreted it as a “mentoring moment” because she was a new attorney unsure how to handle this unique situation. 

Joan Butz, a court reporter in Dugan’s courtroom, testified that she  was irritated when she heard that ICE had returned. “That pisses me off,” she remembered telling one of the other staff. Butz was captured on audio talking with Dugan about “down the stairs,” in a  conversation that wasn’t cleanly recorded. Butz testified that she offered to show de la Rosa the exit near the jury box, saying she just wanted to be helpful. Butz admitted, however, that she believed the correct exit would have been the staircase, and that the wrong exit would have been into the hallway where the agents were waiting. 

Prosecutors rested their case Wednesday, allowing the court day to conclude almost two hours earlier than usual. On Thursday, defense attorneys are expected to call several more witnesses. 

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Judge Hannah Dugan leaves court in her federal trial, where she faces charges of obstructing immigration officers. (Photo by Isiah Holmes/Wisconsin Examiner)

The gallery was packed shoulder-to-shoulder Monday morning as Milwaukee County Circuit Court Judge Hannah Dugan entered the courtroom of U.S. District Judge Lynn Adelman not as a judge, but as a criminal defendant. Dugan is accused of obstructing federal agents in their efforts to arrest a Mexican-born man who was in the country without legal authorization, and who appeared in Dugan’s misdemeanor criminal court back in April. If convicted in what Adelman signaled would be no more than a week-long trial, Dugan could face six years in prison.

Attorneys on both sides of the trial painted very different pictures of Dugan during their opening statements, which can include statements which do not have to be demonstrated by evidence. 

Opening statements from prosecutors lasted nearly an hour, with the lawyers saying that Dugan “knew what she was doing was wrong.” Repeatedly, prosecutors pointed to courtroom audio transcribed by the FBI which captured Dugan saying, “I’ll get the heat,” when talking to her courtroom staff about how to respond to the fact that immigration agents were waiting in the hallway to arrest Eduardo Flores-Ruiz, a man appearing before her on misdemeanor charges of battery and domestic violence. 

Prosecutors called the Milwaukee County Courthouse “a safe place where arrests are routine,” allowing federal agents to confront targets who have passed through security screening and are unarmed. An arrest team of six federal agents from the FBI, DEA, Border Patrol, and ICE wearing plain clothes and carrying concealed weapons were attempting to blend into the normal hustle and bustle in the courthouse. Prosecutors said that an FBI agent told a Milwaukee sheriff’s deputy, who was serving as a bailiff for Dugan’s courtroom, that they were there to arrest Flores-Ruiz. “Everything was proceeding in a routine way,” prosecutors told the jury, until the court clerk told Dugan that agents were in the hallway for an immigration arrest. 

Jurors watched mute video compiled from security cameras showing Dugan, accompanied by fellow Circuit Court Judge Kristela Cervera, walking down the public hall in their judge robes to find out what the agents waiting outside the courtroom wanted. Both judges can be seen pointing to the chief judge’s office, with agents then following Cervera to consult with Chief Judge Carl Ashley. 

When Dugan returned to her courtroom she called Flores-Ruiz first out of the at least 33 cases she had on the docket, setting a court date and telling Flores-Ruiz he was welcome to attend remotely over Zoom. After that, prosecutors allege that Dugan and her court staff directed Flores-Ruiz to an exit in the courtroom which led to a non-public hallway. At the end of the hallway Flores-Ruiz could either take a staircase leading down to the fifth floor, or go through a door which led back out to the public hallway where agents were waiting. 

Flores-Ruiz and his attorney exited through the door and walked  right past the federal agents. Some of the agents trailed Flores-Ruiz to the elevator, while the rest of the arrest team left Ashley’s office. Cameras outside the courthouse captured agents running down a sidewalk after Flores-Ruiz and his attorney. 

Dugan is accused by prosecutors of “dividing” the arrest team by directing them to the chief judge. They say that Dugan had “strongly held views” about immigration enforcement in courts which led her to “cross the line,” and that the now-suspended judge had “orchestrated” Flores-Ruiz’s “escape from federal law enforcement.” 

Prosecutors claimed Dugan told Cervera to keep her robes on during the interaction, and that Cervera and Flores-Ruiz’s defense attorney Mercedes De La Rosa were both uncomfortable with Dugan’s wishes to confront the agents. 

Dugan’s defense team emphasized that the door Flores-Ruiz used to exit the courtroom was just 11 feet from the courtroom’s main entrance. They also discussed the upheaval the Trump administration’s deportation operations had caused at the Milwaukee County Courthouse before the interaction with Dugan. ICE arrests had occurred in late March and early April, alarming county judges. The defense displayed emails from courthouse personnel they said demonstrated the “paranoid” atmosphere at the courthouse and which described concerns about people not showing up to court and suspicious vehicles parked outside that looked like they belonged to federal law enforcement. 

Courthouse was developing a policy on ICE

At the time of Flores-Ruiz’s arrest, Chief Judge Ashley was drafting a policy on how to respond to immigration enforcement coming inside the courts. Judges had been invited to a training presentation on the matter which Dugan was unable to attend, but she had been briefed on its main points. 

The draft policy noted that administrative warrants of the type federal agents presented to arrest Flores-Ruiz are not treated the same way as judicial warrants. Whereas a judicial warrant would give the agents full access to the building, administrative warrants limit them to the public areas of the courthouse. Court staff were also instructed to direct immigration officers to their immediate supervisors, which Dugan appeared to be doing by directing them to Ashley, her attorneys said, adding  that the chief judge needed to be notified if a warrant is executed. 

Ashley had also issued a press release after the rash of ICE arrests saying in part that “the court must remain a safe haven,” Dugan’s attorney Steven Biskupic noted, as images of courthouse emails, messages, and press releases were presented  to jurors on two screens. Dugan did not obstruct the agents, or give direction to anyone else to do so, her attorneys argued. 

Federal agents testify

Three federal agents took the stand Monday and gave lengthy testimony, starting with Erin Lucker of the FBI. Lucker was not involved with the immigration arrest, but helped gather and analyze video and evidence to charge Dugan. Using audio from courtroom microphones, Lucker created a transcript and timeline of events from the time Dugan first approached the agents until Flores-Ruiz was arrested outside. 

The audio was very poor in places, and Judge Adelman reminded the jury that the audio is evidence, not the transcript, and that if they could not understand what is said on the audio, they were not allowed to rely on the transcript instead. In a portion of the audio, Dugan can be heard talking to court staff about the exit to the hallway, with a voice saying “down the stairs,” though some of what’s being said was inaudible. Prosecutors also said that the alleged victims of the domestic violence and battery charges Flores-Ruiz faced were kept waiting in the courtroom to wonder what happened after he left. 

In response to questions from Dugan’s defense attorneys, Lucker said she had no firsthand knowledge of the courthouse itself or what business there usually looks like. She had not participated in an arrest team like the one assembled for Flores-Ruiz, she said. She also responded to the defense that she wasn’t aware that before January 2025 immigration enforcement officers did not, as a matter of policy, target people for arrest at courthouses. 

Defense attorneys also pointed out that a video Lucker helped produce shows a walkthrough of Dugan’s courtroom and the non-public hallway outside ends with the filmer walking down the stairs, not taking the entrance to the hallway which Flores-Ruiz took. Lucker said she hadn’t walked down those stairs, and was unaware that to get out of the building you’d need to pass by multiple security checkpoints. 

Testimony revealed that federal agents had been surveilling Flores-Ruiz at his home and followed him to the courthouse. Defense attorneys questioned why a traffic stop wasn’t made. The task force agents used an encrypted Signal chat which they’d named the “Frozen Water Group” to communicate about the ICE operation. 

FBI Special Agent Jeffrey Baker,  one of the plain-clothes agents on the arrest team, testified that he  had only been on the ERO team since February when the team came for Flores-Ruiz in April. Baker said Dugan “divided” the arrest team by leading members into the chief judge’s office, and that when he talked to Dugan “she seemed to be angry at that point.” When he went to Ashley’s office, Baker said he wasn’t told where he was going or why. He was informed that Flores-Ruiz had left the building either by a text or phone call from another agent.

On Tuesday, Baker will be questioned by defense attorneys.

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