Milwaukee County chief judge testifies on third day of Hannah Dugan federal trial

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 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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