Dugan’s ‘tone’ under microscope as fellow judge testifies against her in federal trial

The federal courthouse in Milwaukee, Wisconsin. (Photo by Isiah Holmes/Wisconsin Examiner)
Testimony from federal agents continued into the second day of Milwaukee Circuit Judge Hannah Dugan’s federal trial, where Dugan faces charges of obstructing immigration officers and concealing a man they were trying to arrest outside her courtroom in April. Prosecutors repeatedly asked agents about Dugan’s tone when she spoke with them, which they described as upset, angry, direct and stern. A colleague of Dugan’s, Judge Kristela Cervera, who was with Dugan when she confronted agents in the hallway outside her courtroom, also testified that Dugan’s demeanor during the encounter made her uncomfortable.
On Tuesday, FBI agent Jeffrey Baker testified about his encounter with Dugan as part of the six-man arrest team that entered the Milwaukee County Courthouse in April in search of Eduardo Flores-Ruiz, a 30-year-old Mexican-born man who was in the country without legal authorization.

During Baker’s testimony, details emerged about a woman the agents encountered in the hallway whom they believed was a public defender and who noticed them and began taking pictures of the agents before Dugan arrived and spoke with them. Images of a Signal Chat used by the arrest team which had been named the “Frozen Water Group,” a reference to ICE, revealed that agents texted that the woman had “been around for more than one of these before.” Another message stated “she was talking sh*t about us with another attorney about how we are not very covert.”
The prior arrests the agents were referring to had occurred at the courthouse from late March to early April, fueling concern among Milwaukee County judges about how to ensure the courthouse remained a safe and orderly place to conduct business. Testimony and text messages suggest that the prior arrests had all been made by the same team Dugan spoke with on April 18.
Defense attorneys highlighted the agent’s choice of profile images for the “Frozen Water Group” chat. One agent had chosen an image of a skull over a pill bottle crossed by two syringes with a thin blue line flag in the background. Brian Ayers, a Drug Enforcement Administration (DEA) agent, who said that this was his account in the Signal chat, testified Tuesday that the logo belonged to the DEA opioid task force. Another showed a man licking the barrel of a handgun. Ayers testified that he followed Flores-Ruiz down the hall, and rode the elevator down with him and his lawyer without revealing that he was a federal agent.
FBI agents Phillip Jackling, Customs and Border Protection agent Joseph Zurao, and ICE deportation officer Joseph Vasconcellos, who were all part of that Signal chat, described Dugan coming out to ask whether they were there to attend court hearings, and pointing them down the hall to Chief Judge Carl Ashley’s office. Jackling described Dugan as “very direct, and she seemed upset,” and said that leaving the rest of the arrest team in the hall “caused me to have a little bit of uncertainty about what was going to happen next.” Zurao said that Dugan told the agents to “get out” or “leave”.
Vasconcellos said that he was unnerved by the attorney photographing them, and that because he’d been stabbed, shot, and suffered nerve damage in his neck over the course of his career, he had concerns that their plan to use the courthouse as a “safe place” to arrest people had gone south. “I was honestly concerned that we had had our pictures taken and the staff knew who we were,” Vasconcellos testified. He’d texted in the group chat, speaking of the public defender photographing them, “this is going to be a pain in the d-ck.”

Vasconcellos described Dugan as “very stern and upset,” and said when Dugan told them to leave the hall and go to Ashley’s office, “I told her no.” Vasconcellos eventually went into the chief judge’s office, where he and other agents waited to get connected to Ashley over the phone. Ashley discussed the courthouse draft policy governing immigration enforcement in and around the building at length with the agents. When Vasconcellos left Ashley’s office, the rest of the arrest team had already followed Flores-Ruiz outside and arrested him.
Vasconcellos testified that he was aware that judges could speak sternly and that he was not familiar with Dugan and didn’t know if that tone was normal for her. Defense attorneys highlighted that only DEA Special Agent Ayers told FBI investigators that he heard Dugan yelling at the team, something none of the other task force agents described in their testimony. Ayers also refuted testimony from Zuaro, who claimed to have told Ayers to “get your ass out in the hallway in case he comes out,” an assertion that was not documented in reports and interviews conducted by investigators. Nile Hendrix-Whitmore, a victim witness advocate with the Milwaukee County District Attorney’s Office, also testified that she did not hear any yelling or arguing when Dugan spoke with the agents.
Judge testifies about discomfort with Dugan
Later in the day, Judge Cervera took the stand. Cervera recalled that she had a busy schedule on April 18, and had arrived to court early to begin working on her cases. She’d left the building to move her car and as she walked back she ran into Dugan who was presumably doing the same. Not long after she arrived back to her courtroom, Cervera testified that Dugan came in and beckoned her over. “I thought something bad had happened,” said Cervera. “It was embarrassing to be summoned in that way.”
Cervera testified that Dugan gave the impression that “it was urgent” and that Dugan “seemed irritated.” When Cervera began to remove her robes, she testified that Dugan told her to keep them on, which she did because Dugan was a more senior judge. “I didn’t want to walk into the hallway with my robe,” Cervera testified, though she said she didn’t tell Dugan that she was uncomfortable.
When the two approached the agents and Dugan asked whether they had a judicial warrant, Cervera said that “her irritation seemed to progress into anger.” Cervera said that Dugan was “expressing her views to the officer” and that she thought Dugan “could have been a little more diplomatic.” Nevertheless, Cervera testified that the interaction was “pretty straightforward and quick,” and that she had her own questions about the kind of warrant the agents had. Dugan told them that a judicial warrant signed by a judge, not an administrative warrant signed by an ICE officer, would be needed, Cervera testified.
Cervera escorted the agents to Ashley’s office and recalled looking back and not seeing Dugan follow them. “I felt abandoned,” she said on the stand. “I thought she left me.” As Cervera looked over the warrant herself, she noticed other agents coming into the hall leading to the chief judge’s office. When Cervera took a short cut through Dugan’s court to get back to her own room, Cervera noticed that Dugan was hearing cases. “I was irritated at that point,” she said, repeating that she felt “abandoned” by her fellow judge.
Bits and pieces of what happened then made it to Cervera, including Flores-Ruiz being arrested outside, and attorneys pumping their fists telling her, “You go, Judge,” and saying, “Judge, you’re ‘goated’ now,” a reference to the term “Greatest Of All Time.” Cervera testified that one attorney, the same who took pictures of agents in the hall, told her, “We knew what you guys were trying to do.” The next day, she heard that the FBI would be getting involved. “I was shocked” and “mortified,” she testified. “Judges shouldn’t be helping defendants avoid arrest.”
Sometime after April 18, Cervera recalled running into Dugan in an elevator. “I didn’t want to run into her at this point,” Cervera testified. Dugan allegedly told Cervera that she was “in the dog house with Carl,” referring to the chief judge. “She seemed eager to tell me about what happened on Friday,” Cervera said.
Defense attorneys questioned Cervera about whether she knew ICE agents were waiting outside her courtroom as well, which she denied. When she got home on April 18, she Googled Vasconcellos’ name, and warned her sister — who is also an attorney who had cases with clients at the Milwaukee courthouse coming up — that ICE was more active in the building. Defense attorneys noted that when she was called to a grand jury, Cervera did not reveal that she had warned her sister about the federal operations.
Cervera said on the stand that she was talking to her sister about what appeared to be “sweeping arrests” happening around the country, and that she’d never heard of ICE arrests at the courthouse prior to March. Multiple members of the arrest team testified that they had only been transferred to ICE Emergency Removal Operations (ERO) duties in early 2025, after President Donald Trump took office.
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