Tipsheet

Here's the Day Two Recap of Judge Hannah Dugan's Trial

Amy Curtis
Amy Curtis  |  December 16, 2025 10:15 PM

The trial of Milwaukee County Judge Hannah Dugan began yesterday with opening statements from the prosecution and defense, as well as testimony from both FBI and ICE agents.

Here's a summary of the day's testimony:

The day began with the defense's cross-examination of FBI Special Agent Jeffrey Baker, who said he and other agents were armed and in plainclothes, planning to arrest illegal immigrant Eduardo Flores-Ruiz after his April 18 hearing before Judge Dugan, and that other agents had been conducting surveillance outside Flores-Ruiz's home that morning. Baker said agents did not arrest Flores-Ruiz when he left his home because they couldn't positively identify a man who left the residence.

Baker told the court he was confused when Dugan directed agents from the public hallway to the chief judge's office, as it was the first time that had ever happened.

The government then called FBI Special Agent Phillip Jackling to the stand. He said he was at the Milwaukee County Courthouse to arrest Flores-Ruiz, and there was an administrative warrant for that arrest. He was also in plainclothes and armed with his service weapon.

Dugan approached Jackling and asked whether they had a judicial warrant; they did not. Jackling said Dugan's tone was "very direct" and that she "seemed upset." Dugan directed Jackling and the other agent to the chief judge's office.

The arrest team was separated after being directed to the chief judge's office, Jackling said, and eventually left the area, where another agent informed them that Flores-Ruiz had entered an elevator, and yet another agent followed him.

Jackling said outside the courthouse that he attempted to identify himself as an FBI agent to Flores-Ruiz, who fled. Jackling chased Flores-Ruiz, who another agent caught.

Defense questioned Jackling about the use of the Signal group chat on April 18, and Jackling said he was unaware that using the app was not recommended. 

On redirect, Jackling said the agents tried to be discreet, but Dugan's targeting of the agents and her removal of them from the public hallway made their presence known. Jackling also said the bailiff told him that the bailiff had not notified Dugan about why agents were present.

After a short morning break, the prosecution called Joseph Zuraw, a supervisory officer with Customs and Border Protection (CBP), to the stand. Zuraw testified that, when he went through courthouse security, he was asked to present additional identification after presenting his CBP credentials. He joined the other agents on the sixth floor, and the group was on Signal discussing how someone on the sixth floor was taking pictures of them.

The video showed Flores-Ruiz walking past Zuraw and the other agents on the way to the hearing, and Zuraw sent a message in the Signal chat that Flores-Ruiz had arrived.

Like the other agents, Zuraw said Dugan's tone was "direct," and she was "visibly upset" when she confronted agents in the public hallway and moved them to the chief judge's office. When Zuraw tried to explain why he was there, Dugan cut him off.

While in the vestibule of the chief judge's office, a deputy informed Zuraw that Flores-Ruiz's case had been "moved up" in Dugan's courtroom and was underway. Zuraw also said the arrest team was separated during this time, and noted ICE/CBP had made arrests in the courthouse "without incident" in the past.

Following Zuraw, the prosecution called Joseph Vasconcellos, an ICE deportation officer. Vasconcellos was previously a border patrol agent. Vasconcellos told the court he was aware that Flores-Ruiz had been previously deported in 2013.

Vasconcellos testified that fingerprints taken from Flores-Ruiz when he was booked in the Milwaukee County Jail matched those taken in 2013 and that "biometric confirmation" indicated Flores-Ruiz was not allowed back into the country and had no pending immigration hearings. 

He also testified that officers can face dangers while making an arrest, and that he's been shot and stabbed during his work.

Vasconcellos told the court that a supervisor told him they could arrest Flores-Ruiz after his hearing in Dugan's courtroom, and Vasconcellos said he told the court agents would not enter the courtroom. He also testified that Dugan confronted agents in the public hallway and seemed "upset" before directing them to the chief judge's office. He also said that despite the team being separated, he did not call off the arrest.

Like Zuraw, Vasconcellos said he'd made arrests in the courthouse before and had never been told to go to the chief judge's office. Vasconcellos testified that he received a message about Flores-Ruiz being in the public hallway, and that he asked the agent to follow Flores-Ruiz.

Vasconcellos said he was still on the sixth floor when he was informed that agents had arrested Flores-Ruiz outside the courthouse. He also told the court that a deportation officer provided Flores-Ruiz with a document in English and Spanish about his rights, and testified that Flores-Ruiz expressed no fear and did not contest removal from the country.

Milwaukee County Judge Kristela Cervera was next on the stand and said she'd been a circuit court judge since 2021. Cervera said she'd taken an oath not to prejudge a case and follow the law.

Cervera's courtroom is adjacent to Dugan's, and both were assigned to criminal misdemeanor court. She testified that the courthouse is a public building and that anyone may enter for any reason after passing through security.

On the morning of April 18, Cervera said she had overlooked the agents in the public hallway and that it was a busy morning. At some point, Dugan came into her courtroom in her judicial robe and "summoned" Cervera, who said Dugan's demeanor was "urgent" and irritated." Dugan told her that ICE was there and needed to check a warrant.

Cervera also said she was unsure why Dugan was involving her in this matter. She told the court that she was "uncomfortable" wearing her judicial robes in the public hallway because "a judicial robe signals a sense of authority." Still, Cervera followed Dugan into the hallway, where Dugan confronted the agents.

Cevera said she was not familiar with immigration law, but that Dugan's behavior led her to believe a judicial warrant was required to arrest Flores-Ruiz, and that an agent presented a paper warrant in the chief judge's office.

After leaving the chief judge's office, Cervera walked back through Dugan's court to avoid the public hallway. An attorney told her later that one of their clients had been arrested and said, "We know what you guys were trying to do." Cervera testified she was "shocked" and "mortified" that someone believed he was involved in helping Flores-Ruiz leave the courthouse through a restricted area.

Cervera also said the court was developing a policy on immigration arrests, but only a draft was being circulated. She spoke to another judge who said such a policy would "give people a false sense of security" because a courthouse is a public place, and they cannot stop immigration arrests.

On cross-examination, Cervera told the defense she would allow a defendant through a restricted hallway "under a unique set of circumstances," but said the prosecution, on redirect, that helping a defendant avoid arrest was not one of those circumstances.

Milwaukee County Sheriff's Office Sgt. David DeSmet was next on the stand and said he did not recall ICE coming to the courthouse before the Trump administration and that on-duty, uniformed law enforcement were not subject to security screenings when properly identified. He asked the federal agents to wait until after Flores-Ruiz's hearing before making the arrest.

DeSmet testified that Dugan told him it was illegal to arrest people in a courtroom, citing a "Supreme Court decision," and that this information "surprised" him. DeSmet requested the case so he could research it, but Dugan never provided the case law. He also said courthouse arrests are common and that he has conducted them himself.

He said he was "flabbergasted" to learn what happened on April 18 and would be concerned if a defendant were allowed into a restricted hallway. DeSmet also said he was unaware of directives preventing ICE from making arrests in public hallways, and that he wasn't aware of a requirement for agents to go to the chief judge's office. He also said that, outside of ceremonial events, judges didn't wear robes in public hallways.

After another break, ICE Assistant Field Operations Director Cassandra Kubiszewski was called to testify. She said Milwaukee County does not honor ICE detainers, and stopped doing so around 2013, but that ICE has been able to conduct arrests in public areas for "as long as she can recall." Kubiszewski said she was concerned about the April 18 events, including the "less-than-safe manner" in which the arrest occurred.

DEA Special Agent Brian Ayers was called to the stand next. He testified he was aware of the plan to arrest Flores-Ruiz on April 18 and had previously conducted arrests in the courthouse. After some of the agents were directed to the chief judge's office, Ayers remained in the hallway and followed Flores-Ruiz onto the elevator. He did not attempt an arrest due to safety concerns.

Ayers said once outside the courthouse with other agents, Flores-Ruiz tried to run when an agent announced himself to make the arrest. Ayers ran after Flores-Ruiz and apprehended him.

The prosecution then called Nile Hendrix-Whitmore to testify. Hendrix-Whitmore is a witness advocate with the Milwaukee County District Attorney's office. As part of her job, she accompanies victims in court and explains the court process to them.

She was scheduled to meet with victims on cases before Dugan on April 18, and she was assigned to work with the victims in the Flores-Ruiz case. However, she was moved to another courtroom, and someone else would be covering Dugan's courtroom that day. She met with the victims in the Flores-Ruiz case and informed them of this.

Hendrix-Whitmore said she saw Dugan and another judge (Cervera) in the hallway in their judicial robes, something she hadn't seen before. She was later informed about what happened in Dugan's courtroom.

She also said Dugan seemed "frantic" in the hallway.

The court was adjourned for the day just before 4:30 p.m. Central time.

The trial resumes at 9 a.m. on Wednesday.