The second day of Judge Hannah Dugan’s trial unfolded with testimony from FBI, ICE, CBP and DEA officers about an April 18 courthouse arrest of Eduardo Flores-Ruiz, unusual courtroom interactions, and whether federal agents followed proper procedure when a judge confronted them in a public hallway and directed them to the chief judge’s office.
The day opened with cross-examination of FBI Special Agent Jeffrey Baker, who described plainclothes agents planning to arrest Flores-Ruiz after his hearing. Agents had been conducting surveillance outside Flores-Ruiz’s home that morning, and Baker said they did not detain him leaving the residence because they could not positively identify a man who left the house.
Baker told the court he was surprised when Judge Dugan moved agents from the public hallway into the chief judge’s office, calling it the first time he’d seen that happen. That exchange set the tone for testimony that emphasized confusion over judicial direction and the practical challenges of making an arrest in a busy courthouse.
The government next called FBI Special Agent Phillip Jackling, who said agents had an administrative warrant to arrest Flores-Ruiz and were armed while conducting courthouse work. Jackling testified that Dugan asked if they had a judicial warrant, which they did not, and that her tone was “very direct” and that she “seemed upset.”
Jackling said agents split up after Dugan sent them to the chief judge’s office, and that an agent later followed Flores-Ruiz onto an elevator after he left the courtroom area. Outside the courthouse Jackling attempted to identify himself as FBI and Flores-Ruiz fled; another agent caught him after a short pursuit.
The defense drilled Jackling about the use of a Signal group chat on April 18, and Jackling admitted he did not know using the app had been discouraged. On redirect he said the attempt to be discreet was undermined when Dugan singled out the agents and moved them away from the public hallway, which made their presence more obvious.
Customs and Border Protection supervisory officer Joseph Zuraw testified that courthouse security asked for extra identification when he entered and that the arrest team was messaging on Signal about someone taking pictures of them on the sixth floor. Zuraw also said Dugan’s tone was “direct” and that she was “visibly upset” when she stopped agents in the hallway and cut him off when he tried to explain why they were there.
Joseph Vasconcellos, a deportation officer with ICE, explained that fingerprints taken when Flores-Ruiz was booked matched prints from his 2013 deportation, and that “biometric confirmation” showed he was not allowed back into the country. Vasconcellos also noted officers face real dangers making arrests and testified that he has been shot and stabbed during his career.
Milwaukee County Judge Kristela Cervera described how Dugan entered her courtroom in robes and “summoned” Cervera into the hallway with an “urgent” and irritated demeanor. Cervera said Dugan told her ICE was there and they needed to check a warrant, and that she felt “uncomfortable” wearing her robe in a public hallway because “a judicial robe signals a sense of authority.”
Cervera said Dugan’s behavior left the impression that a judicial warrant was required to make the arrest, and an agent later did present a paper warrant in the chief judge’s office. Afterward Cervera learned that an attorney had told a client “we know what you guys were trying to do,” leaving Cervera “shocked” and “mortified” that someone thought judges helped a defendant avoid arrest.
Sgt. David DeSmet of the Milwaukee County Sheriff’s Office testified he asked federal agents to wait until after the hearing to make the arrest and said he was surprised when Dugan cited a “Supreme Court decision” that she said made courthouse arrests illegal. DeSmet said Dugan never provided the case law and that courthouse arrests had been common practice.
ICE Assistant Field Operations Director Cassandra Kubiszewski testified Milwaukee County stopped honoring ICE detainers around 2013, but that arrests in public courthouse areas have long been possible. She said she was concerned by the “less-than-safe manner” of the April 18 arrest and that the sequence of events deserved scrutiny.
DEA Special Agent Brian Ayers said he followed Flores-Ruiz onto an elevator but did not attempt an arrest there for safety reasons, and that Flores-Ruiz tried to flee outside the building when an agent identified himself. Ayers gave chase and helped apprehend Flores-Ruiz after the announcement of an arrest.
The prosecution also called Nile Hendrix-Whitmore, a victim witness advocate, who said she saw judges in robes in the hallway and that Dugan appeared “frantic.” Hendrix-Whitmore had been reassigned that day but still met with victims in the Flores-Ruiz case and later heard about the arrest.
The court adjourned just before 4:30 p.m. Central time, and jurors heard about a split among courthouse practice, officer safety concerns, and differing views on when and how arrests should be handled in public spaces. The trial is set to continue at 9 a.m. on Wednesday as witnesses return to clarify the chain of events and the legal questions raised by that April day.
