Milwaukee County Judge Dugan trial: Live updates Tuesday, Dec. 16

MILWAUKEE - Testimony continues in the trial of Milwaukee County Judge Hannah Dugan, who federal prosecutors accuse of helping an undocumented man evade capture at the courthouse earlier this year, on Tuesday, Dec. 16.

Live updates from Tuesday, Dec. 16

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FBI Special Agent Phillip Jackling 

Government re-direct: Agents efforts to be discreet

10:19 a.m.:

Jackling testified that a Signal group chat primarily took place before Eduardo Flores-Ruiz arrived at the courthouse and primarily discussed that people had recognized them despite efforts to be discreet.

The special agent said the arrest team's effort was meant to be low-key, but that did not happen once Dugan instructed them to see the chief judge.

10:09 a.m.:

Jackling testified that he was unaware of any interm policies at the Milwaukee County Courthouse that required agents to check in with the chief judge's office before they conducted any immigration arrests in the public hallway.

The special agent said he was not irritated when Dugan and fellow Judge Kristela Cervera came to speak to them because he respected that judge's have a certain authority. He said she directed them to the chief judge's office.

Jackling went to a vestibule outside the chief judge's office and said nobody told him he could leave that area but he later left on his own. 

Defense cross-examination: FBI involvement in ICE operation

10:03 a.m.:

Defense Attorney Jason Luczak cross-examined Jackling, who testified he had been involved in a previous ICE arrest at the Milwaukee County Courthouse.

Jackling said, in his role with the FBI, it was "new to me" that someone like himself would be involved in an immigration enforcement operation.

Luczak showed a Signal group chat to the court that Jackling and other agents were using on April 18. The image icons for some agents were not photos or initials, but one showed a man licking a gun. Jackling testified that he did not know at the time that the app's use was not recommended. 

Government questioning: Arrest outside Milwaukee County Courthouse

9:57 a.m.:

Agents regrouped outside the courthouse. Jackling testified that he called out "Flores-Ruiz" and said "F-B," trying to identify himself as a member of the FBI, when Flores-Ruiz ran.

Jackling testified that he was involved in the foot chase of Flores-Ruiz, and that Flores-Ruiz ran in front of a vehicle – causing the agents to pause. A different agent ultimately caught Flores-Ruiz, and he was taken into custody. Other agents eventually made their way over.

Government questioning: Agents separated on sixth floor

9:52 a.m.:

Jackling testified that the arrest team became separated after Dugan directed them to the chief judge's office. He said he felt "uncertainty" about the situation, and it was not part of the arrest plan for the agents to be separated.

While in a vestibule area outside the chief judge's office, Jackling said he did not know where Eduardo Flores-Ruiz was. He ultimately left that vestibule area and spoke with another agent in the public hallway, where he was informed another agent had followed Flores-Ruiz into an elevator. 

Government questioning: Dugan speaks to agents at courthouse

9:44 a.m.:

Jackling testified that he identified himself to courthouse security when he arrived on April 18. He was in plainclothes and armed with his service weapon. When he and a fellow agent arrived on the sixth floor, where Eduardo Flores-Ruiz was scheduled to appear in Dugan's courtroom, they informed the bailiff that they were there and planned to make the arrest after the appearance.

The special agent and a fellow agent were sitting on a bench when Dugan came up to them. He testified that she asked why they were there, she was told they were there to make an arrest, and she asked if they had a judicial warrant – which they did not. He described her tone as "very direct" and said "she seemed upset."

Jackling said Dugan told them to go to the chief judge's office, and another judge accompanied them there. He "briefly" stayed in a vestibule area outside the chief judge's office. He said he did not see Dugan again.

Government calls FBI Special Agent Jackling to testify

9:40 a.m.:

Attorney Kelly Brown Watzka, for the government, questioned Jackling. He testified that he primarily investigates "violent gangs" but had been assigned to work on immigration enforcement from February 2025 to June 2025.

Jacklin testified that there was an administrative warrant to arrest Eduardo Flores-Ruiz at the Milwaukee County Courthouse on April 18, and he was one of six agents on the arrest team.

FBI Special Agent Jeffrey Baker

Government re-direct: Agents became separated at courthouse

9:36 a.m.:

U.S. Attorney questioned Baker after the defense's cross-examination. Baker testified that he was one of six agents on the sixth floor of the Milwaukee County Courthouse to arrest Eduardo Flores-Ruiz.

Baker testified that he and his fellow agents were together but became separated after Dugan instructed them to go to the chief judge's office. 

Defense cross-examination: Video from inside, outside courthouse

9:23 a.m.:

The defense questioned Baker about his saying in a report that he ran after a fellow agent, who had followed Eduardo Flores-Ruiz toward an elevator. Video was shown in court of him walking toward the agent, and he testified that he remembered running at some point in the day and made a mistake in the report.

Baker testified that agents were communicating with one another and agreed to arrest Flores-Ruiz on 10th Street after he had exited the courthouse on April 18.

Flores-Ruiz ran across 10th Street and was taken into custody. Baker said he was not sure whether Flores-Ruiz stopped on his own or an agent tackled him.

Baker testified that additional agents were outside the courthouse in vehicles, but those agents were not part of the six-person arrest team. 

Baker was seen on video holding a cellphone. He testified that he would not have been on his phone for personal reasons, but did not recall specifically what or who he was communicating about or with.

Defense cross-examination: Agents sent to chief judge's office

9:18 a.m.:

Baker said he and other agents at the courthouse were confused when Dugan directed them from the main public hallway to the chief judge's office. He said it was the first time he had experienced something like that when attempting a courthouse arrest.

While in a vestibule area outside the chief judge's officer, Baker said he did not see Flores-Ruiz and his attorney exit into the public hallway and did not recall whether he was looking for them through a window in the door that led into the public hallway.  

Defense cross-examination: Agents outside Eduardo Flores-Ruiz's home

9:14 a.m.:

Baker testified that other agents were conducting surveillance outside Flores-Ruiz's home on the morning of April 18, before he was scheduled to appear in court. He said agents did not make a positive identification on a man who left the residence, and therefore did not attempt an arrest. 

Defense begins to cross-examine Baker

9:01 a.m.:

Defense Attorney Nicole Masnica cross-examined Baker, who first took the stand as a witness in the government's case against Dugan on Monday afternoon.

Baker testified about his involvement in ICE arrests. Specifically, he was part of the team of federal agents sent to the Milwaukee County Courthouse to arrest Eduardo Flores-Ruiz. He said it was his second arrest at the courthouse.

Baker said he notified courthouse security about his presence, because he and other agents were armed and in plainclothes, and alerted a bailiff that he was there to make an arrest after Flores-Ruiz's hearing on April 18.

Judge Adelman calls court into session

9:00 a.m.:

The 13-person jury was brought into the courtroom for a second day of testimony in the trial. Judge Lynn Adelman told them they will "try to keep moving along."

Bonus coverage from Tuesday, Dec. 16

Dugan charged

The backstory:

A federal grand jury indicted Dugan, and she pleaded not guilty, in May.

The grand jury's two-count indictment accused Dugan of helping an undocumented man, Eduardo Flores-Ruiz, evade federal agents who were at the Milwaukee County Courthouse to arrest him on April 18. It also states Dugan obstructed those agents in the process.

Flores-Ruiz was in Dugan's courtroom for a misdemeanor battery case. Prosecutors said Dugan told federal agents to go to the chief judge's office down the hall, and she is then accused of telling Flores-Ruiz and his attorney to leave her courtroom through a back door as federal agents waited outside the courtroom to arrest him.

Agents arrested Flores-Ruiz outside the courthouse after a brief foot chase that day. Dugan was arrested by federal agents at the Milwaukee County Courthouse on April 25. 

The Wisconsin Supreme Court later suspended Dugan indefinitely after she was arrested and charged. Flores-Ruiz later pleaded guilty to illegally reentering the U.S. and, in November, was deported.

Federal Judge Lynn Adelman is overseeing the Dugan trial. 

Complete coverage

Dig deeper:

FOX6 News will stream special coverage of the Dugan trial each day on FOX LOCAL. The app is free to download on your phone, tablet or smart TV. 

• Day 1: Opening statements; FBI agents, ICE supervisory officer testify
• Dec. 11: Judge Dugan trial: Jury seated after day of questioning
• Judge Dugan trial: How did we get here?
• Judge Dugan trial: Who is Eduardo Flores-Ruiz?
• How does federal court work?
• Courthouse immigration enforcement policy questions remain

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