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 Eduardo Flores-Ruiz evade capture at the courthouse earlier this year, on Tuesday, Dec. 16.

Live updates from Tuesday, Dec. 16

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Milwaukee County Judge Kristela Cervera

Government questioning: Uncertainty about immigration policy

2:06 p.m.:

Cervera testified that she was aware of a draft policy that was circulated, but nothing was conveyed to her that any binding policy for judges to handle immigration arrests at the courthouse had been finalized. 

The judge said she recalled discussing a possible policy with a fellow judge, who said a policy would give people a false sense of security because the courthouse is a public place and they cannot stop arrests.  

Government questioning: Cervera learns about what happened

1:58 p.m.:

Cervera said, after leaving the chief judge's office, she walked through Dugan's courtroom – where Dugan was already conducting court – to avoid walking down the public hallway in her judicial robe as she tried to return to her own courtroom.

Cervera said an attorney later told her one of their clients "was arrested" and "we know what you guys were trying to do." The judge testified she did not know what they were talking about, but the chief judge later filled her in about what happened. 

Cervera said she was "shocked" to hear that and "mortified" that someone might think she was involved in helping Flores-Ruiz leave court through a restricted hallway.

Government questioning: Cervera escorts agent to chief judge's office

1:49 p.m.:

Cervera said she was not familiar with immigration law but under the impression, based on Dugan's actions, that the agents did need a judicial warrant. She then helped escort an agent to the chief judge's office. She believed they were going to show a warrant to the chief judge.

Cervera testified she looked back and did not see Dugan and was "amazed" that she was not following them. 

Cervera said an agent presented a paper warrant once they were in the chief judge's office and looked at it while they waited to find out who they could talk to, because she knew the chief judge was not there. She later learned the agent spoke to Chief Judge Carl Ashley over the phone.

Government questioning: Dugan, Cervera address agents

1:41 p.m.:

Cervera testified that a judicial robe signals a sense of authority. She said she felt uncomfortable wearing it in the public hallway, because it is not common, and was hesitant to go into the hallway.

The judge testified that Dugan asked agents who they were, and an agent identified himself – telling Dugan they were there to conduct an arrest and had a warrant. She said Dugan quickly repeated three times that the agents had to have a judicial warrant.

Cervera said she did not see a warrant, but the interaction happened very quickly. Dugan told the agent to go to the chief judge's office. 

Government questioning: Dugan notifies fellow judge about ICE

1:33 p.m.:

Cervera said she was "pretty busy" on the morning of April 18, but she did not recall exactly how many cases, and lots of people were coming and going. 

When shown surveillance video, she testified that she and Dugan walked past federal agents in the public hallway. She said the agents did not draw her attention. At that point, she said she and Dugan had not yet conducted court business for the day.

Cervera testified that Dugan came into her courtroom, wearing her judicial robe, and "summoned" her. She said she was concerned something happened, and they went into Cervera's chambers. 

Cervera said Dugan told her that ICE was there, and they needed to check a warrant. She was not sure why Dugan involved her and described her demeanor as "urgent" and "irritated."  

Government questioning: Public vs. restricted areas of courthouse

1:29 p.m.:

Cervera testified that the Milwaukee County Courthouse is a public building and, once they pass through security, "technically" anyone is free to enter the courthouse for any reason. 

Cervera testified that there are restricted areas, such as a judge's chambers, in the otherwise public building. She said there is a restricted hallway that jurors are allowed to use but would need to be let into.

Government begins questioning Milwaukee County judge 

1:25 p.m.:

Attorney Kelly Brown Watzka questioned Cervera, the Milwaukee County judge seen on surveillance with Dugan at times on April 18, in the government's case. 

Cervera has been a circuit court judge in Milwaukee County since 2021, and testified that she took an oath to not prejudge a case and follow the law.

Cervera testified that Milwaukee County judges are assigned to a specific docket. She is assigned to criminal misdemeanor court – which can include retail theft or battery, among other things. Her courtroom is adjacent to Dugan's courtroom, and she said Dugan was assigned to criminal misdemeanors as well.

ICE Deportation Officer Joseph Vasconcellos (cont.)

Government re-direct: Conversation with Ashley

1:22 p.m.:

Vasconcellos again stated that, in his conversation with Chief Judge Carl Ashley, he was not told he could not make an arrest in the public hallway. He reiterated that Ashley discussed a draft plan that had not been finalized.  

Defense cross-examination: Conversations with Dugan, Ashley

1:09 p.m.:

Vasconcellos testified that he did not have a chance to show the warrant he had until he was in the chief judge's office, and that he did not interrupt Dugan to present it as a sign of respect but informed her that he had an administrative warrant. He later testified that anyone, including the public, could ask to see a warrant.

The deportation officer said he did not know Dugan prior to Aug. 18 and, while she seemed stern, could not say whether that was her normal demeanor.

Vasconcellos testified that it was his understanding that court officials did not know Chief Judge Carl Ashley was not in his office when Dugan directed agents to speak with him. They talked on the phone.

The deportation officer said, in the conversation with Ashley, that Ashley had not yet determined and informed ICE about a draft policy related to immigration arrests. Vasconcellos testified that he was not specifically told whether he could or could not conduct an arrest in the public hallway on the sixth floor.

Defense cross-examination: Confusion at Milwaukee County Courthouse

1:00 p.m.:

Defense Attorney Nicole Masnica cross-examined Vasconcellos, first questioning him about forms that were filled out after Flores-Ruiz was arrested.

Vasconcellos testified about things he found unusual on the day he and other agents went to the Milwaukee County Courthouse to arrest Flores-Ruiz. He agreed that there seemed to be confusion with courthouse security when he arrived on April 18.

The deportation officer testified that there was an understanding with courthouse staff to not arrest Flores-Ruiz until after his court appearance. 

Government questioning: Flores-Ruiz in custody

12:54 p.m.:

Attorney Keith Alexander continued to question Vasconcellos in the government's case when the court returned from lunch.

The deportation officer said he gave Flores-Ruiz a document, which was in both English and Spanish, to review his rights. He testified that Flores-Ruiz expressed no fear of being removed from the country and did not contest.

COMPLETE COVERAGE: Federal trial of Milwaukee County Judge Hannah Dugan

Judge calls for break

12:05 p.m.:

U.S. District Judge Lynn Adelman called for a lunch break. Court should resume around 12:50 p.m.

ICE Deportation Officer Joseph Vasconcellos

Government questioning: Flores-Ruiz leaves, detained outside

12:03 p.m.:

Vasconcellos said he was still on the sixth floor of the Milwaukee County Courthouse when he was informed that agents detained Flores-Ruiz outside the courthouse on 10th Street.

The deportation officer said he then drove to where Flores-Ruiz was detained, identified himself, showed Flores-Ruiz and his attorney a copy of the warrant, and placed Flores-Ruiz in the back of his vehicle. 

Government questioning: Private conversation with chief judge

12:00 p.m.:

While on the phone with Ashley, Vasconcellos said the chief judge was aware that a warrant had been presented. He asked the chief judge if the conversation could be moved to a more private area.

Vasconcellos said the chief judge told him that he'd been sitting on a draft policy, but it had not been sent to ICE. 

The deportation officer said the chief judge never told them they could not conduct an arrest operation in the public hallway, and Vasconcellos told the chief judge they "always respected" a judge's courtroom.

Government questioning: ICE officer on phone with chief judge

11:53 a.m.:

Vasconcellos said he previously had an administrative warrant to conduct an arrest at the Milwaukee County Courthouse and had not previously experienced anything like being directed by a judge to go to the chief judge's office.

The deportation officer said he was buzzed into the chief judge's office alone, and later asked a fellow agent to come in as a witness to a phone call with Chief Judge Carl Ashley. Other agents remained in a vestibule area outside the office.

Vasoncellos said he was in the office when he received a message from an agent, who was still in the public hallway, that Flores-Ruiz had exited into the public hallway. He asked that agent to follow Flores-Ruiz.

Government questioning: Arrest team outside Dugan's courtroom

11:45 a.m.:

Vasconcellos testified that he became concerned when he saw a public defender who appeared to be taking pictures of himself and other agents. He said it was unusual.

The deportation officer said agents were communicating when Flores-Ruiz arrived on the sixth floor, and he said he told them via message, "this is going to be a pain in the d***," because of the pictures being taken even though courthouse security knew what they were there to do.

Vasconcellos said Dugan came into the public hallway and asked if they had a judicial warrant, and he said they had an administrative warrant. He said she seemed "upset" and did not ask to see the administrative warrant before directing them to go to the chief judge's office. 

Vasoncellos testified that, while the six-agent arrest team had been split into different areas of the sixth floor, he did not call off the arrest. He said they were split up because Dugan had told them to go to the chief judge's office.

Government questioning: Considerations upon entering courthouse

11:39 a.m.:

Vasconcellos testified about the dangers officers can face while making arrests. He said he had been shot at and stabbed in his career. He explained that courthouses require people to go through a security checkpoint, where they are screened for weapons, making them safer places to conduct arrests.

The deportation officer was one of six federal agents at the Milwaukee County Courthouse, and he testified they had six agents to ensure the safety of themselves and the public.

Vasconcellos testified that he informed courthouse security of his reason for being there: to conduct an immigration arrest. He said security initially said he would need an escort through the courthouse, but a supervisor informed him that he could proceed without an escort and asked that they arrest Flores-Ruiz after his hearing. Vasconcellos said he conveyed agents would not enter the courtroom.

Government questioning: Documents authorizing immigration arrest

11:32 a.m.:

Vasconcellos said Flores-Ruiz's fingerprints were taken when he was booked into the Milwaukee County Jail, and his fingerprints matched those taken in 2013. 

The deportation officer testified that the "biometric confirmation" of fingerprints indicated that Flores-Ruiz was in the country, and that records from his prior deportation indicated he was not allowed back into the country and had no pending immigration hearings. He indicated as such in a document.

Vasconcellos said his superior determined, based on that document, there was probable cause to remove Flores-Ruiz and authorized a warrant commanding agents to arrest Flores-Ruiz.

Government calls ICE deportation officer to testify

11:27 a.m.:

The government called Joseph Vasconcellos, a deportation officer with U.S. Immigration and Customs Enforcement, to testify. He was previously a border patrol agent.

Attorney Keith Alexander questioned Vasconcellos. The officer testified he was aware Flores-Ruiz had previously been deported in 2013.

CBP Supervisory Officer Joseph Zuraw

Government re-direct: 

11:25 a.m.:

On re-direct, U.S. Attorney Richard Frohling asked Zuraw to reiterate that he was two sets of doors away from the public hallway when Flores-Ruiz emerged. 

Defense cross-examination: Flores-Ruiz exits into public hallway

11:23 a.m.:

Defense Attorney Jason Luczak questioned Zuraw about a report that did not mention which door Flores-Ruiz took into the public hallway. Zuraw testified that he did not see which door was used because he was in the chief judge's office at the time, but knew from fellow agents which door it was at the time he filed the report.

Defense cross-examination: Chief judge's office, bailiff's comment

11:14 a.m.:

Defense Attorney Jason Luczak cross-examined Zuraw, questioning him about statements that were included in a report written by another agent. 

Zuraw testified he was brought back to the chief judge's office to be a witness, because he believed there was something unusual going on about whether they could arrest Flores-Ruiz. 

The supervisory officer testified that a deputy, who was the bailiff for Dugan's courtroom, informed him that he, the deputy, had not informed Dugan that the agents were there to arrest Flores-Ruiz.

Government questioning: Agents separated on sixth floor

11:12 a.m.:

Zuraw testified that six agents were assigned to the arrest team, which helps ensure that the operation is safe for everyone involved – agents, the subject, the public. Having too few agents can hinder safety.

The supervisory officer said the agents on the sixth floor of the Milwaukee County Courthouse became separated. Initially, he testified, they planned to make the arrest with all six agents in the public hallway. He said they had done so without incident in the past. 

Government questioning: Agents directed to chief judge's office

11:04 a.m.:

Zuraw arrived outside the chief judge's office and waited in a vestibule area. He said another agent went into the chief judge's office and had to be "buzzed in." Dugan did not join them in that area.

While in that area, Zuraw said a deputy came in. He said the deputy informed him that Flores-Ruiz's court case had been "moved up" and was underway. Zuraw then told another agent, who was with him in the vestibule, to go back into the public hallway.

Zuraw said another agent directed him to come through the door into the chief judge's office, and he was buzzed in. Chief Judge Carl Ashley was not there but was on the phone.

The supervisory officer testified that the chief judge and a fellow federal agent were discussing a "memorandum of understanding" to work out how agents would make ICE arrests at the courthouse complex. At no point did he hear the chief judge say they could not make an arrest in the public hallway.

Government questioning: Dugan speaks to agents in hallway

10:57 a.m.:

Zuraw testified that he heard Dugan speaking to two other agents who were seated across the hall from him on April 18. He said he recalled hearing her ask them if they were there for a court appearance before she told the agents to go to the chief judge's office. He described her as "visibly upset" and her tone as "direct."

The supervisory officer said Dugan then approached him. He testified that she asked him if he was there for a court appearance, and he said no. She then told him "get out" or "leave" while pointing down a hall toward the chief judge's office. He said he tried to tell her who he was and why he was there, but she cut him off and told him to go to the chief judge's office.

Zuraw testified that he complied but did not know why he was being sent to the chief judge's office. He said that had not happened to him while conducting an immigration arrest at the courthouse before or since. 

Government questioning: Eduardo Flores-Ruiz arrives for hearing

10:53 a.m.:

Video from the Milwaukee County Courthouse showed Eduardo Flores-Ruiz and his attorney walk directly in front of Zuraw, toward Dugan's sixth-floor courtroom, while he was seated on a bench. He testified he sent a message to a group chat informing fellow agents that Flores-Ruiz had arrived.

Government questioning: Zuraw arrives at courthouse

10:45 a.m.:

Zuraw testified that he arrived at the Milwaukee County Courthouse and went through a security checkpoint, where he was asked to show additional identification after showing his CBP credentials. He was then allowed, without any additional escort, to continue through the courthouse complex.

The supervisory officer said he went to the sixth floor and saw other members of his team already there. He said they had a Signal group chat, where agents were discussing that someone on the sixth floor was taking pictures of them.

Zuraw testified that CBP authorizes the use of Signal, but it was under review at that time, and he said he saved and provided messages to the FBI.

Government calls CBP supervisory officer to testify

10:40 a.m.:

The government called Joseph Zuraw, a supervisory officer with Customs and Border Protection (CBP), to testify. CBP, like ICE, operates under the U.S. Department of Homeland Security. 

U.S. Attorney Richard Frohling questioned him. Zuraw testified that he was assigned to assist ICE from February 2025 to April 2025, but his primary role his to assist the FBI with counter-terrorism investigations.

Zuraw reviewed a field operations worksheet, which is a document agents use when conducting an immigration arrest. 

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Judge calls for break

10:24 a.m.:

U.S. District Judge Lynn Adelman called for a 10-minute break.

FBI Special Agent Phillip Jackling 

Bailiff speaks to agent

10:23 p.m.:

During the government's re-direct, Jackling testified that a bailiff informed him that he had not alerted Dugan about why agents were there – and that Flores-Ruiz's case was being pushed through.

The defense re-crossed Jackling, and he testified that he had prepared to testify in the case but had to be reminded about what the bailiff told him.

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 office, 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 would "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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