Jurors hear from string of federal agents on day 2 of Dugan trial

Jurors heard from a string of federal agents on the second day of a high-profile trial against Milwaukee County Judge Hannah Dugan.

Tuesday’s first witnesses included FBI Agents Jeffrey Baker and Phillip Jackling, Supervisory Customs and Border Protection Officer Joseph Zuraw and Deportation Officer Joseph Vasconcellos.

Those agents were part of the six-person arrest team assigned to take Eduardo Flores-Ruiz into custody following his scheduled appearance at the Milwaukee County courthouse on April 18.

Dugan, 66, faces charges of obstructing or impeding a proceeding and concealing an individual to prevent his discovery and arrest.

The charges stem from her decision to usher Flores-Ruiz through a side door of her courtroom on a rainy April morning. Those actions came after the federal agents had announced their plans to arrest Flores-Ruiz for being in the country illegally.

Did Dugan obstruct an arrest?

Agents eventually took Flores-Ruiz into custody outside the courthouse, after running after him on foot. The 31-year-old from Mexico pleaded no-contest to a misdemeanor domestic battery charge in November, and he was deported shortly thereafter.

Dugan’s attorneys have argued that she didn’t obstruct anything. During cross-examination, defense attorneys seemed to suggest that federal agents had multiple opportunities to arrest Flores-Ruiz throughout the day on April 18. The defense also made several attempts to cast doubt on agents’ professionalism.

On Tuesday, defense attorneys once again referenced a group chat that agents on the arrest team for Flores-Ruiz had been using on the encrypted platform Signal. That chat was titled “frozen water” — seemingly a playful reference to ICE, the acronym for Immigration and Customs Enforcement. The defense showed pictures of the icons that some of the agents used in the chat, including one showing an agent with his tongue sticking out, appearing to lick a gun.

Assistant U.S. Attorney Kelly Brown Watzka tried unsuccessfully to get U.S. District Judge Lynn Adelman, the federal judge overseeing the case, to shut down questions about the Signal chat.

Watzka suggested that the chat didn’t have “anything to do” with Dugan’s conduct on April 18.

Prosecutors emphasize how agents were separated

Throughout the day on Tuesday, prosecutors emphasized how dangerous arrests can be and stressed Flores-Ruiz’s violent history.

Repeatedly, prosecutors told jurors that courthouses are secure locations because of the metal detectors at the doors.

Prosecutors argued that agents were put in a precarious position because the arrest team was split up after Dugan “ordered” agents to the chief judge’s office.

The controversy embroiling Dugan began two days before Easter when the team of six arrived at the courthouse in plain clothes. They were carrying guns, but were able to bypass the courthouse metal detectors after showing identification to court security.

After arriving at Dugan’s courthouse on the sixth floor, agents said they notified the court’s bailiff about their plan to carry out an immigration arrest.

Witness: Bailiff said ‘I didn’t dine you out’

Later, Zuraw, a border protection officer, testified that the bailiff told agents “I didn’t dine you out.”

Zuraw said he took that to mean that the bailiff was saying that he didn’t tip off Dugan about the presence of ICE.

Vasconcellos, the deportation officer, said court security initially told him he would need an escort through the courthouse. After Vasconcellos spoke with that person’s supervisor, a sergeant with the Milwaukee County Sheriff’s Office, the sergeant said an escort wouldn’t but needed, but requested that agents wait until Flores-Ruiz’s hearing was over before taking him into custody.

Vasconcellos told the sergeant that agents would comply with that request, Vasconcellos testified.

Security footage shows Dugan and Judge Kristela Cervera, another Milwaukee County Judge who has an office on Dugan’s floor, confronting federal agents in the courtroom hallway while wearing their black robes.

Prosecutors said it was “unusual” for judges to be wearing their official robes outside of the courtroom while in the court hallway.

Cervera also testified Tuesday, saying Dugan’s actions that day left her feeling ‘irritated’ and ‘abandoned’ by Dugan.

Agent texted colleague: ‘This is gonna be a pain’

After agents arrived at the courthouse’s sixth floor, Dugan asked agents about a warrant and directed them to speak with Chief Judge Carl Ashley. Agents described Dugan’s tone during that exchange as “stern,” “upset” and “angry.”

At one point, Vasconcellos texted his colleague “This is gonna be a pain in the dick.”

Vasconcellos said he was referencing how factors were arising that seemed like they were going to complicate the arrest. He said that included the presence of a woman — later identified as a public defender — who was in the courthouse hallway taking pictures of the plainclothes federal agents.

At Dugan’s behest, multiple members of the arrest team went to Ashley’s office. Ashley was not in the courthouse at that time, so Vasconcellos spoke to Ashley on speakerphone while Zuraw listened in.

Ashley told the agents he was working on a policy that would address ICE arrests at the courthouse, but that policy was still in draft form, the testimony indicated.

After other agents went to Ashley’s office, one member of the arrest team, a U.S. Drug Enforcement Administration agent, had stayed behind in the hallway outside Dugan’s courtroom. That agent was in plainclothes, and prosecutors have alleged that Dugan didn’t realize that woman was a federal officer.

In addition to testimony from the agents and Cervera, jurors heard from Milwaukee County Sgt. Dave DeSmet, who discussed courthouse arrests. They also heard from ICE Assistant Field Director Cassandra Kubiszewski and Drug Enforcement Agent Brian Ayers.

The final witness Tuesday was a victim witness advocate, who arrived at court on April 18 with the victims in Flores-Ruiz’s domestic violence case.