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5 new things we’ve learned in Judge Hannah Dugan’s trial so far

USA TODAY Network via Reuters Connect//December 18, 2025//

The prosecution and defense teams at Judge Hannah Dugan's federal obstruction case trial. (USA TODAY Network via Reuters Connect)

5 new things we’ve learned in Judge Hannah Dugan’s trial so far

USA TODAY Network via Reuters Connect//December 18, 2025//

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In Brief

  • Federal prosecutors revealed new testimony from nearly 20 witnesses in ‘s trial.
  • was suspected of felony strangulation but charged with misdemeanor battery.
  • ICE agents coordinated an arrest through a Signal chat dubbed “frozen water.”
  • Dugan’s clerk admitted calling an ICE agent a “fascist” during the courthouse arrest operation.

Much of the evidence introduced in Milwaukee County Judge Hannah Dugan’s federal trial was already known to the public, such as Chief Judge Carl Ashley’s communications on ICE policy.

But previously unknown information has also been revealed through the testimonies of nearly 20 witnesses called by the prosecution in the first three days of the trial.

That includes a text message sent by Dugan’s fellow Judge Kristela Cervera and Dugan’s clerk Alan Freed testifying that he called an ICE agent a “fascist” on the morning of April 18.

Here are five new things we’ve learned from the trial so far:

Flores-Ruiz was suspected of felony strangulation

First Assistant U.S. Attorney Richard Frohling said Eduardo Flores-Ruiz, the undocumented immigrant Dugan is accused of helping, was suspected of felony strangulation and suffocation, based on a federal arrest document at the time.

Joseph Vasconcellos, a deportation officer with ICE, testified that federal forms indicated Flores-Ruiz “has a predilection for violence.”

Flores-Ruiz was charged with three counts of misdemeanor battery — not felonies — the day he appeared before Dugan.

According to a criminal complaint, Flores-Ruiz hit his roommate more than two dozen times in the head and choked him for several seconds. Two women who tried to intervene were hit by Flores-Ruiz as well.

He had no previous criminal convictions, according to court records. The prosecutor was exploring a possible deferred prosecution agreement for Flores-Ruiz.

Flores-Ruiz, 31, pleaded no contest and was convicted of one count of misdemeanor battery in that case in October. He also was convicted in federal court with illegal re-entry of the United States. He has since been deported.

Agents were in Signal chat called ‘frozen water’

Testimony from multiple agents revealed there was a “frozen water” Signal chat among members of the arrest team at the courthouse as they gathered to arrest an undocumented immigrant.

“Frozen water” was meant to be a humorous reference to ICE, or U.S. Immigration and Customs Enforcement.

Joseph Zuraw, a Customs and Border Protection officer, testified he believed the government was reviewing use of Signal, an encrypted messaging app, at the time.

Over objections from prosecutors, Dugan’s defense team asked an agent about other high-profile cases involving federal officials using Signal.

The defense attorney didn’t go into detail but he likely was referring to the case involving Defense Secretary Pete Hegseth and others, who mistakenly included a magazine editor in a chat about battle plans. The leak sparked fears about the potential mishandling of classified national security information.

Judge Cervera texted her sister about ICE being in courthouse

Under cross-examination by Dugan’s defense attorney Steve Biskupic, Milwaukee County Circuit Judge Kristela Cervera testified she texted her sister, an attorney, that federal immigration agents were in the courthouse on April 18, shortly after she and Dugan spoke to agents in the hallway.

“You told her that ICE was in the building,” said Biskupic.

“That’s fair,” Cervera said.

“Warn her?” Biskupic asked.

“Yeah, sure,” the judge testified.

Asked about the text again, Cervera said, “It was more about what was happening in our country at the time that ICE was doing sweeping arrests.”

Chief Judge Ashley grilled on ICE arrest policy

Dugan defense attorney Steve Biskupic questioned Chief Judge Carl Ashley about his draft policy for handling immigration arrests at the — and changes he made to it.

Biskupic asked Ashley to read much of his draft policy, and public comments about , including lines raising concerns about such arrests in courthouses.

Biskupic noted that Ashley in his draft policy for handling immigration arrests at the Milwaukee County courthouse was close to one from San Francisco but left out a key line: “Enforcement agents are allowed to conduct their operations in the Court’s Public Areas.”

Biskupic questioned Ashley, saying he made “the conscious decision” not to put it in the Milwaukee draft policy.

“It was not included,” Ashley responded.

Dugan’s clerk called an ICE arrest team agent a ‘fascist’

Alan Freed, Dugan’s clerk, testified he called a member of the ICE arrest team a “fascist.”

In the courtroom, Freed had been shown footage of him walking past one of the agents who was on his way to Ashley’s vestibule. The prosecution asked what Freed said to the agent.

Earlier in his testimony, he was asked about ICE’s presence in the courthouse.

“I was upset and a little bit outraged,” Freed said.

This article originally appeared on Milwaukee Journal Sentinel

 

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