Judge Hannah Dugan leaves court in her federal trial, where she faces charges of obstructing immigration officers. (Photo by Isiah Holmes/Wisconsin Examiner)

The gallery was packed shoulder-to-shoulder Monday morning as Milwaukee County Circuit Court Judge Hannah Dugan entered the courtroom of U.S. District Judge Lynn Adelman not as a judge, but as a criminal defendant. Dugan is accused of obstructing federal agents in their efforts to arrest a Mexican-born man who was in the country without legal authorization, and who appeared in Dugan’s misdemeanor criminal court back in April. If convicted in what Adelman signaled would be no more than a week-long trial, Dugan could face six years in prison.

Attorneys on both sides of the trial painted very different pictures of Dugan during their opening statements, which can include statements which do not have to be demonstrated by evidence. 

Opening statements from prosecutors lasted nearly an hour, with the lawyers saying that Dugan “knew what she was doing was wrong.” Repeatedly, prosecutors pointed to courtroom audio transcribed by the FBI which captured Dugan saying, “I’ll get the heat,” when talking to her courtroom staff about how to respond to the fact that immigration agents were waiting in the hallway to arrest Eduardo Flores-Ruiz, a man appearing before her on misdemeanor charges of battery and domestic violence. 

Prosecutors called the Milwaukee County Courthouse “a safe place where arrests are routine,” allowing federal agents to confront targets who have passed through security screening and are unarmed. An arrest team of six federal agents from the FBI, DEA, Border Patrol, and ICE wearing plain clothes and carrying concealed weapons were attempting to blend into the normal hustle and bustle in the courthouse. Prosecutors said that an FBI agent told a Milwaukee sheriff’s deputy, who was serving as a bailiff for Dugan’s courtroom, that they were there to arrest Flores-Ruiz. “Everything was proceeding in a routine way,” prosecutors told the jury, until the court clerk told Dugan that agents were in the hallway for an immigration arrest. 

Jurors watched mute video compiled from security cameras showing Dugan, accompanied by fellow Circuit Court Judge Kristela Cervera, walking down the public hall in their judge robes to find out what the agents waiting outside the courtroom wanted. Both judges can be seen pointing to the chief judge’s office, with agents then following Cervera to consult with Chief Judge Carl Ashley. 

When Dugan returned to her courtroom she called Flores-Ruiz first out of the at least 33 cases she had on the docket, setting a court date and telling Flores-Ruiz he was welcome to attend remotely over Zoom. After that, prosecutors allege that Dugan and her court staff directed Flores-Ruiz to an exit in the courtroom which led to a non-public hallway. At the end of the hallway Flores-Ruiz could either take a staircase leading down to the fifth floor, or go through a door which led back out to the public hallway where agents were waiting. 

Flores-Ruiz and his attorney exited through the door and walked  right past the federal agents. Some of the agents trailed Flores-Ruiz to the elevator, while the rest of the arrest team left Ashley’s office. Cameras outside the courthouse captured agents running down a sidewalk after Flores-Ruiz and his attorney. 

Dugan is accused by prosecutors of “dividing” the arrest team by directing them to the chief judge. They say that Dugan had “strongly held views” about immigration enforcement in courts which led her to “cross the line,” and that the now-suspended judge had “orchestrated” Flores-Ruiz’s “escape from federal law enforcement.” 

Prosecutors claimed Dugan told Cervera to keep her robes on during the interaction, and that Cervera and Flores-Ruiz’s defense attorney Mercedes De La Rosa were both uncomfortable with Dugan’s wishes to confront the agents. 

Dugan’s defense team emphasized that the door Flores-Ruiz used to exit the courtroom was just 11 feet from the courtroom’s main entrance. They also discussed the upheaval the Trump administration’s deportation operations had caused at the Milwaukee County Courthouse before the interaction with Dugan. ICE arrests had occurred in late March and early April, alarming county judges. The defense displayed emails from courthouse personnel they said demonstrated the “paranoid” atmosphere at the courthouse and which described concerns about people not showing up to court and suspicious vehicles parked outside that looked like they belonged to federal law enforcement. 

Courthouse was developing a policy on ICE

At the time of Flores-Ruiz’s arrest, Chief Judge Ashley was drafting a policy on how to respond to immigration enforcement coming inside the courts. Judges had been invited to a training presentation on the matter which Dugan was unable to attend, but she had been briefed on its main points. 

The draft policy noted that administrative warrants of the type federal agents presented to arrest Flores-Ruiz are not treated the same way as judicial warrants. Whereas a judicial warrant would give the agents full access to the building, administrative warrants limit them to the public areas of the courthouse. Court staff were also instructed to direct immigration officers to their immediate supervisors, which Dugan appeared to be doing by directing them to Ashley, her attorneys said, adding  that the chief judge needed to be notified if a warrant is executed. 

Ashley had also issued a press release after the rash of ICE arrests saying in part that “the court must remain a safe haven,” Dugan’s attorney Steven Biskupic noted, as images of courthouse emails, messages, and press releases were presented  to jurors on two screens. Dugan did not obstruct the agents, or give direction to anyone else to do so, her attorneys argued. 

Federal agents testify

Three federal agents took the stand Monday and gave lengthy testimony, starting with Erin Lucker of the FBI. Lucker was not involved with the immigration arrest, but helped gather and analyze video and evidence to charge Dugan. Using audio from courtroom microphones, Lucker created a transcript and timeline of events from the time Dugan first approached the agents until Flores-Ruiz was arrested outside. 

The audio was very poor in places, and Judge Adelman reminded the jury that the audio is evidence, not the transcript, and that if they could not understand what is said on the audio, they were not allowed to rely on the transcript instead. In a portion of the audio, Dugan can be heard talking to court staff about the exit to the hallway, with a voice saying “down the stairs,” though some of what’s being said was inaudible. Prosecutors also said that the alleged victims of the domestic violence and battery charges Flores-Ruiz faced were kept waiting in the courtroom to wonder what happened after he left. 

In response to questions from Dugan’s defense attorneys, Lucker said she had no firsthand knowledge of the courthouse itself or what business there usually looks like. She had not participated in an arrest team like the one assembled for Flores-Ruiz, she said. She also responded to the defense that she wasn’t aware that before January 2025 immigration enforcement officers did not, as a matter of policy, target people for arrest at courthouses. 

Defense attorneys also pointed out that a video Lucker helped produce shows a walkthrough of Dugan’s courtroom and the non-public hallway outside ends with the filmer walking down the stairs, not taking the entrance to the hallway which Flores-Ruiz took. Lucker said she hadn’t walked down those stairs, and was unaware that to get out of the building you’d need to pass by multiple security checkpoints. 

Testimony revealed that federal agents had been surveilling Flores-Ruiz at his home and followed him to the courthouse. Defense attorneys questioned why a traffic stop wasn’t made. The task force agents used an encrypted Signal chat which they’d named the “Frozen Water Group” to communicate about the ICE operation. 

FBI Special Agent Jeffrey Baker,  one of the plain-clothes agents on the arrest team, testified that he  had only been on the ERO team since February when the team came for Flores-Ruiz in April. Baker said Dugan “divided” the arrest team by leading members into the chief judge’s office, and that when he talked to Dugan “she seemed to be angry at that point.” When he went to Ashley’s office, Baker said he wasn’t told where he was going or why. He was informed that Flores-Ruiz had left the building either by a text or phone call from another agent.

On Tuesday, Baker will be questioned by defense attorneys.

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