Inset: Milwaukee County Judge Hannah Dugan in court (WTMJ/YouTube). Background: Surveillance video shows Milwaukee County Judge Hannah Dugan speaking with ICE agents before Eduardo Flores-Ruiz’s detainment (WDJT/YouTube).
Hannah Dugan, a former judge in Wisconsin, faced a setback on Tuesday when a federal judge decided not to overturn her conviction for obstructing ICE agents during an arrest in a courthouse last year.
In his detailed 32-page decision, U.S. District Judge Lynn Adelman explained, “The defense’s challenge lies in the nature of the event—it was not an impromptu street encounter but rather a planned operation aligned with agency protocols, including an arrest warrant specifically for Eduardo Flores-Ruiz.”
Judge Adelman further noted, “Dugan equates this situation to standard police procedures, such as executing warrants and making arrests. She contends that ICE functioned as a typical law enforcement agency in this scenario. However, this view overlooks the unique authority ICE holds, which allows it to issue its own warrants and carry out removals independently, as demonstrated in Flores-Ruiz’s case, without court intervention.”
At age 67, Dugan was charged last year with assisting Flores-Ruiz in avoiding ICE officers after his appearance in her Milwaukee County Circuit Court related to a domestic abuse case. Prosecutors argued that Dugan obstructed the ICE agents’ efforts during the courthouse operation by facilitating Flores-Ruiz’s escape through a jury door following a hearing. Flores-Ruiz, a Mexican national, was facing charges of misdemeanor battery.
The charges against Dugan included allegations of misleading ICE agents by insisting they required a judicial warrant to detain Flores-Ruiz. This incident took place on April 18, 2025, leading to Dugan’s criminal complaint within a week, followed by a formal indictment in May 2025.
A federal jury found Dugan guilty in December of one count of obstructing or impeding a proceeding before a department or agency of the United States, a felony. Jurors found her not guilty of one count of concealing an individual to prevent his discovery and arrest, a misdemeanor.
Dugan’s legal team filed a motion for a new trial in late January with claims that recent court cases, including one in November 2025, established a “common-law privilege” that bars civil arrests from happening inside courthouses. “This privilege specifically precludes ICE courthouse arrests for deportations or removal,” the motion said. Federal prosecutors insisted that was not the case with Flores-Ruiz.
“Arrests at the courthouse are a common practice and can be made in a public hallway with or even without a warrant based on probable cause,” the DOJ said in its response. “Because she knew ICE could operate in the hallways, Dugan prepared a sign for her courtroom door, stating that if any attorney, witness coordinator, or court official felt unsafe coming to court in person, they could request to appear by Zoom.”
Prosecutors pointed out that Dugan did not raise the privilege argument or legality of immigration arrests at courthouses before her trial, even though the “facts necessary to make such an argument” were alleged in her indictment.
“Dugan did not argue, in her voluminous pretrial motions to dismiss, that the indictment failed to state an offense because Flores-Ruiz was privileged from arrest in the courthouse,” the DOJ said. “Thus, Dugan cannot now invoke a ‘longstanding’ privilege to argue that there was ‘no crime’ ‘as a matter of law’ unless she can show good cause for her earlier failure to object on this ground.”
The government alleged that Dugan was “wrong about the scope of the privilege,” claiming it does not apply to actions “by the sovereign that address uniquely sovereign interests.”
In addition to the privilege argument, Dugan’s team claimed jurors were improperly instructed by Adelman when asked whether Dugan needed to know who ICE agents were looking for that day in order to convict her, as well as the meaning of the term “pending proceeding.” Dugan’s definition of the term “proceeding” was too narrow, according to Adelman.
“Defendant proposed the jury be instructed that: An effort to arrest a person, or to execute an arrest warrant of any kind, is not a ‘proceeding’ within the meaning of the crime charged in Count 2,” Adelman noted in his ruling Tuesday. Dugan’s lawyers had said that “as used in that count, the term ‘proceeding’ means an actual administrative or judicial process apart from an attempt to arrest someone that was pending at the time, or at least was reasonably foreseeable to the defendant,” per Adelman.
“I instructed the jury as follows,” Adelman said. “‘Pending proceeding’ simply means any process taking place in the manner and form prescribed for conducting business by or before a department or government agency, including all steps and stages in such an action from its inception to its conclusion,” the judge recounted.
Adelman said that the arrest Dugan obstructed was ultimately part of an ICE investigation “seeking to determine whether Flores-Ruiz had violated federal law by returning to the United States without permission.” Her lawyers had argued in filings that she should not have been charged because there was no “pending proceeding” against Flores-Ruiz and only a warrant for his arrest.
Adelman said that Flores-Ruiz’s case “did not involve a contested hearing in front of an immigration judge or other authority,” because Flores-Ruiz declined to challenge the previous removal order or make an asylum claim. “At oral argument, defendant noted that ICE goes out every day to try to arrest people on the street,” the judge wrote. “Given the estimated 10 million undocumented persons in the United States, does that mean there are 10 million pending proceedings?”
Dugan’s legal team called Adelman’s decision “wrong” in a statement to The Associated Press.
She faces up to five years in prison but is expected to get probation, per the AP. Flores-Ruiz was deported in November 2025.
A sentencing date has not been set yet.
