Showdown Unfolds: Trump DOJ and Judge Clash Over ICE in Sentencing Memos

Amidst a brewing legal storm, federal prosecutors are seeking a “serious sentence” for Hannah Dugan, a former judge in Wisconsin, who last year was convicted of interfering with ICE agents during an arrest at a courthouse. As her sentencing nears, Dugan remains defiant against the prospect of harsh punishment.

The impending sentencing, scheduled for July 8, has become a battleground between Dugan’s defense team and the U.S. Justice Department, both submitting markedly different proposals for her fate.

Federal prosecutors argue that Dugan’s actions constituted a grave offense deserving of severe consequences. Conversely, her defense contends that the Justice Department’s heavy-handed approach aims to instill fear and publicly shame individuals who oppose ICE operations in county courthouses. They are advocating for her to receive credit for time served, noting that her actual detention lasted less than a day.

In their sentencing memorandum, Dugan’s attorneys highlight her unblemished record and longstanding contributions to the community, emphasizing, “For nearly seven decades, Hannah Dugan has been an exemplary member of this community.” They maintain that the event was an isolated incident, unlikely to recur, and assert that her arrest and subsequent public exposure amount to sufficient deterrence. “There is no need for further deterrence, either specifically or generally,” they concluded.

Dugan, 67, was indicted last year for helping an immigrant named Eduardo Flores-Ruiz evade ICE officers shortly after he appeared in her Milwaukee County Circuit courtroom in connection with a domestic abuse case. Federal prosecutors alleged during her trial that Dugan impeded ICE agents during the attempted courthouse immigration bust by helping Flores-Ruiz, a Mexican national who was facing misdemeanor battery charges, leave through a jury door after a hearing.

Dugan was accused of “falsely” telling ICE agents they needed to obtain a judicial warrant to take Flores-Ruiz into custody. The incident occurred on April 18, 2025, and Dugan was charged in a criminal complaint less than a week later and formally indicted in May 2025. A federal jury found Dugan guilty in December 2025 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.

“A serious sentence is necessary to reaffirm a foundational principle of our criminal justice system: no one is above the law, particularly those entrusted with administering it,” the DOJ says in its sentencing memo. “Anything less risks sending the opposite message — that personal loyalties, subjective viewpoints, or self-interest can supersede legal duty.”

Federal prosecutors argue that judges are “entrusted with tremendous discretion, but there is a line they cannot cross,” according to the DOJ’s sentencing memo. “They may disagree with the law, question policy, or sympathize with those who appear before them. But they cannot use the power of judicial office to obstruct federal law enforcement officers to help someone evade arrest,” the memo says. “The defendant crossed that line.”

Prosecutors say “that, combined with her lack of remorse or sense of accountability,” warrants a sentence that reflects the “serious nature of her conduct” and its broader impact on the justice system. Dugan’s team, meanwhile, says she “has been punished enough,” per their memo.

“Whether deserved or not, the ongoing residual effect was to force Hannah Dugan into life as a recluse,” her lawyers say. “Based on actual threats and a legitimate fear of those threats against her and those associated with her, she moved out of her home. She gave up her usual life of attending community events, including public religious services. Security measures needed to be taken before she could travel, even to her required court proceedings in this case. These effects will persist well into the future regardless of the sentence this court imposes.”

Dugan’s attorneys add, “The nine-year judicial career of Judge Dugan (and almost 40-year legal career) came to an end because of approximately five minutes of immediate reactions to learning that an ICE enforcement action was to take place on the sixth floor near her courtroom.”

Prosecutors say Dugan was ultimately “entrusted with authority and responsibility that few citizens possess” and “rather than honoring those obligations, she used her position to interfere with the lawful administration of justice,” according to the DOJ’s sentencing memo. “That betrayal magnifies the seriousness of the offense,” the memo states.

“This is not a case involving a momentary lapse in judgment followed by reflection or remorse. Instead, the defendant has continued to characterize her conduct, which a jury found criminal beyond a reasonable doubt, as appropriate, justified, and legally permissible,” prosecutors say. “To be clear, the government does not seek punishment for the defendant’s exercise of her constitutional right to trial. Rather, the Court simply should consider the defendant’s continued minimization of her conduct and persistent refusal to acknowledge wrongdoing when evaluating the need to promote respect for the law.”

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.”

A federal judge ruled last month that Dugan’s conviction would not be overturned. She plans to appeal her case to the 7th Circuit Court of Appeals, regardless of the sentence she receives.

“The defendant’s refusal to acknowledge the wrongfulness of her conduct raises legitimate concerns about respect for the law and suggests a continuing belief that her personal disagreement with federal immigration law justified her obstruction of lawful government functions,” federal prosecutors concluded in their sentencing memo. “That mindset does not reflect well on the defendant and heightens the need for the Court’s sentence to promote respect for the law and restore confidence that the justice system holds itself accountable. Public officials must understand that they cannot substitute personal viewpoints for legal duty.”

Dugan reportedly faces up to five years in prison, but prosecutors noted in their memo that the average sentence imposed is 16 months. Dugan’s lawyers submitted nearly 20 letters of support for a sentence of time served. The DOJ has not recommended a specific sentence, only that it be “serious.”

“As former ambassador and mayor Tom Barrett wrote in his letter to the court, the guilty verdict in this case alone caused Hannah Dugan to resign her judicial position: ‘For her, it was an extraordinarily deep price to pay,'” her team’s memo concludes. “Joseph Wall, referring to the intentional and unnecessary public humiliation of Dugan’s arrest, echoes the sentiment that she already has been punished enough.”