Milwaukee Judge Hannah Dugan faces charges for aiding undocumented immigrant escape

A federal grand jury in Milwaukee handed down an indictment against County Circuit Judge Hannah Dugan on May 13, 2025, thrusting her into a high-profile legal battle. The charges stem from an incident on April 18, where Dugan allegedly attempted to assist an undocumented immigrant, Eduardo Flores-Ruiz, in evading arrest by federal Immigration and Customs Enforcement (ICE) agents. This case has ignited tensions between local judiciary officials and federal authorities, spotlighting broader debates over immigration enforcement tactics. The indictment marks a rare instance of a sitting judge facing federal charges, drawing national attention.

The controversy unfolded in a Milwaukee County Courthouse, where Dugan, a veteran judge elected in 2016, presides over misdemeanor cases. The case has raised questions about courtroom protocols, judicial authority, and the presence of federal agents in local courthouses. Key details include:

• Dugan faces two charges: obstructing a U.S. agency and concealing an individual to prevent arrest.
• The charges carry a maximum penalty of six years in prison and a $350,000 fine.
• Witnesses, including court staff and another judge, testified before the grand jury.
  This incident has also sparked protests and criticism from local officials, who argue the arrest of a judge in a public courthouse sets a troubling precedent.

Charges against Judge Dugan

On May 13, a federal grand jury of 20 members convened at the Milwaukee Federal Courthouse, returning a two-page indictment against Dugan at 5:10 p.m. before U.S. Magistrate Judge Nancy Joseph. The document accuses Dugan of obstructing a U.S. agency by interfering with ICE agents’ efforts to apprehend Flores-Ruiz and concealing an individual to prevent his arrest. These charges, while serious, typically result in shorter sentences for nonviolent offenses, though the maximum penalties are substantial. Dugan’s defense team issued a statement asserting her innocence, expressing confidence in her vindication at trial.

The indictment followed a day of testimony from several witnesses, including Alan Freed Jr., Dugan’s court clerk, and Mercedes de la Rosa, the former attorney for Flores-Ruiz. Milwaukee County Judge Kristela Cervera, whose courtroom is adjacent to Dugan’s, also appeared, accompanied by defense attorney Michael F. Hart. None of the witnesses commented publicly when approached at the courthouse. Acting U.S. Attorney Richard Frohling’s presence during the proceedings underscored the case’s significance, as it is unusual for a high-ranking prosecutor to attend such hearings.

Incident at the Milwaukee County Courthouse

The events leading to Dugan’s indictment occurred on April 18, 2025, at the Milwaukee County Courthouse. Eduardo Flores-Ruiz, a 30-year-old undocumented immigrant, was scheduled to appear in Dugan’s courtroom. A six-member ICE arrest team arrived on the courthouse’s sixth floor to apprehend him. According to the criminal complaint, de la Rosa, Flores-Ruiz’s attorney, photographed the agents and informed Freed, Dugan’s clerk, of their presence, describing their locations and attire. Freed relayed this information to Dugan, setting the stage for the confrontation.

Dugan allegedly left her courtroom to confront the ICE team in a public hallway, informing them they required a judicial warrant, not an administrative one, to arrest Flores-Ruiz. The complaint further alleges she directed the agents to leave the hallway and proceed to Chief Judge Carl Ashley’s office. While most agents followed this directive, one remained behind. During this time, Dugan is accused of expediting Flores-Ruiz’s case off the record and instructing him and de la Rosa to exit through a non-public jury door. This door led to an adjacent hallway with access to public elevators.

Role of other courthouse personnel

Judge Kristela Cervera played a notable role in the incident, according to the criminal complaint. She escorted the ICE team to Ashley’s office to discuss their warrant and speak with Ashley by phone. However, she left one agent behind in the hallway, who later spotted Flores-Ruiz and de la Rosa exiting via the jury door. This agent followed them into an elevator, leading to Flores-Ruiz’s eventual arrest outside the courthouse at West State Street and North 10th Street. Cervera’s involvement has drawn scrutiny, though she has not been charged and declined to comment when seen at the federal courthouse on May 13.

Alan Freed Jr., Dugan’s court clerk, also emerged as a key figure. A former employment law and disability rights attorney, Freed was informed by de la Rosa of the ICE agents’ presence and passed this information to Dugan. His actions have been detailed in the complaint, but he faces no charges and remained silent when approached by reporters. The involvement of courthouse staff highlights the complex dynamics at play during the April 18 incident, raising questions about communication protocols in high-stakes situations.

BREAKING: Wisconsin Judge Hannah Dugan indicted by a grand jury for helping an illegal escape ICE pic.twitter.com/X6xMWeW7Gy

— End Wokeness (@EndWokeness) May 13, 2025

Arrest of Eduardo Flores-Ruiz

Flores-Ruiz’s arrest marked the culmination of the courthouse confrontation. After exiting through the jury door, he was spotted by the remaining ICE agent and pursued outside the courthouse. Federal agents apprehended him on a downtown Milwaukee street, concluding a chase that began inside the courthouse. Flores-Ruiz, now held in federal custody at Ozaukee County Jail, is expected to receive a new public defender before his next hearing on May 14. His case is part of a broader federal crackdown on undocumented immigrants, intensified under the Trump administration’s immigration policies.

The arrest has drawn attention to ICE’s tactics, particularly their operations in courthouses. A CNN report from May 6, 2025, documented at least 12 instances of ICE arrests on or near courthouse grounds across states like Virginia, Illinois, and Wisconsin. Federal officials defend these operations, noting that courthouses provide a controlled environment where individuals are likely unarmed and have passed security checkpoints. However, local officials and advocates argue such actions undermine public trust in the judicial system.

Dugan’s arrest and public reaction

One week after Flores-Ruiz’s arrest, on April 25, 2025, Dugan herself was arrested at the Milwaukee County Courthouse. Handcuffed and taken into federal custody, she appeared before a federal magistrate in a highly publicized move announced by FBI Director Kash Patel on the social media platform X. The arrest of a sitting judge in a public courthouse sparked widespread criticism from local officials and protesters. Milwaukee County Chief Judge Carl Ashley expressed concern over the manner of Dugan’s arrest, calling it a troubling precedent for judicial independence.

Protesters gathered outside the courthouse in the days following, decrying what they described as an overreach by federal authorities. Community advocates argued that targeting a judge for her courtroom decisions could deter others from upholding due process. Meanwhile, federal officials maintained that Dugan’s actions warranted accountability, emphasizing that no one is above the law. The polarized reactions reflect broader national debates over immigration enforcement and the role of the judiciary.

Legal proceedings and next steps

Dugan is scheduled to enter a plea at a hearing on May 15, 2025, before U.S. District Judge Lynn Adelman, who was assigned to preside over her case. Her defense team has signaled a vigorous defense, with their statement emphasizing Dugan’s confidence in being cleared of the charges. The indictment’s brevity omits several details from the earlier criminal complaint, focusing solely on the two charges of obstruction and concealment. Legal analysts note that the case’s outcome could hinge on interpretations of Dugan’s intent and the scope of her judicial authority.

The grand jury’s proceedings were marked by secrecy, as is standard practice. U.S. Magistrate Judge Nancy Joseph reminded jurors of their oath to maintain confidentiality after the indictment was returned. The vote tally was not disclosed, though Joseph confirmed that at least 12 jurors supported the indictment, meeting the required threshold. The absence of charges against other individuals, such as Cervera or Freed, suggests the federal government’s focus remains solely on Dugan.

Broader implications for courthouse operations

The incident has prompted discussions about courthouse protocols and the presence of federal agents in local judicial settings. Milwaukee County officials have called for clearer guidelines on how ICE operations should be conducted in courthouses to avoid disrupting judicial proceedings. Some argue that federal agents’ presence could intimidate defendants and discourage them from attending court, undermining access to justice. Others contend that courthouses are appropriate venues for arrests due to their security measures.

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Nationwide, similar incidents have fueled debates over sanctuary policies and immigration enforcement. In states like Massachusetts and Pennsylvania, local governments have pushed back against ICE courthouse arrests, citing concerns over public safety and judicial integrity. Wisconsin, with its diverse urban and rural populations, has seen growing tensions over these issues, particularly in Milwaukee, a city with a significant immigrant community.

Community and official responses

Local government officials have rallied in support of Dugan, with several issuing statements condemning her arrest. Milwaukee County supervisors and city aldermen have called for a review of federal arrest practices in courthouses, arguing that such actions erode public confidence in the judiciary. Community organizations, including immigrant rights groups, have organized rallies to protest what they view as an attack on judicial independence. These groups have also highlighted the broader impact of ICE’s tactics on Milwaukee’s immigrant communities.

Federal officials, however, have defended their approach. In public statements, ICE representatives have emphasized that courthouse arrests are a routine part of their operations, particularly for individuals with immigration violations. They argue that such arrests are necessary to enforce federal law and ensure public safety. The Trump administration’s hardline stance on immigration has amplified these efforts, with officials citing increased deportations and detentions since the start of 2025.

Judicial authority and ICE operations

Dugan’s case raises complex questions about the intersection of judicial authority and federal law enforcement. Legal experts note that judges have significant discretion in managing their courtrooms, but actions perceived as obstructing federal agents can lead to serious consequences. The allegation that Dugan misled ICE agents about warrant requirements has been a focal point of the indictment, with prosecutors likely to argue that her conduct exceeded her judicial role.

The case also highlights the challenges of balancing local and federal priorities. Milwaukee County, like many urban jurisdictions, has sought to maintain cooperative relationships with immigrant communities while navigating federal immigration mandates. The confrontation between Dugan and ICE agents underscores the tensions that arise when these priorities conflict, particularly in high-stakes courtroom settings.

Details of the indictment

The two-page indictment is notably concise, focusing on the specific actions Dugan allegedly took on April 18. Key allegations include:

• Confronting ICE agents and providing false information about warrant requirements.
• Directing agents to leave the hallway and visit Chief Judge Ashley’s office.
• Expediting Flores-Ruiz’s case off the record to facilitate his exit.
• Instructing Flores-Ruiz and his attorney to use a non-public jury door.
  These actions, prosecutors argue, constituted a deliberate effort to thwart a lawful arrest, though Dugan’s defense is expected to challenge the interpretation of her intent.

Ongoing developments in Flores-Ruiz’s case

Eduardo Flores-Ruiz remains in federal custody, with his legal proceedings moving forward separately from Dugan’s. His next court date, scheduled for May 14, will likely involve the appointment of a new public defender, as de la Rosa has withdrawn from the case. Flores-Ruiz’s arrest has drawn attention to the broader experiences of undocumented immigrants in Milwaukee, many of whom face heightened scrutiny under current federal policies. Advocacy groups have called for his release, citing concerns about due process and the circumstances of his arrest.

The case has also shed light on the role of public defenders in immigration-related cases. De la Rosa’s actions, including photographing ICE agents and alerting courthouse staff, have been scrutinized, though she faces no charges. Her withdrawal from the case reflects the complexities of representing clients in high-profile immigration disputes, particularly when federal and local authorities are at odds.

Local judiciary’s response

Milwaukee County’s judicial leadership has responded cautiously to the case, balancing support for Dugan with the need to maintain public trust. Chief Judge Carl Ashley, who was indirectly involved in the April 18 incident, has emphasized the importance of judicial independence while acknowledging the need for cooperation with federal authorities. Other judges, including Cervera, have refrained from public comments, likely due to the ongoing legal proceedings and their proximity to the case.

The incident has prompted internal discussions within the courthouse about how to handle similar situations in the future. Some judges have advocated for training on interacting with federal agents, while others have called for policies to limit ICE’s presence in courthouses. These discussions are ongoing, with no formal changes announced as of May 13, 2025.

National context of courthouse arrests

The Dugan case is part of a broader pattern of ICE operations in courthouses across the United States. Reports from states like New Hampshire and North Carolina indicate that federal agents have increasingly targeted courthouses to apprehend undocumented immigrants. These operations have sparked legal challenges and policy debates, with some jurisdictions implementing restrictions on ICE’s access to judicial facilities. In Wisconsin, the issue remains contentious, particularly in Milwaukee, where community advocates have long criticized federal immigration tactics.

Data from immigration advocacy groups suggest that courthouse arrests have risen since the Trump administration’s return to power in 2025. While exact figures are difficult to verify, the CNN report from May 6 provides a snapshot of the trend, identifying cases in multiple states. These arrests often target individuals attending routine court hearings, raising concerns about access to justice and the chilling effect on immigrant communities.

Milwaukee’s immigrant community

Milwaukee’s immigrant population, which includes significant Latino and Southeast Asian communities, has been deeply affected by the case. Local organizations have reported increased fear among undocumented residents, many of whom are hesitant to engage with the court system. Community leaders have organized forums to address these concerns, offering legal clinics and know-your-rights workshops to support residents navigating immigration challenges.

The case has also galvanized advocacy efforts, with groups like Voces de la Frontera calling for reforms to protect immigrants from courthouse arrests. These organizations have emphasized the need for local policies to limit cooperation with ICE, arguing that such measures would strengthen community trust. Milwaukee County officials have expressed openness to exploring these proposals, though no concrete actions have been taken as of May 13.