MILWAUKEE — A federal judge postponed the sentencing of former Wisconsin Judge Hannah Dugan on June 3, 2026, to consider arguments seeking to overturn her jury conviction for felony obstruction related to helping an immigrant evade U.S. Immigration and Customs Enforcement (ICE) agents. U.S. District Judge Lynn Adelman did not issue a ruling during the hearing and gave no indication of when he might decide whether to overturn the conviction.
Dugan, 67, was convicted by a jury on December 19, 2025, of felony obstruction for actions taken during an April 18, 2025 incident at the Milwaukee County courthouse. On that date, ICE agents arrived to arrest Eduardo Flores-Ruiz, who had reentered the country illegally and was scheduled to appear before Dugan in a state battery case. Dugan confronted the agents outside her courtroom, told them their administrative warrant was insufficient, and directed them to the chief judge’s office. After the agents left, she led Flores-Ruiz and his attorney out through a private jury door. ICE agents spotted Flores-Ruiz in the corridor, followed him outside, and arrested him after a foot chase.
Dugan’s attorney, Steven Biskupic, argued that her conviction should be overturned because a federal appeals court recently ruled in a Virginia case that ICE’s detention of an immigrant who later escaped did not constitute a "pending proceeding" under federal obstruction law. "Our primary argument is this was an invalid theory of conviction," Biskupic said. Dugan’s attorneys contend there was no "pending proceeding" against Flores-Ruiz at the time, only an administrative arrest warrant, which they argue does not meet the legal definition required for obstruction.
Acting U.S. Attorney Richard Frohling countered that the Virginia case is factually different and does not apply to Dugan’s situation, adding that other legal precedents support her conviction. "The court should stick with its ruling," Frohling said. He also noted that timing for a decision is uncertain, stating, "It could be a couple minutes, it could be a couple years. It all depends on the context."
Dugan resigned from her position as a Milwaukee County circuit judge two weeks after her conviction. She was acquitted of a separate misdemeanor charge of concealing an individual to prevent arrest. Dugan faces up to five years in prison and a fine of up to $350,000, though federal sentencing guidelines generally recommend probation for defendants with no criminal history convicted of nonviolent crimes.