When Judge Hannah Dugan arrived to work at the Milwaukee, Wisconsin, courthouse shortly before 8 am on April 18, she did not anticipate becoming embroiled in the Trump administration's offensive against sanctuary cities, much less arrested in a courtroom a week later for allegedly attempting to help an undocumented migrant evade deportation.

On the morning of April 18, one of Judge Dugan's first cases involved Eduardo Flores-Ruiz, a 30-year-old Mexican who had been working as a cook in Milwaukee for over 10 years. He lacked legal residency status, but immigration enforcement falls under federal, not local, jurisdiction – something courts and local police are not supposed to take into account. The cook was appearing for a preliminary hearing, accused of assaulting his roommates on the evening of March 12 during a dispute over loud music. It was a routine case for the judge, who had 25 other cases on the docket that day.

Dugan, 65, is a respected judge in Milwaukee. Elected in 2016 and easily re-elected in 2022, she is one of the few female judges in the US to have been elected to the bench – unlike federal judges, who are appointed by the executive branch, state judges are chosen by popular vote. She served as president of the Milwaukee Bar Association. A former law professor at Marquette University, the city's Jesuit university, she also led the Catholic Charities migrant aid organization. According to friends, she participated in a seminar in Kyiv on American democracy a few years ago. Since the war began, she has never missed a protest in support of Ukraine.

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