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Lucas: A tale of two ICE-avoiding judges

By Eric November 15, 2025

In a striking case of judicial accountability, Milwaukee County Judge Hannah Dugan is set to stand trial next month on federal obstruction of justice charges. Dugan is accused of facilitating the escape of Eduardo Flores-Ruiz, a wanted illegal immigrant, from her courthouse to evade U.S. Immigration and Customs Enforcement (ICE) agents waiting outside. This incident, which involved Dugan allowing Flores-Ruiz to exit through a side door, has drawn significant attention, particularly in light of previous similar allegations against Boston Municipal Court Judge Shelley Joseph, who was never prosecuted for her own actions in a comparable situation. If convicted, Dugan faces a potential six-year prison sentence, underscoring the message that no one, including judges, is above the law.

The context surrounding these cases highlights a concerning trend in judicial conduct and the handling of immigration issues within the U.S. legal system. Judge Joseph’s case, which dates back to 2019, involved her allowing a twice-deported illegal immigrant, Jose Medina Perez, to escape the courthouse in a similar manner. Despite being indicted and suspended with pay, the charges against her were dropped following the change in administration after President Joe Biden took office. The subsequent investigation concluded that Joseph was not directly responsible for the escape, a finding that has drawn criticism and raised questions about the integrity of the judicial system. In contrast, Dugan’s impending trial represents a stark difference in how such cases are being pursued under the current administration, emphasizing the importance of accountability in the judiciary.

As both cases reveal the complexities of immigration enforcement and judicial responsibility, they also highlight the broader implications for public trust in the legal system. The contrasting fates of Judges Dugan and Joseph serve as a reminder of the ongoing debates surrounding immigration policy and the role of the judiciary in upholding the law. While Judge Dugan prepares for trial, the outcome may have significant repercussions not only for her career but also for the perception of judicial integrity in handling cases involving illegal immigration. As the legal proceedings unfold, the public will be closely watching how justice is served in these high-profile cases.

It is good that the judge who let a wanted illegal immigrant out the back door of the courthouse to avoid waiting ICE agents will stand trial.

No one is above the law, including judges.

So, the judge will face federal obstruction of justice charges when her trial begins next month and, if found guilty, could face six years in prison.

That is the way politicians say the system works or is supposed to work.

Only in this case the judge is not Boston Municipal Court Judge Shelley Joseph who was once charged with the same thing, but Milwaukee County Judge Hannah Dugan.

While Dugan may go to prison, Joseph walks.

Like Joseph before her, Dugan is charged with federal obstruction of justice for letting wanted illegal immigrant Eduardo Flores-Ruiz, 31, sneak through a side door of her courthouse to avoid waiting ICE agents.

Flores-Ruiz was arrested after a foot chase and has since been deported to Mexico.

After seven months in detention, Flores-Ruiz promised never to come back. Before shipping out, he said, “I am grateful and happy I was able to work here,” which is something you do not ordinarily hear from illegal immigrants.

Joseph, a Democrat, was appointed to the bench by Republican Charlie Baker, who later found her actions “extremely troubling.” He said, “Judges are not supposed to be in the business of obstructing justice.”

Joseph was sitting in the Newton District Court when she was indicted on obstruction of justice charges in 2019 for allowing twice-deported illegal immigrant Jose Medina Perez, 38, to exit the back door of the Newton courthouse to also avoid ICE agents waiting out front to scoop him up.

Medina Perez’s escape came after Joseph participated in a 52-second unrecorded conversation with Medina Perez’s defense counsel and an assistant district attorney.

The charges were brought by then U.S. Attorney Andrew Lelling, who was appointed by Republican President Donald Trump. Joseph was suspended with pay pending the outcome of her trial.

Only there was no trial.

No sooner was Democrat Joe Biden elected over Trump in 2020 than Biden’s U.S. Justice Department dropped the charges.

This came about after the case was referred for “review” to Democrat U.S. Attorney Zachary Chuna of Rhode Island, a Biden appointee. Lelling by then, of course, was gone.

Chuna, as if on schedule, in September 2022 recommended that the Justice Department drop the charges against fellow Democrat Joseph, which it did.

Cunha said that “the interests of justice are best served” by sending the matter to the Massachusetts Commission on Judicial Conduct, which investigates judicial misconduct.

The commission appointed Attorney Denis J. McInerney to conduct a hearing on the matter.

McInerney, in his report last week, which reads like fan mail, said that Joseph was innocent of any wrongdoing because she had no idea what was going on in front of her nose in her own courtroom.

So, she should be reprimanded but not thrown off the bench.

“I find that Judge Joseph did not know about — much less authorize — the escape plan and did not mislead court authorities following the incident, McInerney said. Besides, Joseph, he said was a “new and inexperienced” judge.

And since the “incident,” Joseph, according to McInerney, has “repeatedly demonstrated” that “she is a thoughtful, diligent and conscientious judge underserving of the harsh public criticism she has received in connection with this matter, and entirely worthy of the opportunity to finally move on from it.”

Forget the dropped charges and the reprimand. Judge Joseph is so good that Gov. Maura Healey ought to appoint her to the Supreme Judicial Court.

Veteran political reporter Peter Lucas can be reached at: peter.lucas@bostonherald.com

Judge Shelley Joseph is not facing any trial. (Herald pool file)

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