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Lucas: A tale of two ICE-avoiding judges

By Eric November 19, 2025

In a controversial case that has captured public attention, Milwaukee County Judge Hannah Dugan is set to stand trial next month on federal obstruction of justice charges for facilitating the escape of a wanted illegal immigrant from her courtroom. Dugan is accused of allowing Eduardo Flores-Ruiz, a 31-year-old undocumented immigrant, to slip out a side door to evade waiting ICE agents. If found guilty, Dugan could face up to six years in prison, reinforcing the principle that no one is above the law, including judges. This situation echoes a similar incident involving Boston Municipal Court Judge Shelley Joseph, who was previously charged with obstruction of justice for a comparable act but ultimately escaped trial due to the dismissal of charges by the Biden administration’s Justice Department.

The case against Judge Dugan stems from her decision to allow Flores-Ruiz to avoid deportation after he had been apprehended following a foot chase. After spending seven months in detention, Flores-Ruiz was deported back to Mexico, expressing gratitude for the work he had done in the U.S., a sentiment not often echoed among individuals in similar situations. Dugan’s actions have sparked a debate about judicial accountability, especially considering that her predecessor, Judge Joseph, was also implicated in a similar obstruction of justice case involving another undocumented immigrant, Jose Medina Perez. While Joseph faced charges in 2019, the subsequent political shifts led to the dismissal of her case, raising questions about the consistency of legal repercussions for judges in similar circumstances.

The contrasting outcomes of these cases highlight a troubling narrative in the judicial system regarding accountability and political influence. While Judge Dugan prepares to face trial, the lack of consequences for Judge Joseph, who was exonerated by a report that deemed her an inexperienced judge unaware of the escape plan, suggests a disparity in how judicial misconduct is addressed. This incident has sparked discussions about the integrity of the judicial system and the implications of political affiliations on legal proceedings. As Dugan’s trial approaches, it remains to be seen how the courts will navigate the complexities of justice and accountability for those who are entrusted with upholding the law.

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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