01.22.2025

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Rewarding loyalty? Longtime local police union boss with a knack for stirring the pot seen as Trump’s pick for a plum federal post

Say the words U.S. marshal, and an image of Tommy Lee Jones in “The Fugitive” may come to mind.

As the second Trump administration kicks into gear, Jerry Flynn, a long-time police union boss from Lowell, is being eyed for the post of U.S. Marshal for the District of Massachusetts.

And say what you want about Flynn, but the police union chief is no Sam Gerard, the relentless, no-nonsense lawman portrayed by Jones in the 1993 movie.

Now, we can’t speak to Flynn’s younger days as a cop in Lowell, when, according to his bio, he was “awarded numerous citations and commendations for bravery and for the capture of dangerous criminals.”

But as the head of the New England Police Benevolent Association for years, maybe the only thing the one-time Lowell cop has been in relentless pursuit of has been one sordid controversy after another.

Jerry Flynn

Nothing really compares to an infamous 1998 bus trip that Flynn was involved with as head of Lowell’s police union, which sparked a $2 million federal lawsuit and judgment against the labor group.

Flynn and a busload of officers traveled into Boston to attend a political rally, afterwards stopping for drinks at J.J. Foley’s, a favorite watering hole for police and reporters in the South End.

However, as the bus made its way back to Lowell in the early morning hours, things quickly got out of hand.

Vanessa Dixon, a Lowell officer at the time, fled the bus in the middle of downtown Boston after being bombarded with crude sexual comments and suggestions by a group of fellow officers, according to court documents.

Flynn, as head of the police union, failed to take effective action to shield Dixon from the abuse, according to a federal appeals court ruling.

That said, while the union was hit with more than $2 million in damages, Flynn escaped with just a $1 judgment for discrimination.

Nothing if not scrappy, Flynn also won a $40,000 settlement from the city of Lowell after being suspended for 30 days following the bus trip.

Flynn argued he had no part in the harassment Dixon had suffered and that his civil rights had been violated.

Meanwhile, a long-time Trump supporter, Flynn made headlines again in 2020 for comments made during the heated presidential campaign between Trump and Biden.

He referred to U.S. Rep. Alexandria Ocasio-Cortez of New York as a "bar fly stripper" and derided now former Vice President Kamala Harris as a "racist pig" and "lunatic" who was "out of her ever living f------ mind," Business Insider reported.

Now, with Trump back in the White House, Flynn appears poised to receive a plum federal appointment as the U.S. Marshal for Massachusetts.

(Flynn’s union, the New England Police Benevolent Association, was one of the first to endorse the president back in 2015.)

Late last month, Flynn officially retired as head of the New England Police Benevolent Association in preparation for being nominated by the Trump administration, Inside Lowell reports.

We’ll see what happens. But in a conservative field like policing, it would seem like a reasonable bet there are other law enforcement leaders who could also do the job, but without Flynn’s penchant for controversy.

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