Forget Boston Mayor Michelle Wu in 2025.

Boston City Councilor Ed Flynn should think about running against Gov. Maura Healey in the 2026 Democrat primary.

It could be a more winnable fight. Instead of running against a progressive mayor he would be running against a progressive governor.

Flynn could begin by regularly jogging around the city neighborhoods the way Boston Mayor Ray Flynn, his father, used to do when he was mayor from 1984-1993. Nobody knew the neighborhoods better.

Ray Flynn resigned as mayor in 1993 after President Bill Clinton named him ambassador to the Vatican where he served until 1997. So instead of jogging around Boston, he jogged around Rome.

Ray Flynn always wanted to run for governor, but never did. Maybe his son will run for him, although Ed Flynn seems to have his eyes set on City Hall and not the State House.

Healey, running for a second term, would of course be an odds-on favorite to defeat any Republican challenger, just as she made short work of GOP challenger Geoff Diehl in 2022.

The GOP does not account for much in Massachusetts anymore.

And Ed Flynn thus far has shown only interest in running for mayor of Boston, not governor of Massachusetts.

“I’m going to consider it (a run for mayor), consider my options and how I can be helpful to the residents of Boston,” Flynn said.

Still, a Democrat challenger like Flynn in a primary would represent a whole new challenge for Healey if she is still around, that is.

She could be gone if Kamala Harris is elected president. She could become Harris’ U.S. Attorney General and leave the governorship to Lt. Gov. Kim Driscoll.

As U.S, attorney general she could continue to hound Donald Trump the way she did when, as Massachusetts attorney general, she sued then President Trump some one hundred times.

Now as a Harris campaign surrogate, she is hounding Trump on the anti-Trump national television news shows where she is a welcome guest.

A Trump 2024 victory would therefore be a major political setback for Healey.

There would be no cabinet appointment as there would be no Harris administration. She would then be faced with finishing out her term and contemplating running for re-election.

More importantly, a Harris defeat could have serious negative effects for Massachusetts as well when it comes to the distribution of federal funds for immigration, for instance, or for building two new Cape Cod bridges.

Seeking re-election in 2026—if she is inclined to do so—Healey could face serious problems dealing with a Trump administration and could be vulnerable in a Democrat primary running as the progressive that she is.

Trumpian politics tend to be personal, and payback is a bitch.

You can just hear a Democrat opponent challenging Healey saying, “ I can work with the Trump administration, Governor Healey can’t.”

A moderate, regular Boston Democrat like Ed Flynn—a neighborhood guy like his father– in a contested primary could seriously challenge Healey, who is vulnerable when it comes to basic issues like the costly flood of illegal immigrants who have swarmed into Massachusetts disrupting neighborhoods and schools.

Once only a Boston issue, illegal immigration has become a problem for communities outside of Boston as Healey has placed immigrant families in neighborhoods and communities across the state with the taxpayers footing the bill and coping with the fallout.

As a South Boston city councilor, Ed Flynn, like his father, has been dealing with basic neighborhood issues for years, and he could bring a solid neighborhood perspective to the governor’s office.

What is Massachusetts if not a large neighborhood?

In addition, Ed Flynn is a U.S. navy veteran (23 years) and is being supported by the newly formed Veterans for Ed Flynn.

If elected he would be the first veteran elected governor in 50 years, the last being Michael Dukakis in 1974.

It is far-fetched, to be sure. But it was once far-fetched to think that Donald Trump would be elected president, lose, and then be elected again.

We live in strange times.

Peter Lucas is a veteran political reporter. Email him at: peter.lucas@bostonherald.com.

Gov. Maura Healey (Photo By Matt Stone/Boston Herald, File)
Mayor Michelle Wu (Photo By Matt Stone/Boston Herald, File)