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Road not taken: A successful developer and a natural pol, Tom O’Brien would likely have been a more formidable challenger to Boston Mayor Michelle Wu

It’s mid-September, and we should be in the middle of a heated, high-stakes mayoral race in New England’s largest city and economic engine.

But we’re not, because 2025 is the year the election for the city’s top job got cancelled in Boston, with challenger Josh Kraft dropping out after a nearly 50-point pummeling by Mayor Michelle Wu in the city’s preliminary vote.

So it’s only natural to wonder if things could have turned out differently with a different candidate, namely Tom O’Brien, the politically savvy, powerhouse developer who briefly flirted with a mayoral run last spring before abruptly pulling back.

Tom O’Brien

A recent Boston magazine piece, “What Really Happened to Tom O’Brien’s Mayoral Run?” suggests that O’Brien got cold feet thanks to fear of retribution from City Hall and pressure from investors to stay on as head of HYM Investment Group.

We could have told you that. O’Brien has had great success with the NorthPoint project, now home to thousands of people in East Cambridge, and with the Bulfinch Crossing high-rise development near Government Center.

But he is highly vulnerable to pressure from Wu and city officials as work has stalled on other projects in his portfolio, like plans to build a new neighborhood at the old Suffolk Downs racetrack.

Rendering of plans for a new neighborhood at Suffolk Downs.

Tellingly, state Sen. Lydia Edwards, a close Wu ally and fellow Democrat, hints not so subtly in the piece that the city should consider taking O’Brien’s Suffolk Downs acreage by eminent domain, given that just one apartment building has gone up so far.

Of course, little if any private sector housing is being built anywhere in Boston right now, and the incumbent mayor’s policies have played a significant role in that. But, no matter.

“You have to keep your head up and keep moving forward,” O’Brien told Contrarian Boston, when asked about the implied threat by Edwards, whose state senate district includes East Boston and Suffolk Downs. “I don’t really look back.”

But would O’Brien have fared any better against Wu, whose poll numbers surged amid her defiant stance against Trump and his draconian crackdown on illegal immigration?

Probably, if for no other reason than that O’Brien, unlike the earnest but awkward Kraft, is a natural politician who has also honed his skills guiding major projects through Boston’s contentious permitting process.

Boston Mayor Thomas M. Menino was a sharp judge of political talent. And let’s just say he pretty clearly saw a potential rival in O’Brien, who served as the late mayor’s development chief in the 1990s before being forced out and going into the private sector.

In an interview with Contrarian Boston, O’Brien didn’t rule out a run for office at some point in the future, though he added that it “certainly won’t be happening in 2025.”

“I care deeply about the city,” O’Brien said. “It’s been my home all my life. I have worked here for 35 years on a range of different projects that have hopefully improved the civic life of the city.”

O’Brien certainly could have made a stronger, pro-growth, pro-jobs, pro-economic development argument than Kraft, who tried but failed to tack to Wu’s left on rent control and other issues.

“I love doing this work,” O’Brien said of his work as a developer in Boston. “I will still continue to be up every single day. I love it.”

But thanks to her skillful playing of the Trump card, Wu may have just been about unbeatable this year, no matter who ran against her.

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