Bobby Cappucci, the happy warrior running for Boston mayor

Some are born to political greatness. Some have greatness thrust upon them.

And then there are those who aspire to political greatness, but like a donkey pursuing a carrot tied to a stick held by its rider, find that savory morsel forever receding into the middle distance.

Such is the case with perennial candidate Bobby Cappucci, who is running for Boston mayor (again) this year. I first encountered Bobby some three decades ago, when he was one of the flock trying to succeed Speaker Tip O’Neill in the Eighth District. Every candidate had devised a reason to run that distinguished him or her, but Bobby’s was unique.


“What this district needs is a strong, forceful leader, someone like Bobby Cappucci,” he opined. “And I think I can be that person.”

He was a conservative in a left-leaning district, and there were times when the going was so tough you felt a little sorry for him. “I must tell you, Bobby Cappucci is pro-life,” he would say when the abortion issue arose, a disclosure often greeted with boos or hisses. Then came a candidates’ forum at St. Francis de Sales Church in Charlestown. The audience was an older, conservative crowd, one where Bobby’s antiabortion stance could, at long last, win him some favorable notice. When the inevitable question was posed, a beaming Bobby Cappucci was ready. Unfortunately, Bobby Cappucci’s tongue was not.

“I’m proud to say that Bobby Cappucci is pro-choice,” it proclaimed.

That declaration was met with a distinct murmur of displeasure. It soon dawned on a crestfallen Bobby what his treacherous tongue had done.

“I mean, pro-life, pro-life,” he said, then lamented: “Bobby Cappucci makes these mistakes.”

Alas, the moment, which in a larger sense was never there, could not be reclaimed. In September, when the primary votes were tallied, Bobby joined the ranks of those crushed by Joe Kennedy II.


In 1987, however, Bobby hit electoral pay dirt: Lowering his sights, he got elected to the Boston School Committee. His otherwise unremarkable tenure was marked by a propensity for attending warm-weather educational conferences on the public dime, and a controversy over Bobby trying to land a school department post for a relative, an incident he now claims he doesn’t recall.

But just as he was learning the ways and wiles of a true Boston pol, fate intervened, and in the unkindest of ways: Mayor Flynn persuaded the Legislature to eliminate the elected school board in favor of an appointed panel.

“I always wanted a political career, and it was cut short when they abolished the school committee,’’ Bobby observed a few years ago, explaining why he was launching yet another long-shot mayoral candidacy.

But now he’s back, and with a more carefully crafted rationale.

“The fire is in my belly, I believe I would have a different agenda than the present mayor, and it would be irresponsible of me not to try to be the next mayor of Boston,” he told WBZ’s Jon Keller recently.

That agenda? Perhaps you’ve seen his community-newspaper ads with this pitch: “All Lives Matter. No Sanctuary City. Help Every Neighborhood.” Except that Bobby has put quotations marks around “All,” “No,” and “Every,” much in the manner of a pizzeria that boasts of world famous pizza but then — from want of either gastronomic or grammatical confidence — qualifies that claim by inserting quote marks around “world famous.”


So if you’re looking for a conservative mayor, Bobby may be your man. And if Bobby, 72, goes down to yet another defeat, will he run again?

“I doubt it,” he says, “but you never know the future.”

I don’t doubt it. Not while East Boston’s happy warrior has a single bone in his body persuaded that (1) public life needs a leader like Bobby Cappucci and (2) that he can still be that person.

Scot Lehigh can be reached at Follow him on Twitter @GlobeScotLehigh.