“Democracy is the worst form of government, except all those other forms that have   been tried from time to time.” — Winston Churchill

Jacob Ventura. Credit: Ropes & Gray

In August of 2021, then Ward 3 Councilor Hugh Dunn was facing criminal charges for OUI and leaving the scene of an auto accident. He was also wrapped up in a scandal involving whether three New Bedford police officers gave him special treatment when responding to an early-morning accident in the downtown New Bedford bar district.

Even so, not a single candidate came out of Ward 3 to oppose the three-term councilor’s re-election bid. Such is the fear of incumbency in a city like New Bedford, where the voter turnout is almost always low.

Such is also the state of affairs in the city’s sleepiest ward politically. 

Unlike all of the other New Bedford wards, Ward 3 has never been defined by a single, easily identifiable neighborhood or section of the city. It is a hodgepodge of enclaves located in the geographical center of New Bedford, but with each area located far from the others by car or by foot. It stretches from the most challenged residential neighborhood in the city along the grimy Hicks-Logan waterfront to the middle-class single-family and garden apartments west of Route 140.

As a consequence of these less-than-optimum boundaries, the political representation in Ward 3, in my opinion, has often been weak, and especially so since the departure of the hardworking and New Bedford-loving former Councilor George Smith two decades ago.  

What Ward 3 lacks in neighborhood cohesiveness, however, it may more than make up for in its attractiveness to politicians looking for a political career or an office to run for.

Hugh Dunn, a Democrat originally from Worcester who had worked for Congressman Bill Keating and attended UMass Law in Dartmouth, moved into the ward from another section of the city before he ran and easily won its seat. And yes, he won the spot in another one of these low-turnout special elections.

This year, Ward 3 may have already attracted an even newer ward resident for a special election.

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In early November, and less than a month after Dunn beat the drunk-driving charge and did not contest the charges of leaving the scene and negligent operation of a motor vehicle, his friends at WBSM-AM broke the story that the good elected official was resigning his Ward 3 seat. His explanation was that it had just become too difficult for him to commute to Boston, where he has a new job as a lawyer for a prestigious personal-injury law firm.

I hope that before Councilor Dunn leaves, he finally explains to his constituents exactly what happened the night of his accident.

New Bedford residents had hardly caught their breath from the news about Dunn, however, when South Coast Tonight politicos Marcus Ferro and Chris McCarthy again broke another story about Ward 3. 

The latest story, written by Ferro, is that longtime Republican Party activist Jacob Ventura, who also describes himself as a personal friend of Councilor Dunn’s, was exploring a run for the Ward 3 seat.

You may remember Ventura from a number of his previous public activities. He ran unsuccessfully as a Republican twice, in 2017 and 2018, for the state Senate seat in the district centered up around Attleboro. He was criticized during that race by his opponents for being a “carpetbagger” because he had moved into Attleboro (from Dartmouth) in June, and then ran in a September special election for the Senate seat.

Fast forward to this month and Ventura is again being criticized as a carpetbagger by at least one of his potential New Bedford opponents in the Ward 3 race, this time for moving into New Bedford (again from Dartmouth) shortly before exploring a run for the Ward 3 race.

Ventura, who described himself to me as “bi-coastal” for a time in recent years, told me last week he doesn’t remember exactly when he moved into Attleboro for the Senate race but that he did not move to that city to run for the office.

He said that he had moved into the same New Bedford apartment complex (Wamsutta Mills), where Hugh Dunn lives, in mid-September. He registered to vote in New Bedford one week ago on Nov. 28, and took out papers to run for Ward 3 the following day, on Nov. 29.

Odd. Dunn is resigning his seat because he is a Boston lawyer and says the commute from his Wamsutta apartment is too difficult, but Ventura, who is also a Boston lawyer, says the same commute won’t be a problem for him. He mentioned something about Dunn working in litigation while he is working as a private-equity attorney and can operate from home. Ventura said he himself usually commutes to Boston three days a week.

Ward 3 City Councilor Hugh Dunn. Credit: Hugh Fanning / The New Bedford Light

Ventura works at the international law firm Ropes & Gray and acknowledged there were several issues he would have to recuse himself from because of the firm’s interactions with the city.

I don’t know. On the night I interviewed Ventura, he said he was staying in a Boston hotel.

Ventura said he is currently the roommate of Christopher Sheldon, a Republican who ran against incumbent Democratic Congressman Bill Keating in 2012. He is looking for his own apartment in the Wamsutta complex, Ventura said.

“I took Hugh’s dog out for a walk the other day,” Ventura said, but no, he would not want to live in Dunn’s apartment even though it may be empty soon. He believes it is a one-bedroom, he said.

The would-be candidate explained that he very much considers himself a New Bedford guy because he grew up in the city until he was 7½-years-old, when his parents moved just over the city line to Dartmouth. The reason? Like a lot of people who move there, his parents did so because of the town’s school system, he said.

Ventura told WBSM that his roots in the city go deep as he is a descendant of Sgt. William Carney, an escaped enslaved person who fought with the first all-Black regiment in the Civil War, and he told me that he is a descendant of Amos Haskins, the first Native-American whaling captain.

I’m not sure what the connection there is to Ward 3 but it’s certainly an historical connection to New Bedford.

“I’ve always been interested in the public service element,” Ventura said. “I’m fortunately in a situation where I can think about running for New Bedford City Hall.”

He said that although he hasn’t made a final decision to run yet, he would have “a team” out gathering signatures this past weekend. He definitely knows how to run a campaign, that’s for sure. Although the state Office of Campaign and Political Finance lists him as only having $33.54 cash on hand in his campaign report, it also lists him as having raised $213,154.02 during his previous campaigns. None of the other potential Ward 3 candidates has listed any money raised yet.

Ventura said that with the short-window for the Ward 3 race (the preliminary election is Jan. 24 and the final Feb. 28), he will probably have to finance this campaign himself. Other potential candidates in the ward said the same.


But based on Ventura’s history, he has experience running a political operation and will certainly have the ability to get a message out. And in an interview with me, he let it be known that his opponents — one of whom has already criticized him pointedly for running in the Ward 3 race when he has little history there — will pay a price for describing him as a carpetbagger.

“Anyone who calls me a carpetbagger, we’re going to hit back, and we’re going to hit back hard,” he said.

Ventura also suggested that the press should investigate a social media reporter who has visited his parents’ Dartmouth home to try to determine if he still lives there, and that person’s “connections to certain people at city hall (sic).” As far as living in Dartmouth, he told me he does “spend some time” at his parents home and that the social media reporter “was pretty much harassing the place.” The reporter is Carlos Felix of the Facebook site New Bedford Live. Ironically, he is the same individual who was on site the night of Hugh Dunn’s accident.

Felix left me a recorded message that he was too busy to talk but said “Something smells fishy.”

He described Ventura’s parents as clueless as to what is going on and called Ventura “a carpetbagger.”

“He has a known track record of moving into areas, or pretending to move into areas, to run for political office,” he said.

Ventura made it clear that he also has not taken kindly to my own columns on the Dartmouth Republican Town Committee’s involvement during the controversy over whether the town of Dartmouth should eliminate its Dartmouth Indians’ mascot, and research on that fact originally done by Democratic activist David Ehrens. “New Bedford Light tax exempt status is another one of those issues,” that should be investigated, he wrote me in a text.

This guy means business.

New Bedford City Hall. Credit: Jack Spillane / The New Bedford Light

For the record, it’s not just me whose eyebrows have been raised by the way Ventura has tried to run for the Ward 3 office and previously the one in Attleboro.

Kathy Dehner, a former Ward 3 councilor and owner of a real estate business that has developed several key buildings in the historic district, has also taken out papers in the race. She flat out charged that Ventura had moved to the city to run for the office.

“It’s a stepping stone to move on to something else,” she said. “And I find that offensive, I really do.”

Shawn Oliver, a state correction officer who is also running, said that he had wanted to run against Dunn last year, after the publicity about the driving charges, but that it was not a good time as his family was involved in renovations to his house.

He questioned unnamed candidates’ devotion to the ward seat without mentioning any particular name.

“Do you truly want to be involved in this city and listen to residents or are you trying to pad a resume and run for the Senate or something? Which is all well and good but the city needs something else,” he said.

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Robert Cabral, the former owner of Ash Away Hearth and Chimney who has taken out papers for the race, also expressed skepticism and referred to an unnamed carpetbagger on his Facebook page.

“You know they already have a candidate they want to win,” he said. Asked who “they” are, he said “powerful people in the city.”

Two other potential candidates — Robert Bromley, a financial analyst for the Rhode Island Senate and longtime official at the Fort Taber military museum and John F. Robinson, a retired music teacher who taught across Southeastern Mass. and Rhode Island — avoided direct criticism on the residency issue, but they both seemed to reference it indirectly by emphasizing that they had spent much of their lives as residents of Ward 3.

Myself, I certainly understand the residency concerns of folks who have long lived in the city. But I also think their importance can sometimes be over-emphasized. For example, Barney Frank had no real connections to the South Coast at all but he became beloved down here because he respected and listened to what people needed and wanted. Perhaps Mr. Ventura would be like that, given his family’s connection to the area.

I do think, however, that the exception to this rule might be a ward race in a municipality where having the time and energy to follow-up on constituent services is everything. The reason a city divides its legislative body between at-large councilors and ward councilors is because people with deep and longtime connections to different parts of the city are more likely to know, and more importantly, care, about what their fellow residents want. That doesn’t mean a hard-working, empathetic individual from outside cannot accomplish the same thing. They can. But I think it would be less likely.

Particularly devastating for Ward 3, I think, after suffering through a succession of city councilors who didn’t hold office for very long, would be another one who is on their way to somewhere else and has other big-time responsibilities.

The very minority Massachusetts Republican Party has been talking for years about the need to build the party from the ground up. That means running for city council and school committee and other local races. It’s a great idea and perhaps that is what Mr. Ventura wants to do. The theory is that that is how you build the farm team to run for state rep, Senate and congressional seats when they are available.

Local elective offices, of course, are technically not partisan. There is no ‘R’ or ‘D’ or ‘L’ after your name when you run for a local office. But I think people deserve to know something about your political philosophy by knowing that background, and your membership in a political party identified with a particular philosophy of government provides that.

Of the other would-be candidates, Dehner, Bromley and Robinson are registered as Democrats and Oliver and Cabral are unenrolled, which means they are not a member of any political party.

Jacob Ventura strikes me as a smart, hard-working, competent individual. He might make a good city councilor and he might not. It’s hard to say how any individual will do until they occupy the job.

What is not encouraging, however, is the way Ventura has tried to finesse the fact that he does not have any long-term connections to Ward 3, and that this is now the second political district he has looked at running in where he had no long-time residence. His “hit back hard” remark also sounds like a threat to me, although I suppose it’s part of the political game.

The history of Ward 3 has been a troubled one when it comes to representation in recent years. It is going to need a good, grounded representative this time around. Let’s hope it gets one.

Email Jack Spillane at jspillane@newbedfordlight.org.

Editor’s Note: David Ehrens is a founder of The Light. Our newsroom is wholly independent of founders, board members and other funders; they have no influence over news content.

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