City Council Candidate Chat: Thomas Dooley

This is the 28th in a series of conversations with candidates for Boston City Council. Real estate broker Thomas Dooley is running in District 8.

David S. Bernstein: Why are you running for the city council seat?

Thomas Dooley: I am running because my dear friend Mike Ross is no longer available. The last 15 years I’ve chosen not to run because I valued our friendship more than any political aspirations I might have. I am the person primarily responsible for opening an elementary school in my neighborhood—it is today the Park Street School, which is the Park Street Church. I called Emerson College back when they were divesting themselves of 16 properties. I had 2,000 parents with lots of money, and they told me “Tom, you find us the building, we’ll buy it, clean it up, get it ready to go.” Mayor Menino refused to meet with us. We then joined hands with the Park Street Church. I said private, public, I don’t care—let’s get it done. One of the parishioners bought the building for $6 million, said pay me back when you can. It is now open, paid for; the project was $18 million. I can’t do any more than that as a private person. As a city councilor, I’ll be in a position to re-open elementary schools across the city. I don’t care what it takes. We’re spending $150 million a year on busing. That’s insane. The entire school population that’s being bused is entirely poor black and Hispanic kids. Nobody wants busing any more. There’s nothing left to integrate or desegregate. The city has a 13 percent [school-age] population of Caucasians—those are all in the exam schools, and those kids don’t take the bus. So I say upgrade the facilities.

What is preventing the opening of new schools or expansion of existing schools as you’re describing?

Mayor Menino. It’s like us getting out of Vietnam, like John Kerry said—who wants to be the last person to admit that we made a four-decade, $4 billion mistake and destroyed the social fabric of Boston? I’m from Jamaica Plain. 1970, when they announced integration, we, and a quarter-million other people, including black people, everybody with money, sold their house and got the hell out of Boston. This city emptied out. Or, the Yankee WASP establishment—which I’m not part of—they put their kids in private school or parochial school. I can’t afford the Park Street School any more. It’s $20,000 a year. My kids are over at the St. John’s School in the North End, at $4,000 a year. That’s all I can do.

So, if Mayor Menino is the problem, he isn’t going to be there any more. Do you think the mayoral candidates—including the one you just described as your “dear friend”—would make significant progress in this area?

I know all the city councilors, moreso the ones that were there a few years ago. They’re all cowards. They’ve allowed Mayor Menino to terrorize them for 20 years. They never stand up to him. They’re all concerned about keeping their jobs. I’m in a position, as a city councilor representing the most affluent part of Boston, I will say what needs to be said to the mayor of Boston.

You also talk about business, and believe that there needs to be significant reduction in regulation and cost of doing business in the city. Can you give me specific examples?

All these [other candidates] speak about “I’ll do this, I’ll create jobs, a chicken in every pot, accessible quality education for everybody.” I’m looking across the panel thinking, “what are they talking about?” Some of these people have never had real jobs. Some of them have never had a business, created a business, employed people—I’ve created three businesses, and had 60 employees altogether since 1991. I’m specific. We have a swimming pool on the Esplanade. It’s closed. The legislature won’t allocate the funds to re-open it. I would reconstruct it as a year-round, indoor swimming pool, go to Suffolk University, and tell them “tell the Trustees they need to pay for this, and we’ll introduce a men’s and women’s swim team at Suffolk; you’ll have kids from around the world applying to Suffolk just so they can swim on the swim team.” And have a daytime pay-to-swim for adults, and free for children. I would even introduce swimming into the Boston city school curriculum. Boston is a swimming city—a sailing-swimming city. Kids should know how to swim. If they fall off a boat in the Charles or in the Harbor they shouldn’t drown because no-one ever thought to teach them to swim. When I was a kid everybody learned to swim. It was just part of your childhood.

You run a brokerage called Louisberg Properties; you make deals with some of the wealthiest people in Boston. But the district also includes some poorer and working-class residents. Do you think you understand and can represent the needs of both?

Yes. In what was our family business, Dooley Brothers, I spent a couple of summers on a trash truck in Lexington. Throwing barrels, which is one of the roughest labor jobs there is. I’m coming from an industrial, working-class kind of family. There’s nothing beautiful about the trash business. I grew up in a very modest culture.

Near the top of your website you write about ending the negative rhetoric of class warfare, and stopping the dividing of our society into hostile camps. It sounds like you’re rejecting the Occupy Wall Street mentality, but isn’t there a legitimate difference between the classes, even within your own district?

My opinion is that we’re alienating a certain part of our population because if somebody has worked hard, done well, and become comfortable in life, the last thing they’ll ever do is run for office. I don’t know that Boston has done well the last 40 years, more or less excluding 10 percent of its population. Nobody wants to touch government affairs. I was discouraged from running, by my own parents. I said: “we can’t all just sit on Martha’s Vineyard hoping people back in Boston take care of our affairs. Some of us have to actually just stop working, stop making money, and go into city government for two years or four years and try to impose some law and order to what’s going on.” I could just keep doing what I’m doing, and be perfectly happy, and either Nichols or Zakim becomes the new City Council. But I don’t think that they really know or completely care about anything. I’m very concerned about violence in Boston. I think it’s wrong that on this side of the city we have a zero tolerance rate for violent crime, but we are turning a blind eye to shootings every other day in Roxbury and Dorchester.

I wanted to ask you about that; you mention on your materials about a zero tolerance policy encompassing the entire city of Boston. What do you mean by that?

If you want to know the names of a couple of black girlfriends I’ve had, I’m a real open-minded guy. Do you think that there is a dual standard in Boston, where the city administration, because they are politically able to get away with it, allow for a certain amount of violence, murder, and mayhem where black people live? And are we in fact losing our black population, where it’s almost as if they’re becoming an endangered species? Many, many blacks that we see in Boston, they have African or Caribbean roots. The school population has shifted from the late 80’s, when a majority were black Americans, and now it’s Hispanic. And it’s not as if the population has changed all that much, it’s just that they’ve had so many shootings, there are a lot of people who just aren’t around and never became parents.

One other thing from your materials: you mention the keeping of stenographic records by the City Council, and the failure to make them public. There’s an individual in public who has championed that issue, and I’m wondering why you feel it’s important.

I had no idea, I was unaware of it, and I had a phone call—it may have been from the same person. It was explained to me that this is a funded operation to make it easier for the public to know what’s going on. I think it’s part of the whole Menino method of operation. When I heard about it, I said absolutely, we have to do this.


Read more Boston City Council Candidate Chats. This interview has been edited for length.