David S. Bernstein: You have considered running for office before; why are you in at this time, for this seat?
Jack Kelly: Combination of a couple of different things: unique opportunity of the seat opening up for two people, and given my own personal stature in life I thought it was the perfect time to give it a go. If I didn’t do it, I knew that if I make it to 75 years old I would have regretted it. It was just timing—and I think a lot of stuff in politics is timing.
You’ve worked for the city as a neighborhood coordinator; is it something from that experience that makes you think you would be good as a city councilor?
Yeah, yeah. It’s a combination of my biographical experience and my government experience, and also my other professional experience, why I think I have a very diverse way of coming at the City Council. There’s nothing traditional of how I got to this point, for the classic Irish politician. That’s why I think I could be a really good city councilor, just like I was as a neighborhood coordinator: the combination of new Boston/old Boston—I can be both. I also can tap into every single neighborhood, into more economically depressed areas like Mattapan, and some of the Latino communities, because of what I’ve been through. I uniquely, in my opinion, really understand what it’s like to lose people, and to deal with the serious, serious issues that we see in the city of Boston. When I was a neighborhood coordinator for the mayor, I said I’m going to bridge old Charlestown and new Charlestown, and I effectively did that, in my opinion. And my support within Charlestown is evidence of that. The mothers group, and all of these people that they don’t think would be inclined to go with me, are just as excited about what I’m doing as anyone who was brought up here.
That Charlestown Mothers Association, which is seen as part of the new Charlestown—groups like that are emerging as very powerful political players. What are they asking for that is different from what the city has done in the past?
I don’t think they’re different from any other group in democracy throughout time. They have an interest in whatever their interest is, so they organize around that. Just like any other group does. Anybody who doesn’t live in Charlestown has a misconception of what that actually is. The mothers group is actually a mixture of traditional Charlestown people and newer residents. It’s very mixed. And that’s refreshing because Boston needs to be like that. Boston has settled to a point where the old-school people who have decided to stay, they’re staying. People like myself. We live here; I have a condo here, we’re staying. The issues that I’m facing as a 32-year-old person, who’s considering getting married one day, maybe having kids here, do I want to stay in Boston, are the same exact issues someone from Ohio is dealing with if they moved here.
You call for investing in improving Level 3 schools, improving substance-abuse and rehab services, re-entry programs, early learning—that adds up to a certain amount of money, in what have been pretty difficult budgeting times. Do you think we need to find ways to spend more money?
Yeah, I do, and there’s a couple of different ways to do this. We have to look into other departments that need to be cut. I also think that we have to have an honest conversation about revenue. It’s very difficult to talk about taxes, because most people who are taxpayers, who sort of casually pay attention to this stuff, they get reflexively against anything that’s being raised for taxes. We’ve seen that with the transportation bill, with the governor. You see how the individual state legislators, how they had to deal with that, because they don’t want to deal with their constituents. But if you really want to improve the school system, we really have to go into the neighborhoods that are holding us back and invest in making their neighborhoods healthy, so that they can then have a neighborhood school, and then the rest of us can have a neighborhood school. Because if we cannot improve the school system in Mattapan, if I cannot convince a parent in Mattapan that their child is going to go to a good neighborhood school, how are we ever going to fix this problem? One of the things I think we can do, with medical marijuana coming into effect, I want to take the tax revenue from that and put it into some of these programs that I mention.
That’s interesting that you’re open to that; you’ve been very open about your own past addiction problems. You’ve talked about your addiction; Marty Walsh has talked about his problems with alcohol; other candidates have talked about times they’ve dropped out of school—is this some sort of millennial-generation, Facebook-era over-sharing, or is this a good political trend?
I think it’s good. People want to know our imperfections because they have a lot of imperfections. The thing that I’ve been through, it’s very up front, and it’s very dramatic in the sense that I lived on the streets for a while. No matter what economic class they’re in, or culturally where they are or where they’re from—people go through stuff, David. People go through stuff with their marriage, people have had trouble with their kids. People want to know that this person I’m going to vote for, who I’m trusting my decisions to be made to, yeah, they’ve been through some stuff too. And in politics, there’s a romantic component to politics—people want a good story. Barack Obama had a good story. They want to know there’s an element of hope that they’re voting for. If you can’t vote for me because I’ve had addiction problems, and I did drugs, and I got arrested before, you have every right as an American citizen to do that. But at least I’m telling you what it is. I’m not hiding anything.
One of the criticisms of Menino is the sense that he has used city employees, and city services, as a way of building and maintaining political power. You ended up getting caught in that, as a neighborhood coordinator—
—The Boston Globe, I remember it well.
Yes. That Globe article, in 2009, sort of made you the poster boy for what it was trying to describe as Menino’s people, like you, using favors as a way of currying political favor or allegiance, and also threatening people suspected of not being supporters of Menino. Is this the way the city works, and should voters look at you as part of that system?
No they shouldn’t. First off, I left Tom Menino’s administration, left without a job, because I felt that I had the required experience and had done a good enough job, and it was time to move on because I wanted to do something else. I think that my actions speak louder than words. That story was not the truth. That was a situation where someone was trying to make me look politically bad, and make their particular candidate look good. And when the Globe actually looked at that story, they had nothing. If you actually read what happened in there, none of that was real, at all. Nothing in that story was real. I never threatened anybody. Except for the one particular kid that was promised a job and was going to get it if he threw me under the bus, other than him, there was nobody else that could verify their story. There were people that had the mayor’s opponent at the time, Michael Flaherty’s house signs on their house, and when they went and spoke to them, every single one of them said Jack has been nothing but gracious to us throughout this whole process. I never once even intimated that they weren’t going to be helped because of politics. That’s not anything that I’m about. My philosophy is a lot different in that respect because I don’t believe in a politics of payback or power politics. It’s not my style. I come from a neighborhood, David, where we have no political infrastructure. Zero. Most people in Charlestown have no clue about politics. It’s not like South Boston, or parts of Dorchester, or West Roxbury. It’s just not. I know most people will never look at it like that, because it’s just like hey, Irish Catholic, they’re the same way. But it’s true. We’re not a political town. So my instincts are not reflexively political, ever. That story was laughable. In fact, the way I look at the story, David, it basically said I did a really good job.
Read more Boston City Council Candidate Chats. This interview has been edited for length.
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