🏛 Halls of Power is brought to you by Legislata, an informational platform for politics. Keep up with bills, share press releases, keep your team aligned, and even get through your inbox quicker. Sign up for free at app.legislata.com.

Welcome to the first episode of of Halls of Power, a podcast and newsletter from Legislata that explores what working in the political ecosystem is actually like and advice about how to better navigate it.

We’ll be bringing you weekly conversations with people about their careers, what they’ve seen, why they made the choices they did, and what they wished they had known if they could have done it again.

Today, we’re talking with Jake Wilson, a Councillor-at-Large for the city of Somerville, MA, who won election in 2021 and was in office in 2022 when the Green Line Expansion was finally completed, bringing rapid transit to the city after decades of delays.

It was the rare time when an elected official could celebrate a clear win for the community. We talk about what led him to run, what a municipal campaign is like when you don’t do much until the preliminary election is over, and what it means to go straight from civic festivities to a protest.

You can listen to the conversation above, or read a lightly edited transcript below.

Chris Oates

When we think about working in government, we often think about people in Washington, running from crisis to crisis or managing some disaster. But a lot of governing happens at the local level. And not every moment is a crisis. Today, we're going to be speaking with someone who recently ran for and won office at the city level in Massachusetts, and then was in office when that city experienced a real victory. The city is Somerville, Massachusetts, it's right next to Boston and is where I used to live. And the victory was the extension of the rapid transit system into that city. We're going to talk about what it's like to run a campaign as a local level, trying to balance your day job in the campaign, and then what it's like to be in office when people are actually happy with what the government is doing. Counselor-at-large Jake Wilson of Somerville, Massachusetts. Thanks so much for being here.

Jake Wilson 1:22

Thanks, Chris. Yeah, it's great to be here with you. Thanks.

Chris Oates 1:25

I looked at your website. And you started off in Iowa, and then moved to Philadelphia, and then to the Boston area, and Somerville, and I'm just wondering, at what point in that journey did you first get involved in politics?

Jake Wilson 1:40

I'll tell you, I always have followed politics, I've always wanted to, to, you know, to dip my feet in the water and try it. It took me a little bit longer to take those first steps that I probably had envisioned back as a teenager. But I got here eventually, it really stems from just a general zeal for talking to people and trying to solve problems with you know, in this case, medium and long term solutions. As a city councilor, we rarely can solve something, you know, it's not on us to solve something in the in the moment, we have a city staff for that. But what we can do is try to get creative and innovative on the policy side and look to solve big problems by thinking big and working with our legislative and policy analysts to try to come up with good solutions.

Chris Oates 2:40

And I saw on your biography that you were the head of Somerville youth soccer for three years. And I have to imagine like there's no better training ground for elected office in municipal government than dealing with soccer parents.

Jake Wilson 2:52

That's really perceptive. Actually, it sometimes shocks people when I tell them what good preparation it was for this. Perceptions can can be very different from reality in terms of what's involved in youth sports administration. Soccer was big. We had, by the time we grew it from about 799 kids to almost 1200 by the last season that I was involved in the planning. That's a decent chunk of the city right there. When you talk about that, it's probably also a decently big part of why I got elected, running at-large, I had citywide name recognition through families. Soccer families tend to be social, have a lot of friends and neighbors who they talk to, and no one thing gets you elected, but I put a big weight on it. Basically I showed I could run a pretty big nonprofit in the area.

Chris Oates 3:58

Lots of folks in democracies these days are talking about the lack of civic space. And they often say youth sports is one of those last remaining ones that in every single town in America, there are some youth sport leagues and like that brings people together.

Jake Wilson 4:18

Yeah. And I'll tell you, it's tough. In the most densely populated city in New England, it's can be tough finding that recreational space. And that's one of the things that I ran on. It's one of the things I was honestly I got my start in community organizing around athletic fields in school yards and recreational space. I think it's a really important thing for communities for families, for everyone, that we have these these shared spaces, and it's going to be something that I'm going to continue to work on here in office.

Chris Oates 4:50

I saw this on your LinkedIn, is this true? You're a minority owner and a second division Danish soccer team.

Jake Wilson 4:57

That's true. That's a new thing. My wife and I bought, I will say, a very small percentage of Danish football club that's currently in the third tier over there for the club that has had some success in its history. They have nine Danish titles to their credit in their history. So we're part of a consortium that came in there and then did a takeover in late November. And yeah, we're looking to hopefully restore that club to its rightful place is one of the more prominent clubs in Denmark.

Chris Oates 5:30

As someone who's seen nearly everything from Welcome to Wrexham and who would absolutely buy a soccer club. If I had the money. I'm very envious, but that's a whole other podcast. I don't want to get.

Jake Wilson 5:40

It's the probably the dumbest and funnest investment that I will ever make.

Chris Oates 5:45

I mean, if it gets you some free tickets and a flight to Denmark, I'd say that's worth it.

Jake Wilson 5:48

It's getting me to Valencia for warm weather training next month. So that's something

Chris Oates 5:54

That is fantastic. So you were running youth soccer, and then you decide to run for office. And I'm just curious, what was the thought process behind, I'm actually running for office. I know a lot of people think about it, we talk about it, maybe I will, maybe I won't. But what was the decision of, I'm going to do it, and I'm going to start working on it now.

Jake Wilson 6:12

Yeah, I mean, I'll be honest, I thought about running and talked to the, at the time, the outgoing ward councilor here for ward four, the late Walter Pirro. But we had there were two very, very good candidates already. Already in the race one with citywide name recognition, another one who I thought very highly of, and I just decided it wasn't really the time. I had a young, very young child at the time. And I knew the kind of work involved with with campaigning, and I knew I just, I didn't have that to give at that point. I was working full time and the primary caregiver for for a young child, so it wasn't in the cards, but you know, it's kind of stayed with me. And the current ward councillor for my ward is very good at his job. I had no intention of challenging him. And it was really some some board members on the soccer board who came to me. I know, every every elected official likes to to portray, you know, I was drafted, I was called upon. I kind of actually really was like some folks put it in my ear, who basically said, like, Hey, you seem good at this stuff. Have you ever thought about running for city council? And I said, Yeah, my ward councillor is really good, though. Well, you should run citywide. Like I said earlier, you have name recognition from soccer. And that stuck with me, and I decided to do it. I was a very non traditional candidate, because I've not been involved in local Democratic committee, City Committee politics at all. Despite being a Democratic socialist, myself, I've not really been involved electorally, with Boston DSA. So I didn't really fit into any of these sort of groups. And so in some circles, there was some consternation, like who is this guy? Why is even running. But the people who knew me who'd worked with me, I've been very involved in both education, and youth sports, as we've talked about, and people who who dealt with me in those circles, they thought I had a much better chance of winning than folks who would not know me from those circles. I struggle with perfectionism, and I wanted to have like a really good campaign video. It held up launching the campaign probably by a month or two, beyond where it should have and then it was starting to get to be a crowded field. And finally, I had people screaming at me if you're gonna do it, get in the race. So I pushed out a video that was good enough, announced and then said about the process of trying to figure