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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 out the landscape as a newcomer in running for office. And it's, it can be daunting. Let me tell you.
Chris Oates 9:02
That campaigning period was a year, two months? I mean, I'm curious how long the election cycle is in Somerville.
Jake Wilson 9:10
Well, it's, it's funny, you should ask. It started early in 2021. In March or so, and I think I announced in April, but and then you pulled papers, I want to say it was late May and then you pulling papers means you gotta get the official signature pages from the committee, election Commissioner's Office. Then getting those nomination papers signed. And then you eventually returned them and get certified on the ballot. However, the transition process from Somerville soccer, I shouldn't have been surprised by it, but just given when you bring in someone new, and this was someone you know, who came from a really good background in sports information. Very good and a sharp person, but just the knowledge transfer, bringing in someone who's new to the organization took a lot longer than I had planned on. I was doing candidate forums, I was filling out candidate questionnaires, but I wasn't knocking on doors. And a lot of people who knew me and were rooting for me grew very alarmed that I, you know, they thought I wasn't taking the campaign seriously. In reality, I was doing the planning for the fall season of soccer, which is the big lift. I was not only doing it, but having to explain it to a new executive director. And as anyone knows, who's done that it takes about three times as long to do something and explain it to someone as it would to just do it yourself. So yeah, that that dragged on and through the preliminary and the night of the preliminary election, September 14, it was seven weeks out from the primary, I got lucky in that someone there were going to be nine candidates at large, only eight of us, which is the maximum that you can have without requiring a preliminary election, only eight of us got certified. So we didn't have a preliminary if we'd had a preliminary I might have been out at that stage. Because I had not had the time to go knock doors-
Chris Oates 11:31
Just to explain it to people, Somerville doesn't have a primary and then a general it has for at-large candidates a preliminary election. And so eight can make it through the preliminary, which is effectively the primary, to carry on to the general in November.
Jake Wilson 11:45
Yeah. We're looking at ranked choice voting here. The system we have is honestly not that bad. It's not quite as good as ranked choice voting. But you know, it's probably the next best thing. Yeah, it's a way of ensuring that there are basically 2x people, two times as many people as there are winners in an election on the final ballot for the for the municipal election. So there's a preliminary election, usually early to mid September, shortly after Labor Day, that narrows it down to that maximum for the final ballot.
Chris Oates 12:19
So for your race because there were four at large councilors and eight people certified. There was basically no preliminary, you were on the ballot for November without having to do anything other than collect your signatures.
Jake Wilson 12:30
Yes. And that was a very good thing for me, because I mean, I might have made it through I don't know, it would have been cause for concern, let me tell you, because I had really not raised money I you know, I really had not, I've not really fully campaigned. And then it was the night of the preliminary. I remember vividly emailing the some of the soccer board and saying, I cannot help out anymore with anything the season had begun at that point. And I had said, you know, there are seven weeks and my campaign is a disaster right now. And I have to devote myself entirely to fixing this and getting it on track. And then I basically lived campaign mode those final seven weeks. There's a perception out there that I didn't knock doors and that's definitely not true. It's true up until the preliminary election, but I'll tell you, I knocked a lot of doors and those final seven weeks I pretty much I probably averaged four to four and a half hours asleep in those seven weeks. And I lived that campaign. So I put in a lot of work on the campaign it all just was concentrated in this final seven weeks.
Chris Oates 13:42
It's fascinating because hopefully one of the things we're doing in this podcast series is showing what it's actually like working in this world and your day job doesn't just go away because you want to run for office. You still have responsibilities from your previous life.
Jake Wilson 13:59
Well mine did. When I cut the cord with that I was full time campaigning. I would go to bed with like racing thoughts, you know, one or 2am wake up at 6am Like with a jolt of adrenaline like you know, in panic mode up out of bed down to the home office. At that point I was planning my morning - not to go too into the weeds on this.
Chris Oates
But let's go let's go into those weeds.
Jake Wilson
We use Vote Builder. It is the database the Democratic Party in Massachusetts uses. I had to register as a Democrat to get access to it. I've been a proud independent because of annoyances I have with the Democratic Party. And I got really good advice from a current colleague who will remain nameless who told me to get over myself that my my little one-man protest wasn't being noticed by anyone. I should just get over myself and register as a Democrat. It’s really good advice. And I thank that person for it. And it proved, it proved to be excellent advice. And it getting Vote Builder and the minivan app was hugely helpful. So I would basically plan, you know, which doors I was going to knock? And then I would be out there from basically 9am. I'm one of these weird intermittent fasters. So I didn't need to stop for lunch, I could keep going. And I pretty much went from 9am to in many cases, sunset. And yeah, and I would on weekends, too, I would tend to, to knock a ton of doors as well. So I do that. I'd come home, eat some dinner, eight or nine o'clock. Go back down to the office, respond to emails, and that is oftentimes the only time I could respond to emails then. And plot the next day and you know, try to sleep at like one or two and rinse and repeat.
Chris Oates 16:03
And then what was election day like? Did you did you find out the results on election day?
Jake Wilson 16:08
Yeah, yeah. Election day, it's funny. So knocking all these doors and doing so late in the process gave me a pretty unique perspective. What I joke about is like anecdotal polling to the point, I have witnesses for this, I successfully predicted the order of finish for the eight of us in the in the at-large race, because you can you talk to enough people you can tell. And I was pretty confident about it. So I knew I had a chance to win. I remember running into some folks who, you know, didn't know me didn't think I, you know, didn't think I should be running. I remember saying, you know, I think I have a shot and they looked at me like I had three heads. I knew it was basically down to me and one other candidate for the fourth spot. And I thought that I knew I had a real shot when someone who was part of the Our Revolution, DSA slate, messaged me, and complimented me on the campaign and said, they were hearing a lot of support for me on the doors. And because of how good an organization they have in terms of canvassing, that told me that it was likely showing up in their voter data that I that I had support. I knew I'd done really good mailers. We spent a lot of money on mailers, because I did them late in the process. I did all the copy for them. Someone who does a lot of congressional campaigns did the design. And I know from talking to voters that those mailers, the three of them hit, they were really well designed, really appreciated that work. And I put a lot of effort into the content. And I know those maybe that was second to the youth soccer experience in terms of what got me into office. I know those mailers made a real impact.
Chris Oates 18:08
It's just always interesting talking about municipal elections because, you follow congressional national news from the midterms or the presidential and you have constant polling, constant updates. But NBC is not polling Somerville.
Jake Wilson 18:23
We have zero polling in Somerville. On election day, I went into it knowing I had a chance thinking I might actually have the inside track on the fourth spot. And I just remember it being a blur. I tried to hit all 21 precincts - some have shared polling stations. I want to say it was like 13 or 14 separate polling stations and I couldn't make it to all of them. There weren't enough hours a day, but I made it to a lot of them. And I just really remember I didn't eat, just sort of going on adrenaline. And I remember the one I ended up at. I was told to go to a big one at the end, like a polling location with multiple precincts. I picked the Somerville Community School for the closing. I waited too long to go inside because it had locked the doors. Because if you're there they can give you a printout of results. And I thought that'd be a good sort of bellwether. But I missed that. So I drove home and I had people some campaign folks and I wanted to get together with them. And we thought we'd be watching returns. But as I'm driving home on that 10 minute drive, I get a call from from my wife, who said, almost everything is in, you're up 500 votes with three precincts left. And I said, What precincts are they? And she, I don't know how she knew which ones maybe she'd looked it up. And I did some quick math. And I was like, I think I'm safe. I think I think I've got this. And by the time I got home, I want to say within five or 10 minutes, those other those straggling precincts had come in. I got a call from then Mayor Curtatone congratulating me. It was surreal, like people hadn't even arrived yet. And I already knew I had won. I will say on a personal note, I have my child, my oldest child was a big supporter of the candidate who finished fifth. And when I did, I saw this coming, I knew it was down to me and this other candidate. When this other candidate lost my child was in tears. And so it was weird. I get emotional talking about it, actually. It was this weird feeling of like euphoria. And then I have a child who's you know, I think that my child would rather that this person beat me honestly. So that was really kind of a gut punch while celebrating this thing, but yeah, and then people showed up on my back deck, and we had a weird, thrown together ragtag election night party. I sent a fairly inebriated resignation email to the soccer board, because I can't I had to. You can't be on a nonprofit board like that and be a city councilor. So resigned at about 2am after a decent amount of bourbon and woke up the next morning. Like, whoa, let's do this.
Chris Oates 22:19
That's a great election night story. Okay, so you're you're in office. And let's jump forward to now the Green Line Expansion. This had been for those who don't know, the Green Line Expansion had been proposed decades ago, it had gone through a whole process. It was running way over budget, it was cancelled, it was started again. When I was living in Somerville, the construction was happening. So we knew it was eventually going to be built, or at least, we hoped so. But at what point on City Council, did you have a sense like, oh, it’s happening and it's happening now? It's not going to be delayed for another couple of years. We can start planning for it.
Jake Wilson 22:53
Well, I mean, like you say, there have been so many deadlines, so many false dawns, I basically adopted a view of I’ll believe it when I see it. Yeah. I mean, they announced the date in March of the Union Square one. And I think I tweeted this out on social media, like, Alright, I'm seeing it, I believe it. I'm on a Green Line train, it's really happening. And that one was fun. But that's that's one station. And then the attention quickly turned. I mean, what's really going to be transformative for Somerville is having the the E line go right through the spine of the city. When they announced the date, that's probably when it started to get real. It got very real waking up at 4am on December 12, and then heading over to Tufts and riding on that first train. And that's that's when the the ultimate realness set in.
Chris Oates 23:59
And was there any kind of celebratory events that the council was involved in? Or were you preparing for something? Was it was it a big party? Or was it just kind of another day in the office but it'll be a pretty good day.
Jake Wilson 24:11
It was an inter governmental celebration. Current and previous mayor's were there at 430 at Tufts. I don't know if I can remember any other colleagues got up for it? Maybe 600 people there. We rode it all the way to JP because it's the first train so you can either get off and wait outside for the train to come back or you just stay in the warmth of the train. It was a pretty cool day so I just wrote it to JP and we came back and in true MBTA fashion, the train became disabled at Park Street station. And yeah, then we then we got off at Ball Square and that's where they the city had organized a morning rush hour celebration. Yeah, that was great. Lots of joy, brass bands, so many faces I know. Just general euphoria. I also took part in a protest immediately after that, for the Community Action Agency of Somerville protesting against the lack of protections that have been put in place around housing affordability and the displacement crisis that we have. It's been a real public policy failure in our state and in our region here, that we've experienced all the downsides gentrification-wise, that the Green Line is brought in without any of those, those protections put in place. And it's created a very perverse situation where the very people who this was brought here for - transit equity for the working class folks who need this - a lot of them are gone, because they have gotten pushed out of the city. So you know, it can be a sober, sobering, you know, upsetting moment, and it can be a moment of joy at the same time, like, both things can be true. And I'm fine, I can embrace that. That paradox. I'm okay with that. I'm okay with nuance. And that sums it up right there for me.
Chris Oates 26:04
It's interesting, because you're on the one hand, you are an elected official of Somerville celebrating a governmental accomplishment. On the other hand, you are someone who has a series of issues and policies that you want to advance. And you don't want to miss an opportunity to do that.
Jake Wilson 26:20
Yeah. And to your point at the very start of this. It can be it can be a tough business, sometimes it can be frustrating, you can it can leave you feeling powerless. And that's why it's really important to seize those victories, even small victories. In this case, a giant victory, a transformative victory. We have to celebrate those. It lets you refill your emotional tank, it gives you the fuel to fight on and reminds you that wins are possible. Like we can have good outcomes if we fight. And the you know, the GLX is is a testament to that, right? This was decades, we're not exaggerating, decades of advocacy. One of the first things I did in Somerville when I moved here in 2005 was attend a rally at the old high school auditorium. I had my green glow necklace on. And people literally yelled at state officials about them dragging their feet about this. So yeah, that's a good, good illustrative point of the power of organizing and the need for persistence.
Chris Oates 27:31
As someone who's worked on winning campaigns and losing campaigns, you always need to appreciate what it feels like to win because it doesn't always happen. Okay, so that was really, really interesting. But I want to before you go have a few questions. What is politics actually like the West Wing, Veep, or House of Cards?
Jake Wilson 27:50
What is it most like? Probably most like Veep. I mean, I know about the other shows, I'm familiar with them. It's just weird. Like, there's no job description, really. No one tells you how to do this stuff. We have a councillor’s college where it's sort of like a crash course and how the different departments work. But like, you sort of just have to kind of feel your way through it.
Chris Oates 28:14
And what was in the political sense, what's been your best day in politics?
Jake Wilson 28:19
Oh, that's a great question. My best day in politics, probably just from a relief point of view, the day we passed the budget for FY 23. As a new councillor, you have to learn about municipal finance and then I was a member of the finance committee. So you're the ones actually carrying out this whole thing. I was the Finance Chair. So I was having to plan these meetings and run them. And it was a really steep learning curve. My wife was away for work at a conference one week when we had four meetings that went from 6pm until midnight during June. So I remember feeling pretty euphoric when budget season officially ended with us officially approving the FY 23 budget. I won't take credit for it. It was innovations that were done with with staff, with the budget director in particular. But we we did set a modern record, going as far back as I could find it for the fewest minutes spent in committee meetings. Sorry, that's kind of an anticlimactic answer to your to your question.
Chris Oates 29:48
No, if that was your best day, then that was your best day. I mean, this is what life in politics is like. It's sitting in budget meetings.
Jake Wilson 29:55
Actually. You know what? I've got one for you. My kids go to the Healey School just down the road. Prior to getting involved in city council, my first real involvement with city government was leading a parent coalition at the school who pushed successful in the end but after a lot of effort to get the city to, to renovate it to build a new and actual school yard, their soccer field, younger kids equipment, older kids equipment. If there's a if there's a better school yard, anywhere in the area, I'd love to see it, I'd put this up against anything, they spent $6.4 million on it. And it happened for an area, I might get emotional talking about this again, I actually teared up at the speaking at the ribbon cutting ceremony on November 30. Because my kids go to the school. I coached these kids. It's an area not used to good things happening to it. And this, I know how much it means to the neighborhood, to the kids at that school, the message it sends to them that they really do matter when they get something nice like this. And I got really emotional talking about it, I had to actually cut my remarks short, or I was going to be full on crying at the lectern, they're on camera. But you get an emotional talking about it. But yeah, that that has to be the for me the best moment.
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