The evolution of Stephanie Pollack

Why a life-long Democrat became one of Charlie Baker’s biggest backers

Photographs by Frank Curran

STEPHANIE POLLACK AND Charlie Baker are the odd couple of Massachusetts politics. Pollack is short and Baker is tall. She’s a lifelong Democrat and he’s a lifelong Republican. She supported Deval Patrick in 2010; Baker was running against Patrick during that race. She’s a progressive with a history of pushing higher taxes to support transportation; he’s a fiscal conservative with a history of opposing such measures.

Yet if Gov. Charlie Baker wins reelection, he may have Pollack to thank. As Baker’s secretary of transportation, Pollack is overseeing the governor’s signature first-term issue—the turnaround effort at the moribund and change-resistant MBTA. How well she does may well determine how Baker fares in 2018.

Pollack and Baker met for the first time when the governor interviewed her for the job. They went into the interview wary of each other, but both of them emerged impressed. “He basically said, all my friends are going be mad at me if I hire you. I said, a lot of my friends will be mad if I take the job. And we were both right,” says Pollack.

Any lingering reservations of their friends notwithstanding, the two seem to get along well. Last year, they appeared in a comedy sketch, portraying the Blues Brothers on a mission to fix the T. In March, they took a tour of a prototype of a new Orange Line car. As Baker was leaving the event, he came over to Pollack and said, “See you, kiddo.” When a reporter expressed surprise at the governor’s use of the term kiddo, Baker smiled and said: “You should see what she calls me.”

Transportation advocates have generally not attacked Pollack for joining forces with the Republican governor and opposing new revenues for the T.  Rafael Mares, a vice president at the Conservation Law Foundation, where Pollack worked for nearly two decades and helped file a number of legal actions against the MBTA, says it is understood that Pollack has to be a team player. “We don’t go after her personally. We go after the policy,” he says.

Pollack’s knowledge of transportation issues is legendary. She’s built her internal database up over time, first at the Conservation Law Foundation and then over years as a consultant and nearly a decade at the Dukakis Center for Urban and Regional Policy at Northeastern University. Words pour out of her at times, almost always in complete sentences. At meetings of the T’s Fiscal and Management Control Board, she is the one who provides a broader policy context for presentations by T staff. But she also regularly delves into the minutiae of projects and programs.

Joseph Aiello, the chairman of the T’s Fiscal and Management Control Board, says he is constantly astounded at the breath of her knowledge. “Of all the people I’ve met in my life, she’s got one of the biggest CPUs [central processing units] in her head that I’ve ever seen,” he says.

Pollack, 56, grew up in East Hanover, New Jersey, and now lives in Newton.  She is the mother of three 20-something millennials named Hana, Yitzi, and Beni and the wife of a health insurance executive (and former physician) she met at MIT, where she earned degrees in mechanical engineering and public policy (odd pairing, yet she says it was a necessity because her father would only pay for an engineering degree) before going on to Harvard Law School.

What follows is an edited transcript of our conversation.

COMMONWEALTH: How would you describe the old you, the transportation advocate?

STEPHANIE POLLACK: When I was an advocate, I always was something of a contrarian in that I wouldn’t necessarily take the position that was conventionally seen as an advocacy position.  When I worked on childhood lead poisoning, I actually enraged a lot of people in that world because I took the position that we actually had to help landlords because ultimately if we didn’t help landlords pay to fix lead-paint problems that meant higher rents for the families. That was something that we should be just as worried about as the fact that their kids were lead-poisoned. I have been a person who has always tried to see all sides of an issue and to focus most on the people aspects of issues. I don’t think any of that has changed. I do think that there is a certain conventional wisdom among advocates in every area. In transportation advocacy, that conventional wisdom was that the only limiting factor that mattered was the availability of revenue. While I like to think I poked at that assumption, I now realize that I didn’t look deep enough to understand what was really getting in the way of ensuring that folks in Greater Boston had the transportation system and, in particular, the public transit system that they need.Com.Pollack-016

CW: What was getting in the way?

POLLACK: The T would always say that if it didn’t have more money, it wouldn’t be able to deliver all these great projects. I was just as focused on projects as all the advocates, and we would go to bat to get more resources for the T. My assumption was that some of that money went to run the system, but some of it went to actually build things. Now, having seen what goes on from the inside, as far as I can tell it pretty much all went into a giant operating hole and there wasn’t a lot of focus on capital investment. So when we were debating raising the gasoline tax in 2013, all the examples of what was going to happen to that money involved capital construction projects. But, in fact, the MBTA’s internal pro forma assumed that hundreds of millions of dollars of that money was going to go to the operating side and wasn’t going to go to capital construction projects.

CW: People are always trying to reconcile Stephanie Pollack the advocate and Stephanie Pollack the transportation secretary. There’s this sense that you’ve buried your real self, the advocate, to work for a no-new-taxes Republican governor. Which Stephanie Pollack is the real one?

POLLACK: I’m only familiar with one Stephanie Pollack. I’ve always thought of myself as a person who tries really hard to listen and learn and look at data and be open to re-examining preconceived notions.  So I don’t think I’m a different person. I do think that who your boss is forces you to ask different questions. When my boss was a nonprofit advocacy group, I didn’t ask the same number of questions about effective service delivery or accountability as I have to because I work for a governor who expects all of us to be accountable and to use every dollar of resources well. So it’s not irrelevant that I am a transportation secretary for Gov. Charlie Baker. But it doesn’t change who I am. It does change some of what I focus on.

CW: Have you had many philosophical disagreements with the governor on transportation policy?

POLLACK: We haven’t had many philosophical disagreements because there are two overarching philosophies that shape why I took this job and why I think he offered it to me. We’re in complete accord on both of them. One of them is that transportation is ultimately about economic development and people’s quality of life. The transportation agencies are not free to build the things that are important to them, but are responsible for building a system that works for the people who use it. That was the very first conversation we had the very first time we sat down to talk. That view continues to be, I would say, a minority view among many transportation professionals. So that philosophy helps us because then if you’re having a conversation about a specific project or a specific request from a city or a town, we’re both having the same conversation. Is it a good investment? What’s the return on investment? How is this going to help?  We may disagree on the answer to that question, but we’re asking the same question.

CW: What’s the second philosophy?

POLLACK: It’s this interesting point of consensus between people who see themselves as fiscal conservatives and people who, as I do, see themselves as progressives. It’s about spending government dollars wisely. I think one of the biggest problems with transportation agencies – not just in Massachusetts, but nationwide – is our constituents do not believe we spend every dollar we get well. This need for government to function well is where fiscal conservatives and progressives should be able to find common ground. Progressives may want that money spent well so that they can put more dollars into government and fiscal conservatives may want that money spent well so that they can leave more money in people’s wallets. But in both cases it’s really important to focus on delivery. For me, that has given me a blueprint for what my job is in running the transportation agencies.

CW: You recently said you didn’t think the Legislature would provide more money for transportation. Have you asked for more money?

POLLACK: I haven’t asked because I don’t think we’re at the point yet where we can make the honest argument on the operating side and the capital side that we’re spending the resources we have in the best way possible. But I would also note, having been on the outside asking for more money far longer than I’ve been on the inside working, that there are not people lined up to volunteer more dollars to invest in the nuts and bolts of the transportation system. I don’t know what the answer is to the question of when or if there will be a time to ask, but I do know that the notion that there is a willingness to make unquestioning investments in transportation through higher user fees or other taxes is not supported by the actual behavior of voters or people who answer polls.

CW: How do you plan to vote on the millionaire’s tax if it makes it on to next year’s ballot? The money is supposed to go to education and transportation.

POLLACK: No comment.

CW: As we talk, you’re getting a lot of pushback on the proposal to eliminate weekend commuter rail service. Do you think that proposal went too far?

POLLACK: I understand as well as anybody how hard it is to talk about cutting service. Obviously, service cuts should be a last resort. I’m very proud of the fact that the Fiscal and Management Control Board and the T have been able to get as far as they’ve been able to get in closing the operating budget deficit without any real changes to service. I also have to say, as someone who has followed the T’s trajectory on service cuts for many years, that I’m actually proud of the fact that, for once, the T is talking about commuter rail and not the buses, which is historically where service cut proposals have come. One question we have to ask ourselves when we put service cuts on the table is what would happen if we eliminated this service. Would the people who use it have alternatives? We’re talking here about weekend commuter rail service in a system that provides rapid transit well into the suburbs, which on weekends are not that tough to access. I understand why you need to be on the commuter rail for coming in from the western suburbs on weekdays, but on weekends you could go to Riverside and take the Green Line, or Alewife and the Red Line, or Wonderland and the Blue Line, or Quincy and the Red Line. The T is not talking about eliminating transit service on the weekends. We’re talking about eliminating, or suspending for one year, a low-ridership, high-subsidy service. I don’t know how that conversation is going to end up, but I think it would be almost irresponsible not to at least have the conversation about why we are running a service that so few people use that it costs three times what the late-night service that was canceled costs.

CW: The Fiscal and Management Control Board meets practically every Monday. You’re there most weeks, as are the T’s top management and staff. I’ve never seen anything like it in state government. Are those meetings, and all the time and staff resources they consume, worth it?

POLLACK: I’ve known for a long time how central the success of the MBTA is to Greater Boston and, indeed, all of the Commonwealth. But one of the frustrations of many transit advocates is that the T seemed to be an extraordinarily unappreciated agency. What is so wonderful about the Control Board and its meetings on Mondays is that we are investing that much time and effort in having the conversations that are happening. The meetings are the agency and its stakeholders working through complicated issues that have been left unresolved, in some cases for decades, because we’ve finally gotten to the point where we realize that we have to. Yes, it takes tons and tons of staff time and effort to gather the data and figure out how to present the data and queue up the options and anticipate the questions. But as I go through that process every week, I just keep thinking to myself isn’t it a wonderful world where people are so concerned about making the T work that they’re willing to put in that level of effort.Com.Pollack-035

CW: Originally, it seemed like the meetings were live political theater. But increasingly it seems like many in the audience have already seen the presentations and know what’s about to happen.

POLLACK: What the Control Board decides is happening in real time at the meetings. That’s what the state’s Open Meeting Law requires and that’s what we knew would be the ground rules when the board was set up. One of the things that we’ve learned over the arc of time is that there are constituencies and stakeholders that are particularly close to particular issues and it’s in everybody’s best interest to have them come up to speed in advance of the meetings so when they comment and raise issues and questions that they’re in a position to do it well. One of the complaints we got is that public comment comes at the beginning of the meeting. How can we comment if we don’t have the agenda? So we now email the agenda to people in advance so they have an opportunity to think about it or give someone a call to learn what’s going on. If there’s a specific group of stakeholders, we do meet with those folks beforehand. The Control Board members are certainly not allowed to do any deliberating, but that doesn’t mean they can’t be briefed by staff. And it doesn’t mean staff can’t be talking to others so we can use the time in public sessions on Mondays to have the best possible dialogue among the Control Board members and between the Control Board members and the stakeholders.

CW: You’re preparing to hire a new general manager/CEO. How important is that hire to the future of the T?

POLLACK: The frequent turnover in leadership at the MBTA is clearly one of the things that has kept the agency from addressing its long-standing problems and succeeding. It’s my hope we can find the right leader for the T at this moment in its transformation and that that person will actually stay in their position for at least three years if not longer. It’s really important because it’s been a long time since the general manager of the T served out the entire period of their contract, and I think it’s something that the T needs.

CW: Did you give any thought to taking that job yourself?

POLLACK: I haven’t given serious thought to that position because in my current job I have the best of both worlds. I spend part of every single day working with the T’s leadership and the Control Board to make the T better, but I also get to work on a lot of other transportation issues that I care about just as much.

CW: But whomever you hire is likely going to be paid more than you and the governor?

POLLACK: If salary were a driving force in my career, I don’t think I would have spent two decades at the Conservation Law Foundation.

CW: You mentioned earlier that you’re a progressive. Are you a Democrat?

POLLACK: I have been a Democrat since I registered to vote at age 18.

CW: Any plans to change parties?

POLLACK: I don’t really see any reason to unless someone were to challenge Gov. Baker in the primary, in which case I’d pull a Republican ballot in a heartbeat to vote for him.


In a funny video last fall, Stephanie Pollack and Gov. Charlie Baker played the Blues Brothers on a mission to save the T.

CW: Why do you, as a progressive, support Baker?

POLLACK: The governor is not just a person who has demonstrated his ability to make government work. It’s because he’s got the right reason for making government work. When Jim Braude recently asked him whether he had a vision, an issue that’s been bouncing around with the governor and me for a while, the beginning of his answer was we have to make sure public transportation works for the people who need it most. That’s my vision, too. It’s important for we progressives to always be thinking about the people who need the government to work for them. But I would argue that it’s equally important for the government to work. That’s why it has been such a privilege to work for Gov. Baker. It’s not enough to care about the right issues and the right people. We have to deliver.

CW: What’s happening at the T is likely to be an issue in the race for governor. It’s interesting he’s got you, a Democrat, watching his back on that front.

POLLACK: There’s no question that the progress that we do or don’t make in fixing the T is going to be an issue in the campaign because the governor has made that a central focus of his term in office. He deserves a lot of credit for that because, honestly, there are a lot of pieces of that we don’t control, starting with the weather. To actually say, I’m going to tackle this issue that has been festering for decades—not years, decades—and I’m going to make a commitment that we’re going to show tangible progress, that’s a pretty risky thing to do. We’re not the first people to start down the road of making the T a better agency. I’d like to be the first ones to actually finish it.

CW: How does it feel to always be the smartest person in the room on transportation issues?

POLLACK: I don’t think of myself as the smartest person in the room and I know I’m not when I’m in the room with the governor because it’s scary how quickly he grasps things and how many issues he has to keep track of. I tell people that if you ever want to test your ability to process and synthesize a lot of information on almost no sleep, an MIT undergraduate education is a good way to try that.

CW: To keep up, are you constantly reading?

POLLACK: I don’t actually read as much as I would like. When I was at Northeastern, I had the time to read whole reports and pore over the data. Now I read the executive summary and set the report aside in the hope that someday I will get the chance to read it. So I actually feel not as well informed in some ways as I used to be. I guess I’m just blessed that I synthesize information well. I do a lot of reading in the morning, late at night, on the weekends, or while I’m traveling. It takes a lot of hours.

CW: Do you read for fun?

POLLACK: The only pile that’s bigger than my pile of unread work reading is my pile of unread personal reading.  I am a happier person when I am reading something for my own personal pleasure, but I can’t actually remember the last time I did that.

CW: How does your Jewish faith affect your work?

POLLACK: I am an observant Orthodox Jew, which means a lot to me and my family. I could get into an Orthodox 101 conversation, but in terms of how this affects my job, being an Orthodox Jew means I keep kosher and that I try to be home for Sabbath before sunset on Fridays.  Except in the case of emergency situations, I do not make phone calls or send emails on the Sabbath and other Jewish holidays.  For me, Sabbath is an electronic timeout that gives me time to think about something other than transportation. My staff, the governor, and others have all been helpful and understanding in making sure that I am able to fulfill all my responsibilities while remaining true to my faith and I deeply appreciate their support.

CW: How long will you remain as transportation secretary?

POLLACK: I will stay in my job as long as the governor will have me.

CW: You’d stay through a second term if the governor is reelected?

POLLACK: If there were a second term and the governor asks me, I would absolutely stay on. I once asked a gentleman who served a governor from day one of the first term to the last day of the second term how he accomplished as much as he did. He said we really started hitting our stride in the sixth year.

CW: Who told you that?

POLLACK: I’d rather not share his name since I never asked him if I could use that story.

CW: What gets you most excited? Building the Green Line extension? Creating a new neighborhood with Harvard at the Allston-Brighton toll area?

POLLACK: Transportation is at this fascinating moment because all of a sudden the possibilities of how people can get where they’re going are opening up. We’re investing in our transit system. We’re building complete streets for people who are walking and biking and using transit, not just driving. We’re watching all kinds of business-model companies, whether they’re car-sharing companies like Zipcar or ride-sharing companies like Uber. What interests me the most is how you fit all these pieces together to create an ecosystem in which people have really great options for getting where they need to go. There’s a public transit piece of that. The T will always be the high-volume backbone of a place that gives people great transportation choices, but for me the most interesting thing is how the whole can be more than the sum of the parts.

CW: Can you and the MBTA focus on the future very much given the day-to-day pressure on the agency to put out fires?

POLLACK: I hope that we are already focusing on it somewhat. At the moment, MassDOT is in the process of completing a statewide bicycle plan, a statewide pedestrian plan, a statewide rail plan, a statewide freight plan, and the Focus 40 plan for the T. One of the reasons that I am pushing the staff and the consultants on all of those exercises is it’s where we have the opportunity to really think forward and outside the box. We can put ideas on the table that may not come to fruition while we’re here, but that will lay the groundwork for other people in the future.

Meet the Author

Bruce Mohl

Editor, CommonWealth

About Bruce Mohl

Bruce Mohl is the editor of CommonWealth magazine. Bruce came to CommonWealth from the Boston Globe, where he spent nearly 30 years in a wide variety of positions covering business and politics. He covered the Massachusetts State House and served as the Globe’s State House bureau chief in the late 1980s. He also reported for the Globe’s Spotlight Team, winning a Loeb award in 1992 for coverage of conflicts of interest in the state’s pension system. He served as the Globe’s political editor in 1994 and went on to cover consumer issues for the newspaper. At CommonWealth, Bruce helped launch the magazine’s website and has written about a wide range of issues with a special focus on politics, tax policy, energy, and gambling. Bruce is a graduate of Ohio Wesleyan University and the Fletcher School of Law and Diplomacy at Tufts University. He lives in Dorchester.

About Bruce Mohl

Bruce Mohl is the editor of CommonWealth magazine. Bruce came to CommonWealth from the Boston Globe, where he spent nearly 30 years in a wide variety of positions covering business and politics. He covered the Massachusetts State House and served as the Globe’s State House bureau chief in the late 1980s. He also reported for the Globe’s Spotlight Team, winning a Loeb award in 1992 for coverage of conflicts of interest in the state’s pension system. He served as the Globe’s political editor in 1994 and went on to cover consumer issues for the newspaper. At CommonWealth, Bruce helped launch the magazine’s website and has written about a wide range of issues with a special focus on politics, tax policy, energy, and gambling. Bruce is a graduate of Ohio Wesleyan University and the Fletcher School of Law and Diplomacy at Tufts University. He lives in Dorchester.

CW: I notice that before answering a question you tend to pause for quite a while. Sometimes it’s for several seconds. Are you thinking of what you are going to say before you speak?

POLLACK: My middle child, he’s an introvert. He ended up in the state finals for the mock trial competition for the Commonwealth of Massachusetts. They were held at Faneuil Hall. He was only a sophomore. He asked a question that he had asked a million times before and a lawyer from the other high school team objected. The judge said you have to rephrase the question. My son stood there. I actually timed it; it was over 30 seconds, where not a single word came out of his mouth because he was clearly thinking the whole thing through. I thought to myself how courageous it is for a 16-year-old to stand in Faneuil Hall in front of hundreds of people and think instead of just having the words come out of his mouth. I have actually tried to model my own behavior on that day, watching my son do it, because I came to the conclusion that I didn’t leave myself enough time to think sometimes.