The Three Ds of Dan Dain

1632: Boston is home to the first public school. Four years later, Harvard becomes the first institution of higher education in the colonies. The first regularly issued newspaper, The Boston News-Letter, drops in 1704. In 1840, the first women’s rights and Black civil rights movements in the nation are sparked.

The world’s first publicly supported free municipal library, The Boston Public Library, opens in 1848. Alexander Graham Bell makes the first phone call in 1867. 1897 offers the first running of the Boston Marathon, the world’s oldest annual 26.2; and the nation’s first running of an underground metro system, for those less committed to cardiovascular wellness.

And we didn’t even get into that whole “birthplace of American revolution” thing.

Yet this storied city of firsts had nocomprehensive historical overview to its name. No single book, no nothing. It’s a bit outrageous if you think about it. It was to Dan Dain.

“My professional interest is in what makes cities successful,” says Dain, a commercial real estate lawyer at Dain Torpy in Boston. “When my clients make proposals to build, they’re essentially making a future prediction that when the building is open, there will be office tenants who want to rent the space or residents who want to live there. They’re betting on the continuation of what has been a 30-year period of high urbanism in Boston, which I define as a period when people want to live, work, play, study and shop in the city. I started wondering, ‘Could we look to the past as a guide to those policies and practices that would help Boston continue to be successful?’”

Prior to this 30-year period, in the 1980s, the Brookings Institution declared Boston “‘the most blighted city in the country,’” Dain says. “The population in 1950 was 801,000. In 1980, the population was 570,000. The city lost 230,000 people and a similar number of jobs. I was curious why Boston swung through these periods of great success and decay, and whether those lessons could be applied to today’s challenges.”

That’s why, in 2017, Dain found himself reading books on various elements of Boston history. He was soon dedicating his weekends to notetaking, but the notes led to more questions, which led him to buy more books, which led him to realize there was no singlevolume that traced the history of Boston from its first peoples to today.

So he got to work. In 2023, into the oeuvre of Boston firsts came A History of Boston, Dain’s 800-page deep dive into the city he loves—the most comprehensive volume that exists.

Dain, soft-spoken and even-measured, thoughtfully chews on questions before answering; and boy, does he have answers. When the conversation fleetingly turns to cycling and true crime, he waxes on the origins of biking in Boston and the sensational 1849 murder of Dr. George Parkman, the scion of a wealthy family whose dismembered body was found in a Harvard science lab.

In June 2024, the Independent Publisher Book Awards presented Dain with the bronze medal for best nonfiction in the Northeast region. He’s in high demand on the historical lecture circuit. Friends and colleagues are astounded by his treatise. But, he says, the best kudos he’s received was an email from a local high school history teacher. “He said it was one of the best books he’s ever read,” says Dain.

Dain shoved a magnifying glass into nearly 400 years’ worth of Boston nooks and crannies, but the author’s most pressing pursuit was to identify the practices and policies that coincide with success.

“My conclusion is that cities depend on innovation; cities that stop innovating become stagnant,” he says. “’Innovate’ is broad. There’s economic or business innovation. There’s cultural innovation, political innovation. The question then became, what are those policies and practices that provide the framework to innovate?” The answer, he says, are the “Three Ds:” Density, diversity and good urban design.

“Urban design is the architecture or social infrastructure that creates the spaces where lots of people come together; when they come together, as residents or businesses, that’s the density. And you need people from different backgrounds and experiences, whether it’s racial diversity or socioeconomic diversity, families or single people, young or old,” he says. “If you bring the Three Ds together, social science research indicates that decision-making and economic outputs are improved, and innovation is encouraged. That’s the grand plan.”

Dain had no grand plan for the law. A Newton kid who grew up in the Boston suburbs, he was a poli-sci major who gravitated to law school due to logic, not love. “It seemed like the natural next step,” Dain says. The University of Michigan Law School saw the logic turn to something akin to ‘like,’ but he still didn’t feel enamored with the work.

“I started my career at an amazing firm where I still have many close friends, Goodwin Proctor, as a commercial litigator doing business disputes,” he says. “I wanted to win, but I didn’t feel strongly about whether one company beat another company and money moved around.”

It was at Goodwin Proctor in the late ’90s that Dain met former U.S. Attorney Andrew Lelling, who’s now back in private practice with Jones Day. “We were associates staffed on this brutally awful case,” Lelling says. “We hit it off. He was low key, super smart, and had a good sense of humor—three things required to work on awful cases like this one. He was a better civil litigator than me. I learned a lot from Dan about the nuts and bolts of being a civil litigator.”

Lelling says Dain’s special sauce is his outlook. “He is the ultimate pragmatist. He doesn’t have to win at trial, he doesn’t have to do anything. He just wants the practical result, which is on balance with the best his client can do in a given situation, which I think is a reflection of his personality. He’s a solution-based guy who doesn’t get too worked up about things.”

Which doesn’t mean he isn’t passionate. “Dan actually does stuff,” Lelling says. “I’m lying in bed, binge-watching Breaking Bad, and here’s Dan calling me up like, ‘Hey, you want to go see the Rolling Stones?’ We just did that together recently. Or he gets home at 6 or 7 every night and spends hours writing a book when the rest of us are drinking a beer. When I think about that, how huge a project the book was and how many nights and weekends that book took because he has a demanding day … it’s outrageous.”

In the mid ’90s, Dain’s career started coming into focus. “I started getting cases involving land use, and to me, that was the most interesting thing I’d done yet, because the subject of the dispute was tangible, something I could visit, that I could tell my family about, something that affected how we live. It was my community, and I believe that we should encourage development.”

He soon devoted his career entirely to land use, and in 2006 co-founded Dain Torpy.

Joseph Feaster Jr. met Dain on a panel on how to increase minority hiring. The duo then began to partner on other presentations to affinity law groups. As the partnership grew stronger, Feaster recalls Dain saying, “One of the ways in which I could increase diversity is to convince you to come to the firm.”

“So I did, with another Black lawyer, Timothy Fraser, a 20-year practitioner,” remembers Feaster, now of counsel at the firm. “Dan has remained committed to diversity hiring, and we’ve brought in women and people of color across the board. This has been a marriage made in heaven.”

What sets Dain apart, Feaster says, is his support of all the out-of-firm activities his lawyers engage in.

“Being supportive of people is in Dan’s DNA,” says Feaster. “I’m very active because of my longtime involvement politically, my organizational involvements, particularly in the areas of mental health. I do a lot of speaking, and Dan has attended many of those engagements. I recently received a Lifetime Achievement Award from the Massachusetts Black Lawyers Association, and Dan was there because Dan always is. He provides extraordinary leadership and is a true Renaissance man, which I describe as a cultured man of the world, who is knowledgeable, educated, and proficient in a wide range of fields. And his book, particularly about people who were oppressed, from Native Americans to the Middle Passage—it’s an honest assessment of the history of Boston. It’s a vehicle for ongoing conversation.”

Dain has closely watched shifts in public policy over the course of his career. In the 20th century, policies aligned to encourage low-density suburban living over high-density city living.

“Consider things that we don’t really think about, like the home mortgage interest deduction, which is a subsidy for home ownership, and therefore mostly suburban. We don’t subsidize rentals in cities,” he says. “Our tax code encourages people to move out of cities and live in low-dense areas instead of high-dense areas.” The way education is financed, too, via property taxes, encourages people to live in low-density suburbs, he notes. And then there are the more obvious policies, like the National Interstate and Highway Act.

“The amount of money that we invest in essentially financing an auto-centric way of living and don’t put a similar investment into public transportation is yet another deterrent,” he says. “We expect that public transportation will pay for itself, but we don’t expect that drivers are going to pay to maintain the highways, other than some very modest tolling.”

Yet many who do live in cities view his developer clients as public enemy No. 1.

“There remains tremendous hostility to density. I think most would say, ‘Sure, we should build more housing, but my neighborhood is dense enough.’ We go into these communities and they say, ‘We really want the housing your client is proposing, but can you make it less dense?’

“We’re in a housing crisis, which has a major impact on the economy and the environment. We’ll say, ‘Look, if there’s some specific harm that’s going to be caused by building here, let’s talk.’ But if there’s just this abstract of ‘it feels too big,’ that should not be overriding the desperate need for housing, particularly housing with access to public transportation or walkable jobs.”

Dain says pushback comes in the guise of theoretically good ideas. Let’s say people are opposed to his client taking down trees.

“But if you don’t take down a small number of trees to build a hundred units very densely in an urban area, those people are going to live somewhere,” he says. “So we can put them in an urban area that’s close to public transportation and jobs and lose a small number of trees, or we can put them in single-family homes in the suburbs in which every one- or two-acre lot will require taking down a large number of trees. … Those people are going to get in cars not just for work, but for shopping or to take their kids to soccer. Dense development gets opposed on environmental grounds, but it’s misguided: The densest neighborhoods are the greenest places per capita and have the lowest per capita carbon consumption.”

Dain is primed to tackle other contemporary land use problems, like the challenge of pursuing the post-COVID “Holy Grail” of converting empty office units into residential spaces. “The city would love to encourage it, but there are problems,” he says. “One is, even if a building is 30 percent empty, which is a high vacancy rate, you still have 70 percent of it filled, and you can’t convert to residential unless you go down to zero.” To add to the challenge, such leases are staggered, so one would have to contend with an increasingly declining occupancy rate and then invest a lot of capital converting to residential, which isn’t easy. “Residential office buildings have a much wider foot plate than do residential buildings, and the plumbing tends to be in the core,” he says. “So you have large bathrooms in the core of a building, but people like smaller bathrooms throughout their units, so they don’t lay out very well for residential.”

In his free time, Dain contributes to the Three Ds via the Restaurant Investment Group, which he co-founded. The group’s mission is to offer novel investment strategies to get the next hot Boston restaurant up and running in dense urban areas. If you eat at MIDA or Mooncusser, you can thank Dain in part for their existence.

From his office windows, Dain can’t quite see the Radian building, a curved, 26-story glass tower that overlooks the Rose Kennedy Greenway, but it’s a residential building he worked hard on, and is proud of. What he can see, however, is Dewey Square and South Station, and other new projects being built.

“I just love looking out and seeing people walking,” he says. “I love to see cranes over the city and activity going on that brings people into Boston. I have a view out toward Logan Airport, so I can see airplanes coming in. It all reminds me of what we’re doing here, and makes me feel grateful to see that work alive.”