The Bridge Builder

Developer Tom O’Brien is changing the face of Boston with a rare compassion and a community-minded approach

Tim OBrian

Tom O’Brien, developer and founder of HYM Investment Group, overlooks Suffolk Downs, where his firm is redeveloping  161 acres of East Boston and Revere into a commercial and residential complex.

Story by Alyssa Giacobbe
Photographs by Faith Ninivaggi

There are few things developer Tom O’Brien loves more than a community meeting, even the ones where people disagree with him, which are most of them.

O’Brien, JD ’93, attended almost 450 meetings, ranging from one-on-one discussions in people’s kitchens to large public presentations, in laying the groundwork for the redevelopment of Suffolk Downs. The former horse-racing site where East Boston meets Revere is, under O’Brien’s lead, one of the largest redevelopment projects in Boston’s history.

“They stand up to ask a question. They’re angry, they’re frustrated, sometimes they have bad information, or they haven’t really thought it through,” he says. Those are the people he wants to talk with most of all.

O’Brien, has been a meetings enthusiast ever since he served as director of the Boston Redevelopment Authority (BRA)—the city’s urban planning division since renamed the Boston Planning & Development Agency—where once or twice a week he’d meet with residents in neighborhoods throughout Boston and stay for as long as it took to answer every question. “I can’t say it’s always fun, because there are tense moments,” he says. “But getting to know people, listening to them, it’s what I enjoy most about my career, I suppose.”

O’Brien is one of Boston’s most prominent developers, with a portfolio that includes a hand in building, essentially from scratch, some of the city’s most thriving neighborhoods, including parts of East Cambridge, Brighton, and the South Boston waterfront. His development firm is elevating Boston’s skyline with a major redevelopment of the Government Center Garage. And the upcoming redevelopment of Suffolk Downs is set to transform 161 acres of East Boston and Revere into a commercial and residential complex that will include 5.2 million square feet of new office space and hotels, two new retail squares, 10,000 apartments, including a significant amount of affordable housing, and 40 acres of new parkland. O’Brien’s team anticipates the project will contribute to the creation of some 14,000 new jobs. As of early September, the project was moving toward a Boston Planning & Development Agency board vote at a planned Sept. 24 special hearing.

It is ambitious, complex, transformative and represents everything O’Brien loves about being a real estate developer.

“I would say if it’s big and complicated and other people are shying away from it, then it’s probably right for us,” he says of his HYM Investment Group’s ideal endeavor, and Suffolk Downs certainly qualifies.

Post Pandemic

Beyond the fact that COVID-19 has made Tom O’Brien’s job logistically much more difficult—his construction sites are required to follow safety protocols that limit the number of workers at one time and include mandatory daily temperature testing—the pandemic also has raised larger questions about the future viability of cities. The virus has disrupted city and work life and left many wondering to what degree those disruptions might become permanent. Those are big questions for a developer of some of the biggest office and residential sites in Boston.

O’Brien isn’t worried. It’s something he’s thought about every day for years—he’s spent his career making cities more livable for all sorts of people under all sorts of conditions, and he doesn’t buy that cities are doomed. O’Brien has just started selling luxury condominiums in the newly constructed Sudbury residential tower in Bulfinch Crossing. He expects the number of international buyers may drop but says there are still plenty of people who want to live in a downtown Boston building with a pool deck, sky lounge, fitness center, pet spa, and a 48th-floor private rooftop garden. “Generally, we feel like the market has stabilized and people are still out there looking to try to buy new homes,” O’Brien says.

He says the One Congress office tower project that will anchor the Bulfinch project is in an early enough phase to make changes, such as elevators being controlled by a phone app “so you don’t have to touch anything.”

“For pretty much all of humankind, people have wanted to work together,” O’Brien says. “Just before COVID-19, what was really driving the real estate business is the concept of people working collaboratively. I think the idea that we would give all that up doesn’t seem like a natural progression in terms of human history. So I have faith: We’ll get back on that path.” —Greg Gatlin

Day Hero

Top: The soaring, 600-foot-tall One Congress glass office tower, designed by Pelli Clarke Pelli  Architects, will enliven Boston’s skyline. Bottom: Suffolk Downs will transform 161 acres of East Boston and Revere into a commercial and residential destination, with office space, hotels, two new retail squares, 10,000 apartments, affordable housing, and 40 acres of new parkland. Renderings courtesy of: The HYM Investment Group, LLC

Suffolk Downs


Among urban developers, O’Brien is the anti-bulldozer. He’s a bridge builder in a field known for being competitive and cutthroat, where victories are often earned by some measure of force. He has earned a reputation for his compassion and community-mindedness and has managed to succeed without straying from the strong moral sense instilled in him by his parents and reinforced by his role as husband and father.

“Tom is a family-first person,” says Doug Manz, HYM’s director of development. “That’s funny to say when you’re talking about a business perspective, but, fundamentally, family informs everything he does.”

Boston’s Government Center Garage was built in the 1960s and is the largest parking structure in the city. It is also, in O’Brien’s view, the most unsightly—an alienating, Brutalist-style concrete divider between the city’s North and West ends and Downtown Crossing that casts a figurative and literal shadow on Boston. “The garage was a terrible idea when it was built,” says O’Brien. “And it’s been a burden to the downtown ever since.”

Tom’s focus has always been on building the community around any given project.”

—Doug Manz, HYM’s director of Development

For decades, ever since he served as director of the BRA, and perhaps even before that, O’Brien has dreamed of making better use of the space. As he walks through the build site on the corner of Congress and Sudbury streets, he reminisces about taking the Orange Line to the Haymarket MBTA station as a kid to watch hockey games at the old Boston Garden. “As far back as I can remember, nobody thought about wanting to live here, go out to eat here, that sort of thing,” he says. “It was come for work or a game and get out.” Some 10 years ago, O’Brien got his chance when his firm won the bid to redevelop the garage as part of the creation of Bulfinch Crossing, a mixed-use development that will, in O’Brien’s words, bring daylight to that part of the city for the first time in half a century.

Like Suffolk Downs, it is a long, slow haul with many moving parts and many problems to be solved. O’Brien organized and attended more than 50 meetings with community leaders and neighborhood groups for Bulfinch Crossing’s pre-build process, leading to the winning bid 10 years ago. When completed in 2022, the development will include six new high- and mid-rise buildings, with more than 1 million square feet of office space, some 800 residential units, a retail corridor, and a public square. A planned 50-story glass office tower designed by Pelli Clarke Pelli Architects is slated to rise about 600 feet with a stunningly graceful facade that, together with the already built Sudbury residence tower, will enhance the city skyline.

O’Brien grew up in Scituate, Massachusetts, the middle son of Anne and John O’Brien, MBA ’81, who raised their children to value education, family, and faith. There were two basic house rules growing up, says O’Brien: To love God, and to do that by loving other people. “The basic idea, and it really is very basic, was to try to listen and to be kind and to do what you can to positively affect people’s lives,” he says.

O’Brien and his brothers spent many weekend afternoons knocking on doors with their father, a local political devotee who would canvass for one candidate or another. “My parents were really inspired by people in the church who were active in trying to create social change,” says O’Brien. “There was the sense that government, and politics, can make a difference in people’s lives.”

After graduating from Brown University, where he played football (along with his younger brother, Bill, who is now head coach of the NFL’s Houston Texans), O’Brien went to work for AIG in New York City. Finance, he quickly realized, was not the right path. He returned home to work for the Michael Dukakis presidential campaign, which set him in a different direction, eventually landing him at the Massachusetts Industrial Finance Agency (MIFA), where he worked with manufacturers seeking to expand their facilities and learned the ins and outs of government financing.

He felt at home working in government and politics—he liked people, and they liked him, and he had a patience for navigating systems. Figuring a law degree would help support a career either on the front lines or behind the scenes, he attended Suffolk Law at night while working at MIFA during the day.

”Going to law school at night is definitely a badge of honor,” says O’Brien, who fondly recalls the impact of camaraderie with his law school peers and the relationships he built with professors such as the late Honorable John E. Fenton, Jr. and the late Victoria Dodd.

The grueling schedule and challenging coursework gave O’Brien a new sense of professionalism. “It really helped me become a different person,” he says. “It honed my skills to be able to write well, it made me a person who could formulate and make an argument.”

O’Brien wasted no time applying those skills when in 1992, his third year in law school, he served as the campaign manager to his older brother who was seeking a seat in the Massachusetts State Senate; John D. O’Brien, Jr., JD ’85, won that year and served a total of four terms representing Merrimack Valley.

O’Brien credits his law degree with significant career milestones. After passing the Massachusetts bar in 1993, MIFA named him general counsel, which O’Brien believes put him on the radar of Tom Menino, then the city’s new mayor, who was looking for a chief of staff at the BRA.

O’Brien was only 29 years old but quickly rose through the ranks to become the agency’s director in less than a year. He was a star from the start, which worked both in his favor and against; he quickly understood that the key to success in politics is knowing how to toe the line, a job he, a consummate middle child, did well. He learned how to be good but not too good; to shine without outshining; to build bridges.

“At the BRA we had the planning side and the economic development side,” remembers Kanna Kunchala, a senior vice president at City Year, who served as O’Brien’s assistant at the BRA. “Sometimes, the sides didn’t agree, but Tom was really good at helping them find common ground. And getting people to compromise. He just figured out a way to get everybody to agree.”

He particularly excelled at sharing credit, often an uncommon trait in government.

Kunchala remembers when O’Brien landed on the cover of the Boston Globe magazine as part of a story about his work with the BRA and its impact on the city—the headline: Where is Tom O’Brien Taking Boston? “I thought he wasn’t going to come to work for a week, like, he just hated it,” Kunchala laughs. Not much has changed since: Kunchala recalls his former boss’ discomfort at a more recent United Way ceremony honoring O’Brien’s professional and philanthropic contributions toward racial and income equality, including his work as cofounder of the Massachusetts Business Immigration Coalition. “Everyone was talking about how great he is, and I said to him, ‘You just want to crawl under the table right now, don’t you?’”

O’Brien spent seven years at the BRA. He is perhaps best known for having overseen the development of the Seaport, though he is personally proudest of bringing grocery stores to neighborhoods that had long gone without. He would hold weekly community meetings across Boston to find out what people wanted. As Kunchala recalls, O’Brien was patient.

“He was able to win people over by sheer perseverance. He just stood there and just took every question,” he says. “It just meant a lot to everybody in the neighborhood, because they were like, ‘Whatever happens, this guy definitely cares.’”

A Suffolk Family Affair

Tom O’Brien and his wife, Patricia, MBA ’87, met on a blind date that got off to a rough start.

O’Brien, in his penultimate year as a Suffolk Law evening student at the time, was literally running late because he had to turn in a course paper. He made a full sprint for the Donahue building on Temple Street, where the Law School was located at the time, dropped off the paper, then ran to a Faneuil Hall bar to meet his date, about 10 minutes late. “She was not happy with me for being late to a first date,” he recalls. Things seem to have worked out. Within a year and a half, as O’Brien was getting ready to graduate in 1993, they were married. Theirs is a family filled with Suffolk connections.

Patricia earned a Suffolk MBA, prior to meeting Tom in 1991, and went on to have a successful career as an executive at Verizon. His brother, John D. O’Brien, Jr., preceded him at Suffolk Law, earning his juris doctorate in 1985, before going on to serve four terms in the Massachusetts State Senate. O’Brien’s father, John, completed Suffolk’s Executive MBA program, graduating in 1981.

Their shared Suffolk experience has become a point of pride for the O’Brien family.

“Suffolk for us has really been a wonderful place in which you can pursue an advanced degree while continuing to work or continuing to find your way in the world,” says O’Brien, now one of Boston’s leading real estate developers. “Suffolk is a school that’s both located in the heart of Boston, but also, in many respects, it is the heart of Boston. When you look around through the ranks of business and the ranks of government, the most senior positions, and the most respected positions in the Commonwealth of Massachusetts … they are often held by Suffolk graduates.”

Tim OBrian

O’Brien describes his wife, Patricia, MBA ’87, as his mentor—the most professionally influential person in his life. “She’s always been the person pushing me to live up to the ideals that we talk about,” he says.

“She’ll say, ‘if you care about creating more affordable housing, what are you doing about it? if you care about being an anti-racist, what are you doing about it?’”

O’Brien was working at the BRA when he and Patricia began to start a family, adopting their first child, Lucas, from Colombia. Their second, Nina, was born the following year in Guatemala, and after that Tomas, from Ecuador. “Lucas was an amazing gift to us, and we realized that no matter how this child came to earth, he was meant for us and we were meant for him,” says O’Brien. “And we recognized there are a lot of families who are built in ways that are perhaps not as predictable. So we went through the process quickly.”

Around that time, rumors began to swirl that Menino felt threatened by O’Brien, who was talented, driven, and perhaps worst of all, universally well liked, and in 1999 O’Brien was ousted from the BRA.

It proved to be less a setback than an opportunity. O’Brien went to work for Tishman Speyer, a New York-based real estate investment firm, where over six years he learned how to finance real estate and raise capital. Then he worked two years at JPI Companies, a national developer, where he met Manz and Paul Crisalli. Eventually, the three began to discuss forming their own company to create transformational, transit-oriented urban projects.

“Tom’s focus has always been on building the community around any give n project,” says Manz. “He wants the company to be more than just a business.”

In 2010 they launched HYM, an acronym inspired by O’Brien’s fourth child, Marisol, who had come to O’Brien and Patricia from Guatemala in 2000 and died in 2008 following a long illness with a rare genetic disease called leukodystrophy.

“When Marisol was younger, before she lost her voice, she would put her arms up and say, ‘Hold you me,’” says O’Brien. “Her words would get mixed up. The best part about the name is being in big presentations and seeing it up on a slideshow, and I smile and think of her. As we’ve grown, people think HYM is some big national real estate conglomerate or something when, you know, it just stands for ‘hold you me.’

O’Brien and Patricia had always been active in their parish, but when Marisol became sick they began to wonder what, exactly, the purpose of her life had been. They joined a group for grieving parents at St. Anthony Shrine in Boston and began to call on prayer to help cope with the loss.

“The tragedy of losing a child brings you to a variety of different places, but we believe that Marisol’s purpose in our life was for us to become closer as a family, hopefully become closer to our faith, and to be kinder and better listeners to people,” he says. “We feel her presence frequently. Typically, when I’m going into a big meeting or something important, I’ll whisper her name and say, ‘Daddy needs your help a little bit.’ It just brings me a sense of peace.”

The role O’Brien’s children play in his work can’t be underplayed; their fifth child, Dureti, came to them from Ethiopia. O’Brien has received numerous awards recognizing his efforts at improving relations among racial, religious, and ethnic groups, including the Abraham Joshua Heschel Interfaith Relations Award by the Anti-Defamation League, and he frequently testifies on behalf of the Massachusetts Immigrant and Refugee Advocacy Coalition (MIRA).

“I’ve run out of words to thank Tom for the work he’s done,” says Eva Millona, MIRA’s CEO. “The fact that he adopted five children and made a home and provided for people who came from a most vulnerable place—that decision alone I think speaks volumes to who Tom is.”

He serves on the boards of organizations committed to the development of underprivileged youth, like the Ron Burton Training Village and the East Boston Social Centers, and has been a strong proponent of workplace diversity since HYM’s start. The company is comprised of 50% women and 30% minority team members, which in the real estate development world is unusual. “I think he’s really trying to do work to lift up the whole city as much as he can,” says Justin Pasquariello, East Boston Social Centers’ executive director.

Someone in O’Brien’s position and with his abilities could easily be caught up in his ego, points out Father Tom Conway, the executive director of St. Anthony Shrine. “But he’s just always looking out for other people,” he says.

O’Brien collaborated with Conway to propose an open-air plaza at Winthrop Square, with a new St. Anthony Shrine church, a new friary and ministry center, and a new downtown Boston school in addition to the requisite high-rise residential and office tower. Another developer ultimately won the bid, but Conway was struck by O’Brien’s care for the community in developing his bid.

“He uses his connections for the benefit of other people—and obviously for the benefit of his own business, too—but, you know, other people aren’t left behind,” says Conway. “I’m seen as a religious leader in Boston, and I’m taken aback by how good he is.

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