What Really Happened to Tom O’Brien’s Mayoral Run?

On a Monday morning this past March, Tom O’Brien was in his office at HYM Investment Group checking his emails when his phone rang. It was his public relations representative, Susan Elsbree, calling with unwelcome news—the secret O’Brien had been guarding for months was about to become very public. Columnist Shirley Leung from the Boston Globe had just called, Elsbree told him, and whether O’Brien wanted to comment or not, she was writing a story about his considering a run for mayor.

O’Brien’s mind raced. Someone must have talked. He flashed back two days to Saturday—his daughter at her favorite Dorchester hair salon, getting ready for college tours. While she prepped inside for the next phase of her life, he sat in his car outside on Bowdoin Street returning calls, including one to a friend from Boston’s nonprofit sector. On the call, O’Brien told his enthusiastic supporter, whom he declined to name, that he was exploring his next phase: running for the city’s top job.

Over the course of the previous two months, O’Brien—one of Boston’s most influential real estate developers, a fixture of civic life, the consummate father of five children adopted from Latin America and Africa—had talked to many people around town about challenging Boston Mayor Michelle Wu and candidate Josh Kraft in the mayor’s race. Remarkably, it hadn’t yet leaked to the press. Now, though, that was all about to change.

From his Beacon Hill office, O’Brien watched as the story went online, later describing it as a “pretty positive” article. Then his phone started buzzing. In the hours that followed, supporters called to express enthusiasm, and colleagues reached out with questions. Then it was time for O’Brien himself to make a call. That evening, he says, he dialed Wu and told her he was, in fact, considering a run, and apologized that she didn’t hear it from him first. They had what he describes as a cordial conversation. Meanwhile, the very idea that O’Brien was considering running for mayor set people in the business and civic worlds of Boston into an outright tizzy.

It is no secret that real estate developers in Boston have been at odds with Wu pretty much since she took office. The mayor has imposed new regulations on the development sector while simultaneously overseeing one of the most economically challenging periods in our city’s history for the business of putting up buildings. Which made O’Brien’s position all the more surprising: He was one of the few developers to support some of her most controversial proposals aimed at the developer community. “Most of us were like, “WTF, why would he be doing that?” said one Boston real estate developer. “Because he has a full, ongoing business and because of the fact that he had been an ally of Mayor Wu.”

Two-and-a-half weeks later, O’Brien and Patricia (Tricia)—his wife of more than three decades and the biggest supporter of his political ambitions—were leaving church when his phone buzzed. Another Globe story. This one revealed that his announcement was imminent and that he would be making it in East Boston. Three days after that, he released a statement—but it wasn’t the one political observers expected. “After many conversations with people I know, trust, and admire, I’ve decided not to pursue a political candidacy at this time,” it read. “Instead, I will continue my work with the HYM Investment Group and my engagement in Boston’s charitable and civic life.”

Theories multiplied like rumors in a high school hallway: Kraft got to him. Wu got to him. Threats were made. Promises were extended. Deals were cut.

The turn of events left acquaintances, businesspeople, and politicos slack-jawed. If the news that O’Brien was running had been the source of much talk among the chattering class, the news that he wasn’t became catnip. Theories multiplied like rumors in a high school hallway: Kraft got to him. Wu got to him. Threats were made. Promises were extended. Deals were cut. One theory suggested O’Brien’s almost-run was part of a deep-city conspiracy between him and Wu to rally support for her.

Regardless, O’Brien went quietly back to the business of trying to get buildings into the ground, saying nary a word about the whole affair. But in a city that loves its political intrigue, the mystery persisted. “It’s our own ‘Who Shot J.R.,’” says one local political consultant. “Only we found out the answer to that—I doubt we will ever know in this instance.”

Over the course of several months of reporting, though, a clearer picture emerged of who O’Brien is, what he really wants—and why he walked away before the race had even begun.

At Suffolk Downs, developer Tom O’Brien has staked out one of Boston’s biggest developments ever: 10,000 units of housing plus hotels, retail, and green space. / Photo by Tony Luong

The only surprise about O’Brien’s near-run for mayor was that he didn’t do it sooner. He and his two brothers were raised on a cocktail of faith, family, and politics that swirled together into the unswerving belief that life was to be lived for and in service of others. (Football was arguably the cherry in that drink—O’Brien played at Brown University, and his younger brother Bill is Boston College’s head football coach.) “I think it has long been part of his DNA to want to serve in an elected role,” says a Boston real estate attorney who has known O’Brien for 30 years and is not free to comment publicly due to the nature of his work. “He has been mulling since age 10 whether to run for public office.”

O’Brien’s father served as a local selectman in Scituate and read three newspapers a day. When O’Brien was a tween, he was a Globe delivery boy who devoured the headlines each morning on his route. “I became a newspaper addict,” he says. “In our house growing up, we talked about politics all the time.”

The result of that civic-minded upbringing? O’Brien seems engineered for politics. His regal good looks and the slight wave in the sweep of his hair evoke an air of JFK-if-he-had-lived-to-62. And then there is the deliberate cadence of his speech. “Just listen to him—he sounds like a politician waiting to happen,” another Boston real estate developer told me. Meanwhile, he found in his wife, Tricia, a woman as passionate about politics as he is and someone who, from day one, has encouraged him to run for office.

O’Brien’s first foray into politics came after graduating from Brown (where his parents and brothers also attended) with a history degree. In what his older brother John describes as a pivotal moment, O’Brien quit his first post-college job at an insurance company in New York to join then-Governor Michael Dukakis’s presidential campaign. After Dukakis lost, O’Brien enrolled in night school at Suffolk Law and was soon back in politics, managing his brother John’s successful 1992 state Senate campaign as a side project. The following year, O’Brien entered government himself as the chief of staff to the director of the Boston Redevelopment Authority (BRA). It was the first year of Tom Menino’s transformative mayoral tenure—an era when City Hall convinced developers and investors to bet on what had been a backwater town and turn it into a booming metropolis.

It was an exciting job for which O’Brien was grateful, but the lure of elected office remained as he embarked on his new career. Soon after taking the job, he and Tricia talked seriously about moving down the Cape, where his parents lived, so he could run for a state Senate seat in Barnstable. He opted to stay at the BRA, and in 1997, he was named to the agency’s top post, making him arguably the second-most-powerful man in city government at age 34.

During his tenure at the BRA, O’Brien established himself as someone who excelled at—and enjoyed—meeting with community members affected by development projects. “We would go to these community meetings and there’d be people upset—‘I want this, I don’t want that’—and Tom always calmly and patiently answered every question. I was a 25-year-old kid, and I wanted to be done and go out in Boston, and he always said, ‘I am going to be the last one to leave,’” says Kanna Kunchala, who served as O’Brien’s special assistant.

O’Brien also proved he could strategically navigate Boston’s complex power structure to get deals done. The one he may be best known for is laying the groundwork for the Boston Convention and Exhibition Center in the Seaport, which drove development throughout the neighborhood—part of a master plan to transform the neighborhood that O’Brien oversaw during his tenure.

O’Brien’s work earned him significant press coverage and even landed him on the cover of the Sunday Globe Magazine. When the issue arrived on his doorstep that Sunday morning, his wife read the article and told him she thought it was wonderful, he recalls. His response was that he considered it a disaster. “There is one person reading it right now in Hyde Park who is not going to be happy that I’m on the cover,” he told her.

The attention—and perhaps his own ambition—came with consequences. “There was a sense of, ‘What’s Tom O’Brien going to be, what’s he going to do?’ Some of that I let fester a little in a way that I should not have,” O’Brien admits. There was even talk that O’Brien might challenge Menino in 2001, something he says he never would have done to the man who gave him a life-changing professional opportunity.

If Menino was looking for an excuse to get rid of him—as journalists at the time suggested—he found one when news broke in the fall of 1999 that O’Brien had signed off on his chief of staff’s purchase of a subsidized Charlestown condo intended for people earning far less. O’Brien was forced to resign. As Globe columnist Joan Vennochi wrote at the time, O’Brien’s exit was a political execution for the crime of not staying on Menino’s good side. She described him as “smart but a little too cocky, aggressive but a little too arrogant, focused but a little too ambitious.”

O’Brien spent the next decade working for two national real estate development firms, Tishman Speyer and JPI. For someone driven by faith and public service, Kunchala says, the move to the private sector was surprising. Still, it provided a less stressful environment and the opportunity to support his growing family. By the time he left the BRA, he and Tricia had adopted three children: Lucas from Colombia in 1995, Nina from Guatemala in 1997, and Tomás from Ecuador in 1999. He later adopted Marisol from Guatemala in 2000, traveling alone to Guatemala City to bring her home. (Later, in 2013, O’Brien and Tricia would adopt their fifth child, Dureti, from Ethiopia.)

Then tragedy struck. At age three, Marisol was diagnosed with a rare, genetic neurodegenerative disease that progressively robbed her of her speech, her mobility, and eventually her life. She passed away at age eight in December 2008. In the dark months that followed, O’Brien found himself firing some 70 people from JPI and then losing his own job as the financial crisis rocked the country.

It was during that difficult period that he decided to start something of his very own, founding the HYM Investment Group along with two people he’d worked with at JPI. Not many know the origins of the company’s name: It stands for “Hold You Me”—what Marisol would say when she wanted to be held, her disease scrambling her words.

As the BRA director under Mayor Tom Menino, O’Brien was part of the planning of the Seaport, November 25, 1997. / Photo by John Blanding / The Boston Globe via Getty Images

The first time I met O’Brien, he didn’t start off talking business or about his billions in development projects—he led with his faith, family, and the five adopted children at the intersection of both. We were in his corner office at HYM Investment Group, and when I turned around on his couch to look at the photo wall behind me, he pointed out each of his kids with tender affection and pride.

Moments later, he opened the shades on the window opposite me that had been drawn against the 90-degree heat, and I realized his bird’s-eye view of downtown Boston doubled as a different kind of brag wall. Through the window: two gleaming HYM towers built where the Government Center Garage—that light-blocking eyesore—once straddled Congress Street. Two more buildings are still slated to go up on the site, known as Bulfinch Crossing, but already, HYM’s work has transformed that corner of the city. Off to the left and inland, I could also see Cambridge Crossing, a 45-acre former rail yard for which HYM laid the groundwork to convert it into a new neighborhood; it also constructed its first building.

Far off to the right, beyond the runway at Logan and just to the left of the 35-foot-tall Virgin Mary monument atop Orient Heights in East Boston, sits an open patch of land that was once the Suffolk Downs thoroughbred racetrack on the Revere-Boston line. There, O’Brien has staked out one of the largest development projects in Boston’s history—a planned 10,000 units of housing, plus hotels as well as office, retail, and green space. “What I love doing is projects that try to improve the city somehow,” he said. “I know it sounds kind of hokey.”

In a field where success is typically measured by profit margins, O’Brien frames development as civic work that happens to make a profit. When we later toured P3—a long-vacant Roxbury parcel that HYM plans to develop—he sounded like a politician trapped in a developer’s body. O’Brien told me he was drawn to the site because he sees its development as a chance to address some of Boston’s troubled racial history: the eminent domain seizures—including the land P3 is being built on—redlining, and blockbusting that stripped the Black community of generational wealth through homeownership.

It’s one thing to talk about addressing racial history—it’s another to put money behind it. Reverend Jeffrey Brown of Twelfth Baptist Church says O’Brien shocked him with an unexpected proposal: HYM and Brown’s company, My City at Peace, would partner 50-50 on the project. O’Brien has also brought in several local Roxbury business owners and community leaders, with plans to house the organization Embrace Boston. The strategy? Attract academic labs from Longwood institutions, just a mile away. Those labs would provide community jobs while subsidizing 144 affordable units for homeownership to help close the racial wealth gap. “Working on these civic issues, that’s what I love,” O’Brien tells me as we stand in the middle of P3 with Brown. “It’s not really about how much money you make. It’s more about the impact you can make in the community. It’s faith-driven and family-driven.”

Meanwhile, at Suffolk Downs, state Senator Lydia Edwards says, O’Brien showed a clear commitment to fighting housing discrimination. After Edwards—who represented East Boston on the Boston City Council at the time—got stricter fair housing standards passed in 2021, O’Brien voluntarily applied the new rules to his project even though Suffolk Downs had already been approved under the old standards. “That doesn’t happen,” Edwards says of a developer retroactively adopting stricter standards that would expose them to more scrutiny.

That sensitivity shapes how O’Brien runs his company. Women and people of color make up more than half of HYM’s workforce, reflecting O’Brien’s commitment to diversity long before DEI became trendy—and after it became politically fraught. “To make the decision to adopt five children of color, that to me speaks volumes of his character and his commitment to the power of inclusion,” says public relations maven Colette Phillips, who also notes that he is extremely—if quietly—philanthropic.

Edwards points to one other way O’Brien stands apart from typical developers. While many in his industry have been highly critical of Wu’s housing policies, O’Brien publicly supported her proposed commercial real estate tax increase designed to avoid raising residential taxes. He also backed a plan for a transfer fee on large real estate transactions that would fund affordable housing. One development industry insider said some developers couldn’t understand why he would support policies that hurt the sector. “They didn’t like that,” O’Brien says, adding that within the developer world, “I think they see me as less corporate.”

More recently, though, the dynamic has shifted. His previous support of Wu policies nearly morphed into a direct political challenge. And as difficult economic conditions for development stretched into a third year, O’Brien’s projects have suffered—and his reputation as a fair-minded developer who gets things done is showing cracks.

Tom O’Brien was planning chief under former Mayor Thomas Menino and is now an influential developer in Boston. This spring, he almost ran for mayor. / Photo by Tony Luong

While ambitious, O’Brien’s multibillion-dollar vision for Boston’s future has in many ways become a case study in development quagmire. The day we visited Suffolk Downs, he could show me only 475 units where 10,000 should eventually rise—after five years and three quarters of a billion dollars invested in the acquisition, infrastructure, work, and lone completed building on the massive site, Amaya. After touring it, O’Brien led me to where the next building, Portico, should have broken ground more than a year ago. Instead, vegetation tussled in the wind behind a chain-link fence. “It’s killing me,” O’Brien said, exasperated. The delays on Portico, he explained, were pushing back the timeline for everything on the site.What has happened at Suffolk Downs is representative of the broader story unfolding across Boston’s real estate sector, which is weathering a perfect storm. Inflation has driven up the cost of building materials and the cost of cash itself. With interest rates rising, large pension funds that invest in development projects nationwide now demand a 6.5 percent return on their money—up from 5.5 percent when Suffolk Downs was planned, O’Brien explains. Tariffs on materials aren’t helping either.

Suffolk Downs’ development was approved under Marty Walsh’s administration, which required 13 percent affordable housing in new projects. But all projects approved under Wu must include 17 percent affordable units, and she has also introduced costly green-energy standards. Cranes have all but disappeared from the city skyline over the past two years, and fewer units of housing have been built than in any year since 2011.

O’Brien tells me that under current economic conditions, Portico no longer pencils out using the traditional funding methods—meaning it won’t hit the magic number of 6.5 percent return on capital needed to secure construction financing. Meanwhile, he says, pension funds are flocking to cities like Seattle, Chicago, and Nashville, where development costs are lower and government incentives are higher. Some Boston developers are following that capital, developing projects in other states. When I asked O’Brien if he would do the same, he practically shuddered. “This is my home,” he said.

O’Brien is hardly the only one who is frustrated with the delays at Suffolk Downs. “People are wondering what the hell is going on,” Edwards told me. “It’s a 20-year project, and we are five years in, and we have one building…I regret not saying, ‘You can’t have this project approval in perpetuity; if you don’t do anything here, the zoning goes back to zero, and you have to start all over again or sell the thing.’ I’m currently trying to get the city to purchase the project, to make them an offer they can’t refuse.”

The building trades are frustrated for different reasons. After Amaya was completed last fall, a labor leader said, O’Brien tried to renegotiate the project labor agreement requiring union workers on the Suffolk Downs project—breaking with the company’s longtime practice—something, the leader said, that was presumably a result of mounting investor pressure over delays. Negotiations ultimately saved the original deal, the leader said, but only after the unions had to “grovel and beg to get back to the table” and agree to more concessions.

Still, the damage was done to the building trades’ decades-long relationship with O’Brien. “He had always stood shoulder to shoulder with the building trades and said, ‘I wouldn’t do a project without unions,’” the union leader said. “But when times got tough, the first thing he did was turn on his friends, and that really was disappointing. The squeaky-clean guy that Tom always portrays got some dings in him as far as I’m concerned.” For his part, O’Brien says he switched general contractors on the project, and the new company, Suffolk Construction, worked with the unions to find solutions that honored the original agreement while accounting for the changed financial environment.

The situation is equally challenging at P3 in Roxbury, where HYM has yet to break ground and is still raising capital for the predevelopment phase. Beyond the industry-wide obstacles, O’Brien has bet on academic and medical research labs to subsidize the housing. But this is hardly the time for universities to expand lab space, given federal research funding cuts.

Some people around town believe O’Brien is in deeper trouble than he lets on. “O’Brien got in over his head,” says a former City Hall employee who is familiar with the development process. “Suffolk Downs, Parcel 3, neither of them is close to being done. And there is a massive hole in the ground where the Government Center Garage was. I don’t know what is going on with Tom O’Brien, but in my opinion, he is on the verge of losing Suffolk Downs.”

O’Brien disputes this assessment. He points to Revere’s recent approval of a tax break for HYM’s Portico construction project, which at presstime he predicted might get under way by Labor Day, making it the first major housing project in the Boston area to break ground in three years, he says. He also vowed he wasn’t giving up on P3 and says progress on the two remaining buildings at Bulfinch Crossing, where the Government Center Garage was, is ongoing. What is certain, though, is that for one moment this spring, he was willing to walk away from it all to pursue another prime piece of real estate: that singular office on the fifth floor of City Hall.

Now, as the managing partner and public face of HYM Investment Group, he is overseeing the planned development of another new neighborhood at Suffolk Downs. / Photo by Tony Luong

The conversation that would lead to one of Boston’s biggest political what-ifs began with Tricia almost walking out of Cricket’s in Faneuil Hall in 1991. She’d been waiting 30 minutes for a tardy O’Brien to show up for their first date (he says he wasn’t that late). But when he finally arrived, they dove immediately into the kind of deep talk most couples save for months down the road—about their faith, politics, and their drive to be of service to others. It was a conversation, O’Brien says, that they have never stopped having.

Last fall, the stakes felt higher as O’Brien grew increasingly concerned about the city’s future—not just housing, but the public school system and city finances. He told me their decades-long dialogue follows a reliable pattern: He’ll comment on some civic issue facing Boston, then turn to Tricia and say, “Geez, someone needs to do something about that.” And Tricia looks at him and says, “Well, Tom, why don’t you do something about it?”

I witnessed this dynamic firsthand in the living room of their apartment in the Sudbury, a luxury building HYM erected as part of the Bulfinch Crossing project. Through their windows, the Custom House Tower clock kept time over the harbor in the distance. “I always felt he should run for office,” she told me. “He knows the city better than anyone.”

In January, something shifted. O’Brien looked at the situation in Boston and said to himself, “It’s my time.” Tricia was immediately behind him as his top supporter while he began exploring a run, making phone calls around town that yielded encouraging support—enough to convince him he had a real shot at victory. One of those calls was to Harry Collings, a former longtime executive at the BRA, who urged O’Brien to run because, he says, O’Brien is a smart guy who always listened to people in the community when he was at the agency. “I thought he would be a good candidate, it would be a good campaign, and he would be a good mayor,” Collings says.

Collings wasn’t alone in thinking O’Brien would make a great mayor. Yet even some of O’Brien’s biggest supporters weren’t convinced he should run. One close friend questioned whether he truly wanted to be the person to take on Boston’s first mayor of color. Meanwhile, Ricardo Louis of Privé Parking, who considers O’Brien his mentor and is involved in the P3 project, also had reservations. “It was like: Tom, this isn’t your race. You already have something great going on that I think you should focus on, and that’s development,” he says.

Some suggested the timing wasn’t right—that he simply didn’t have enough of it. “I said, ‘With all due respect, are you running this year? Because it’s March,’” Edwards recalls of their phone conversation after reading about his mayoral plans in the paper. Edwards also had concerns about his public presence. “I told him you have opinions about really good things—race relations, housing, schools—why weren’t you speaking out about those issues in the run-up to the mayor’s announcement?” she recalls. “I told him if you want to run, you can’t just be a developer who is a nice guy running for mayor; you have to be more than that.”

But for some in O’Brien’s orbit, even that description no longer fit. When O’Brien let the labor leader know he was considering running, he didn’t receive the promise of an endorsement. “We felt he did the trades dirty over Suffolk Downs,” the leader said. “I heard he called several trades and that he got shunned from a few different spots.” According to Elsbree, O’Brien was still exploring the race during those calls and hadn’t publicly committed, so endorsements weren’t part of the equation yet.

Meanwhile, people around Boston wondered about his motivation for running against a mayor he had once supported. “I think over time, the economics didn’t work for him with Suffolk Downs, and that’s when it seemed like he started to sour on the mayor. Was it because his project didn’t work out?” mused one person active in civic life. “You know, she is the mayor of the city, not just of his project.”

Over the course of my reporting, people were surprisingly reluctant to speak on the record about O’Brien’s near-run. Some declined to say anything that might sound negative about someone they consider honest and decent, while others were hesitant to praise someone who had challenged their current business partner—City Hall.

A few days after he and Tricia saw that second Globe story revealing his planned announcement site in East Boston, and less than a week before the campaign launch, O’Brien was at HYM when he made his decision. Pulling Tricia into his office, he told her he had decided to call off his run. Sitting there, underneath the photos of their children, her jaw clenched with emotion. They both put their phones aside, left the office, and walked around the city before dinner. “I wish he had run for mayor,” she told me that afternoon in their apartment. “I understand why he didn’t. I absolutely agree with the decision, but I don’t think there would have been a better mayor than him. I just don’t.” His statement went out a few days later, saying he would not run. But the question remained: Why?

Pulling Tricia into his office, O’Brien told her he’d decided to call off his run. Her jaw clenched with emotion.

About seven weeks after O’Brien announced he wasn’t running for mayor, he and Tricia went to Sunday mass at St. Cecilia Parish in the Back Bay. They were both lectors that morning. When O’Brien’s turn came to take the lectern toward the end of the service, he read a prayer that ended: “For the intentions we hold in the silence of our hearts, we pray.”

As I sat in the pews under the soaring ceilings of the church, the morning light streaming through the windows, I wondered about O’Brien’s intentions, about his secrets. I was not the only one. The news that he was not running had set off speculation across the city, with all manner of theories about what really happened during those three weeks in March.

During my reporting, several theories emerged. The local political consultant who knows O’Brien said he’s a competitive guy who likes to win—and while O’Brien would have made a good mayor, coming in second to Wu wouldn’t have sat well with him, which is where he likely would have landed.

O’Brien’s friend who questioned whether the developer really wanted to be the white guy challenging the city’s first mayor of color said that was surely part of O’Brien’s decision. The labor leader suggested the lack of union support could have made him reconsider.

Some speculated that he and Kraft—or Kraft’s father, Robert—had cut a deal. Others wondered what Wu might have promised or threatened. Then there was the theory that O’Brien was working with Wu all along, only running to make it appear that not one, but two, white men were trying to unseat her, generating more sympathy for the mayor.

When I first asked O’Brien directly, he told me he initially thought his business was ready for him to pass the torch to his partners. Some of his investors, he said, believed in him and supported whatever he wanted to do. But as the mayoral run became more real, it turned out his company wasn’t ready to go it without him—and some investors pushed back.

Still, some people aren’t buying the idea that O’Brien, the former top city planner, hadn’t worked all of that out beforehand. “Did the meticulous planner not plan enough?” mused one former City Hall source who remains tuned in to local politics. Or, the source wondered, “Did he get a message from the Hall saying, ‘If you do this, you will be decimated’? Tom’s a good guy. If you threaten him, it’s one thing, but if you threaten his business and all the good people who work there, that would be another.” That message, if it existed, the source added, would never come from the mayor herself, but from someone around her—or be delivered by a friend in O’Brien’s industry.

I put these theories to O’Brien to see what he thought. The one about his run being a conspiracy to support Wu earned a hearty laugh. No, he said, it wasn’t because he was a white guy. Yes, he said, he was competitive, but no, he didn’t think he would finish second. And, no, no one sent him a horse head, or promised him project approvals in exchange for dropping out.

So what was it, I asked? “I think if it was just Tricia and I who were at risk, if it was just the two of us, then I definitely would have run. But it was beyond us. It was another group of people who I was putting at risk.”

O’Brien said it was people’s jobs that would be vulnerable—plus investors’ money. When I asked him whether he meant that they would be at risk because of his absence from the company or because there would be blowback or vengeance exacted on his company if he ran, he told me, “A little bit of both.” He said there were calls he received, not from Wu or anyone in her administration, but from “political people,” adding, “Listen, I know how this town works, and I know a lot of people. Some of the calls I was getting were from people who were calling with an agenda, is what I would say.”

With his candidacy in this year’s mayoral race now behind him, O’Brien has returned to developing, trying to get his projects off the ground. But that conversation between him and Tricia seems far from over. “He’s only 62,” she told me that afternoon in their apartment, ever hopeful.

I asked O’Brien if one day in the future he still might run for office.

“It’s still a bug in me. It’s still an illness in me,” he said. “So who knows?”

First published in the print edition of the September 2025 issue with the headline: “What Really Happened to Tom O’Brien?”