The Next Mayor of Boston?

City Councilor Michelle Wu, a Chicago native and Harvard Law grad, has emerged as one of the city’s most effective politicians.

Elise Amendola / AP

Michelle Wu wanted to free the T. On a subfreezing February morning, the Boston city councilor was handing out flyers at the Park Street subway station. In a soft voice, she urged bundled commuters to sign a petition opposing the Massachusetts Bay Transportation Authority’s proposal for a 6.3 percent fare hike, part of her campaign to make the T free. The gold-domed state house rose behind her. Below, one of the notoriously failing trains slowed to a stop.

For weeks, Wu had been making her case, sometimes with her youngest son on her hip as she told local reporters that Boston needed to do better for climate and community. She didn’t present concrete plans for alternative funding so much as urge the MBTA and lawmakers to seriously discuss the possibilities. “Making the investment in fare-free transit would not only nourish our future, but also align with our history,” Wu wrote in an op-ed in The Boston Globe, referencing the state’s establishment of the first public school, park, and library in the country. Wu knew her audience, reframing the city’s history as a roadmap for how to move forward.

In the past, no member of the Boston City Council, long a rubber stamp for the mayor, had ever led such a crusade against the MBTA. But Wu embodies the kind of political change that’s making waves in Washington, D.C., and cities across the country. Ayanna Pressley, Alexandria Ocasio-Cortez, Ilhan Omar, and Rashida Tlaib defy the status quo in Congress. Once considered a long shot, the presidential candidate Pete Buttigieg has become a 2020 sensation, with his opposition to the Electoral College and fresh approach to Christianity and gay rights. This month, Lori Lightfoot was elected Chicago’s first black female and openly gay mayor.

As the Democratic Party rapidly diversifies, young, progressive women of color such as Ocasio-Cortez, Pressley, and Wu—Pressley’s former council colleague in Boston—have ignored calls to “wait your turn” and have run for office pushing progressive policies.

As Peter Beinart wrote in the fall following Pressley’s victory as the state’s first black woman elected to Congress, politics are no longer local, for “the part of America you’re from matters less than it once did, and the kind of America you believe in matters more.” The kind of America that new Democrats believe in is often an activist one, which is visible in traditional, hidebound Boston, where the city council overwhelmingly passed Wu’s resolution to support the Green New Deal earlier this month.

With Pressley, the first woman of color elected to the city council, having moved on to the national level, the Boston City Council remains an incubator of new politics. Ten years ago, no woman of color had ever served on the council. Today it’s composed of seven white men (three of whom are departing in this year’s election) and six women of color, including its president, Andrea Campbell, who succeeded Wu last year.

Wu is an example of this transformation. She is not from Boston. A Taiwanese American, she is the council’s youngest member, at 34. In a 19-way race for councilor-at-large seats in 2013, her first political run ever, she came in second. Just a few years later, she was elected unanimously as the first woman of color to serve as council president. And now people are already talking about her as the next mayor of this traditionally Irish Catholic city, which, for all its progress, remains one of the two most populous cities in the country (the other being Indianapolis) that has yet to elect a mayor who is not a white man, despite being majority-minority for the past decade.

Wu stands out from many of her political peers because of her particular leadership style. Unlike Pressley, Wu isn’t known for being an impassioned speaker. Unlike Ocasio-Cortez, Wu would never be described as a “bomb-thrower and agitator.” For most of her life, she didn’t think of herself as a leader; her report cards once urged her to participate more. “It sort of takes people by surprise how she is able to take command of a room, a situation, or a group of people to get things done,” says Roger Lau, who worked as the political director of Elizabeth Warren’s Senate campaign during the time Wu served as its constituency director.

But Wu has emerged as one of the city’s most effective and diplomatic politicians. She has negotiated with the mayor on issues such as government transparency, short-term-housing-rental regulations, and green energy, earning a reputation for both hyper-detailed policy work and humility in the face of a prideful city. When we met for coffee after Wu’s morning of petitioning, she deflected from commenting on “old” and “new” Boston, tucking her shoulder-length black hair behind her ears, eyebrows sloped up. “Even the folks who some people would call ‘Old Boston’ today were ‘New Boston’ at one point in their family’s history, right?” Wu said.

On another cold February day, 50 years earlier, Senator Ted Kennedy addressed a crowd gathered in Government Center for the inauguration of a new city hall. “Urban life in the United States has come to a critical point of decision, caught between the narrowing walls of change and decay on one hand and, on the other, priorities created for another age,” Kennedy warned. The brutalist-style City Hall was meant to usher in a new Boston and leave behind the corruption and economic woes of the 1950s. But five years after Kennedy’s speech, in 1974, Boston was rioting over the integration of its public schools.

When Wu entered her office for the first time, in January 2014, the pink missed-call slips on her desk from disappointed constituents indicated people’s worry that “New Boston” had still not yet arrived. Wu had promised her vote for city-council president—her first as an elected official—to Bill Linehan, a five-term councilor from South Boston who was thought to represent the old guard. (At the time, Linehan’s latest media flare-up was for saying that an elected official from South Boston should host the neighborhood’s Saint Patrick’s Day breakfast rather than the state senator per tradition; many viewed this as an attempt to prevent the new senator, the first woman and person of color to represent the district, from hosting.) The Globe editorial board called Wu’s support for Linehan “a head-scratcher, at the very least” and her reasoning “honest enough but politically naïve.”

Caught between campaign and office staffs, Wu inexpertly fielded the onslaught of criticism herself. Wu, as she still does today, stood by her decision, explaining that she cast her vote because of Linehan’s administrative ability to lead the council and urging the city to avoid dichotomizing “New Boston” and “Old Boston.” “I reject the notion that Boston is a city hopelessly divided by neighborhood, income level or political outlook,” she wrote in a statement at the time. “The only way we can move the whole city forward is by working together—even if that means reaching beyond the confines of what’s easy or comfortable.”

Though she lost some supporters, Wu gained the respect of many initial disapprovers because of her loyalty to her word. As Wu told me, the incident stressed all that she had to learn about “how deeply racial disparities and divisions were right under the surface of that conversation and so many other policy conversations we have across the city.”

Like Wu, many of Boston’s political groundbreakers—Pressley, Warren, Attorney General Maura Healey, and former Governor Deval Patrick, among others—did not grow up among Boston’s historic disparities and divisions. As much as their “outsider” label complicated breaking in, it also perhaps made these candidates more willing to challenge Boston’s status quo.

Pressley, who was raised in Chicago like Wu, told me that she was so accustomed to seeing diversity in Chicago politics that she didn’t realize the unlikelihood of her candidacy in Boston; by contrast, Wu wasn’t even aware of political role models, commenting in a 2016 interview that people often told her she should become a figure skater like Michelle Kwan, one of the few Asian American women to achieve mainstream success.

Her immigrant parents remained distant from politics and taught Wu, the eldest of four, the value of hard work and to keep one’s head down. When Wu arrived in Boston in 2004 to study economics as an undergraduate at Harvard, she didn’t even think of herself as a Democrat or a Republican.

Unbeknownst to Wu, Boston politics at the time were prefiguring her own career trajectory. In 2005, the Pennsylvania-raised Sam Yoon made history not only as the first Asian American on city council, but also as the first-ever candidate to win an at-large seat on his first run, as Wu would do less than a decade later.

In 2007, Maureen Feeney became the second woman to serve as city-council president (Wu, the third).* And while 2009 brought Pressley to the council—a historic win as the first woman of color—that year’s mayoral race demonstrated that there was a clear limit to how far “New Boston” could go. “Running against the mayor was like running against an institution that was almost synonymous with Boston,” says Yoon of his campaign against Thomas Menino, the mayor with a 73 percent approval rating.

Menino won decisively, becoming the city’s longest-sitting mayor, an unsurprising triumph considering that an incumbent hadn’t lost reelection since 1949 (when the corrupt mayor even served part of his term from prison).

Around this time, Wu had her own watershed moment. She was working as a consultant in Boston post-graduation when her mother suffered a mental-health crisis so severe that Wu moved back to Chicago to care for her and Wu’s 10-year-old and 16-year-old sisters. As Wu said, “she went from being the mom who was always the class parent … to not even wanting to engage with family members.”

For a long time, Wu couldn’t talk about what happened without crying; the stigma of mental illness made it even more difficult. At 23, she was responsible for her mother’s health care and her sisters’ education (she became the legal guardian of the youngest). She opened a tea shop in Chicago with her boyfriend (now husband) to help support the family, hoping that her mother would run it one day. Complete with book-themed teas (“Barack’s AudaciTea”), the shop was a catalyst for Wu’s future advocacy for small businesses. After slogging through city permitting for months, Wu closed the shop less than a year after opening once she realized that her mother would not soon be well enough to take over.

Wu moved back to Boston to attend Harvard Law School, bringing her family with her. (Wu’s mother is doing better, and she still lives in a two-family home with Wu, her sisters, her husband, and their two children.) As a law student, while raising her then-teenage sisters and finding her mother health care in Boston, Wu threw herself into politics, always seeming “a little surprised by how good she was,” as her professor and mentor Elizabeth Warren told me.

As an intern for Menino, Wu worked to make the restaurant permitting process accessible and helped establish Boston’s food-truck program. When Warren ran for senator in 2012, Wu volunteered, then worked full-time, for the campaign as its constituency director, all while finishing law school, studying for the bar, and preparing to get married. She was late to graduation because she was organizing a campaign event at North Station, so she hopped on the T in her cap and gown, only to commute back after the ceremony to continue working.

When the campaign ended, Wu announced, to the surprise of many, that she was running for city council in the fall of 2013. “Even my siblings told me … they weren’t sure this was the best idea, given my personality, being on the soft-spoken and shy side,” Wu said. As “someone who really wanted to make people happy, wouldn’t this be really negative, and all this public speaking?”

But as she wore out multiple pairs of shoes and her voice while campaigning, Wu learned how to tell her story, emphasizing her firsthand experience with education, health care, and small business as a way of promising that she would and could make city bureaucracy more transparent and accessible. She often thought of, though never spoke of, something her mother had once written down: “Remind Mimi”—her nickname for Wu— “to help people and think about government.”

At first, Wu was competing against an incumbent for an at-large seat, but the dynamics changed quickly when Menino announced that he would not seek reelection. Dozens of people entered the mayoral race, including two of the sitting councilors-at-large, freeing up two spots. Wu now had a better shot at an open spot, but she still had to beat out 18 candidates. She didn’t just beat out the others—she came in second for total votes, trailing Pressley, an incumbent, by less than one percentage point.

Wu was primed to work on the “inside,” thanks to her time with Menino and Warren. But Wu comes across as milder than both of her mentors (Menino, though beloved, was known for his temper), a quality that seems to have helped her build consensus on progressive issues.

In her first term, Wu was already challenging Mayor Marty Walsh, urging the City to withdraw its 2024 Olympics bid (citing its lack of transparency) in language that appealed to Boston’s pride. “In the drive to prove our status as a world-class city, let’s stay true to our democratic legacy and what Boston has already given to the world: informed independence and true debate,” she wrote in a post for WGBH, a local public-radio station. That summer, pressured by councilors and citizens, the City withdrew its bid.

Last spring, Wu led her colleagues in pushing Walsh to tighten short-term-housing-rental regulations. Councilor Lydia Edwards, who also worked on the stricter policy, says that Wu, newborn in arms, would not back down during these negotiations, but instead offered Walsh opportunities to collaborate. Wu won—the mayor signed a firmer proposal and the governor later contributed a state policy—but not without incurring the wrath of Airbnb.

The rental giant sent thousands of emails to Bostonians calling Wu out by name for aligning “with big hotel interests against the interest of regular Bostonians,” along with an inaccurate list of her policy points. With an army of supporters, Wu quickly shot down Airbnb on Twitter for “spreading fake news.” The company soon softened its language. (It did, however, file a lawsuit against the City earlier this year, as it has previously in New York and San Francisco.)

Wu would not confirm that she has plans to run for the mayor’s office, but political pundits and strategists I spoke with said she would be a clear favorite. Granted, she is young enough that a move like this wouldn’t necessarily come in the next mayoral election, in 2021.

And while some speculate that she may follow Pressley’s federal trajectory or head into the private sector, Wu has additional reforms to city politics she’d like to pass. In addition to curbing the mayor’s power, she has voted to check her own power by opposing pay raises and the lengthening of councilors’ terms, measures that both failed. “The people of the city are changing faster than the political structures,” says David Bernstein, a longtime journalist and columnist at WGBH. But in being able “to work with the powers that be while also working with and for the outside structures,” as Bernstein says, Wu has chipped away at the city’s institutionalism.

As a new mother in her first term in office, Wu spearheaded Boston’s first paid-parental-leave policy for city employees, which Barack Obama later praised. As council president, she restructured its committees and established a monthly councilor lunch to try to promote collaboration. And this summer, she substituted the mayor’s proposal to regulate lobbying in City Hall for a stricter one. If Wu were to become mayor, the change wouldn’t just be demographically historic—she would, perhaps, help redefine the notion of absolute mayoral power.

Wu has not acted alone. Walsh has helped facilitate this stronger relationship with the council. City Hall is less insular than it was under Menino, and the mayor’s word, once a golden ticket, no longer automatically wins a city councilor a seat, as the loss of Walsh’s chosen candidate in 2017 showed. Walsh himself is in some ways an untraditional Boston mayor; a genial underdog, he is unmarried and a recovering alcoholic. Still, Walsh’s story is familiar: An Irish Catholic labor leader, he was long considered “the unofficial mayor of Savin Hill” and only recently moved just four miles out of his childhood neighborhood.

Particularly with an approval rating as high as Walsh’s, an incumbency is tough to crack, even if Wu thrice winning a citywide seat suggests that she could be a stronger candidate than her precursors. Moreover, the council’s ability to work with the mayor and its increasing diversity could either give Wu traction or suggest that change has already happened. As the Globe’s Spotlight team wrote in its 2017 series on racism in Boston, “We have deluded ourselves into believing we’ve made more progress than we have.” The mayor’s seat in particular highlights this stagnancy: There have been just four mayors in the past 50 years. “Opportunities to seize power occur here once in a generation,” the Globe wrote.

The stakes of trying to seize this power have been high. “When I ran, people constantly pointed out how people like me don’t run for Boston city politics—whatever that means—but by the time Michelle came around, I’m not sure if that was the buzz around her,” says Yoon, who ran for mayor in 2009 and lost. (Yoon now works in D.C. as the executive director for the Council of Korean Americans.) His advice if Wu were to run for mayor? “Have a Plan B,” he said with a sharp laugh.

Later that February day, at a public meeting on the fare hikes, Wu stood at a podium and faced a long table with two men from the MBTA. Nearly 200 people, many waiting to speak, sat behind her. “Imagine the opportunities and the access that would open up for generations in our city,” she said with a practiced cadence. “This is the approach we should be pushing toward, not a regressive fare hike on the backs of working families.”

Though Wu’s comments received enthusiastic applause, less than two weeks later, the MBTA announced the implementation of the fare hikes. A sliver of compromise emerged—the buses, the MBTA’s mode of transportation that tends to support the city’s lowest-income neighborhoods, would remain the same price and overall fares would not rise again for another three years, longer than in the past. When we spoke by phone a few weeks later, Wu seemed undeterred. She was already moving forward with efforts to make the Bus 28 route free.

* A previous version of this article misidentified Maureen Feeney as Maura Feeney. We regret the error.