BOSTON — Michelle Wu was weeks away from her first City Council election when she lost her voice.
Her supporters watched apprehensively. Wasn’t it enough of a challenge that, in a city of backslapping, larger-than-life politicians, their candidate was a soft-spoken, Harvard-educated policy nerd? Or that, in a city of deep neighborhood loyalties, she was a newcomer? Now, at crunchtime, she could barely make herself heard above a rasp.
But it became clear, when Election Day arrived, that they need not have worried. Ms. Wu, then 28, had put the pieces in place, learning Boston’s political ecosystem, engaging voters about policy, cobbling together a multiracial coalition. This was not about speeches. She would win in a different way.
On Nov. 2, when Ms. Wu, 36, faces off against another city councilor, Annissa Essaibi George, in Boston’s mayoral election, she could break a barrier nationally.
Though Asian Americans are the country’s fastest-growing electorate, Asian American candidates have not fared well in big-city races. Of the country’s 100 largest cities, six have Asian American mayors, all in California or Texas, according to the Asian Pacific American Institute for Congressional Studies.
Ms. Wu, a protégée of Senator Elizabeth Warren, began her political career in this city as it was turning a corner, its electorate increasingly young, well-educated and left-leaning.
She proposes to make Boston a laboratory for progressive policy; to reapportion city contracts to firms owned by Black Bostonians; to pare away at the power of the police union; to waive fees for some public transportation; and to restore a form of rent control, a prospect that alarms real estate interests.
“In nearly a decade in city government, I have learned that the easiest thing to do in government is nothing,” she said. “And in trying to deliver change, there will be those who are invested in the status quo who will be disrupted, or uncomfortable, or even lose out.”
Critics says Ms. Wu is promising change she cannot deliver, since several signature policies, like rent control, require action by state bodies outside the mayor’s control.
“Michelle talks, day in and day out, about things that are not real,” said Ms. Essaibi George, who has run as a pragmatic centrist and is an ally of former Mayor Martin J. Walsh. “My style is to be accurate in the things I say out loud, and to make promises I can truly keep.”
Polls since the preliminary election have shown Ms. Wu with a substantial lead over Ms. Essaibi George.
Others warn that Ms. Wu lacks allies within Boston’s traditional power centers and will run into resistance, even on everyday matters.
Ms. Wu says that she is ready for those battles, and that the course of her life has compelled her, gradually, in the direction of taking greater risks. For example, she was not supposed to go into politics to begin with.
A family unravels
Ms. Wu was born shortly after her parents immigrated from Taiwan, intent on setting the next generation up for success.
Han Wu, a chemical engineer, had been offered a spot as a graduate student at Illinois Institute of Technology. But he and his wife, Yu-Min, barely spoke English, and so, from the age of 4 or 5, their oldest daughter, known in Mandarin as Wu Mi, served as their interpreter, helping them navigate bureaucracy and fill out forms.
At her suburban Chicago high school, she was Michelle. She stacked up A.P. classes, joined the math team and color guard, and earned perfect scores on the SAT and ACT exams. As co-valedictorian, she wowed the audience at graduation with a piano solo from Gershwin’s “Rhapsody in Blue.”
Her sister Sherelle said their parents encouraged them to range widely but expected mastery.
“They always made us feel that we could do anything, but whatever we chose, we had to be the best,” Sherelle Wu, a lawyer, said. “You know, I could have been an artist, but I had to be Picasso. My brother played the cello, and he could be Yo-Yo Ma.”
Politics, however, was off the table; their parents, raised by parents who fled famine and civil war in China, viewed it as a corrupt, high-risk vocation. They wanted Michelle to go into medicine, along a “pipeline of tests and degrees to a stable, happy life,” she said. When she left for Harvard — something her parents had hoped for her whole life — Ms. Wu was not sure whether she was a Republican or a Democrat.
It was while she was at Harvard that her family came unraveled.
Her father had lived apart from the family starting when she was in high school; her parents would eventually divorce. Her mother, isolated in their suburban neighborhood, began acting erratically, shouting at the television and dialing 911 to report strange threats.
Ms. Wu, newly graduated, had started a fast-track job at the Boston Consulting Group when Sherelle Wu called and said, “We need you home, now.”
Ms. Wu rushed home and was shocked by her mother’s condition. She has described finding Yu-Min standing in the rain with a suitcase, convinced a driver was coming to ferry her to a secret meeting. She examined her daughter’s face closely, seeking evidence that she was not an android.
“You’re not my daughter anymore, and I’m not your mother,” Ms. Wu’s mother told her.
Ms. Wu marks this period as the crossroads in her life, the point where she let go of the script that her parents had written for her.
“Life feels very short when that kind of switch happens,” she said.
Thrust into position as the head of the family, Ms. Wu, then 22, dove in. She became a primary parent to her youngest sister, who was 11, eventually filing for legal guardianship. She managed psychiatric treatment for her mother, who was diagnosed with schizophrenia, and opened a small tea shop, thinking her mother might take it over.
Then, frustrated by the bureaucratic obstacles she had encountered, she enrolled at Harvard Law School, bringing her mother and sister back to Boston with her. This time, she intended to stay.
A political baptism
Ms. Warren, who taught contract law, remembers Ms. Wu coming to her office hours in her first semester of law school.
Ms. Wu had come to apologize for some academic shortcoming, though Ms. Warren had not noticed any. “She felt she hadn’t done her best and wanted me to know she had not intended any disrespect,” Ms. Warren recalled.
As they sat together, Ms. Wu told the story about how she had come to care for her mother and sisters. Ms. Warren listened, marveling. “Michelle was doing something in law school that, in 25 years of teaching, I never knew another student to be doing,” she said.
That marked the beginning of a close relationship between Ms. Wu and Ms. Warren, who would become Massachusetts’s progressive standard-bearer. Asked this summer why she endorsed Ms. Wu over other progressives, Ms. Warren responded simply, “Michelle is family.”
In law school, Ms. Wu began expanding her networks in government. During a legal fellowship in Boston City Hall, she designed a streamlined licensing process for restaurants and started a food truck program, attracting the interest of Thomas M. Menino, the mayor at the time.
When Ms. Warren decided to run for Senate, Ms. Wu asked for a job on her campaign. John Connolly, a former city councilor who ran against Mr. Walsh in 2013, credits her with “a phenomenal, genius-level understanding of field politics,” similar to Mr. Menino in her “photographic memory of the nooks and crannies of Boston.”
“She can tell you the six places Albanians socialize in Roslindale,” he said.
She went on to win an at-large seat on Boston’s City Council in 2012, making her only the second woman of color to serve on the Council, after Ayanna Pressley.
Almost immediately, she was in hot water with progressives. In the election for City Council president, Ms. Wu had pledged her support to William P. Linehan, a leader of the Council’s conservative faction and one of her early supporters.
Shortly before the vote, Ms. Pressley jumped into the race, and it became an ideological showdown. A parade of progressive heavyweights tried to persuade Ms. Wu — at 28, the youngest councilor ever elected — to switch her vote. She recalls “thousands and thousands” of phone calls and emails that left her “in bed crying, devastated and shaken,” unsure she even wanted the position she had just won. Still, she did not budge.
The vote cast a shadow over her victory: Many progressives saw her choice as an act of political self-interest, and conservatives, who repaid the favor by backing her for City Council president in 2015, were disappointed that she resumed voting with progressives, Mr. Linehan said in an interview.
“She gets elected, and goes back to the people who were abusing her, because that was her political future,” he said. (He is supporting Ms. Essaibi George in this race.)
Others in the city, though, recall watching the young politician with new interest, surprised by her toughness.
“She is so nice, people sometimes mistake her niceness for softness,” Leverett Wing, one of her early supporters, said. “It showed she wouldn’t succumb to pressure. It showed she had the mettle to lead the institution.”
‘She had a long game’
Over four terms as city councilor, Ms. Wu has built a reputation for immersing herself in the nitty-gritty of government, reliably showing up at meetings on unglamorous matters.
“The word that is coming to mind here is ‘methodical,’ and that’s almost dismissive — I don’t want to paint a picture of someone who says, ‘I’m going to be mayor and I’ll just tick all the boxes,’” said Chris Dempsey, an activist and former state transportation official. “It’s the consistency with which I have seen her show up and work on issues and build constituencies and start conversations.”
She captivated young progressives with far-reaching proposals like a citywide Green New Deal and fare-free transit, campaigns she rolled out on TikTok, Instagram and Twitter, alongside dispatches from her campaign headquarters and her two young sons.
“All my classmates started to talk about Michelle Wu,” said Benjamin Swisher, 22, a senior at Emerson College, adding that her candidacy “shows that young people can do it, that we have the ideas to push this country forward and create that new America.”
Ms. Wu can be sharp elbowed, and often brought her criticisms of Mayor Walsh straight to the press or social media, to his irritation. In 2020, after she criticized a city coronavirus fund, he remarked that it would be better “if the city councilor just took time out of her schedule just to give me a call and maybe go on a call to talk to us.”
In September 2020, she was the first candidate to declare a run against Mr. Walsh, at a moment when polls showed he was heavily favored to win.
Four months later, President Biden chose Mr. Walsh as labor secretary, and the stars lined up.
“This has been thought out and played out and planned out for years,” said Peter Kadzis, a commentator for GBH radio. “She had a long game to get into the office, a much longer game than anyone I’ve ever known who has become mayor.”
Her success at mounting an electoral challenge does not mean she will be able to perform well as mayor, her critics warn. She could face pushback from powerful players in the city’s development sector, who may seek to block her agenda.
“The nuts and bolts of how that government runs, and the city workers — she’s going to have her hands full trying to control them and manage them,” said Mr. Linehan, the former city councilor. “Are you going to bring in some people from Harvard to manage them? You’re going to get a reactionary response.”
“She’s Ms. Outside,” he added.
Ms. Wu allows that there are challenges ahead. But no leap seems more vertiginous than the one she took when she was 22, and decided not to follow the plan that her parents had so carefully plotted out.
“In some ways, maybe the biggest risk of all,” she said, “was choosing to step away from that.”
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