Nearly 200 years after Boston elected its first mayor, the city recently swore in its first female mayor and its first mayor of color, almost by accident. Two-term mayor and former union boss Marty Walsh left his post in March to serve as secretary of labor in President Joe Biden’s administration, leading then-City Council President Kim Janey to become acting mayor. Just 12 years ago, the city elected its first woman of color, Ayanna Pressley, to the City Council. In 2018, Pressley also became the first woman of color to represent Massachusetts in Congress. 

Now, Janey and five other candidates, all of whom are people of color and self-described progressives, are running to serve a full four-year term as mayor in a race widely seen as the christening of the “New Boston”: The city is close to becoming a majority-minority city, and all six candidates are quick to point out that Boston is no longer the mostly white, mostly Catholic city it once was. (The race is nonpartisan, so candidates are not technically affiliated with the Democratic Party, but the city is overwhelmingly Democratic: 82% of Boston voters cast their ballots for Joe Biden last November.) The deadline for candidates to enter the race was last week, kicking off a critical period of campaigning before a September primary that will send the top two vote-getters to the November general election.

“The community of Boston is in a period of transformation, and asking questions about what kind of city it wants to be going forward, both as an urban center and as the hub of a region,” said Jeremy Burton, executive director of the Jewish Community Relations Council of Greater Boston.

While the candidates come from diverse personal and family backgrounds, most have relatively similar electoral histories and political views, leading to questions of how voters will ultimately differentiate between them. Five of the six major candidates serve in city government, and three of the candidates — Michelle Wu, Andrea Campbell and Annissa Essaibi George — currently serve on the Boston City Council, as did Janey until earlier this year. A fifth candidate, John Barros, served as chief of economic development under Walsh. The final candidate, Jon Santiago, is a state representative and emergency room doctor. 

“If you’re a progressive Democrat or a liberal Democrat, you by and large like all these candidates,” said Erin O’Brien, associate professor of political science at the University of Massachusetts Boston. “There seems to be pretty substantive policy agreement on the major issues. I think [the race will be] more personality driven.”

For the most part, all six candidates are highlighting a robust, equitable economic and public health response to the COVID-19 pandemic as a key focus of their campaigns. Other major issues include education and teacher pay, access to housing, adapting to and mitigating climate change and expanding transit options.

State Rep. MD Jon Santiago shows support for presidential candidate Elizabeth Warren at a morning press-conference in Boston to support Warren’s plan to handle infectious disease outbreaks on Feb. 27, 2020. (Jonathan Wiggs/The Boston Globe via Getty Images)

In a city where unions remain dominant, one major change is that none of the candidates are actively seeking the endorsement of the city’s police union. Essaibi George is the only candidate who has spoken out against the movement to defund the police, as she believes the city’s police force should be reformed, not defunded. 

“[Essaibi George] has done it in terms that are much more palatable to progressives and less so to the police union,” O’Brien explained. “But I really feel like the police union is used to having political clout, and their clout isn’t anything these candidates want.” 

Other unions in the city have not coalesced behind a single candidate, as they did when Walsh first ran in 2013. The construction union endorsed Santiago, and the nurses’ union endorsed Barros. The firefighters’ union endorsed Essaibi George, as did William Gross, former commissioner of the Boston Police Department. 

Polling has been limited in the race, with more than three months until the primary, but a late April poll found that 36% of voters remain undecided. Wu narrowly leads Janey and Essaibi George, but each had only about 15% support. 

The Greater Boston Metropolitan Area is home to about 250,000 Jews, but only about 10-20% of the area’s Jewish population lives in the city of Boston, with the rest scattered in the surrounding suburbs. Still, members of the Jewish community in suburbs like Newton and Brookline closely follow city politics. “Broader Boston serves as a real center of the region, and what happens in Boston — the success of its educational systems, the health of its economy, the vibrancy of transportation, the leadership the city provides — sets the tone for the region,” explained Burton. 

In conversations with community leaders, Burton has not seen Jewish community members coalesce around a particular candidate. “To the extent that they settle on candidates, they are sort of all over the place, so nobody has emerged yet as a clear favorite candidate,” he said. In part, this has to do with the diversity of the city’s Jewish community, which Burton described as three-pronged: an Orthodox immigrant community in Brighton; a more secular, older community downtown comprised of empty-nesters; and a younger, progressive, LGBTQ-friendly community largely residing in the southern part of the city. “They are not necessarily seen as one distinct, highly visible community,” Burton noted. 

“If you’re a progressive Democrat or a liberal Democrat, you by and large like all these candidates,” said Erin O’Brien, associate professor of political science at the University of Massachusetts Boston.

Many of the candidates have engaged with the organized Jewish community in some form, either by speaking at panel discussions hosted by Jewish groups or appearing at events including Holocaust remembrance ceremonies. Two candidates — Janey, the current mayor; and Campbell, a city councilor — have traveled to Israel with the Boston JCRC, and Barros participated in a trade mission to Israel as a member of Walsh’s administration in 2014. 

Unlike the ongoing mayoral race in New York City, where all eight Democratic candidates have weighed in on the recent violence in the Middle East, the Israeli-Palestinian conflict has not crossed into the Boston race. But across the Charles River, the Cambridge City Council held a seven-hour meeting Monday night on a resolution that Burton described as aligned with the Boycott, Divestment, and Sanctions (BDS) movement against Israel. The council is slated to vote on the resolution Tuesday evening.

“One of the issues that’s being raised in the community is in fact that they largely haven’t done orders like this targeting other companies or countries (or at least not in many, many years),” Burton told JI. JCRC’s website notes that “there are hundreds of American companies that are working overseas and engaged in transactions that could be tied to questionable human rights practices,” and the “focus on Israel betrays a deeper and concerning animus to the world’s only Jewish state.”  

City Councilor Annissa Essaibi-George stands for a portrait in Savin Hill, the Dorchester neighborhood where she grew up, in Boston on Jan. 27, 2021. (Erin Clark/The Boston Globe via Getty Images)

The only candidate who responded to questions from Jewish Insider about the resolution — and how they would vote if it came before them as mayor — was Barros, who did not answer the question. “The City of Boston is a diverse and inclusive community, and as mayor I would work to make sure our purchasing power reflects our values,” Barros said. 

Who are the candidates hoping to become Boston’s next chief executive? Four of the six major candidates — all but Janey and Campbell — spoke with Jewish Insider about their campaigns. 

Michelle Wu

Councilor Michelle Wu got her start in politics while working on the Senate campaign of her Harvard Law School professor and mentor Sen. Elizabeth Warren (D-MA). Like Warren, Wu’s campaign is full of plans — “many, many plans,” she told JI — and also like Warren, she argues that she has the experience necessary to get the job done. Wu is the longest-serving city councilor in the race, but she says the city needs change from the top to truly serve all its residents. “I believe that the way to deliver transformational change is to rethink our approach and recognize how intersectional our issues are,” Wu said. 

Her election to the city council in 2013 made her the second woman of color to ever sit on the body, alongside Pressley, and she noted that people urged her not to run. “There were many, many well-meaning mentors, advisors and politicos around town who all told me not to do it,” Wu said. “It was with the best of intentions that people were saying, ‘You won’t get elected: You’re a first-generation American woman, young, not born in Boston. It’s not possible.’ And at that time, when you looked at the makeup of the city council, that made complete sense.” 

Wu’s grandparents fled mainland China for Taiwan to escape civil war, and her Taiwanese-born parents then immigrated to the U.S., where she was born. “I can’t remember one instance where we discussed politics or current events at the dinner table,” Wu recalled, adding that “in my family’s multi-generational immigration story, politics was fear and famine, and war and corruption, and all of the many things that we were supposed to stay far away from growing up.” 

After attending Harvard as an undergraduate, she returned home to Chicago to care for her younger sisters as their mother dealt with a mental health crisis. “All of a sudden, the bubble around us that had kept us completely walled off from politics and government bursts, and I had to deal with government all the time in extremely frustrating ways,” Wu said. She had witnessed people call the police on her mother, and she also had to learn to manage local government bureaucracy in Chicago when she opened a small business to support her family. 

Wu has advocated for limiting funding for police, and instead rerouting it to mental health or social services. “I am one of the candidates in this election cycle that has committed to not accepting donations from the police union. We are in a moment of national reckoning on systemic racism that Boston must show leadership on,” she said. 

She noted the strong partnerships between Jewish and Asian populations in the city, and credited Boston’s Jewish community for its activism dating back decades. “I feel very grateful for the efforts and the work that has been done with civil rights and antisemitism that has really laid the groundwork and continues to be the foundation for so much anti-racism work here in our city,” Wu said. “There are so many incredible community leaders and organizations building community, not just to connect members of the Jewish community, but really to create community across the board.” 

Annissa Essaibi George

Councilor Annissa Essaibi George spent 13 years as a teacher at Boston public schools, a unique perspective she wants to bring to Boston’s top job. “Teaching in the classroom, teenagers gave me, I call it, a front-row seat to the people of Boston,” Essaibi George said. “When I taught high school, 11th and 12th grade, you sort of see the end result when systems fail our kids and fail our families.” 

She ticked off some of the challenges she witnessed from that vantage point: “The impacts of substance use disorders on our kids and on our families; the impact of trauma; the impact of poverty; the impact of food insecurity; the impact of not being able to access healthcare, whether it’s physical healthcare or mental health care; [and] the impact of not having access to a high-quality education.”

“The community of Boston is in a period of transformation, and asking questions about what kind of city it wants to be going forward, both as an urban center and as the hub of a region,” said Jeremy Burton, executive director of the Jewish Community Relations Council of Greater Boston.

Born and raised in Boston, Essaibi George is a first-generation immigrant, the child of a Tunisian father and a Polish mother. Her mother had been born in a displaced persons camp in Germany after World War II. “My grandmother, as a teenager, was taken to work in a labor camp in Germany, and my grandfather was in the Polish army and was a prisoner of war,” she explained. Essaibi George grew up largely within Boston’s Polish community, and she was raised Catholic, but she also grew up learning about Islam and Tunisian culture from her father. Her campaign office is located in her grandparents’ old house, where her grandfather once owned and operated a TV and radio repair business. 

“I share a common thread, I think, with most Bostonians, certainly those that are first-generation Americans, as a daughter of immigrants,” Essaibi George said. “Boston is rich in its ethnic and cultural diversity.” Should she be elected, she hopes to “first and foremost [build] a cabinet and an administration that is diverse and reflective of Boston to best tackle … systemic inequities.” 

Essaibi George views police reform as part of addressing inequality in the city, but “I don’t support defunding the police,” she said, adding that many voters have told her they also hope to see more police officers. “I’ve heard how important public safety is, and we’ve seen some significant violence recently in our city. I have residents calling for more public safety, for more police, for a heightened presence of police officers across our city.” Shootings and homicides were up in 2020 — the city had 57 murders, compared to 37 in 2019 — but overall crime was down in the city. 

Essaibi George expressed a commitment to combating antisemitism in Boston. “At the city level, we have a certain responsibility to be very intentional when thinking about and working against racism, antisemitism or hate,” she said. “A number of years ago, the Holocaust memorial in Boston was damaged, and as a city we came together to support our Jewish community and to support and honor what that memorial recognizes, remembers and reflects upon.” 

Jon Santiago

As an emergency room doctor and a state representative, Santiago has had a busy year serving people at Boston Medical Center and in the state house. He knows that if he becomes mayor, he’ll have to put his medical career on pause — but that’s what he’s always wanted, he said: “That was always the game plan. I wanted to practice medicine for six to 10 years, but my eyes are always on the bigger picture, on those root causes [of the city’s critical problems],” he explained. “The way I look at problems is through a very comprehensive lens.” 

When a gunshot victim enters his emergency room, Santiago said he considers the factors that could have led to that moment. It’s “a number of factors of a comprehensive, larger nature,” he said, including “housing, transportation, economic opportunity, education” that could ultimately contribute to who gets shot. “It’s not a coincidence why almost all the gunshot victims are young, Black or brown males.” 

Born in Puerto Rico, Santiago moved to Boston as a toddler, and first began to see how public policy could impact health outcomes when his uncle contracted HIV. “Boston has been a place of opportunity where if you work hard, if you dream big, good things can happen. For me, it’s always been this inspirational place, but at the same time, it’s been a place of tragedy,” he said. “It’s a place where my uncle likely became infected with HIV and passed away from AIDS later on, leaving his son, my cousin, to become an AIDS orphan.” Seeing his uncle get sick and die led to his decision to go to medical school. Santiago later served in the Peace Corps in the Dominican Republic and studied as a Fulbright scholar in Paris. 

Santiago presents himself as an outsider, having beaten a 36-year incumbent in his election to the state house in 2018, and he thinks Boston needs a mayor who does not come from within city politics. “The question I asked myself is, was I happy with the situation the city of Boston is currently faced with right now?” Santiago said. The answer was no. “There’s probably about 30-plus combined years of City Hall experience in those five candidates, not just years of experience, but also in leadership positions, multiple city council presidents, the chair of a department there,” he added. “The question for me is, Why are we going to the same people who have been in charge of the system — who enabled the system?”

Although Santiago has expressed support for reallocating money from the Boston police budget, he shied away from referring to his position as defunding the police. “I think that the term ‘defund the police’ is a term that has not served anything, anyone or any community,” he said. “I’m a person of color. I grew up in urban America for a number of years. I know what it feels like to be intimidated by cops,” Santiago noted, adding that he also sees the other side of the issue: “I understand the role that the cops do daily because I work with them in the emergency room. I see them each and every shift, and I respect the work they do.” 

Like the other candidates, Santiago is running as a progressive. But he is also pushing a message of unity and understanding across political differences. “I think we have a lot more in common with each other, and I just believe in this American pragmatism,” Santiago argued. “I want to bring a sense of belief that Boston is a place where things can happen, where people can come together and work to achieve and address these complex issues.”

Santiago said that he met with members of the Jewish community at the urging of some Jewish members of his staff. “Their issues are very much intertwined with everyone’s issues — housing affordability, transportation, equity, education, how can we fight for a city that is responsive, and that reflects all of our interests,” he noted. “I’ve developed relationships with them. I’ve knocked on their doors and spoken with their community leaders, and will continue to do so.” He said he spoke with Jewish day schools in the area about the challenges of operating during the COVID-19 pandemic. “We’ve been back in the community several times since then, to really engage them and to learn from them,” Santiago noted. 

John Barros announces his campaign for mayor of Boston, in a crowded Haley House Bakery Cafe, on Thursday, April 25, 2013. (Pat Greenhouse/The Boston Globe via Getty Images)

John Barros 

Although John Barros has never held elected office, he is the only candidate to have previously run for mayor — and the Boston Globe endorsed him in 2013. That race also had a historically diverse field, though it culminated with Walsh’s victory. Barrow joined Walsh’s administration early on to oversee economic development issues. “I’m not running to make history. I’m not running because I feel like I need to be elected as a Black man. I’m running because I feel like I am ready to help the city meet the moment,” he told JI. 

The economy is his expertise, and his main focus. He wants to “help our small businesses get back on their feet and get ready to help get our economy back in order, and then help to make the economy more inclusive, make those who are participating in the growth of our city more diverse,” he said. He also wants to prioritize creating Black-owned and women-owned businesses, and to “create opportunities for us to bridge the wealth divide gap in Boston.” He added that Boston faces many of the same challenges now as when he ran for mayor in 2013 — pandemic aside — but one major change is “the urgency is now different when you talk about transit and climate justice. It wasn’t part of the conversation back then.”

Barros’s political resume highlights his time as a community organizer, but he is also a small business owner himself. The son of immigrants from Cape Verde, in Western Africa, he owns a Cape Verdean restaurant called Restaurante Cesaria in Dorchester. “During the pandemic, we knew firsthand what it meant to try to survive as a small business and keep families employed. It was really difficult,” he said. “We had to make some tough cuts. The management left some paychecks on the table to make the right decision and try to keep the team in place.” 

In that role, Barros had to navigate thorny ethical issues. “One of the toughest things for the restaurant is, I was able to manage the direct relief program from city government to small businesses, but because obviously I was a part owner of that business, [the restaurant wasn’t] able to receive any assistance,” he said. He praised that program and the resilience of Boston’s restaurants: “Restaurants and other places provide meeting space, networking space, places for people to connect, and they are really an important backbone to our community building,” he noted. 

His parents came to the U.S. to build a life with better educational opportunities for their children, and he took their lessons to heart, becoming a community organizer at age 14. “I became a community organizer in my neighborhood, and started to do work in improving my neighborhood and improving the city,” he explained, later doing the work full-time and helping create urban parks and agricultural spaces. “I can’t say I’ve always wanted to be mayor. It is not true. I never thought I could be. I felt that government wasn’t for me, it was for someone else,” he said. 

Barros has also expressed support for reallocating funding from the police, but he told JI he believes police must be partners in reform. “I think I can work with police to get those reforms. I started working with police on police reform matters as part of the Walsh administration,” he said. “It’s work that you do by bringing police to the table and having the hard conversations about what needs to change, and that’s the only way it can happen. Because the police, like everyone else, have bargaining units, have contracts.”

Barros highlighted his opposition to antisemitism and a commitment to fighting hate crimes in the city. “The Jewish community has seen an increase in crime, and we have to stand up against that and be firm in a zero-tolerance policy,” he explained. “It is a threat to all communities if we don’t stand up for the hate crimes being perpetrated to other communities.”