When Renata Caines’s mother asked if she wanted to open a cannabis shop in Boston, Caines was immediately on board. “A family business would truly make a difference for us,” said 31-year-old Caines. But Caines had the feeling that “if we’re going to do this, we’re going to do this right.”

For Caines, that meant applying for an economic empowerment grant designated for those disproportionately affected by the war on drugs, hiring employees who have been hurt by the criminalization of cannabis and, ideally, opening the store in Roxbury — a neighborhood of Boston home to many of the city’s Black households, who have a median net worth of $8 compared with White families’ $247,500.

But under an executive order by Mayor Marty Walsh (D), city of Boston employees — such as Caines’s mother, who works at a city community center — cannot seek marijuana business licenses in the city. Caines and her mother now plan to open the store outside of Boston, a disappointment, given that Caines wanted her business to build generational wealth in her neighborhood, making sure that, as she put it, “the folks closest to pain are closest to power.”

“Racial justice is really important in a city like Boston, where we are a minority-majority city, and we haven’t seen the leadership to reflect that,” said Caines, who is Black.

But Caines was excited to learn that Boston would soon have new leadership. Once Walsh leaves his post in the coming months to serve as President-elect Joe Biden’s labor secretary — if Walsh is confirmed by the Senate — City Council President Kim Janey, a Black woman, will become acting mayor. For the first time, Boston will have a woman and a person of color in the role.

“Her win is my win,” said Caines, who lives in Janey’s district. “Some things have been legacies and overlooked because the people in power have been the same people in power. … It’s time for change.”

Although Boston is known for its educational institutions and is touted as a Democratic stronghold, the city is notoriously slow to make history when it comes to seats of power. A mayoral incumbent hasn’t lost an election since 1949; in that instance, the bar was low — the sitting mayor had served federal prison time while in office.

“Anybody you talk to who works in Boston politics says that there’s still an old-boys’ network,” said Erin O’Brien, a political science professor at the University of Massachusetts at Boston, whose research has found that Boston is middle of the pack when electing women and people of color to office. “Is it getting better? Yes. Is it getting better at a slower rate than other states? Yes.”

Boston is one of the two most populous cities (the other is Indianapolis) that has yet to elect a mayor who is not a White man, a particularly stark statistic, given that the city has been majority-minority for more than a decade.

Since joining the council in 2018 and becoming president in 2020, Janey, 56, a community activist from Roxbury, has helped lead the council through a variety of education and social justice policies — from prioritizing communities of color in the city’s grant process for cannabis licenses, to advocating for more affordable housing, to voting for deeper cuts to the police budget.

“Should Mayor Walsh be confirmed by the Senate, I am ready to take the reins and lead our city through these difficult times,” Janey wrote on Twitter following Walsh’s nomination. She has not said whether she plans to run once her time as acting mayor ends and Boston votes for a new mayor.

The city is poised to have a woman of color as mayor for the next four years, too; the race is already dominated by two millennial women of color, city councilors Andrea Campbell and Michelle Wu.

“Groundbreaking is one of the best words to describe it, but it’s also unfortunate that it’s 2021, and we’re having these types of conversations where these women could win,” said Alejandra Tejeda, a 23-year-old union organizer. Women and candidates of color have run for mayor before, Tejeda noted, but this is the first year a woman of color’s victory is so likely.

Tejeda is particularly impressed that Campbell and Wu announced their candidacies last fall, when Walsh was still considered a contender, unlike the many mayoral hopefuls now expected to enter the race. “Everyone else wasn’t willing to get past this establishment of Marty Walsh to go out for the community,” Tejeda said.

When mayoral candidate Wu, now 36, started on city council in 2014, she joined now-Rep. Ayanna Pressley (D-Mass.) as one of two women; there were only four people of color out of 13. Today, women and councilors of color hold a majority of the seats.

“When I first started having conversations for running for office a decade ago, the most well-intentioned mentors and advisers at that time told me it was a bad idea, because I would never get elected for reasons that were entirely outside of my control,” Wu said. “Boston didn’t have a history electing people who looked like me.”

According to O’Brien, lawmakers such as Pressley have helped pave the way for Boston’s political transformation. (As she put it: “Once you see one person do it, other people do it and consider it possible.”) In this mayoral race, she said, “it’s a success if women are running against women, because it suggests there’s not just one spot, ‘the women’s spot.’”

While both are liberal, Campbell and Wu distinguish themselves on personal story and policy focus — Campbell speaks often about police reform and education, Wu about climate change and small businesses.

Campbell, 38, a native of Boston who grew up in foster care, talks often about the way the education and mentorship she received at the city’s public schools propelled her to where she is. Her twin brother died at 29 in custody of the state Department of Corrections while awaiting trial.

“How do two twins born and raised in the city of Boston have such different life outcomes?” Campbell said. “I see this run and this race as an opportunity to finally confront generations of inequity that exist in the city of Boston.”

Wu, meanwhile, first engaged with local politics when, at 23, she became the caregiver for her mother, who lives with mental illness, and the legal guardian of her youngest sister; at the same time, she was opening a local business, a tea shop, to support the family.

“I’ve been in those ER rooms night after night, waiting for a mental health bed to open up or fighting for the resources for my sister’s schools … or trying to get a business open with so many barriers for everyday people, who didn’t have the money to hire a team of lawyers and consultants to help smooth the permitting process,” Wu said. “We have what we need to make change in the city, and we have to meet this moment.”

And perhaps the biggest change, women of color in the city said, is the need to address Boston’s racial inequity.

“There’s a national reckoning in this country right now when it comes to race and racism, and we’re feeling that locally, … but there’s also this parallel conversation in the city that latent racism doesn’t exist here, that police brutality doesn’t exist in the city of Boston,” Campbell said. “While Boston is the leader when it comes to higher-ed institutions, our hospital and health-care industry, … I’m also reminding folks that this city still continues to fail thousands of Bostonians.”

Toiell Washington, 23, is hopeful that Wu or Campbell would take major steps to address these inequities as mayor. “Up north, it’s not as blatantly racist as the South,” said Washington, a student at Salem State University and a co-founder of the political advocacy and education nonprofit Black Boston. “It doesn’t look like someone calling you a racial slur in the street. It looks more like you not having the proper access to health care, or when you do, people aren’t paying the same attention to you.”

Washington continued: “If one of [these women] gets into office, then it’s going to be a nice start to dismantling that system.”

And having a woman of color seated in the city’s highest role of power could help change not only policy, but also the makeup of other offices in power. “Once you start to have women serving in these offices, that really does have a cascading effect,” said Jane Swift, the only woman to have served as Massachusetts governor. “Having our first woman, mother, person of color serving as mayor of Boston will accelerate that trend exponentially.”

The true test, as Swift knows, comes once in office. Swift has urged the media to celebrate mayor-to-be Janey’s “firsts,” but then to move on to policy, rather than covering her personal life or the question of: “Can she have it all?” This type of coverage defined Swift’s political tenure in the early 2000s, she said.

“It helps that we’re also about to have a woman vice president who is also a person of color,” Swift said. “Perhaps even though Mayor Janey is a first in Boston, the ceiling has enough cracks and has shattered in enough places that while historic and something for all of us to be tremendously proud of, there’s enough experience by the media and the public that we all have figured out how to appropriately handle our excitement balanced by treating our expectations of her performance fairly.”

Swift recalled one moment when she was governor: She proposed holding a weekly Governor’s Council meeting by conference call rather than in person, because she was pregnant with twins and had to go on bed rest the last week of her pregnancy. “You would have thought in 2001 that I had proposed walking around in a Martian suit for all of the extraordinary attention and outrage that that episode caused,” she said. Swift ultimately held the meeting by teleconference — thanks to the support of the treasurer, a mother herself, who told her own father, a member of the council, to stand down.

Almost 20 years later, the scene looks different. Wu was the first sitting councilor to give birth while in office in 2014, and at times brought her newborn son to council meetings. She said she became “a connection point” for city employees who approached her to share the difficulties of no paid parental leave. With these stories in mind, she helped pass an ordinance for paid parental leave. “We’ve seen the energy for representation and connection to community really transform Boston politics in just a short period of time,” she said.

For now, with Janey set to be mayor, residents hope Boston politics will continue to transform under the direction of a woman of color, setting a new precedent for the way the city addresses inequities in policy and leadership.

Still, “in the same way racism didn’t end when Obama became president, racism is not going to end when one of [these women] becomes mayor, nor is sexism going to go away,” Washington said. “But it is a big start.”

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