The New Insiders of Boston Politics

Rachael Rollins. Steve Tompkins. Ayanna Pressley. An unprecedented number of black leaders are now in power. Does that mean Boston’s race problems are getting better?

Courtesy photos, illustration by Benjamin Purvis

In early October, when 55 young black professionals from 33 states arrived in Boston for a special NAACP “NextGen” leadership conference, City Hall wanted to make a good impression. And for once, it had a large cast of power players to spotlight: William Gross, the city’s first black police commissioner; Rachael Rollins, who had recently won the primary on her way to becoming Suffolk County’s next district attorney; and recently reelected Suffolk County Sheriff Steve Tompkins. Mayor Marty Walsh himself spoke at a swanky kickoff reception inside the private University of Massachusetts Club at One Beacon Street, and Ayanna Pressley, fresh off her victory over U.S. Representative Michael Capuano in the Democratic primary a month earlier, served as the main attraction. “The panelists opened our eyes to pathways we hadn’t thought of,” says Yolanda Melville of Atlantic City, New Jersey, who snapped a picture of herself with the new congresswoman from Dorchester and then made it the banner on her Facebook page. “I think there will be many of us who come back to Boston to contribute in some way.”

For decades now, such a sentiment has been almost unthinkable. Upwardly mobile black professionals have generally wanted nothing to do with Boston, with its largely deserved reputation for racism, segregation, and parochial hierarchies that have shown unique hostility toward black residents. Black business associations have long declined to hold their conferences in Boston. The future first black U.S. president, then the first black editor of the Harvard Law Review, high-tailed it to Chicago after graduating rather than build his career here. Black baseball players have insisted on contracts barring their trade to the Red Sox—allegations of the N-word being hurled at Fenway Park, including as recently as 2017, are just one possible explanation. The city’s racist reputation was even the subject of a deep dive by the Boston Globe Spotlight team in late 2017—and has become a semiregular punch line on Saturday Night Live. In short, accusations of racism have been a blistering retort to the city’s progressive self-image.

Only suddenly, there’s hope that we might finally be able to turn the page. Image rehabilitation, of course, was exactly the point of the NAACP’s October gathering here—but it’s just one step in a multipart plan. Walsh’s office is quietly but eagerly wooing the NAACP to bring its 2020 annual national convention to Boston, where it has not been held since 1982. Michael Curry, senior vice president and general counsel at the Massachusetts League of Community Health Centers and an NAACP board member, says it would be an opportunity to “reintroduce the city to people of color.” Pressley, for one, has become not just one of the leading faces of the Democrats’ diverse new congressional delegation—she’s the best marketing campaign Boston has ever had for one of its most intractable problems. And a successful solution, she tells me, depends on the city as a whole “being intentional about becoming a city that is inclusive and tolerant.”

The roster of black elected officials is the news that made headlines, but if you dare to be a reckless optimist for just a moment, you can see that signs of change are percolating all over the city, suggesting that this moment could be the start of a new chapter. “The conversation on diversity, race, and inclusion is everywhere,” says Cheryl Clyburn Crawford, executive director of MassVote, which registers and organizes voters in historically disenfranchised communities. “I think we are on the verge of something.” Black Bostonians are opening new businesses, guiding capital investment, and rising in management ranks as never before—all stated goals of the New Boston architects. “This is something that the mayor calls out as a priority,” says John Barros, the city’s chief of economic development. “The business community raises this often, when we talk about attracting talent and barriers to attracting talent.”

Transitions, however, are delicate times, especially when you consider the chasm between possibility and real change. “Boston is at an inflection point,” says L. Duane Jackson, a real estate developer and a board member at Massport. “The cosmos is aligned. The actors are in place. We can either recognize the potential of what can be, and alter the course significantly toward diversity and equity, or we can flatline.” Which will it be?

if the city gets this moment right, it might attract people like Pressley superfan Melville, a 33-year-old attorney in New Jersey by way of New York and Virginia. Her boyfriend, a Berklee College of Music graduate, teaches in Boston. They have had conversations about moving in together, which means choosing a city—maybe Boston, maybe Atlantic City, maybe someplace else entirely. For her, Boston isn’t defined by the 1970s busing riots, which gave America the iconic image of a white man attacking a black man with a flagpole on City Hall Plaza, or the 1989 Charles Stuart case, when police wrongfully trolled Mission Hill looking for a black man to blame for murdering a white woman. Melville doesn’t know that the last time the NAACP held its annual convention in Boston, the Boston Housing Authority was relocating three black families who had been firebombed after moving into a white Dorchester neighborhood. To her and many others, Boston is Pressley, and Rollins, and a world of possibility.

Still, Boston is trying to overcome a bleak reality, as a quick scan of the data will tell you. According to one study sponsored by state agencies, taken when Walsh became mayor in 2014, Boston ranked dead last among eight major cities for being “welcoming to people of color.” Among African Americans, it also ranked last in being seen as “progressive.” While nearly half of white respondents said they had lived in or visited Boston, just 20 percent of black respondents said the same. A mere 7 percent of African Americans said they would consider living in Boston, compared with 16 percent of Hispanic and 22 percent of white respondents.

Even worse, U.S. Census and survey data covering 2012 to 2016 shows that black millennials are far more likely to head to Atlanta, Houston, Miami, or even Baltimore than come to Boston, which fails to crack the top 10 most desirable metropolitan areas to relocate to among African Americans despite ranking fifth among white, non-Hispanic millennials. In fact, Curry, of the NAACP, says the current growth pattern of Boston could soon mean it will no longer be a “majority-minority” city. In other words, while we might think of ourselves as living in some kind of progressive wonderland, plenty of people don’t share that view.

Boston’s embarrassing record on race, long a moral problem, is now threatening to become a dire economic one, too. In the past, the city could thrive without a fair share of skilled racial and ethnic minorities, but demographic numbers suggest that will soon become impossible. The percentage of educated, trained, experienced minorities is on the rise—and, on top of that, white professional millennials and post-millennials are looking for diverse cities and diverse companies. Corporations see that and want to locate themselves where that full pool of talent will reside now and for years to come. “From a dollar standpoint, it’s a no-brainer,” Barros says. “We need to be that city, to make sure we attract that millennial talent.” That, however, would require change everywhere from boardrooms to bars, and while it is already happening to some extent, examples that lend themselves to an easy narrative can be hard to come by.

Take November’s election, which city leaders are now featuring front and center in their charm campaign. After the polls closed, Rollins, along with new state Representatives Liz Miranda and Nika Elugardo, went on WGBH’s Basic Black to criticize the lack of establishment party support they received as candidates. Elugardo went so far as to call the state Democratic Party “straight-up racist.” “The people of Boston are changing. That is exciting,” Rollins says. “The power structure is very much the same.”

Things get stickier when you look at entrenched leaders in finance, education, healthcare, and other fields where voters don’t get a say, but whose decisions dictate the tone of the city. “It matters who is in power,” says Andrea Campbell, the city council president. “Whether it is corporate power, political power, or economic power in this city. If that group predominantly represents a single demographic, it’s going to be difficult for people in my [Dorchester and Mattapan] district to feel connected or feel that they can have a place there.” Barros echoes this. “You can’t have upward mobility if you feel isolated in the city,” he says. “It can’t just be politics, it can’t just be business.” Citing the need for more opportunities in education, the nonprofit sector, healthcare, and the business startup ecosystem, Barros continues: “If there is going to be a tipping point, it’s going to be because of a lot of work being done in a lot of different sectors.”

There’s a cultural side to this, too. Many people of color just don’t feel welcome when they’re out and about, says Wynndell Bishop, a political activist who works at Emerson College. “The issue here,” he explains, “has always been mostly social, not professional, for young black men and women.” Nia Grace, the new owner of Darryl’s Corner Bar & Kitchen in the South End, says the same. Young black professionals are her primary customers, she says, and over the years she’s noticed a familiar pattern among new transplants: “They are so enamored and captivated by the growth of the city,” she says. “Then they recognize that it’s not spread evenly across the city.” There are certainly other establishments that cater to an upwardly mobile black clientele—Slade’s Bar & Grill and Wally’s Café in the South End, now joined by Savvor and others—but not enough.

In other words, shedding Boston’s reputation as a city where it’s less than great to be black is a taller order than any one election can fill. “It needs to happen at the midlevel, by nurturing and cultivating careers,” says David Halbert, who is running for an at-large seat on the city council in 2019. “It’s one thing to have diversity; it’s another to have genuine, real inclusion and integration.” Is what we’re seeing the start of a sea change, or just a drop in the bucket?

If you’re skeptical that Boston can really change, fair enough, but there’s one very good reason to be optimistic: precedent. Around the turn of the 20th century, the once-downtrodden Irish wrested political power from the Brahmins by turning out at the polls, making the city’s ruling class look a lot more like the people who lived in it. This Irish political order ruled for most of the century but has been in decline for decades—slowly giving way, election after election, to new political forces.

Also, not so long ago, Boston was able to shed its well-earned reputation for entrenched homophobia. (Remember when organizers of the South Boston St. Patrick’s Day Parade went to the Supreme Court to exclude the LGBTQ community?) It’s worth recalling, too, that it wasn’t just the moral imperative—or even the purchasing power of gay couples—that ultimately prompted corporate and government leaders to help reverse the city’s image. It was also the realization that coming generations would insist on living in cities, and working for companies, that welcomed their LGBTQ friends and relatives. Top-down efforts combined with bottom-up pressures, until—after many years of struggle—Boston reached a tipping point and became one of the premier gay-friendly cities in America. Something similar is happening now, many believe, with race.

The reason many of the black power brokers in Boston that I spoke with are feeling optimistic is because they see a growing insistence that change isn’t negotiable—and it’s coming from all corners of the city. “There is a groundswell of young energy that wants change,” Curry says. That’s coming not just from black residents, he says, but also from white progressives who have no desire to hold onto the old “pale, stale, male” leadership chosen by voters who came before them. And as millennial and post-millennial residents become more prominent, the demand to live in a city with good racial politics is only going to get stronger. “These young people, they’re not going to wait,” says Colette Phillips, president and CEO of Colette Phillips Communications. She recently selected her “Get Konnected! 25 Millennial Leaders and Innovators of Color” from a wide range of public, private, and nonprofit organizations in Boston. “They are fearless,” she says. “They are going to show up,” whether anyone makes room for them or not.

There is, however, a push to make space. For one, Walsh and Governor Charlie Baker have led an effort to grow the number of black-owned businesses. City Hall, especially, has expanded its programs, such as putting its first Small Business Center in Mattapan in 2017, and hosting a Black Millennial Conference in 2018. (Grace, for instance, was able to buy Darryl’s with help and guidance from the city, including the Office of Neighborhood Services.) The Greater Boston Chamber of Commerce has launched new efforts to boost black-owned businesses, including its City Awake program. The New England Venture Capital Association, under the leadership of Jody Rose, is also working with like-minded funders to back African-American entrepreneurs.

Increasingly, diversity has become a stated value for public institutions here that carries real weight. Massport, for instance, has made diversity a key factor in choosing developers—one of four equally weighted categories that are considered—in what’s being talked about as a potential model for the country. The new $550 million Omni hotel in South Boston, being built on Massport land across from the Boston Convention and Exhibition Center, has more than two dozen black investors, plus black-owned businesses involved with contracting, architecture, and management.

Which is not to say all of the city’s problems with race have been fixed. Make no mistake: Black residents I recently talked to still tell me about being unfairly pulled over by police, hounded by store security, or looked at curiously in high-end restaurants. But young black professionals also tell me they no longer feel as ostracized when they go out for drinks with colleagues after work, and don’t feel the same need to gather a large group to “occupy” a nightclub for their own safety. When the Celtics’ Kyrie Irving first moved to Boston in 2017, he was impressed by all the strangers who stopped to help when his car broke down in the rain. For the first time, Irving and other local black sports stars are increasingly praising Boston, not burying it.

Taken alone, each change is minor, though the data points supporting Boston as a more inclusive place are starting to add up. But as several people said to me, there will be one truly telling sign that Pressley, Rollins, and the others are part of a real change: when their examples are nothing extraordinary. “Every time someone like myself is able to cross this finish line in this city,” Grace says, “that’s momentum.”