On a warm summer day, Boston City Councilor Ayanna Pressley paces around in a small circle in Post Office Square, sounding off on Donald Trump. Dressed stylishly—pearls draped over a coral blouse—she bellows without a microphone to a crowd gathered around her. “Donald Trump wants to erase and white-out the gains made by workers!” she shouts, stabbing the air with her right finger and stepping down on black high heels. “By the LGBT community! By women! By immigrants! By people of color!” What starts as a few scattered hollers from the audience turns into a full-throated collective “Yes!” of outraged agreement. By the time she finishes her brief speech, the crowd of young, sign-wielding protesters is cheering wildly—they’re ready to follow her wherever she leads.
The next speaker, U.S. Representative Michael Capuano, has been standing off to the side watching her with hands clasped and a broad grin. “How do I follow that?” he jokes, stepping into the center of the circle in his boxy gray suit. It’s a good question. At the time, Capuano probably never thought he’d have to come up with an answer.
That was two summers ago—back when Pressley and Capuano were on the same team, trying to get Hillary Clinton elected president. Today, Pressley is still whipping up crowds, but now she’s aiming to get herself elected to Congress—ousting Capuano in the process—in what has become the most talked-about race in the state.
On its face, it shouldn’t be so fascinating. On policy, little differentiates Pressley from Capuano; they have different pedigrees, sure, but as outspoken progressives on the left wing of the Democratic Party, there’s almost no daylight between them when it comes to how they’d vote. Some have tried to cast the race as a sequel to Alexandria Ocasio-Cortez’s wild upset in her New York congressional primary against incumbent Joe Crowley—the most surprising result in the country so far this year—but in truth, that description doesn’t quite hit the mark. So what’s all the fuss about?
It’s not that the race is another bellwether of national trends or a referendum on the whiteness and maleness of our representatives—or at least not just those things. The real thrill of this contest is more local: It’s a direct challenge to the way we do politics here. By running against the popular 10-term incumbent, Pressley, a 44-year-old black woman from Chicago, has shaken up a local political establishment that she’d previously always worked within. She’s also broken with Boston’s long-ingrained protocol of waiting for an incumbent to retire, and in doing so has forced questions about what our liberal values are all about. Is loyalty to an ideological ally a “progressive” quality? Is identity representation more valuable than experience? Are passion and intensity important, or just political salesmanship?
For Pressley, the stakes are high—she’s spent her career building credibility with voters and the powers that be. She’s held staff positions with former Congressman Joe Kennedy II and Senator John Kerry, cultivated ties among Democratic leaders and activist groups, run for and won an open city council seat in 2009, and stumped for party candidates, including Clinton. Along the way, she passed up opportunities to run for mayor of Boston (in 2013) and lieutenant governor (in 2014). A loss here could upend her rocket-fueled trajectory.
Capuano, for his part, has been forced into the role of defending the way things have been done before. He’s brought in heavy-hitting endorsements from Mayor Marty Walsh, former Governor Deval Patrick, and Georgia Congressman John Lewis, among others, who have argued that the veteran lawmaker’s experience, relationships, and seniority have real value.
No matter who wins, the race will reverberate through the city, the state, and even the nation. The voters of the seventh congressional district—which includes much of Boston and Cambridge, plus Somerville, Chelsea, Everett, Randolph, and parts of Milton—are among the most liberal and Democratic-leaning in the country. It will be almost impossible not to read the result as a harbinger of what’s to come—both nationally, as Pressley has aligned herself with a rising tide of women of color fighting for higher office, and locally, as a Capuano win might serve as a cautionary tale for the next upstart who wants to challenge an incumbent. The September 4 primary will lead to a great deal of soul-searching about what it means to be a progressive in 21st-century Boston. And ultimately, what we decide will end up saying more about us than it will about the candidates.
At a glance, the contrast between Pressley and Capuano seems as simple as old versus new. A balding, 66-year-old, half-Irish and half-Italian white man from Somerville, Capuano certainly looks the part of Old Boston machine politics. One might mistake him for one of those somewhat regressive, socially conservative Democrats who still linger in pockets of the city but are increasingly outnumbered by New Boston progressives—a description that Pressley most certainly fits. The only problem is, when it comes to Capuano, it also happens to be mostly wrong.
When Capuano tells voters to look at his record, it’s not a dodge—his progressive bona fides are about as strong as they come. As mayor of Somerville, he stood out as a lefty reformer; as a member of Congress, he was a bulldog for workers’ rights, single-payer healthcare, and discrimination protections well ahead of the national Democratic Party’s move to the left. He helped make Somerville one of the first so-called sanctuary cities in the country in 1987. He spoke out against the invasion of Iraq in 2002, cosponsored a single-payer healthcare bill back in 2005, and created the Office of Congressional Ethics. Progressive Punch, a voting record database, gives him a stellar lifetime score of 96 percent. When he ran for U.S. Senate in 2009 (before losing in the primary to Martha Coakley, who then lost to Scott Brown), he was endorsed by Progressive Democrats of America. He even supported the Boston Democratic Socialists of America, sending a congratulatory video message for the group’s 25th annual awards dinner.
Capuano took many of these stances before there was much local institutional support behind him. Progressive Massachusetts, an influential activist umbrella group of 20-plus organizations that has endorsed Pressley in this election, didn’t exist when Capuano first got elected to Congress in 1998. Nor did Progressive Democrats of Massachusetts, Mass Alliance, Emerge Massachusetts, Raise Up Massachusetts, Our Revolution, Democracy for America, or 350 Mass Action—all of which have now become important in Boston politics. “Others that were here are gone,” Capuano notes. “The issues have stayed the same.” To Capuano’s longtime supporters, it’s almost inconceivable that progressives now talk about removing him from office—he was fighting for their causes long before many of them were eligible to vote.
Along the way, he’s shown a rare ability to combine take-no-prisoners rhetoric with collegial, back-slapping politics, to great effect. Though not a top-track House leadership figure in the vein of Massachusetts Democrats Katherine Clark, Jim McGovern, and Richard Neal (potential caucus vice chair, Rules Committee chair, and Ways and Means chair, respectively), nor a media star like Joe Kennedy III and Seth Moulton, Capuano has been a workhorse in Washington, especially under Nancy Pelosi’s leadership. To prove his clout, his campaign points to the funding he’s gained for the district, ranging from the Green Line Extension project in Somerville to the Whittier Street housing development in Roxbury. All of which might explain why his constituents weren’t exactly clamoring for his retirement—there’s plenty of deadwood in the Democratic Party, but Capuano ain’t part of it. But now that there’s an alternative, well, why not consider it? In the words of one voter I spoke with, Dorchester’s Rikibeth Stein (who likes both candidates), it’s “a nice problem to have.”
Pressley has long been one of the undisputed rising stars of city politics—mentioned alongside Attorney General Maura Healey and Boston City Councilor Michelle Wu (both of whom have endorsed her). And while she’s not exactly an outsider, she’s brought her own style to working within the political system here, openly weaving her identity into her politics: She’s made it clear that her experiences—as a woman, as an African-American, as the product of a difficult upbringing in Chicago, and as a victim of abuse—directly inform her policies and approach. She frequently points out that she was the first woman of color ever elected to the Boston City Council (as well as the only woman among 15 at-large candidates when she ran in 2009), and she started her tenure by convincing the council to create a brand-new committee for her to chair, on healthy women, families, and communities. “There is always more that we can do,” Pressley tells me. “There is always more that we must do.”
Even so, some lefty voters look at her record—supporting Hillary Clinton rather than Bernie Sanders in the 2016 Democratic primary, for example—and wonder where she stands. Pat Miguel Tomaino of Cambridge, for instance, is leaning toward Pressley but worries that she’s “not as progressive as Ocasio-Cortez”—even though the two have hatched a plan for “a progressive sub-caucus” within the 78-member Congressional Progressive Caucus if they get elected. But even though Pressley wasn’t in the Sanders camp, she speaks the new language of the ascendant left, peppering her speeches with phrases such as “old leadership paradigm” and “equity agenda.” More pointedly, she’s pushing the argument that race, gender, and class matter in political representation—or, as Pressley puts it on the campaign trail, “The people closest to the pain should be closest to the power.” But will that be enough to distinguish herself and unseat an incumbent as popular as Capuano?
Out of more than 60 yes-no questions on a Progressive Massachusetts questionnaire filled out by the campaigns this summer, Pressley and Capuano differed on just five. They are: Pressley wants to eliminate ICE, while Capuano does not; she agrees with limiting solitary confinement to 15 days and eliminating it for at-risk populations, while he wants to keep it only for protecting an inmate from the general prison population; he supports a federal job guarantee, while she is undecided; she opposes legislation making assault on a police officer a federal crime, while he voted for the Protect and Serve Act in May (explaining that it codified existing laws and did not expand them); and she would make Election Day a federal holiday, while he says there are better approaches to improving the voting process. And that’s all.
When I talked to supporters of Capuano and of Pressley, more than a few confessed that they’ll be happy to see either candidate head to Washington. Many told me they were considering voting for Pressley even though they’re perfectly happy with Capuano’s record. Others say they wish she was running against someone else—someone worthy of ousting. Polls have shown Capuano is ahead by about 10 percentage points, but that lead could evaporate if younger voters show up for Pressley. “I don’t know any supporters of Capuano who are under 40,” says Jonathan Cohn, a leading millennial activist with Progressive Massachusetts, who adds that his generation has “a mistrust of those who were in power for so long.” Older voters, even self-described progressives, believe in sticking with those who have been good to them; many are offended that Pressley is even challenging Capuano.
These days, it’s important to voters not merely what candidates say, but how they say it. They want passionate leaders who show the anger, frustration, and hope that they feel about issues. “The progressive base is getting more sophisticated in Boston,” says Kelly Bates, president of Boston’s Interaction Institute for Social Change. “It’s not just a litmus test on issues. It’s people who understand the interconnectedness of issues.” Pressley might seem to have the edge here, but Capuano counters that he’s been addressing interconnectedness and intersectionality since his days as a Somerville alderman, even if he hasn’t used the language now in vogue. “The terminology might change,” he says, “but not the concept—the idea that you want to address the whole person.”
Whether she wins or loses, Pressley will have made it unlikely that Boston incumbents can go nine reelection campaigns without facing a primary challenge—as Capuano did, before this year. In the end, a contest with so few policy differences and no bad blood always comes down to what we, the voters, project onto the candidates—and the image that voters want to see reflected back. Are we loyal to those who have served us well? Does legislative or personal experience matter more? Are we seasoned and savvy, or young and fiery? On September 4, we’ll all look into the mirror and find out.
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