A Seat at the Table

It was just afternoon on a chilly February day in Boston’s Beacon Hill, and the regulars were placing their orders at Emmets, the iconic Irish pub that has served both meals and gossip to State House politicos for generations. As an older gentleman tucked into his fish and chips, Wilnelia Rivera strolled in, her halo of dark curls emerging from the hood of her coat, and took a seat at the table.

The thirty-six-year-old Rivera, A04, AG14, knows the bar well from nearly a dozen years in Massachusetts politics. But unlike many other patrons, she’s hardly a traditionalist. As the chief political strategist for newly elected Congresswoman Ayanna Pressley, she defied the longstanding convention that rising political stars must wait their turn rather than unseat an incumbent. Instead, she organized a campaign that harnessed the frustration with Washington she sensed under the surface in a minority-majority district.

“Change Can’t Wait” was the slogan with which Pressley, a Boston city councilor since 2010, took on Michael Capuano, a ten-term Democratic incumbent with solid liberal standing. The district where they faced off is so unfailingly Democratic that no Republican ran, which made the primary essentially a battle between the party’s past and its future. Pressley captured 59 percent of the vote in a victory that the New York Times called a “political earthquake.” Pundits swooned over the news that a young black woman—and the first African American to represent Massachusetts—would hold the congressional seat once occupied by John F. Kennedy.

Pressley believes that Rivera’s unique acumen for identifying untapped voters was key to the win. “When you have someone who has a shared experience of being marginalized, of being overlooked and being underestimated, not only in this work but in life, they get that there are people and whole communities that are not participating” in politics, she said. “It’s not because they don’t care, but because no one has extended them a hand.”

J. Phillip Thompson, the deputy mayor of New York City and Rivera’s longtime friend and mentor, suggested that in Pressley, the young strategist found a candidate whose vision matched her own. “Ayanna Pressley’s campaign was intensely grassroots and the pollsters got it totally wrong,” he said, going on to observe that Rivera “was very confident that Ayanna was ahead in this race. And that’s because Ayanna was a candidate who shared with Wilnelia a commitment to really be accountable and engaged with residents at the grassroots level.”

At Emmets, Rivera nibbled on a french fry as she explained that the Massachusetts breed of politics is known for both its parochialism and its deference to relationships. “I have respect, but I’m looking to fly in the face of that playbook,” she said, pointing her thumb over her shoulder in the direction of the State House. “And that makes some people a little uncomfortable.”

But it also has them paying attention. Because wherever Wilnelia Rivera moves next will likely help shape Democratic politics, in Massachusetts and beyond.

Culture Shocks

The way she tells it now, Rivera wasn’t supposed to be born. Her parents had two daughters, ages five and six, and were expecting a third when her mother, Minerva Diffo, and the five-year-old were hit by a car. Both survived, but doctors failed to detect movement in the fetus and told Diffo she would have a stillborn child. A month later, Wilnelia was born, two months premature.

Then Diffo had to make a choice. She’d already relocated from the Dominican Republic to Puerto Rico to marry her husband, a war veteran and a successful architect, but, said Rivera, he was abusive to their family. So Diffo decided to move again. She left him, taking her two older daughters with her and settling in the working-class city of Lawrence, Massachusetts. Rivera stayed in Puerto Rico and was raised by relatives until she was eight. Then she joined her mother and sisters in Lawrence.

While it was odd, at first, to come to the US mainland and live with a family she had known only over the phone, Lawrence was “a little bit of a protective zone,” Rivera said. “English was something people spoke when they had to, but Spanish was all around us. I arrived in a different version of what I was already living.”

Rivera sponged up English in the Lawrence public schools and was tracked into its advanced classrooms. But academics weren’t all she learned. “I remember being a kid and internalizing the negative things people say about Lawrence,” she said. “It politicized me without my knowing.” She also conceived of a different kind of life for herself.

Her basketball coach gave her the first glimpse of towns outside Lawrence when he took her to college basketball games throughout the state. The counselors at Upward Bound, a college prep program for first-generation students, helped her navigate the college application process. And her math teacher, Susan Gerber, J71, AG74, nudged her toward Tufts.

Rivera was admitted to the class of 2004. Arriving on campus, she said, was an even larger culture shock than moving to Massachusetts and learning a new language. “You go from Lawrence to Tufts, it’s night and damn day,” she recalled. “It’s only an hour from home, but it might as well have been China.”
 

'An Island of Misfits'

Tufts exposed Rivera to a racial, religious, and socioeconomic diversity she had never known. Overwhelmed, she retreated into her studies, keeping up the grades she needed to stay on campus while buying time to learn how to navigate this new world. In a lesson that she has carried through to her policy work, she discovered the value of asking for help.

“I was proactive about avoiding the pitfalls that I knew first-generation students face,” she said. So, after getting her first C in a freshman English class, she approached the professor. “I said, ‘I recognize I have a bit of a learning curve, can you tutor me?’” She aced the course.

Rivera eventually hit her stride, pursuing a dual major in international relations and women’s studies and finding a group of friends she characterized as “an island of misfits”—kids with eclectic, nontraditional backgrounds. “We didn’t want to live in a world where everything was so sanitized, it’s just you and your tribe,” she said. “My friends were an adopted gay Jewish guy from Long Island, a Coptic Egyptian who was raised in Western Massachusetts, and a six-foot-tall Kansas-born Chinese immigrant.”

She also found a sisterhood in the Latina sorority at Tufts, Sigma Lambda Upsilon, and its national network of chapters. “I realized when I was at Tufts the deficits that I had—I didn’t have the circle that was going to get me a job,” she said. “I knew I had to find that infrastructure for myself.” And indeed, it was a Sigma Lambda Upsilon sister who encouraged her as she took her first job after graduation—at a training institute for community organizers hosted by the AFL-CIO in Chicago.

In Rivera’s three formative years in that city, her passion for social justice intensified, and others benefited from the savvy that had led to her own success. “I loved the intersection of political, policy, and community,” she said. She grew personally as well. Raised in a traditional Catholic household, Rivera had long grappled with her sexual identity. In Chicago, she became more comfortable with who she wanted to love. “I was one of those gay folks who had to crawl out of the closet,” she said.

Organizing in Massachusetts

Rivera returned to Massachusetts in 2006 and took a job with Neighbor to Neighbor, an organizing coalition committed to empowering underrepresented communities. She worked with immigrants, women, and working-class residents in communities like the one she grew up in, people who rarely get asked about their political interests unless a vote is on the line. She found it challenging but fulfilling, in part because the agenda was dictated by the people she served. Her friend and fellow organizer Malia Lazu pointed out that Rivera “believes in the power of love in organizing,” and added, “You have to believe in the people you’re organizing—that they’re as strong as the bankers or developers” they’re up against.

One of Neighbor to Neighbor’s major victories under Rivera was CORI reform, which makes it illegal for employers to ask about a person’s criminal history on an initial job application in Massachusetts. The group also galvanized frustrated parents to push the city of Lynn to invest in its struggling schools. Those efforts have yielded interpreters and translation services for parents who don’t speak English and a more inclusive environment for LGBTQ students.

Rivera’s leadership was “visionary and innovative,” said Thompson. “A lot of people get cynical about politics, because they’re asked to vote but then the elected officials aren’t really responsible.” Rivera, however, “developed ways of holding elected officials accountable, which keeps people interested in politics and engaged.”

Soon local political operatives were taking notice of Rivera’s triumphs. She got a call from John Walsh, then the chair of the Massachusetts Democratic party, as he was preparing for the 2006 gubernatorial race. “I was working very hard to elect Deval Patrick, and we recognized that Neighbor to Neighbor was doing the work to broaden participation in politics,” Walsh said. He recruited Rivera to use the coalition on Patrick’s behalf.

The candidate would be the first African American to be elected governor of Massachusetts, and the party faced an uphill battle. “The machine had galvanized behind the consensus that we needed to rally behind the next Irish guy,” Walsh recalled. “Finding an organization doing this work and Wilnelia at the forefront was an instant win. As I got to know her and the work, I found myself taking notes.”

Patrick won, and Rivera and Neighbor to Neighbor helped to re-elect him four years later. The climate was very different: the Great Recession had deflated the economy, the Tea Party was ascendant, and Scott Brown had taken the late Senator Ted Kennedy’s seat. But once again, she orchestrated a winning effort, thanks in part to the infrastructure she’d built with Neighbor to Neighbor. “It was the best coordinated get-outthe- vote campaign I’d ever seen,” said Walsh.

That experience, Rivera said, confirmed that her organizing skills afforded her real power. Yet power alone was not enough for Rivera. “I want to question the policy and power-building framework” in government, she said. And that led her back to Tufts, for a master’s degree in urban planning. Her studies gave her insight into the ingrained political structures in the state—and a knowledge of the tools she might use to upend them. “I want to do this work,” she said, “But I don’t want to be a sheep.”

The Pressley Campaign and Beyond

Rivera finished her urban planning degree in 2013 and joined the Patrick administration as director of external affairs. She also toggled between opportunities that seemed to be constantly coming her way. She served as campaign manager for John Barros’ mayoral race in Boston; pushed new education initiatives in Roxbury with RoxMAPP, a program that gives high school students a chance to take college courses; and sought rapid transit solutions under the aegis of the Barr Foundation, a top Massachusetts grantmaker. Then in 2015 she hung out her own shingle. Focusing on millennials, unmarried women, and people of color, Rivera Consulting Inc. has assisted with policy-driven projects in Cambridge, Lynn, and New Orleans. Currently the firm is serving such clients as Maimonides Health Care, which wants to improve health in Brooklyn, and pursuing sustainable urban revitalization for the city of Santa Ana, Panama.

But the biggest recent splash has been the successful campaign of Ayanna Pressley, who came calling in 2017. Rivera had been a friend of Pressley’s since her time with Neighbor to Neighbor and had served on Pressley’s steering committee in Boston City Hall. So when Pressley approached Democratic strategist John Walsh about running for Capuano’s seat, she already had at least one idea about who should be on her team. “The first name on the top of both our minds was Wilnelia,” said Walsh.

“I knew she would bring a movement-building philosophy to the campaign,” Pressley said in February, shortly after a meeting with her new constituents in Cambridge. But would Rivera take the gig? “I knew what would be possible if we had her, but I was not optimistic that she would say yes,” Pressley said.

She needn’t have worried. “Ayanna’s exactly what I thought the district needed,” Rivera said, and in fact when Pressley struggled with second thoughts—aware that “this was a very disruptive campaign and a lot of people were unhappy about it,” and feeling “a sense of protectiveness for political professionals”—Rivera was the one who pushed her to make her run official.

She did it with a gift. The two women shared a role model in Shirley Chisholm, the first African American woman in Congress, who famously said, “If they don’t give you a seat at the table, bring your own folding chair,” and Rivera had a framed portrait of Chisholm that she had carried with her from desk to desk throughout her career. The night before Pressley was planning to announce her candidacy, Rivera presented her with the portrait. “Shirley deserves to go home,” she told her friend.

In the ensuing campaign, Rivera’s approach to securing voters was unprecedented, according to Lazu. Most teams concentrate on “super voters,” citizens who routinely turn out for primaries, she explained. The logic is that reaching for anyone else would be prohibitively expensive. By contrast, Pressley’s only television ads ran on the Spanish language networks Univision and Telemundo, where relatively few super voters were likely to encounter them. “What Wilnelia said is forget traditional campaigns, because we don’t win that way, we win when we organize,” Lazu said.

And they did. Rivera said that on the day of the primary, her team knew they’d won at 3:30 p.m., because the turnout numbers in key districts were so much higher than they’d ever been. “Those are our voters,” she remembers thinking. Later tallies showed that the number of Latino voters went up by 72 percent. A little more than 49 percent of the people who came out to the polls had never voted in a primary. Some reports, Pressley said, now indicate that the campaign helped grow the electorate by 54 percent. “I was crying outside the room and feeling my heart beating out of my chest,” Rivera said of election night, her eyes welling up again at the memory.

Pressley arrived in Washington in a sea of progressive candidates. But she was the one who got Shirley Chisholm’s old office.

Rivera, meanwhile, is continuing Chisholm’s legacy in other ways. She is taking the first steps to create Shirley’s Table, a political action committee working to inspire the next generation to organize campaigns, oversee legislative agendas, and raise funds. She’s starting a podcast, Deep Democracy, to interview movement builders and organizers. And she has a growing list of clients who are seeking gender and reproductive equality. She isn’t certain whether she’ll have a hand in any 2020 campaign, but she hopes people will draw on the resources she’s making available.

“I want us to have a stake in each other,” she said.

Janelle Nanos is a business reporter at the Boston Globe, covering retail, restaurants, and consumer culture.