THE DYNAMIC BLACK WOMAN was well into her 40s and had been working in the trenches of government for years when she shocked the nation with her historic election to Congress, yet that didn’t stop people from labeling her an overnight sensation. She commanded attention by defying the odds, having taken on the establishment of her Democratic Party as much as she took on her opponent. Not only did she refuse to wait her turn, but she creatively forged a new kind of coalition that energized voters out of their apathy and proved the wisdom of her impatience.
And when Shirley Chisholm became the first black woman elected to Congress, she made it clear she was just getting started.
Chisholm’s stunning win in New York in 1968 came six years before Ayanna Pressley was born, and more than a dozen years before the bookish girl would put on her best church clothes and a set of fake pearls and strut around her bedroom pretending to deliver a speech like her congresswoman idol. It came more than four decades before Pressley, by then a Boston city councilor, opened the scrapbook of personal poetry and favorite passages that her rock of a mother had secretly put together for her before succumbing to leukemia, turned to the last tab marked “For Inspiration,” and found a collection of Chisholm’s writing. And it came exactly a half-century before Pressley channeled her idol to make her own history as the first person of color elected to the US House of Representatives from Massachusetts, defying the odds and the wait-your-turn directives of the Democratic establishment on her way to toppling an overwhelmingly favored incumbent. (Adopting Chisholm’s motto, “If they don’t give you a seat at the table, bring a folding chair,” Pressley often wears a lapel pin that reads “BYOC.”)
Still, this whole first thing can be tricky.
The holders of the distinction are proud to have broken the barrier, of course, to bring others joy and to be the shoulders that future leaders will stand on. But they also recognize that, no matter what they go on to do, the first sentence of their obituary has already been written. The goal for them becomes getting enough done to expand the scope of that first line — to add even more nouns and verbs of significance to their biographies.
“I’m a first in my own right, but I’m not the first first,” says Pressley, whose new Capitol Hill office will be Chisholm’s old digs. “It is both a blessing and an honor, and also a unique burden and responsibility, and that’s really what I wake up to every day.”
Alex Cora spent the last year balancing those same blessings and burdens while managing the Red Sox. It started when he got the job — the first person of color to lead the team in the history of a franchise particularly burdened by the sins of the past. Showing little desire to negotiate salary perks — he accepted the low end of the pay scale — he focused on securing a commitment from Red Sox ownership to fly relief supplies to his hurricane-ravaged hometown of Caguas, Puerto Rico. While he took satisfaction in the Puerto Rican pride his appointment unleashed, he made it clear none of it would matter unless he did his job well. In Boston, he and everyone else knows, that means delivering a World Series.
BEHIND-THE-SCENES AT THE COVER PHOTO SHOOT
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Cora did that and more, injecting into his job a refreshing blend of humility, risk-taking, honesty, and accountability, and working to be an effective bridge between players and management. (The team’s principal owner also owns the Globe.) In the process, he became only the second Latino manager in baseball history to bring home a World Series trophy — and the first manager in Sox history to do it as a rookie.
Despite all that success, Cora lives by the Spanish expression No me creo la película, which essentially means I don’t believe the hype about me. “This could all go away,” he says. “I’m not pessimistic. I’m just realistic.” He doesn’t need to look far for sobering reminders. The last two guys to win the Series in their first year managing the Red Sox were eventually shown the door. Ozzie Guillén, who became the league’s first Latino manager to win it all when he led the Chicago White Sox to victory in 2005, is a close family friend. “He’s a great baseball man — and mind,” Cora says. “He’s not managing now.”
As long as Cora is the guy in the hoodie calling the shots in the dugout, he will keep his eyes fixed on the future. As with Pressley, the chase for more nouns and verbs goes on.
For blazing a new style of leadership that is bold yet inclusive, innovative yet respectful of the past, risk tolerant but grounded in smart strategy, Ayanna Pressley and Alex Cora are our Bostonians of the Year. Although they work in different spheres, they share a determination to be not just firsts, but firsts with a purpose.
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ALEX CORA WAS ALMOST 13 when his father died. He revered the man who had taught him pretty much everything he knew about baseball — and life. Understandably, he was devastated by the loss. But at the funeral he refused to let himself cry. Afterward, a man approached Alex to compliment him on his stoicism. “You acted like a man today,” the guy said. As an adult about a decade later, Cora saw a psychologist for help getting through a family crisis. When he related that experience from his father’s funeral, the psychologist told him, “The worst thing you did that day was you didn’t cry.”
Now 43, Cora says: “That was a big lesson in my life. I don’t hold in emotion.”
Emotional intelligence is a cornerstone to his leadership. He can empathize with the people around him without losing sight of the job he was hired to do. Players appreciate his straightforwardness when he has to tell them they’ll be riding the bench or deliver other unwelcome news. On the one hand, he says, “They’re making a lot of money,” so they should be able to take disappointment in stride. But he also remembers what it felt like to be an underused utility player. “Toward the end of my career, on a team of 25, I was either the 24th or 25th guy. But I always wanted managers to be honest with me.”
That understanding of the role emotions play in performance extends to his own psyche in his current job. When he moved into his office, one of the walls was covered with photos of previous Sox managers. As much as he respects his predecessors, he took down all of their photos. “Who wants the reminder that you’ll be on the wall one of these days!”
He also makes sure there’s more than baseball in his life. He and his fiancée, Angelica Feliciano, and their 1-year-old twin boys split their time between Chestnut Hill and Puerto Rico. He also remains in close contact with his 15-year-old daughter and 23-year-old stepson from his first marriage back in Puerto Rico.
At key times during this year’s playoffs, especially when Cora stuck with struggling closer Craig Kimbrel, even a fan base that implicitly trusted the manager’s steely gut began to have second thoughts. Against the Astros, when a trip to the World Series seemed tantalizingly close, Cora’s decision to hand the ball to a shaky Kimbrel seemed to trigger a massive collective groan from Red Sox Nation. Sports personality Bill Simmons tweeted, “I wish I believed in anything as much as Cora believes in Kimbrel.”
When I remind Cora of the panic that was setting in among the fans, he laughs. “We asked a lot of him. He got us six outs.”
Cora’s innovative “rover” approach — strategically using his starters out of the bullpen — broke enough norms in baseball to have the guys in the broadcast booth reaching for the Mylanta. But the willingness of all the starters to step up at any moment underscored the culture of genuine teamwork under Cora.
I tell him the first time the Globe Magazine named a Bostonian of the Year was 2004, when Theo Epstein got the nod for helping the Sox reverse the 86-year-old curse. At the time, Epstein told me he saw 1918 “as the end of the first era of Red Sox dominance. They won five World Series from 1903 to 1918. They were a dynasty. It would be terrific if we could get back to that.” His aspiration seemed just south of ridiculous. Yet if Cora can lead the team to another title next year, the Sox will have exactly matched their dynastic record from a century ago.
His goal is nothing less. “No one has repeated since the Yankees in 2000, but it can be done.”
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AYANNA PRESSLEY WAS raised by a single mother who invested her hopes and ambitions in her only child. Sandra Pressley would remind her daughter there was a reason she was born during Black History Month. “My mother said that God did that on purpose,” Ayanna recalls, “because it was ordained that I would make history one day.”
After her mother died, in 2011, Pressley embraced the belief that we absorb the best parts of our loved ones. “Every time there’s a big milestone, I feel her presence,” Pressley says. “But her absence becomes even that much more pronounced.”
I ask her what parts of her mother she feels she absorbed. The 44-year-old says, “I don’t think I’m an incredibly brave person, so I think anytime I do anything, that’s brave.” (Taking on a 20-year-incumbent against the wishes of party leaders might qualify as one example.) Also: her mom’s love of language — and her clumsiness. “Every time I trip or spill something, I say, ‘Hi, Mom.’ I know that’s her showing up.” (Pressley lives in Dorchester with her husband, Conan Harris, and her 10-year-old stepdaughter, who coincidentally is named Cora.)
There’s one more trait that may surprise anyone who has seen Pressley electrify a room at the podium and assumes she is always on. “I’m an only child, and I was someone who spent a lot of my time with my head down in a book. I was personable but not always sociable,” she says. “My mother was always very sociable. Every now and then, I bring some of that forward, and I know that’s her showing up.”
I was with Pressley on election night, when she seemed nothing but sociable while working a room full of supporters at the Fairmont Copley Plaza. She would do the “selfie shuffle” — walk two paces, get stopped by a fan, offer a warm hug, pose for the camera — and then repeat the sequence, over and over.
But when we moved into a backstage area where Democratic pols gathered before or after addressing the main crowd, I saw a different Pressley emerge, one who resembled the studious child she once was. While most of the other headliners made the rounds, boisterously chatting with each other and aides, Pressley exchanged hi’s and hugs but, for more than an hour, largely kept to herself in the corner. She was easily the most talented orator on the night’s bill — with a few exceptions, the competition was far from stiff — but she was also the one who spent the most time backstage painstakingly editing her speech. “Trying to get it just right for the moment,” she told me at one point.
When she finally took to the podium and immediately lit up the crowd, I wondered how surprised people would be if they had just witnessed the quiet, studious version.
It’s hardly the only surprising thing about Pressley. Because of who she is and the climate in which she ran, some people dismiss Pressley as little more than a practitioner of identity politics. In reality, she wisely uses her experience — as a sexual abuse survivor, as someone whose father battled substance abuse and was in and out of jail — to convey her authenticity rather than to claim title to the seat simply based on her race or gender. She also works hard to be inclusive rather than divisive. She was so skillful at reaching out that I probably shouldn’t have been surprised when scrolling through social media on primary night to see her receive huzzahs even from some Donald Trump defenders. One tweeted: “She follows me. She is now my favorite Democrat. Congrats.”
While some critics have accused her of filtering everything through her lens as a black woman, she says, “It’s not just about my lens. It’s about the people I listen to,” whether that’s a bicyclist trying make the roads safer or a restaurateur trying to keep a small business afloat or a parent trying to cope with the loss of a child to gun violence.
“I am a consensus builder,” Pressley says. “To build coalitions is inconvenient. It is much easier to just surround yourself with a completely homogenous network of people who drink your Kool-Aid.” But groupthink produces terrible policy.
* * *
WHEN SHIRLEY CHISHOLM DIED, in 2005, the first line of her obituary in The New York Times pointed out that she was “the first black woman to serve in Congress and the first woman to seek the Democratic presidential nomination.” Yet the article failed to mention most of her biggest achievements in office, from helping to launch the Special Supplemental Nutrition Program for Women, Infants and Children (WIC) and expanding opportunities for women through Title IX legislation, to cofounding the Congressional Black Caucus and the National Women’s Political Caucus.
Chisholm seemed to anticipate this treatment decades earlier when she responded to a schoolgirl’s question about what it felt like to be a first. “I have mixed feelings,” she replied. “I’m very glad to make history in this country being the first black woman [but] I don’t get terribly excited about it.”
The opening line of her obituary may have been preordained, but the Times concluded the piece with one of Chisholm’s own quotes: “I’d like them to say that Shirley Chisholm had guts. That’s how I’d like to be remembered.”
Ayanna Pressley and Alex Cora still have lots of time to build on their remarkable starts. But this much we know: Some version of that same closer would already apply to both of them.