He extended one through politics. In high school, De Blasio was a student-government geek; in college, at NYU, he became a leading activist, helping form the Coalition for Student Rights, which rallied to protest tuition hikes and organized an overnight sit-in of Bobst Library to demand that it stay open later. He also argued for the superiority of Talking Heads over Blondie with an NYU roommate, Tom Kirdahy. “Bill was very smart but very funny,” says Kirdahy, who remains a friend. “And he had a crush a week.” De Blasio’s interest in politics, and the underclass, deepened as a grad student in Columbia’s School of International and Public Affairs, where he shared one class, in Latin American politics, with Dan Cantor, who years later would team with De Blasio and others to launch the Working Families Party. He soon made two other pivotal friends and mentors: Bill Lynch, the wily Harlem political consultant who masterminded the winning 1989 mayoral campaign of David Dinkins, and Harold Ickes, the combative second-generation Democratic insider. De Blasio volunteered for the Dinkins campaign, then was hired as a coordinator of volunteers; in City Hall, Lynch hired him as a junior aide in community affairs. De Blasio says he learned how not to run an administration during the four tumultuous Dinkins years—“The organizational structure was divided, and there was a real lack of unity, a real lack of singleness of purpose a lot of the time”—but the most significant personal event during that period was meeting Chirlane, a press-office staffer in the Commission on Humans Rights.
De Blasio was persistent; McCray was reluctant. After a few months, she handed him a story she’d written for Essence about being lesbian. De Blasio wasn’t dissuaded. They were married in 1994, in Prospect Park, by a pair of gay ministers; McCray was three months pregnant with Chiara. “The fact that my parents’ marriage turned out so badly was not a great recommender of how easy it was to get it right,” De Blasio says. He tried psychotherapy in his mid-twenties, attempting to sort out his feelings about family. “I took a long time to believe,” he says. “And it’s absolutely connected to meeting Chirlane. That’s what finally made me comfortable, was finding a soul mate, finding someone I could believe that I could actually work it out with. And I was right.”
As his own life has become more public, De Blasio has propelled his family into the spotlight with him. Having cheery, mixed-race kids has paid political dividends, but De Blasio claims his motivation is educational as much as anything else. “You have to understand our family is different in the way we think about things. Chirlane and I met in City Hall; we had both had a history of activism,” he says. “We talked about it in broad ways; it was unspoken that we were going to pursue not only our love, our relationship, but our commitment to the world, and that was going to be a given in our lives … These are kids who, by the time Chiara was 5 and Dante was 2, they had slept overnight in the Clinton White House. [The kids] both got so much out of this experience this year, they got some real-life lessons about how the world works, but they also gained a lot of strength, a lot of confidence, a lot of understanding.”
De Blasio believes that his family would have become media fodder whether they were a prominent part of his campaign or not. And it’s true that everything about this family, as normal as it is in many ways, is inescapably political. Even the house. In 2000, when De Blasio decided he wanted to run for City Council, they moved one block so he’d be a resident of a district with an open seat. Chirlane still loves the neighborhood, but she disdains what she thinks the Bloomberg era has done to it. “The nursery school Chiara and Dante went to, both of them had fairly diverse classes—economically, racially. That was the cool thing. The two mommies, and Asian, and black, and Latino kids,” she says. “That’s not the case now. It’s gone the way of the mom-and-pop stores. It’s wealthier and whiter.”
Now the family may be relocating to the Upper East Side. McCray’s memory of one visit to Gracie Mansion is still vivid. She remembers going to a reception there in 2006 for council members and spouses. Chiara de Blasio—now 18 and a sophomore at a college in Northern California—had just begun middle school, and Bloomberg’s Department of Education had instituted a ban on student cell phones. McCray approached the mayor. “I said, ‘Mayor Bloomberg, you are my hero! Because you instituted the smoking ban, which is so important and has done so much for people who have respiratory problems in this city and for our children. I want to thank you for that. But the cell phones in the schools’—and as soon as I said the words cell phones, he turned his back and walked away from me,” she tells me. “I was so shocked. I had never had that experience before—someone just turning and walking away like that! Bill shook his head and said, ‘That’s just how he is.’ ”