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Senator Kirsten Gillibrand on Trump, Feminism, and Hitting Her Stride in Washington

Vogue: Senator Kirsten Gillibrand on Trump, Feminism, and Hitting Her Stride in Washington

By Jonathan Van Meter

It is a beautiful August morning in upstate New York, and I am driving to meet Senator Kirsten Gillibrand for lunch. Troy, where she owns a home, is a once prosperous, now struggling Hudson River town with harbingers of change on every corner: the lovely café opened by ex-Brooklynites; the elegant tea shop; the oyster bar run by a lesbian couple; a yoga studio. I am meeting Gillibrand at the Illium Cafe, a lively, unpretentious place with burgers and big salads. The senator often comes here for brunch with her husband, Jonathan, and their boys—Theo, fourteen, and Henry, nine. Today she arrives characteristically late (her staff roll their eyes at her inability to stay on schedule), with a young aide, a former Hillary staffer named Alexandria Phillips. Gillibrand is wearing a senator’s version of weekend casual: white jeans, a colorful paisley blouse, and a bracelet with a peace sign dangling from it. Once we are seated, I notice that her sandals are emblazoned with a discreet donkey logo, encircled by red, white and blue stars: Democratic Party flip-flops.

“What makes the Crazy Cobb salad crazy?” Gillibrand asks the waitress.

She thinks for a second and says, “The woman making it is crazy?”

This elicits a big, surprised laugh from the senator, and just like that, the two are yakking like sorority sisters at a reunion. (“I love your top!” “You do?”) Gillibrand has a knack for this kind of easy connection. She radiates concern for regular people, and in her interactions there is an actual, unperformed engagement that people pick up on everywhere. She is the very soul of approachability.

Indeed, a woman has suddenly approached. “I just want to say thank you,” she says.
“Awww, God bless you,” coos Gillibrand.

“God bless you.”

“Local?” asks Gillibrand with typical efficiency.

“Albany,” says the woman. “I’m a teacher, and my husband is a social worker. Thank you for your hard work and service to our state.”

“Oh, my privilege.”

Gillibrand tells me that she has been recognized more in the past six months than in the entire eight years since she was appointed to Hillary Clinton’s former Senate seat. “I’m not sure what it is,” she says. “Maybe it’s just seeped in more.” Or maybe it’s because she has voted against Trump’s Cabinet appointees more times than any other senator and has come out swinging on everything from the president’s statements on Charlottesville to his transgender military ban. In other words, she’s got newfound street cred among lefties and progressives who were unsure of exactly where she stood in Democratic Party politics.

But it is not just Democrats. Over the next couple of days I see others approach her and say some version of “I am Republican, and I really appreciate what you’re doing in Washington.” Even this afternoon, the day after Trump threatened North Korea from his golf club in New Jersey and scared the bejesus out of everyone with his “fire and fury like the world has never seen” voodoo, a frail, elderly Republican lady comes up to Gillibrand looking like she has seen a ghost. She wishes the senator “luck” in dealing with Trump and tells her she was “up all night” because of his press conference from Bedminster. As she walks away, Gillibrand shakes her head and mumbles almost to herself, “Oh, my God, everyone’s worried about North Korea. It’s not . . . it’s not good.”

Just a couple of weeks earlier, John McCain had his dramatic thumbs-down moment in the wee hours on the Senate floor, dooming that month’s health-care repeal that would have thrown millions off their insurance. “These are not small battles,” says Gillibrand. “I feel every voice matters. If the grass roots stops for a minute, we’re going to lose. We are only succeeding by the smallest margin, and on any given day, we could fail. And so many people would be harmed.”

All of the joy has drained from her face. “It’s a heavy feeling being in Washington,” she says. “There are so many important issues at risk. You’re in a fighting stance every day. Because the stuff that comes over Twitter is so horrible. The attack on the transgender troops: disgusting, disgraceful, outrageous. It’s just endless. And then you try to do your day job of finding good bipartisan work across the aisle. . . . You’re doing both all the time. I guess I would describe it as intense. Everything is very intense.”

Gillibrand’s intensity is in her news and radio interviews, her impromptu press conference on the Capitol steps, her speeches at protests, her Twitter feed. She is exceedingly direct and genuine for a politician, especially when speaking about sexual assault in the military, say, or paid family leave, both core issues for her. And she has a populist streak—she has argued for single-payer health care for a decade—that puts her closer to Bernie Sanders than to Clinton. Of course, she’s a quarter-century younger than Bernie and a more likable proposition altogether. “It’s flattering,” she says when I point out that she’s made every Democratic shortlist for 2020. Is the idea of higher office something she thinks about? “I’m entirely focused on 2018. Some of the worst ideas Trump has can be better blocked if we have a majority in the House or Senate or both.”

So I ask about her party—its fractiousness, the lack of a unified message. “I think when people worry too much about the party or the message, they’ve got the wrong focus,” she says. “The message comes from the grass roots and the people, not the party. The people matter most.”
Gillibrand’s friend Senator Cory Booker is also on everyone’s list for 2020. “I’m glad people see her as I see her: a person who has blown away the limited expectations set for her,” he says. “I have no idea what she wants, but would she be an amazing president? Absolutely. I say it all the time: You can’t lead the people if you don’t love the people—and she will go above and beyond for folks. I don’t know if America could hope for a president that cares and loves and works and fights for them more than she would.”

Cecile Richards, president of Planned Parenthood, says, “She came and spoke to our national convention this year, and she just got people on their feet. She has a personality and a drive that people relate to—people outside New York, and that to me is exciting.” Can she imagine Gillibrand running for president? “I can imagine Kirsten doing anything she puts her mind to.”
When lunch is over we head up the hill to Gillibrand’s house. It is nestled on a two-acre slope in a stately 1950s development where the lawns are verdant, the trees are enormous, and no two houses look alike. Gillibrand’s is a midcentury modern, with a kind of knocked-off Frank Lloyd Wright aspect. I arrive about fifteen minutes after her, and she greets me at the front door, which is painted purple, with her Labradoodle puppy, Maple, who sizes me up. “She’s shy around strange men,” she says, and hands me a treat.

Gillibrand’s living room is an undecorated glassy box with dark wood paneling, dominated by a brown leather sectional. A seventies vintage hi-fi stereo belonging to Jonathan, who is 48 and works as a financial manager, sits in the corner, with a sizable collection of LPs on a shelf underneath (mostly soul, disco, and New Wave). Gillibrand and I go out through the sliding glass doors into the backyard, which slopes down to a tennis court. Gillibrand played both squash and tennis at Dartmouth and is still, according to her chief of staff, Jess Fassler, who is sitting in the kitchen eating a sandwich, very good. (“She beats me every time, and it tears at my soul,” he tells me later. “She’s so competitive. Athletics are at her core.”)

As Maple pees in the grass, Gillibrand says, “The court has big cracks in it—see on the right side, there’s a big lump? So Jonny and I hit on the good side; we just pound the balls as hard as we can. I took Henry out yesterday and gave him a lesson. I desperately want to redo it, but it’s $50,000, so we can’t touch it.”

Back in the living room, Gillibrand (with Maple in her lap, chewing on her bracelet), Jess, Alexandria, and I talk for two hours. At one point I remind Gillibrand that she recently said Congress is 20 years behind the rest of the country on most issues, and she levels me with a comically weary look and says, “On its best day.”

Why is that?

“Because they’re in a bubble,” she says. “A lot of members of Congress are isolated. They tend to be affluent. They tend to have a lot of people doing things for them. So sometimes they don’t understand what their constituents are feeling.” As a House member and a young senator, Gillibrand did a lot of what she called “Congress on Your Corner,” traveling around the state, going to farmers’ markets and grocery stores and basically hanging out with people, listening to their concerns. I wrote about her seven years ago and was struck by how effortless it all seemed, and how much she genuinely enjoyed talking about soil conditions or listening to people moan about terrible cell-phone reception in some rural town. These days, she holds proper town halls—and wishes more congressional members did the same. “It’s part of your job,” she says. “Let people be angry, sad—speak to you directly.”

At one I attend later that evening, in a college gymnasium in Troy, there are hundreds of people; every seat is taken. Gillibrand sits onstage in a short-sleeved navy dress and white ballerina flats with a legal pad in her lap, taking notes while her constituents talk. When she comes to the mic, she is thunderous on energy issues that are germane to New York, and at her most clear and persuasive on why she thinks we need a buy-in option for Medicare. When she uses the phrase “Medicare for all,” a man in the back boos her. The room turns around and drowns him out with cheers. At one point a woman stands up to talk about all the hostility in the country between Democrats and Republicans. “What can you do to bring us together?” she asks. Gillibrand pauses for the perfect three seconds and says in her girliest voice, “I made dinner for Ted Cruz the other night,” and brings the house down.

Gillibrand was 43, freshly appointed, when I first met her; now she is 50. Back in the Gillibrands’ living room, I ask about her learning curve, and she is startlingly, refreshingly honest. What were those first weeks in the winter of 2009 like? “Like drinking from a fire hose,” she says. 

“Everybody was out to get us. Other House members were not happy that I was appointed. We were just taking in so much hate.” On top of all of that, she says, “I didn’t know how to do my job well. I didn’t know how to pass a major piece of legislation; I didn’t know how to get colleagues to support my views. It took a lot of asking for advice and learning. One of the lessons is that you have to be able to tell people why you care, and you’re only going to be able to do that if you talk to someone whom an issue is affecting. If you take the time to listen, that is the only way you’re going to be a good advocate. And I didn’t really know that.”

Fassler will tell me later, “Medical marijuana is the perfect example. She didn’t want anything to do with it, didn’t understand it, and then you put her in a room with moms whose kids have seizures without it, and she’s like, ‘Why haven’t we done anything about this?’ She’s been a changed woman on the issue ever since.”

But there is another side to this coin. “I also learned that people need to know you,” Gillibrand says. “They need to decide whether they’re going to trust you. People vote for me who don’t agree with me on all issues, but they trust my judgment or they trust my sense of what’s right and wrong, so they know I’ll do the right thing. That’s how I get Republican votes.”

And she’s gotten a lot of them—she won the House seat in a two-to-one Republican district in 2006 and had landslide victories across the state in both of her Senate races. She has since evolved her positions on gun control and immigration, which she’ll readily admit. “I was elected in a 98 percent white district, and there were a lot of issues regarding diversity and immigration that I wasn’t as sensitive to as I needed to be. On the guns issue, I didn’t have the understanding of how horrible and heartbreaking it is when a stray bullet hits your four-year-old while you’re in a park in Brooklyn. And when you hear that story, you know instantly that you’re going to do something. I certainly should have cared, and I should have informed myself just as a human being, but I didn’t.”

It was Gillibrand’s first signature issue, the repeal of Don’t Ask, Don’t Tell—and the eighteen-month campaign she waged to end it—that changed her stature in Washington. She took up the issue after she was approached by a West Point graduate named Lieutenant Dan Choi, who was being discharged from the National Guard for acknowledging that he was gay. At one point we are talking about why having women in Congress matters, and she tells me this story: “I was on a trip with John McCain, Joe Lieberman, and Lindsey Graham to Afghanistan and Pakistan and Iraq, and John said, ‘No one’s ever come up to me and said they wanted to serve while being gay. No one’s ever come to me and said this was a problem.’ And I didn’t disbelieve him, but why would they? Dan Choi didn’t come up to you to say, ‘Please fix this, this is destroying my soul’; he came up to me. Our lens is different. My presence in the Senate is meaningful because I’m going to have access to different problems.”

DADT was the first time Gillibrand’s colleagues began to realize how tough she can be. “She will go right up to anybody on the floor,” says Booker, “and just get in their face until they say yes in a way that sometimes makes me feel uncomfortable. She is singular in that way. She fights and fights and fights.”

Do you have a sense of what your Republican colleagues think of you? I ask.

Gillibrand looks at me with her spooky blue-gray eyes and says very quietly, “They like me.” Fassler begins making strange noises, like he’s squelching a laugh. “Uhmm, I would say it runs the gamut from like to grudging respect,” he says, smiling. Gillibrand waves him away and says, “I think they like me. But you should call them and ask.”

Which is exactly what I do. “Oh, yeah, I do. Sure I do!” says James Lankford, the junior senator from Oklahoma, with whom Gillibrand not only has introduced legislation but also attends a Bible study. “I like her and would consider her a friend in the Senate. She’s not difficult to work with. Now, she is relentless at times, where she’ll have a certain issue that no one agrees with her on and she’ll keep coming back over and over. . . .”

The next morning we all pile into an SUV for what Gillibrand and her staff call a “road show.” Gillibrand is on a mission to visit all 62 counties in New York State this year, and today we are driving through five of them. Along the way, she will introduce a couple pieces of new legislation and mingle with the good people of the Empire State.

The first thing that comes up is the senator’s complicated relationship to driving. “I don’t mind driving,” she says. “I drove the kids all day yesterday.” Fassler nods and says, “You prefer the minivan,” to which his boss says, “I love the minivan. I can’t harm the minivan.” At our first stop—a mostly deserted elementary school in Montgomery County, where Gillibrand introduces a piece of rural broadband legislation in front of a smattering of local press and muckety-mucks—Gillibrand notices a driver’s-education class under way. She barges in and talks to them for a few minutes, and when she comes out Fassler says to me, “Can you imagine? You’re sitting in driver’s ed and your senator comes in and tells you what a shitty driver she was when she was a kid. She did roll a Jeep when she was sixteen.”

For someone as decisive and athletic and brave as Gillibrand clearly is, she also comfortably inhabits some of the oldest clichés in the book about women, bad driver being the funniest and least among them. She is also self-sacrificial almost to a fault. To take just one example, she insisted that the air-conditioning stay on full blast during our seven-hour drive for the comfort of her male passengers, who were all in suits, even though she herself had on only a sleeveless summer dress. She is deeply maternal, mothering people everywhere she goes. Indeed, as I leave her house one evening, I find she has removed the empty soda cans from my car and put an ice-cold bottle of water in the cup holder.

One way to understand Gillibrand’s unusual mix of utterly modern woman and old-fashioned lady is through the women who raised her. “My grandmother was a strong woman; my mother was a strong woman,” she says. “I feel very comfortable around strong women.” From reading your memoir, I say, it seems your great-grandmother was also a bit of an iconoclast. “Yeah, she kicked her husband out because he was a drunk.” Her staffer Alexandria, who is sitting behind us, laughs. “I push Alex all the time to be stronger. I’m constantly telling her: Be tougher! Interrupt! Use your voice! Don’t let the boys overrule you! State your opinion!”

This, of course, is what makes the idea of a Gillibrand presidential candidacy so tantalizing: She is 20 years younger than Hillary Clinton and does not come with any of her baggage, in particular the endlessly complicated relationship with being a woman running—twice—for the highest office in the land. The feminist writer Rebecca Traister, who has written extensively about women’s liberation, not to mention profiles of Clinton and Gillibrand, sees this as a crucial difference. “Gillibrand understands that she is capable of presenting herself as feminine and maternal in a way that Hillary could never have done and still been taken seriously in politics. Women of Hillary’s generation were expected to excel in male worlds by conforming to male norms.” Gillibrand, who was born in 1966, followed a far more liberated path.

“We were the first generation of girls who were told, ‘There’s nothing you can’t be,’ ” she says. “We had a lot of freedom to own our ambition, to not be embarrassed by it. When my mother was a young lawyer, she couldn’t wear pants into court. There were certain conventions she had to follow. Embracing your femininity wasn’t really rewarded. Today, I think, young women can see those things as strengths, not weaknesses. I do see my gender as one of my greatest strengths: my ability to empathize, to listen, to really care what the other person is thinking and feeling as an important predicate for building consensus.”

We are moments away from the next stop, the Johnstown Historical Society and Museum, which is in the hometown of suffragist Elizabeth Cady Stanton. But just before we arrive, Gillibrand gets all heated up recounting the story from earlier this summer about the Uber board member David Bonderman’s resigning over a sexist remark. “He said something degrading about women on the board, like ‘They’ll never shut up’—some derogatory comment about women talking too much. He was being dismissive and sexist, but what he was referring to is true. Women do talk more! The truth is, it’s one of our assets: It takes maybe twice as many words, but we’ll get to the bottom of the problem!”

I tell her that as a kid, I spent a lot of time talking to my mother and not my father because my mother was talkative and my dad, not so much. “Henry is that way in our family. He takes all his cues from me, so he’s the communicator. You ask Theo, ‘How was your day?’ Good. ‘Anything happen?’ No. You ask Henry, ‘How was your day?’ ‘Well . . . we got to school, and my teacher decided we were going to do a project, and. . . .’ He will give you a 20-minute answer! That’s his nature: listens intensely, wants to know what I did all day long.” When she wants to find out what’s happening at home, she calls Henry. “Otherwise, they would tell me nothing and I would learn nothing!”

We pull into the parking lot of the museum, which is in an old clapboard farmhouse that looks like it hasn’t been touched for 100 years. It is hot and buggy, and there is a sizable gathering standing around in the backyard. At a dais set up in the grass with a small white awning pitched over it for shade, Gillibrand gives a short but surprisingly moving speech, one that feels like the bare bones of a stump speech. She talks about why national paid family leave matters, because without it the “workforce is stuck in the Mad Men era. I have a great bill that makes it affordable. Two dollars a day.” She pushes affordable day care and health care, and then she gets to the one thing that clearly matters to her the most: more women running for office. “Just imagine what it would be like if we had 50 percent of women in Congress? Imagine if we had a woman president.” A mordant chuckle ripples through the crowd, still smarting from Hillary’s excruciating loss. “Things would change, I promise you. There would be different issues raised, different solutions offered. And we wouldn’t still be fighting for access to contraception; we wouldn’t still be fighting for equal pay for equal work. These things would be done, foregone conclusions. Our economies and communities are suffering because we don’t have enough diversity in Congress. I think there is an urgency to this. But I’m very hopeful. Something’s changing. Frankly, we are the suffragists of our generation.”

Coline Jenkins, a descendant of Elizabeth Cady Stanton, steps up to speak about the coming anniversary of women’s right to vote, as that strange ever-present August hum of insects vibrates the air. “You are exercising your right to vote, to hold office in your own name,” she says to Gillibrand. “I’m very proud of you.” Looking a little choked up, Gillibrand says, “I’m proud to be your senator,” and Jenkins says, “I want you to be my president,” and the crowd erupts in laughter and cheers.

Our road show continues—three more counties to go—and at some point I realize that I haven’t asked Gillibrand about her faith. The question takes her back to the days she worked at a big corporate-law firm in Manhattan, feeling deeply unfulfilled. “I felt that I didn’t have a strong enough purpose. At the end of the day, every lawsuit was about money, so in my view, not for the greater good. I had grown up in Catholic school, got plenty of religious education throughout my life, but I hadn’t really homed in on it until then, until I was personally and emotionally lost, a young single woman in New York City. I started going to church and doing a lot of charitable work. And the more I realized what my faith was about, it made me really want to leave the big law firm and focus on public service. It also gave me a purpose that I hadn’t really clarified: that life is not about making money, life is not about self-aggrandizement, life is not about accruing things and power. It’s about being a good wife, a good mother, finding ways to help others who need your help. We all are called to something. I kept feeling like, This is my calling. I really have to serve others. I really have to use my intelligence, my education, my ability to be tough, to be aggressive, to speak out to take on the military or Donald Trump”—she starts to laugh—“or whomever I happen to be taking on at the moment, I have the strength to do that. And I’m not afraid. I am not afraid.”

Which is another way of saying that she’s at peace with losing—she’s not risk averse, which is a rare quality in Washington. “I take calculated risks,” she clarifies. “I measure. I assess risk very intensely. And then I make a judgment. When you play tennis as a kid, you’re going to win sometimes and lose sometimes, and you learn how to behave well under both circumstances. Such a great life lesson because if you’re not afraid of losing, you’ll take a risk—like running for office.” Pause. “Even though it’s a two-to-one Republican district.” Pause. “Even though I might get battered and bruised.” Pause. “I’ll run even if no one thinks I can win except for my mother.