Off the Sidelines

by Kirsten Gillibrand

  I also called my sister, Erin, to discuss it. After I told her that I was thinking about running for Congress and that I didn’t have a great chance of winning, she asked the real question: “Why do you even want to run?”

  The two of us are wired very differently. She’s an amazing natural parent; I need her guidance at times. She’s now a yoga instructor, and before that, for work, she built a pirate ship in Baltimore Harbor, near where she lives, and rented it out for kids’ birthday parties. But since that bonding moment in my early teens, we’d been sharing our truest thoughts and offering advice and unconditional love, so I told her that I felt like I needed to do more with my life. “I’m worried that when I die, God is going to ask me why I didn’t do more,” I said.

  Erin didn’t laugh. She just pointed out all the good I was doing already—for Theo, Jonathan, our family, my church, the charities I supported. But I explained that I felt like I had a wider circle of accountability, more people I needed to help, and that brought her around. Sure, she thought that I was a bit crazy. Erin would not run for elected office for all the money in the world. She dedicates her focus to a tighter, more tangible circle. But she knows me, loves me, and accepts me as I am, so she supported my election bid. To this day she talks about both of us working in the trenches. “Being a stay-at-home-parent, like being a politician, is a dirty job,” she said. “But somebody has to do both. It helps if you have affinity for and love what you do.”

  Finally, I called Hillary Clinton. She telephoned me back one winter afternoon when a friend and I were driving home from pitching my election bid to the ten county chairs of the 20th Congressional District.

  We pulled over to the side of the road so my cell wouldn’t drop the call. After some small talk, Hillary got to the point. “What district are you thinking of running in?” She listened, then asked, “Who are you running against?”

  Hillary was very concerned that my district was heavily Republican and that my opponent had a reputation as a mean guy. She never stated her opinion on my candidacy directly. She just asked a lot of questions that I didn’t have great answers to: “What about the baby?” “What about Jonathan?”

  When I hung up, I knew that she thought I should wait. A race in 2004 was premature and most likely unwinnable. Eventually, Jonathan and I agreed that Hillary’s instincts were right.

  To make sure I’d be ready for the following cycle, I enrolled in campaign-training school. Yes, these schools exist, and anyone can go. Most take place over a weekend and cover subjects such as how to raise money, talk to the press, build a field plan, get out the vote, what to wear and how to present yourself. In 2003, the summer before Theo was born, I attended the weeklong Women’s Campaign School at Yale. Even there, I felt slightly awkward standing up and saying, “I’m considering running for Congress,” because maybe only 10 percent of the women attending intended to be candidates themselves. Most planned to staff campaigns, working in finance or communications.

  At the Yale training, I learned how to stay on point, how to look poised and confident, and how to keep a smile on my face even if a reporter asks a question and inside I am thinking, “Holy shit, what should I say?” I learned that you don’t need everyone to like you and you shouldn’t waste your time trying. You just need 50 percent of the voters, plus one.

  I did a second school in the summer of 2004, through the Eleanor Roosevelt Legacy, where I learned more about organizing contacts and creating circles of supporters, from closest friends on out to acquaintances. There, I met Sam Barend, a twenty-five-year-old running for Congress in the Southern Tier of upstate New York. She was confident and excited, and I wanted to be campaigning alongside her. The third school I attended was run by the Women’s Campaign Fund. There I met Jeanine Pirro, a Republican who was campaigning for attorney general. She famously lost page ten of her announcement speech and took a full thirty seconds to regain her composure, and although I didn’t support her candidacy, my heart was right there with her. Both women lost but weren’t broken by it, and that also felt instructive. I still feared how painful and embarrassing it would be to campaign and lose.

  As I passed on the 2004 cycle and waited for the next round, in 2006, I kept my hand in politics. Through Theo’s infancy, I fundraised for John Kerry and built my credibility with the doyennes of the Democratic Party. My biggest project was starting a new group under the Women’s Leadership Forum for young women interested in politics, called the Women’s Leadership Forum Network. I identified more than a dozen terrific young women to be on our board, placing one woman in charge of events, another in charge of policy, another in charge of outreach. I wanted each to have an important position in order to hone her leadership skills. The Women’s Leadership Forum Network raised money, hosted debate-watching parties, and conducted speaking and advocacy training sessions. (Silda Spitzer attended one before her husband was elected governor, and that’s where I began to respect and admire her.) I took as my job convincing higher-ups in the Democratic Party that young people’s participation was just as important as older people’s, even if the young ones wrote smaller checks. Our group had so much energy and so much potential that I was able to wrangle us up lots of invitations and credentials for the 2004 Democratic National Convention in Boston—hard tickets to get. Theo was eight months old at the time, so I brought him with me. While he strolled along the Charles River with a babysitter, I pumped and dumped breast milk in the hot, sweaty convention center ladies’ room. If you haven’t been to a political convention, they’re just like big sporting events, except they’re several days long and the entertainment is a parade of droning political speeches instead of athletic games. (Envious yet?) The women who traveled with me were younger—no kids yet—so each evening when I returned to the hotel with Theo, they headed to the parties. I even left them at the Fleet Center on the night of the keynote address, while I went back to my hotel room to watch the young Barack Obama on TV. I was so inspired and exhausted that I started crying and whispered to sleeping Theo, “This is such a good speech.”

  After the 2004 elections, Jonathan and I started looking again at a 20th Congressional District race. True to character, Jonathan wanted to see a business plan, a navigable road to success. That meant we needed a poll.

  I called Jefrey Pollock again and asked him to collect data on a possible 2006 race, me versus John Sweeney, a four-term Republican incumbent. Sweeney was a tough campaigner with real financial backing. He’d helped trigger the so-called Brooks Brothers Riot that shut down the recount in Florida during the 2000 presidential election, earning the affection of President Bush (as well as the nickname Congressman Kick-Ass). But Sweeney was dogged by rumors of drunk driving and barroom fights. I was ready for what was sure to be a brutal race, if Jonathan was up for it.

  The poll cost Jonathan and me $10,000, and the numbers Jefrey found were daunting. They showed us losing to Sweeney 57 percent to 14 percent. Jefrey also confirmed that Sweeney would run a nasty campaign.

  But he told us his data showed that over half the voters in the district were undecided. All the Democrats would likely vote Democrat, but only half the Republicans would likely vote Republican, so if we did well with the Independents we could win. Voters in the district weren’t loyal to Sweeney.

  That was good enough for Jonathan. Now I just had to convince everybody else. My mother—who understood my district and, more important, me—thought my decision to run was fantastic. Erin and a few friends knew enough not to underestimate me or stand in my way. Nearly everyone else just humored me and said, “Good luck.”

  Still, I asked everybody in my network for their support.

  Politics is not for the timid or shy. First, I went back to Hillary and was grateful and happy when she agreed to review Jefrey’s poll. We made a phone date and when I called at the appointed time from my campaign office in Albany, she had already talked to Rahm Emanuel, then the head of the Democratic Congressional Campaign Committee. Rahm, she said, thought I was a “
great candidate.” Karen Persichilli Keogh, one of her closest political advisors, whom she’d also talked to, advised the race would be “an uphill climb.” (KPK, as she’s affectionately known, later worked on my first Senate campaign and was an invaluable advisor.) Of course, Hillary was concerned about Theo, our recent move to Hudson, my limited experience in public service, and my opponent’s reputation. Still, what she focused on most was why I wanted to run and how I would feel if I lost. “You should only run if your heart is one hundred percent in it,” she said. We talked about my platform, messaging, and how I should present myself. She described the decision of whether or not to run as a “close call.”

  She shared personal stories about some of President Clinton’s early races, including one where he came from twenty-four points behind to lose by only three, and how he used that opportunity to establish a strong reputation to win down the road. She couldn’t have been more gracious or kind, offering to talk through the race as I made my decision, to explore other avenues for service if I didn’t run, and to help and support me no matter what. (And she and President Clinton did, with fundraising events, stumping in the district, and speaking at huge rallies just before the election.) Her last few words of advice were that I should only run if I was “taking it on out of conviction,” and there would be no guarantees. Campaigns could be nasty stuff, she said. I would have to have a thick skin. If I got in the game, I would have to play to win.

  I definitely wanted to win, and I do have very thick skin. I knew that I was ready, especially with Hillary in my corner.

  Next, I asked every woman I knew who was very experienced in politics to meet one-on-one. I always showed up promptly, neatly dressed, and with a smile on my face and a notebook in hand. The tone of most of the encounters, at least early on, was polite, kind of thrilling (for me), and mildly discouraging. Ellen Chesler, who’d worked on campaigns for a long time, gave me a list of ten more people to call. Susan Thomases, one of Hillary’s longtime friends and advisors, asked, “Do you know all your neighbors in Hudson yet?”

  Such a simple question. I shook my head. Susan said, “When a reporter knocks on your neighbor’s door and asks about you, and your neighbor says, ‘I’ve never met her,’ that’s a bad story.”

  Jane Harman, who at the time was a congresswoman from California, asked, “What’s your platform? What can you do before you run to elevate your name statewide? Can you get on some boards?” She didn’t think my chances were good, but she offered to throw me a fundraiser anyway.

  In August 2005, I registered as a candidate and got to work on the next item on my to-do list: getting to know as many people in the district as possible. A friend would say, “My mother has a bridge group that comes to her house on Thursday evenings. Would you like to meet them?” I’d say, “Yes! Thank you!” Then I’d go, sit down, and speak with the women, asking about their concerns and writing down their answers in blue felt-tip pen on white index cards: SOCIAL SECURITY, TAX BREAKS FOR COLLEGE TUITION, NEW NATIONAL HEALTHCARE MODEL. (This was before Obamacare.) I kept those cards in my purse, just as I had my wedding-planning index card. They became my external brain—a necessity, because I forget things I don’t write down.

  I also set out to meet with leaders of three groups: labor, the Democratic Congressional Campaign Committee, and EMILY’s List. For the first, I met with Suzy Ballantyne, one of the top figures in the New York State AFL-CIO. I figured Suzy would be tough and dismiss me outright, but she listened politely to my then-not-very-polished presentation on why I thought I could beat John Sweeney and said, to my great pleasure, “You know, Kirsten, I think John Sweeney is full of shit. I will help you.”

  Next hurdle: the Democratic Congressional Campaign Committee (or D triple-C, as insiders call it), run at the time by Rahm Emanuel. True to his reputation, Rahm was a hard-ass and a skeptic. He kept giving me outrageous fundraising goals, assuming I’d fall short and thus give him an excuse to bar me from his Red to Blue program, aimed at turning Republican districts Democratic. But I jumped through every hoop, rang every bell, called every number of every contact, and eventually Rahm ran out of reasons not to support me.

  That left winning the support of EMILY’s List, which I knew I couldn’t do unless I had labor and the DCCC on my side. They were the toughest to win over, but when I did, EMILY’s List was invaluable—helping me with staffing, training my finance team, and sending out emails and letters to their hundreds of thousands of supporters, explaining why they should help me.

  In January 2006, a month after my thirty-ninth birthday, I announced my candidacy to a small gathering at the historic and charming Tin Ballroom in Hudson. Later that afternoon, I drove to Saratoga and announced my candidacy again. The next morning, I announced a third time in a maple barn in Delaware County, surrounded by farmers. I was still so green that in Saratoga I spoke for twenty-five minutes (at least fifteen minutes longer than I should have), irritating all the politicians who were standing behind me, including Eliot Spitzer, then attorney general. Afterward, reporters pushed cameras in my face for the first time in my life. Thankfully, I remembered my media training from campaign school: One, smile. Two, breathe. Three, keep it simple. Four, smile again.

  Our campaign was so scrappy. My grandmother had died the week that Theo was born, but our family hadn’t sold her house, so it was a low-cost (and therefore perfect) place for my scruffy band of staffers to live. I imagine she would have loved the energy and chaos. Between five and ten people lived at that house at any given time, some camping out for weeks in sleeping bags on the old white carpet, so focused on my campaign—as opposed to, say, vacuuming—that my mother had to have the entire place recarpeted when my staffers left. Ross Offinger, then twenty-three years old, who started as my deputy finance manager and still works with me today, took a job on my campaign so he could move out of his childhood bedroom at his parents’ Massachusetts home. He ended up living at my grandmother’s for over a year. As our unofficial dean of housing, he installed a foosball table in the living room and, predictably, often woke the whole house at 2:00 A.M. by yelling, “Score!”

  My treasurer, Anne Bradley, who is now my deputy chief of staff, was at a very different place in her life. When she started, she was a principal at Ernst & Young, working for them part-time and remotely while doing her campaign duties for free. At a certain point, being the only real adult in my grandmother’s house, she couldn’t take the collegiate-style crash pad anymore and moved in with my mother. I really appreciated her company, as the average age of my campaign staff was around twenty-five.

  Bill Hyers, my gruff but experienced campaign manager and Anne’s boss, knew how to keep a campaign focused and disciplined, spending money only when he knew it would earn us voters. Toilet paper and other supplies didn’t qualify.

  My role, at the beginning, was to spend days on end talking to people who didn’t think I could win. I called every name of every contact anybody would give me, putting small check marks next to each to remind myself how many times I’d already called. Anybody who was willing, I drew into the campaign. I asked people to throw coffee get-togethers where I could meet voters (and write down their concerns on index cards). If throwing a coffee seemed like too big a request, I’d ask if they could bring muffins to an event someone else was hosting. If bringing muffins seemed like a hassle, I asked if they’d be willing to attend and bring along a friend. People like to help—it’s human nature. From tax lawyers I asked tax-policy advice; from teachers, their thoughts on education policy. Contributing made people feel like part of my campaign, and that made them emotionally invested in it.

  Sweeney hurled everything he had at the race, including a bunch of ridiculous lies. He said that I’d wasted billions of dollars at HUD, that I was a war profiteer, that I wanted to eliminate the child tax credit, and that I was an out-of-touch Manhattanite who hired a maid to polish my silver. He ran campaign ads criticizing all the men close to me—my dad, my brother, my father-in-law, and my husband
. My attitude was “Fuck ’em.” One of the lessons I’d learned from my grandmother was to ignore negative press. Politics, she taught me, is a sport, just like football. You put on your protective gear, get out on the field, and hit your opponent as hard as you can. You should expect your opponent to do the same.

  Jonathan, on the other hand, was enraged. “This is complete bullshit,” he said upon seeing Sweeney’s ads. He turned the TV off in September and didn’t turn it back on until November, when the election was over. He told my staff to remove his name from the daily email of campaign clips. Being British, he was appalled that political ads in the United States were held to no standard for truth.

  To counteract the ugliness, Jonathan and Theo made huge wooden signs with the words GILLIBRAND 4 CHANGE or FARMERS FOR GILLIBRAND painted in red, white, and blue. They then surprised me by placing the signs on lawns along my drive to the campaign office. Lawn signs, I knew by that point, are fairly useless in swaying voters, but they sure did make me feel good. Most satisfying: Sweeney’s negative attack strategy appeared to be backfiring. All by myself, standing on a street corner talking about Iraq policy, I wasn’t that captivating to voters. But once Sweeney started hurling insults at me, people felt offended and paid attention to the race. Nobody likes a man who maligns a new mother. If Sweeney had had the restraint to ignore me, he probably would have won.

  Campaigns are trials of perseverance. Every day, you wake up, examine what other people think of you (never a recipe for happiness), and talk to voters who don’t like you, because if you only talk to your supporters, you’ll never change anybody’s mind and win more votes. I met with every editorial board of every conservative newspaper, eager to convince them I was hardworking and sincere. If we’d planned an event and not enough people RSVP’d yes, we’d call hundreds more until we had a respectable number of attendees. Jonathan tried to keep up morale by regularly supplying campaign headquarters with pizza and beer—and toilet paper when needed.