The assistant was patient and passed me on to the fundraiser in charge of events, who was more skeptical. (Staffers often have to undo offers made by their bosses, many of whom want to say yes to everybody and leave no one disappointed.) After a month of me calling and saying, “Hillary actually asked me to do this. I promise you, I’ll raise fifty thousand dollars! Look, here’s my finance plan for the event!” they finally agreed.
You have never seen someone more fervent about organizing an A+ fundraiser. Hillary had asked me to throw an event for young women, so I was going to throw the best event that anybody had ever attended. I proceeded to enlist seventy co-hosts: all my friends and every young woman I knew with an interest in politics, many of whom I’d met at fundraisers I’d helped organize for other candidates over the past few years. I nailed them down, saying, “This is really important. You have to sell three tickets and buy one yourself.” Regular tickets were $250 and VIP tickets were $500, meaning each host was asked to raise $1,000 minimum. I was preposterously meticulous and micromanaged everything. I must have called Hillary’s campaign office five times to discuss the invitations alone. Did they agree that I should use blue and yellow, as those were Hillary’s favorite colors? I’m sure I drove everyone crazy.
The fundraiser, held in the beautiful and ornate Russian Tea Room, with its rich green walls and gold dining chairs, was my first political success—three hundred women under forty, many rushing to the front of the reception line to ask Hillary passionate questions about education and healthcare. We raised our goal and nearly half as much again. Afterward, Hillary sent me a beautiful signed photo and phoned to thank me for my hard work. We chatted for two minutes. That call meant so much to me.
In the years since then, Hillary has offered me feedback at key times. But before I ran for office, our whole relationship consisted of a series of two-minute conversations. The only exception was a personal call about a year or so after she won her Senate race, to tell me how much she liked my dad. He and Hillary both happened to be at the same small birthday party, and the two of them got to talking and had a blast. My father is a charmer. Men love him; women love him. He’s fun and a good sport.
“Oh, I had a lovely time with your father. He was just so funny! We talked all about you,” Hillary said on the phone. I started laughing, stunned. My father and I did not always have an easy time. This was the first occasion that Hillary and I had ever talked about anything besides politics, and she’d called to gush about my dad.
Three minutes later, head still spinning, I reached my dad. “Guess who just called me!” I said. He chuckled and said he thought Hillary was delightful. A mutual-admiration society!
Being able to ask Hillary for advice at a few very critical times in my political career has been invaluable. I’m not kidding when I say that, until I reached the Senate, the sum total of time she spent talking to me was less than ninety minutes. But that’s all it took for her to help change my life, and I would happily work twice as hard to earn that time again. That is the power of a good mentor. Now when young women interested in politics ask me for my time, I always try to say yes, because Hillary said yes to me.
My Hillary party-planning efforts did not solve my problem of needing to find a way to break into public service. I had already tried and failed to get hired at the U.S. Attorney’s Office for both the Southern and Eastern Districts of New York. I’d also written letters to the Ford Foundation, the Carnegie Corporation, and the Rockefeller Foundation—no response from any of them. My spirits were tanking. I couldn’t even get a full-time job on Hillary’s campaign.
Feeling discouraged, I went to hear Andrew Cuomo, who was then serving as Secretary of Housing and Urban Development under President Bill Clinton, speak at a Women’s Leadership Forum event. He gave a fired-up talk about public service, why it mattered, and how we should all be working to make the world better. To which I responded: “Great.” I wanted the life he was pitching, but no one was giving me a chance.
So after the talk I walked up to Andrew, introduced myself, and said, “Mr. Secretary, I loved your speech. I agreed with everything you said. But I have to tell you, it’s not so easy. I’ve been trying to break into a career in public service for a couple of years now, and I cannot get my foot in the door. Not at the U.S. attorney’s office, not on Hillary’s campaign. I’m hardworking, well educated … and I can’t break in. It really seems to me that it’s an insider’s game.”
“Well, what do you do?” he asked.
“I’m a lawyer at Davis Polk. I’m an eighth-year associate.”
Andrew said, “Would you consider moving to Washington?” (Andrew’s a very direct and provocative person.)
“Of course,” I said, though in the back of my mind I was thinking that I would never move to Washington, because I loved New York, I had a serious boyfriend, Jonathan, and I was up for partner soon. Sure, I’d been dying to break into public service, but now that it was sounding more real, was I willing to walk away from a great, healthy relationship (a big deal for me), a place I loved, and a comfortable, high-paying job?
Andrew said, “Well, if you’re really serious about it, I’ll have my chief of staff call you tomorrow and set up an interview for next week.”
The next day, a Friday, Andrew’s chief of staff called. The following Monday, I flew down to Washington. Andrew interviewed me in his bland government-issue HUD office—navy couches, navy carpet, federal medallions on the walls. We talked for twenty minutes, and then he offered me a job on the spot.
“So, are you going to take the job?” he asked after I’d been sitting in stunned silence for fifteen seconds.
“I just need to think about …”
“Oh, you weren’t serious.”
“I promise I’ll let you know tomorrow,” I said. “I’m really grateful, I think this is just a wonderful opportunity …”
“I’ll make you special counsel. I’ll pay you the highest salary I can under the federal rules, because I know you’re leaving a well-paying job. Will you take it?”
I told Andrew that I really needed just twenty-four hours. Then I flew home to discuss it with Jonathan.
We didn’t live together at the time, so I met Jonathan at his fourth-floor walk-up on the Upper West Side (his apartment number was eight, my lucky number).
“What do you think?” I asked after I explained to him what little I knew about Andrew’s offer.
Jonathan’s response was perfect: “All you’ve ever wanted to do since I have known you is public service. I’ll see you on weekends. Screw Davis Polk.”
If I hadn’t already fallen in love, I would have right then. Jonathan reassured me that I didn’t need to worry about him, even though we’d only been dating a year. So the next day, I spoke with the Davis Polk partner I trusted most and gave the firm just two weeks’ notice, which was nearly unheard of. The partner didn’t say, “But you can’t leave! You’re about to make partner!,” which is what I hoped to hear. (Not that I would have stayed, but it’s always nice to feel wanted.) I put most of my belongings in storage and moved down to Washington, D.C. I knew that if things didn’t work out, I could always come back.
But I didn’t miss corporate law for a second. I got an apartment just two Metro stops from my office and stayed until 8:00 or 9:00 P.M. each night, never leaving before Andrew did. I loved the work. I was helping labor leaders form job incentive programs for single mothers living in housing authorities. I was also working on financing for basic improvements in inner cities. I officially had the bug for public service; there was no turning back now.
Jonathan came to visit me nearly every weekend, and on the ones he didn’t, I went to New York. Andrew, sensing my interests outside HUD, gave me a larger window into politics. For the 2000 Democratic presidential convention in Los Angeles, I volunteered to staff Kerry Kennedy, Andrew’s then-wife. I knew the city well from my years at UCLA, and I had a great time driving Kerry around to all the fancy parties, even just standing by her
side and collecting the business cards of people she met. (I know that sounds pathetic.) Thank God I soaked up that experience, because my stint at HUD was short-lived. The 2000 election cycle didn’t work out for Democrats, and just seven months after I arrived in D.C., my job, like Andrew’s, ended with Bush v. Gore. There would be no appointed positions in Washington for Democrats for four, maybe eight years, so I had to find a new route into public service. Not everybody left the city with grace. Many young disheartened Democratic staffers pried the “W” keys off their keyboards. That way their Republican replacements wouldn’t be able to type the name of their new commander-in-chief: George W. Bush.
Chapter 3
So What If the Cows Outnumber Your Supporters?
A few days after I moved back to New York City, just before Christmas 2000, Jonathan and I took a walk in Central Park. The place felt magical, the ground pristine white and covered in snow, and in a secluded patch of pine trees Jonathan handed me a snowball. Before I had time to toss it toward him, he said, “Open it.”
I crushed the ball in my gloves and found buried in the flakes the most beautiful diamond engagement ring. I felt so elated to know I’d be spending my life with Jonathan. Maybe returning from Washington to New York wasn’t so bad after all.
The next five months were heaven. I took a job as a partner at Boies, Schiller & Flexner, David Boies’s law firm, and negotiated to start in June. So I spent the next four months planning our wedding. (I love weddings, especially officiating; I’ve been honored to conduct ceremonies for Jonathan’s brother, Simon, and his partner, Justo, as well as for two of my staffers and a couple of friends.) I also love to-do lists, so I broke down the job of planning my own wedding into a 10-point action plan:
1. dress
2. reception
3. guest list
4. rings
5. ceremony
6. invitations
7. photographer
8. band
9. flowers
10. cake
I kept a list of these ten items on an index card in my purse, noting a point person and phone number for each. We were married on April 7, 2001, at the Saint Ignatius Loyola Church in New York City, with a hundred or so family and friends. After a two-week honeymoon in Lanai, Hawaii, we came down to earth and started our new life.
One of the reasons David Boies’s firm appealed to me—besides the fact that he, Jonathan Schiller, Don Flexner, and his other partners are brilliant—is that the firm took on cases of national, and sometimes even moral, importance. (David had represented Gore’s campaign in the Supreme Court after the 2000 election. He most recently fought to overturn California’s Proposition 8, which banned gay marriage.) Another draw: Boies’s firm had an office in Albany, and that allowed me to think about moving back home.
By the time I took that job, I’d ventured so far as to tell Jonathan that I might be interested in running for something someday and I’d floated the idea of buying a house upstate. For a few years, we’d been driving up on weekends and in the summers, hiking trails at Bear Mountain, adventuring in the Catskills, eating eggs and hash at the Daily Planet Diner on Route 55, and enjoying romantic Adirondack getaways. “Who knows,” I’d say to Jonathan as we were returning to the city, bouyant and relaxed. “Maybe, possibly, we could decide to live upstate full-time someday …?” I was vague and indirect, unusual for me. The idea of running for office still scared me—and I worried it would scare Jonathan, too.
But Jonathan loved upstate New York, so we started house hunting, heading north most Saturday mornings to the Hudson Valley. Those weekends together, in 2002 and 2003, were some of the happiest we’ve shared. We looked mostly at old farmhouses and always seemed to fall in love with the most impractical ones, including a house with an ancient rainwater-drainage trench in the basement that we nicknamed “A River Runs Through It.”
From the beginning, I wanted Jonathan to choose the house, since I was getting to move back home. That priority never changed, but after a while, if we liked a property, I found myself wondering what district it was in. I wanted, if possible, to buy in the 20th Congressional District, where the incumbent was John Sweeney, a Republican good ol’ boy with a horrible voting record. If we bought farther south I’d have to oppose Sue Kelly—equally conservative, also with a terrible record—but I didn’t want to run against a woman, given how few served in Congress. (Even today, the House of Representatives is only 18 percent women.)
About a year and a half after our wedding, I got pregnant. There’s something about pregnancy that focuses the mind, even as it makes you nauseous, so along with house hunting, I started to think more practically about what it would take to run for Congress and whether I could win. One of the first people I asked for guidance was a pollster named Jefrey Pollock. Several friends had advised me that if I ever contemplated a campaign, I should talk to him first. So I called and Jefrey invited me to his office, in a modest building downtown in New York City, where the creaky elevator opened onto a huge loft space with high ceilings, industrial windows, and old wood floors. Jefrey, sitting behind his well-organized desk, said, “So, how can I help?”
“I’m thinking about running for Congress in the Twentieth Congressional District in New York,” I said. He was the first person, besides Jonathan and my mother, to whom I had spoken those words. Jefrey looked a little concerned.
He walked over to his bookshelf, pulled off a thick paperback, and started reading aloud statistics about voter registration, Democratic performance numbers, and past electoral results. I didn’t know what the numbers meant. He translated: In the 20th Congressional District, a Democrat could expect roughly 45 percent of the vote.
“Do you think I can win?” I asked, trying to get clarification.
Jefrey said, “No. You can’t possibly win. There aren’t enough Democrats in that district.”
This flustered me. “What happens if I run the perfect campaign?” I felt sure Jefrey was underestimating how hard I planned to work.
“It doesn’t matter,” he said. “There aren’t enough Democrats. The district is two-to-one Republican,” meaning it had twice as many registered Republicans as Democrats.
“What happens if I raise two million dollars and really get my message out?”
Jefrey didn’t budge. “It doesn’t matter. That’s not how campaigns actually work.”
Now I was getting angry and impatient. Obviously Jefrey lacked confidence in me, which I didn’t appreciate. “What happens if Sweeney gets indicted?” I asked.
Jefrey didn’t miss a beat. “Well, it depends what he gets indicted for!”
When I told Jonathan about the conversation, he shrugged it off. “Don’t worry,” he said. “We don’t know where we’ll live anyway, and this is not yet relevant for us.”
I was twelve weeks pregnant at the time. My due date felt like a deadline. I had a lot to do. At the top of my list was convincing the senior women in the Democratic Party that I was a worthwhile risk. That started with Judith Hope.
Judith was a legend, the first woman chair of the New York State Democratic Committee and also the founder of the Eleanor Roosevelt Legacy Committee, a group dedicated to training and supporting Democratic women to run for local office. When Judith met me for breakfast in midtown Manhattan, I could tell that she was skeptical. I was too young, too green. Learning that I was Polly Noonan’s granddaughter did reassure her somewhat. (Judith loved my grandmother.) But what really won her over was when, a few months later, I filled my apartment building’s reception room with seventy women under forty to raise money for the Eleanor Roosevelt Legacy. Gaining trust in politics means showing you can deliver. In some ways that event felt like my first real political triumph. Unlike at my Hillary fundraiser a few years prior, I didn’t have a former first lady as my draw.
Pregnancy also turbocharged my nesting instincts. I was determined to be living in a home upstate before baby Theo arrived. Luckily, Jonathan found a perfect house in the town of Hu
dson: a white 1930s colonial with dark-green shutters and views of the Hudson River and the Catskills. The sellers wanted to wait to close until after Christmas, but I insisted on August. My mother served as our lawyer. Theo was born on November 8, 2003, and we were so happy to bring him to our new home.
Boies, Schiller didn’t have a maternity-leave policy before I started there. So I wrote one, granting primary caregivers in the firm three months’ paid leave (and also demonstrating, to myself and others, how important it is for all women to have females in leadership positions). Despite the lack of sleep, Theo’s infancy, for me, was bliss. I’m not a person who likes to just relax; I prefer to do and plan things. So during quiet hours with Theo, I started to think seriously again about running for Congress. When Theo was a few months old, I finally worked up the nerve to ask Jonathan directly how he would feel about the race. I said, “Bunny, I know it’s a lot to ask, and I really need this to be a family decision, but I’ve been thinking a lot again about running for Congress. What do you think? Do you think we could do it?”
I was still soft-pedaling the proposition because I was afraid he’d say no. The ask was huge—running would mean a massive pay cut for me, a devastating loss of privacy for our family, significant emotional discomfort for Jonathan (due in part to negative campaign ads), and a commute to Washington while we had a toddler.
Jonathan weighed the question. “I’m only going to agree if you can show me you can win,” he said, meaning he could get with the idea if he could see a clear path to success. So we agreed to just keep exploring the possibility—which is a good way to do things, but not my usual modus operandi. I typically decide where I want my life to go, then figure out how I’m going to get there and build the case for why it’s a good idea. Jonathan, by contrast, evaluates the pros and cons before starting out. Needless to say, he’s a positive and calming influence on me.
Off the Sidelines Page 5