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The Reintroduction of Kirsten Gillibrand

With Theo in his classroom.  

Gillibrand’s first foray into public service came in 2000, when she ran into then–HUD Secretary Andrew Cuomo at a fund-raiser. She simply approached Cuomo, she says, and explained her desire to get into public service. A representative from Cuomo’s office called her the next day and offered her a job as a special counsel. “I said, ‘Can I think about it?’ ” Gillibrand says. “He said they needed to know by the end of the day. I said yes.”

After George Bush defeated Al Gore that November, however, Gillibrand returned to corporate law, becoming a $500,000-a-year partner at Boies, Schiller & Flexner, working with star Democratic litigator David Boies. She also began raising money for New York Democratic heavyweights like Hillary Clinton and Eliot Spitzer. Gillibrand met Clinton in 1996, and, as she tells it, the pair bonded over their shared experiences as women in the male-dominated world of corporate law. They spoke regularly, if informally, over the next several years, and when Clinton decided to run for Senate in 1999, Gillibrand joined the fund-raising group Women for Hillary.

In 2002, Gillibrand informed Boies, Schiller that she was thinking about running for office. The firm allowed her to transfer from New York to its Albany office, and she established residency in nearby Hudson. “When I was living in New York, I thought about running for City Council or State Assembly, but there were twenty qualified candidates for every opening,” Gillibrand says. “So I thought, ‘I like federal issues. What about Congress?’ I asked Johnny what he thought about raising kids upstate, and he was happy with it. So we moved home. Well, near home.”

Gillibrand’s move to Hudson was carefully calculated. The town is in the southern part of the 20th Congressional District, a region that sprawls to Lake Placid in the north and almost to Binghamton in the west. Registered Republicans outnumber Democrats almost two to one, but Gillibrand learned that Clinton and Spitzer had rolled up large majorities in the district in 2000 and 2002. She theorized that a moderate Democrat could win there under the right circumstances. She contemplated running in 2004, but Clinton, now something of a Gillibrand mentor, suggested the political climate would be better in 2006.

“My parents and husband have been worried about the coverage,” says Gillibrand. “I told them, ‘Give me six months, and I will make it better.’ People meet me, they like me. I work hard.”

With George Bush’s approval ratings at an all-time low, the 2006 electoral environment was, in fact, ripe for Gillibrand. And Republican incumbent John Sweeney was imploding. He had recently been photographed puffy-eyed at a Union College fraternity party and was thought generally to have “gone Washington” by many of his upstate constituents.

Gillibrand hit her mailing lists hard, raising a startling $2 million by the spring of 2006. Still, the Rahm Emanuel–led Democratic Congressional Campaign Committee remained skeptical. In May 2006, Emanuel dispatched Representative Steny Hoyer to check on the race at a fund-raiser. “Hoyer was there, but he seemed checked out,” recalls Bartley. “But then Kirsten got up and start talking about the race and how it was winnable, and people started clapping and he started paying attention.”

Emanuel upgraded Gillibrand’s candidacy from doubtful to winnable on the big congressional map in his office at the DCCC. Resources began to pour into her campaign. Clinton communications director Howard Wolfson signed on to help Gillibrand, and Clinton gave her some of her own coveted fund-raising lists.

Tracking polls showed the race was even going into the final week. Just one week before the election, however, a confidential police report was leaked to newspapers. Rumors had long circulated that state police had been called to Sweeney’s home in 2005 to respond to a 911 call from his wife alleging spousal abuse. The Sweeney campaign contended the timely leak was orchestrated by Gillibrand’s campaign, specifically Wolfson (Wolfson won’t comment).

“We had a press conference about it, and I heard a reporter talking to Wolfson, and he was feeding him details that hadn’t been released yet,” a Sweeney aide told me.

Gillibrand has never denied that her campaign was the source of the leak despite being asked about it several times. She defeated Sweeney by six points.

I met Jonathan Gillibrand at the Dubliner, a Capitol Hill restaurant. A 39-year-old British national, Jonathan has kind eyes, a shy demeanor, and the look of a man who is not unhappy to pop out of the house now and then for a quick pint of Guinness. He is, essentially, the antithesis of his warp-speed wife.

The couple met when Jonathan was dating a friend of Kirsten’s in 1999 and Jonathan was getting his M.B.A. at Columbia. When her friend stopped seeing Jonathan, Kirsten asked if it was okay if she contacted him. They bonded over their shared Catholic heritage and attended Mass at St. Ignatius, on the Upper East Side, on their second date. They were married in 2001.