At Kirsten Gillibrand’s Fox News town hall Sunday night, she was asked how she would win over voters who supported Barack Obama and then voted for Donald Trump. She had a simple answer: “Campaigning everywhere.”

For the New York senator struggling to break through a crowded field of 23 Democratic presidential hopefuls, “campaigning everywhere” means traveling to Iowa, South Carolina, New Hampshire and Georgia.

Thirteen years ago, it meant driving in the snow through the Catskill Mountains while listening to an audio book about Abraham Lincoln.

That was during her first House campaign in 2006, when she defeated Republican Rep. John E. Sweeney by 6 points. Operatives in both parties say her willingness to traverse the sprawling upstate New York district and pitch herself as a moderate helped her beat the odds in a district that had twice as many registered Republicans as Democrats. 

Gillibrand, whose positions on some issues have shifted to the left since then, brings up that race today as evidence that she can win over independents and Republicans.

Put another way: She says it’s proof that she can beat Trump.

“Her origin story in politics is an important one that may not be well-known, but needs to be told for sure,” said John Lapp, the executive director of the Democratic Congressional Campaign Committee during the 2006 cycle.

But that origin story is not a simple one. It’s a story of an ambitious lawyer in relentless pursuit of public office, an incumbent GOP opponent with his own demons, and an electorate growing weary of war and Republican scandals in Congress.

More cows than Democrats?

When Gillibrand talks about her 2006 race on the presidential campaign trail, she recalls her pollster telling her New York’s 20th District had more cows than Democrats. That pollster, Jefrey Pollock, still works on her campaign.

“I was talking to her as a political consultant, but also as a friend, to say, ‘Are you really sure about this kind of crazy thing?’” Pollock said in a recent phone interview.

Sweeney’s district was giant and ruby red. It touched 10 counties and stretched from Lake Placid in the north, down the state’s border with New England, almost to Poughkeepsie. Voters in the district backed President George W. Bush by 8 points in 2004. Sweeney was re-elected that year by 32 points.

Gillibrand, who grew up in Albany, moved back upstate after deciding to run for Congress, she wrote in her book “Off the Sidelines.”

She thought about taking on neighboring GOP Rep. Sue W. Kelly, but decided against it because there were few women in Congress. She settled on Sweeney as her target.

In 2004, Gillibrand considered running against Sweeney but held off after a conversation with Hillary Clinton, then New York’s junior senator. Early in in the 2006 cycle, as Gillibrand gave the seat another look, Pollock conducted a poll for her. The results were not good.

That first survey had Sweeney beating her, 57 percent to 14 percent, she wrote in her book. But she and Pollock also saw an opening with independents and some Republicans who didn’t have strong feelings about Sweeney

Some local Democrats began sensing that Gillibrand had a chance, with voters starting to grow weary of the Bush administration, and a lobbying scandal that had engulfed Congress. Sweeney faced criticism in early 2006 for hosting a pricy ski event with lobbyists in Utah.

Karen Feldman, a Democratic consultant in Columbia County, recalled sitting at Gillibrand’s kitchen table and telling her, “If there ever was a time to do it, now’s the time to do it.”

“We thought [Sweeney] was more vulnerable than a lot of people thought,” said Larry Dudley, who ran the Democracy for America chapter in Glens Falls and was part 20 True Blue, a group that met with Gillibrand when she was exploring a run in 2005.

Sweeney was first elected to Congress in 1988 and he largely supported Bush and party leadership in Congress, according to CQ Vote Studies. Bush dubbed Sweeney “Congressman Kickass” for his role in the 2000 Florida recount.

Still, Pollock wasn’t optimistic there was a path to victory. He said Gillibrand had to put the race in play herself.

“That’s the first thing she did, by raising the amount of money and being aggressive with John Sweeney, who had never faced a real challenge — and certainly not from a woman,” Pollock said.

Bitter battle

According to campaign operatives involved in the race and media reports at the time, the battle was one of the nastiest in the country.

Sweeney tried to paint Gillibrand as a carpetbagger. One local GOP official alleged that she knew more about the price of a Manhattan dog walker than a six pack of beer at Stewart’s, according to the Albany Times Union. (Gillibrand did not own a dog.)

Gillibrand sought to paint Sweeney as a creature of Washington instead of the district, and she capitalized on his own issues. One of her closing ads in the race included references to “drunk driving, arrests, federal investigations,” according to The New York Times.

During the campaign, Sweeney faced negative headlines over a photo of him drinking at a fraternity party. Late in the race, the Times Union reported that he failed to report a trip with an associate of lobbyist Jack Abramoff, potentially violating ethics rules. 

Six days before the election, the Times Union reported that the state police went to Sweeney’s house after his wife called 911, claiming her husband was “knocking her around the house.” No charges were filed.

Sweeney’s campaign initially dismissed the police report obtained by the Times Union as “campaign propaganda.” His team eventually acknowledged the police had been called to Sweeney’s house.

Sweeney said in a recent interview that his own decisions, such as not debating Gillibrand and not revealing the 911 call when it happened, cost him the race, and he particularly lost support among GOP women. But he also blamed fellow Republicans.

The race “had more to do with me, and had more to do with the fracture in the Republican organization,” Sweeney said. Now a recovering alcoholic, he is working as a lawyer after a stint in jail for a DWI.

He accused Republicans aligned with former New York GOP Gov. George Pataki, including the governor’s onetime aide, Patrick McCarthy, of working behind the scenes for Gillibrand after Sweeney clashed with Pataki over homeland security funds.

McCarthy denied doing so. He said he once went to dinner with Gillibrand and her father, a family friend and lobbyist, to discuss the dynamics of the race.

McCarthy said Gillibrand’s victory was a combination of a national environment favoring Democrats (who netted 31 House seats that year), Sweeney’s own issues and a lack of “unforced errors” from Gillibrand.

“I think Gillibrand was underestimated in that race,” McCarthy said. “I think she’s been underestimated by a lot of people since. And they have done so at their own expense.”

Tireless campaigner

To win, Gillibrand needed to secure support from three groups: the DCCC, EMILY’s List and labor organizations, she wrote in her book.

She was “relentless” in imploring DCCC Chairman Rahm Emanuel not to give up on the race, Lapp said. She raised $2.6 million while Sweeney raised $3 million, earning a spot on the committee’s Red to Blue program for strong challengers. The DCCC ran television ads in the race. Former President Bill Clinton traveled to the district twice in the final days of the campaign to bolster Gillibrand.

Suzy Ballantyne, the director of government affairs at the AFL-CIO at the time, recalled Gillibrand diligently meeting with labor leaders early in her campaign. She won the group’s endorsement — a rarity for a 20th District Democrat.

“[Sweeney] was certainly out-organized by her,” Ballantyne recalled.

That determined and relentless approach defined her first House race, according to Democrats involved.

Sean Gavin had just graduated from college when he joined Gillibrand’s campaign in his home district. He worked as her body man and later as a grassroots organizer, living with other campaign staffers in Gillibrand’s grandmother’s house. Gavin later joined her congressional staff and managed her 2012 Senate race, but is no longer in politics.

“She took the time to travel everywhere and anywhere,” said Gavin, who recalled driving through the Catskills in the snow to an event at the outskirts of the district even though they didn’t think many people would attend.

“She was tireless,” Gavin said. “I mean, I was 22 at the time, and she just tired me out, too.”

Some Democrats said Gillibrand’s presidential run is reminiscent of that first race.

“She’s campaigning the same way,” said former Democratic Rep. Michael R. McNulty, who represented Albany. “She’s going around, she’s meeting people in small gatherings. And I think that’s a real strength for her.”

An evolution

Gillibrand does face questions today about how her views have changed since that 2006 race.

At the time, she took more conservative positions on issues such as gun control and immigration. After joining the House, she earned an A- rating from the National Rifle Association. On Sunday, she called the NRA the “worst organization in this country.”

Her critics, including Sweeney, say she’s an opportunist and a “phony,” taking positions that are most beneficial at the time.

Gillibrand has said that she moved to the left after being appointed to the Senate in 2009, and that representing a much more diverse constituency broadened her perspective. She was not well known statewide when she was picked to replace Clinton, who left to become Obama’s secretary of State.

She has argued she took some progressive — and politically risky — positions in her first race. Early on, she called for an end to the Iraq War, even though Pollock’s first poll showed the war popular in the district. Public sentiment ultimately shifted in 2006, with most voters opposing the war.

Gillibrand has also said she campaigned for a version of “Medicare for All” in that first campaign, allowing people to buy into Medicare. Politifact found that claim to be true.

On the presidential campaign trail, Gillibrand notes that, as a more liberal senator, she has still won competitive areas of the state, winning 18 counties in 2018 that Trump carried in 2016.

“We have what we call a ‘Gillibrand Republican’ up here,” said Dudley of Democracy for America. They tend to be GOP women who support abortion rights but split their tickets.

Gillibrand now has to convince Democratic voters that she can replicate that success across the country to defeat Trump.

That first House race is proof that she is “the best candidate to take on Trump,” Gillibrand’s presidential campaign spokesman Evan Lukaske said in a statement to CQ Roll Call.

“Not only did she beat a loudmouth Republican incumbent in Republican territory, but she did so running on progressive policies like Medicare for All,” Lukaske said.

And those who watched her improbable win in 2006 aren’t counting her out.

“There are a lot of very talented people in that race,” McNulty said, “but Kirsten Gillibrand is one of them.”