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How Elise Stefanik Became the Youngest Woman Ever Elected to Congress

Stefanik leaves the Capitol Hill Club with aide Anthony Pileggi. (Bill Clark/CQ Roll Call)

Rep.-elect Elise Stefanik's path to victory in New York reflected the trajectory of the midterms nationally, as Republicans invaded Democratic territory to make double-digit gains in the House.  

But in so many other ways, Stefanik’s dominant win was of her own making.  

Stefanik defeated a wealthy Democrat, Aaron Woolf, by more than 20 points in a district the president carried just a couple years ago. At 30 years old, she’s the youngest woman ever elected to Congress, and New York Republicans now tout her as the future of their party.  

But that’s nowhere close to where Stefanik started the cycle in the upstate wilderness. In late summer of 2013, she drove an F-150 truck to methodically meet local Republican leaders in the vast district represented by a popular Democrat, Bill Owens.  

“I had this 29-year-old political unknown who was introducing herself as willing to challenge an entrenched political incumbent,” recalled Ray Scollin, chairman of the Franklin County Republican Party, who found Stefanik on Twitter before meeting her in a Saranac Lake coffee shop last year. “I know a lot of people who thought of it as laughable.”  

The GOP had been burned before when factions failed to coalesce behind the same candidate in the North Country. The Empire State’s 21st District is one of the largest on the East Coast, extending from the Canadian border to north of Albany. From there, it’s faster to drive round-trip to Manhattan than it is to traverse the district filled with scenic lakes, forests and struggling manufacturing plants.  

Stefanik spent her days working for her family’s plywood company, checking her gmail in between stops and carrying a handful of palm cards to the smallest of GOP functions.  

“She put well over 100,000 miles on that truck," recalled Stefanik's ad-maker, Russ Schriefer. "She’d drive five hours to meet with a half a dozen people.”  

Hundreds of miles to the south, others also had doubts. Some House Republicans expressed concern she had spent too much time in Washington, D.C. A Harvard graduate who worked in President George W. Bush’s White House, Stefanik managed Rep. Paul D. Ryan’s debate preparation when the Wisconsin Republican was the vice presidential nominee. She grew up in the Albany area, but after the 2012 elections she moved to Willsboro, two hours to the north, where her family vacationed during her childhood summers.  

“I remember looking at her résumé and background, and I have to say I was skeptical at first. She seemed, on paper, so young,” said Rep. Ann Wagner, R-Mo., a leader in her party’s efforts to recruit female candidates. “In about 10 minutes, she blew me away.”  

On the spot, Wagner cut a check from her leadership political action committee and offered to help Stefanik with an event. The candidate raised big bucks in her first quarter, but struggled with fundraising in the final months of last year. Keeping a lean staff, she eventually hired her first staffer, Anthony Pileggi, who is a few years her junior, as director of operations in November 2013.  

The race changed drastically in mid-January, when Owens announced his retirement after just two full terms in office. He won a high-profile special election in late 2009, stealing a district Republicans had owned for more than a century. The GOP rallied behind the Conservative Party's choice, accountant Doug Hoffman, over the candidate on their own line, Assemblywoman Dede Scozzafava.  

It wasn’t the last time a splintered GOP killed the party’s chances in the North Country. Third-party candidacies siphoned votes from the Republican nominee, Matt Doheny, in 2010. And in 2012, Doheny lost to Owens by only a couple points.  

“It’s hard to unseat a member of Congress who is doing their job — and he was doing his job,” said Scollin, a Stefanik backer whose son, Matt, works for Owens. “Nobody expected it when Bill dropped out. Nobody.”  

A New Race Hours after Owens dropped out, Doheny started calling local GOP leaders to ask their thoughts on another run. He had spent millions on his previous races, becoming well known around the district. He launched his third bid in late February, scoring support from the Independence Party a day later, effectively placing him on the November ballot no matter what happened in the GOP primary.  

But Stefanik had already coalesced support among local Republicans, who endorsed her  in early February.  

Back on Capitol Hill, tensions over the primary culminated on a cold March morning, as members and their top aides gathered for a recruitment meeting in the key-access-only floor above the National Republican Congressional Committee. The typically tepid meeting escalated to raised voices over one race: New York’s 21st District.  

Several aides in the cash-strapped NRCC, which publicly stays neutral in primaries, saw Doheny — and his wealth — as an asset. But Stefanik had her own allies in the room: Reps. Diane Black of Tennessee and Tom Reed of New York, and Wagner.  

She also had friends with deep pockets in the Empire State. She used her political Rolodex to make inroads with national donors, and other party leaders introduced her to GOP rainmakers in Manhattan, billing Stefanik as a fresh voice for the GOP nationally.  

Still, in early April, even Stefanik’s own polling showed Doheny with a 17-point lead in the primary. Her campaign had reserved their television airtime early, leaving certain weeks open so allies could fill the advertising gaps. They ran $200,000 worth of their own positive spots on Stefanik, plus radio ads in a district where driving is essential.  

Outside help flooded in for Stefanik in the final months before the June primary. Crossroads spent millions blasting Doheny — the only time the group ever played in a primary . New York 2014, a super PAC with roots in the finance industry, spent close to $400,000 boosting Stefanik’s positive image. Doheny spent $250,000 of his own funds ahead of June primary — a relatively small sum for him.  

Stefanik defeated him by 22 points. On primary night, Stefanik’s general consultant and strategy mastermind, Phil Musser, confirmed to her for the first time: If she won in November, she would be the youngest woman ever elected to Congress.  

From Liability to Strength With five figures left in the bank, Stefanik’s campaign turned to the general election. Her new opponent, Woolf, had personal resources and had stockpiled cash from the primary. Both parties had reserved millions in television time for the race, making it one of the most competitive House battlegrounds in the country.  

Stefanik had already honed her message to suit her youthful visage. A self-described millennial, she frequently billed herself as the candidate of “new ideas and a new generation of leadership in Washington.”  

But the campaign’s internal polling, conducted by Linda DiVall and David Kanevsky, showed Stefanik still had trouble with seniors, especially women older than age 65. Stefanik, who turned 30 in July, had to talk about Social Security.  

It didn’t work out well, at first. At a late August news conference, Stefanik walked away when a reporter pressed her  for specifics on raising the eligibility age for future generations. The next day, she held another news conference detailing her position — no changes for anyone older than age 50 — and stayed until every question was answered.  

Woolf told the Watertown Daily Times  he wouldn’t change a thing about the current system, and Stefanik’s campaign responded with a brutal attack ad charging the Democrat’s approach would result in thousands in cuts annually. It thwarted his momentum with seniors.  

"Our advertising was focused on relating the aspirations of seniors for their grandkids' future with the fact that Elise represented most of their grandkids," Musser said. "We turned her age, which some perceived as a liability, into a strength."  

By early September, a Siena College poll showed Stefanik with a 13-point lead over Woolf. A Green Party candidate, bakery owner Matt Funiciello, scored 10 percent. Around the same time, Stefanik brought on Lenny Alcivar, a former digital rapid-response director for Mitt Romney, specifically to target Woolf.  

Some Democrats had counted on Doheny keeping the Independence Party ballot line, siphoning votes from Stefanik. But Doheny endorsed the GOP nominee, and the Conservative Party nominated him for a judgeship in Brooklyn. It was the only way to get Doheny off the congressional ballot, according to state law.  

For once, it wasn’t Republicans who were spoiled by fractions within the party.  

Soon after, Democrats started to give up on the race. First, House Majority PAC pulled its advertisements , and the Democratic Congressional Campaign Committee followed suit by the first week of October.  

The race was effectively over for Democrats, who were quickly shifting resources to protect incumbents. On election night, Stefanik received 55 percent of the vote, Woolf took 34 percent and Funicello had 11 percent.  

“She’s a great match for the district, and so strong that quality challengers will probably shy away from challenging her,” said Bob Honold, a Republican strategist who works extensively in New York.  “Elise Stefanik is going to be in Congress for a long, long time.”  

At her age, it's more than possible.  

This is the second in a five-part series examining the campaigns behind the cycle’s most fascinating races. The first edition examined Rep. John Barrow's defeat in Georgia's 12th District. Related Stories: How Republicans Caught Their White Whale: John Barrow The Best Congressional Campaigns of 2014 How the GOP Did It: Debate Coaches, Media Training, Tech Candidates Get Platform With GOP Weekly Address Roll Call Results Map: Results and District Profiles for Every Seat Get breaking news alerts and more from Roll Call in your inbox or on your iPhone.