How Kirsten Gillibrand’s Presidential Dreams Unraveled

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Senator Kirsten Gillibrand was in a bind.

With less than three weeks until the deadline to get into the fall presidential debates — which she deemed crucial to keeping her campaign alive — she was on track to fall well short. She had neither the 130,000 donors she needed nor the necessary support in the polls. What she did have was a stockpile of cash. So, in one Hail Mary heave, she unloaded $1.5 million on a two-week television buy in the doldrums of August to try to improve her numbers in Iowa and New Hampshire.

“The alternative to not going all in,” said Glen Caplin, a senior adviser to Ms. Gillibrand, “was not a viable alternative.”

The gamble would prove to be a final miscalculation. If the commercials caused any discernible Gillibrand bump, it would go undetected: No Iowa or New Hampshire polls that could have qualified her were even conducted after her ads aired. On Wednesday, with the deadline just hours away, Ms. Gillibrand dropped out.

“It’s important to know when it’s not your time,” Ms. Gillibrand said in a video.

How Ms. Gillibrand, 52, so swiftly went from a rising star of the Democratic resistance and “the #MeToo senator,” as “60 Minutes” had memorably tagged her in 2018, to a 2020 afterthought and early primary casualty is a tale of mistakes, misfortune and a message that did not meaningfully hold sway in a historically crowded field.

Ms. Gillibrand, of New York, entered the race pitching herself as the voice of feminism and the defender of families and women’s equality. She championed a new “Family Bill of Rights,” pioneered a new litmus test to select only judges who supported Roe v. Wade and traveled to Republican-controlled states to protest new restrictions on abortion.

But of the six female candidates, she was the first to call it quits, having found little traction among women or men. She almost never topped 1 percent in a poll. In fact, Ms. Gillibrand ended up as the female candidate with the fewest donors, trailing even the political newcomer Marianne Williamson, despite having spent years trying to build a national following.

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“She was running in a lane of fighting on women’s issues, but other people were running in that lane as well,” Randi Weingarten, the president of the American Federation of Teachers, said. “You had several female candidates who were all bringing their own brand of feminism.”

Ms. Gillibrand said in an interview that she was unsure what the missing piece of her candidacy was. “I don’t know,” she said. “My campaign may well have been ahead of its time.”

Little seemed to click this year.

Her kickoff event was overshadowed by the release of the first snippets of the Mueller report, an unforeseeable development.

Yet she was also prone to self-inflicted wounds. At one Boston fund-raiser, Ms. Gillibrand asked a group of women to contact people on their Christmas-card and school-parent lists to ask for $1 donations to help her make the debate, according to one attendee, who said she and others were appalled by the implication that the women did not have professional circles of their own.

By early August, the downward trajectory was plain to see. Senator Kamala Harris of California was motoring across Iowa in a leather-appointed bus decorated with her campaign logo. A second bus of reporters and aides trailed behind.

Ms. Gillibrand rode in a small R.V. with her campaign sign slapped on the side; her husband was behind the wheel.

She attracted scant crowds (Andrew Yang, a first-time candidate, outdrew her splashy weekend kickoff rally on a rainy work night this spring; both events were in Manhattan). She failed to secure significant endorsements (only one New York member of Congress backed her).

And she was plagued by questions about her past. Her prominent role as the first Democratic senator to call for Al Franken’s resignation dogged her throughout the race, with voters and reporters bringing it up and some Democratic donors denouncing her. And Ms. Gillibrand’s record included policy reversals like her past support of gun rights and her opposition to “amnesty for illegal immigrants” — making her a hard sell for progressives focused on purity and consistency.

Her exact ideological bearing could prove elusive. Was she the upstate congresswoman who flipped a heavily Republican seat more than a decade ago, or the liberal firebrand who voted down nearly every one of President Trump’s nominees?

“There’s a false debate in the party right now,” Ms. Gillibrand said in late August. “Either you have to be an uber-progressive who can inspire the base, or you have to be a moderate who wins those red and purple areas. I believe you have to do both. And my candidacy is both.”

As Ms. Gillibrand’s campaign languished, she began plunging ever more money into Facebook ads, prospecting for donors with money-losing offers like giving away T-shirts for $1.

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Overall, she spent $2.8 million on Facebook — more than $20 for every contributor to her campaign. She ended with fewer than the required 130,000 donors and less than $800,000 in campaign funds.

“The sky-high expectations for her candidacy were also themselves a liability,” Jon Reinish, a former aide to Ms. Gillibrand, said. “When she didn’t shoot to the top right away, the perception game became an albatross she couldn’t shake.”

Ms. Gillibrand’s candidacy did not get off to an auspicious start. She had secured a big booking on her first full day, a spot on Rachel Maddow’s highly rated MSNBC show. The show is typically a friendly space for Democrats, but Ms. Maddow grilled Ms. Gillibrand about her political “transformation.” “She had an A rating from the N.R.A.,” Ms. Maddow said. “She said she wanted to make English the official language of the United States.”

It was the first of many interviews consumed by questions about her record.

She became so adroit at apologizing for her past positions — to her disadvantage, guns and immigration developed into two prominent issues in the Democratic primary contest — that she tried to turn that skill into an asset, comparing it favorably to Mr. Trump’s lack of contrition. But she yielded no ground on Mr. Franken, saying he was not entitled to her “silence” after multiple, credible accusations of sexual misconduct.

“She really did carve a path for unapologetic feminism,” Ilyse Hogue, the president of the abortion-rights group NARAL, said. But, she added, “those who are fiercest and who choose to go toe-to-toe with entrenched misogyny are rarely rewarded.”

Ms. Hogue said that the Franken episode had at times “overshadowed her campaign,” but she predicted that “history will show what she was doing was for the betterment of the country.”

Ms. Gillibrand’s campaign made an early bet that the senator could slowly win over small audiences in Iowa and New Hampshire living rooms. Her $10 million Senate war chest gave her a financial cushion to pursue the strategy. But the early months of the 2020 race showed the national narrative playing out on social media and television, not in coffee shops. That dynamic drove the early states, not the other way around.

“I didn’t see her show up like I know she could have and know that she can,” L. Joy Williams, the president of the Brooklyn N.A.A.C.P., said. “I don’t know why, to be honest with you.”

Her campaign also failed to line up key supporters in New York, such as party officials and members of Congress. One planned dinner for lawmakers at her Washington home was canceled. Some New York donors said they wrote her a check out of obligation but declined to host a fund-raiser. Charlie King, a Democratic National Committee member from New York who is unaligned in the 2020 race, said he never heard from Ms. Gillibrand or her team.

“I heard from several other campaigns,” Mr. King said. “Multiple times.”

Ms. Gillibrand’s lack of small-donor support — the lifeblood of Democratic fund-raising — was evident from the start. Through June, she had topped 2,500 donations in a day only once; Senator Elizabeth Warren of Massachusetts had more than 100 such days.

In May, Ms. Gillibrand’s campaign began to sever ties with Anne Lewis Strategies, the political firm where she had directed $5.6 million in 2017 and 2018, in part to build a digital supporter list. Not enough of those people became 2020 donors.

Months into her bid, Ms. Gillibrand was hemorrhaging money. In the second quarter she spent nearly $2 million more than she raised — by far the worst ratio of any candidate who was not self-funding a run.

Rival campaigns took note. Some began privately discussing how soon would be too soon to try to poach some of the talent that Ms. Gillibrand had assembled in her Troy, N.Y., headquarters.

Ms. Gillibrand had some bright spots. She sipped whiskey with voters, dressed up with drag queens in Des Moines, took spin classes everywhere and arm-wrestled with an Iowa college student. Her team quickly packaged these vignettes into videos posted online.

During her Fox News forum in early June, she was dismissed by the moderator, Chris Wallace, as “not very polite” — a rare viral moment.

“We want women to have a seat at the table,” Ms. Gillibrand said.

“What about men?” Mr. Wallace asked.

“They’re already there — do you not know?” she replied.

In July, her answer defining white privilege ricocheted across the internet and drew plaudits from progressives. But by then the press corps trailing her had thinned. Voters seemed to have settled on a top tier of contenders. It did not include her.

Ms. Gillibrand and her campaign knew the second debate was her last best shot to break through. And they thought they had found a perfect issue to take on the front-runner, former Vice President Joseph R. Biden Jr.: his opposition to a child tax credit in 1980.

But Ms. Gillibrand telegraphed the attack days before the debate. So Mr. Biden came prepared for her premeditated broadside, dismissing her questions about his record on defending women as expediency borne of the fact that she was now running against him.

Ms. Gillibrand received her first 2 percent qualifying poll soon afterward, which helped inspire the ill-fated ad blitz. Her advisers hoped better polling would inspire more donors to chip in.

In recent weeks, her campaign filled inboxes with pleas for cash as often as three times a day. Gloria Steinem signed emails. T-shirts were offered for $1.

“At this point, it’s now or never,” her campaign pleaded on Monday.

It would be her last day on the trail. She took a spin class near San Francisco, canceled fund-raisers in Southern California and then flew to New York to huddle with her family on Tuesday evening.

“I came home, talked to my husband, my two boys, we had a very, very thoughtful and wonderful conversation about what the role of public service is,” she said, “and that mommy is dedicated to serving others, no matter what or in whatever role it is.”

On Wednesday, she broke the news to her headquarters staff in person. They ended the night together at a bar, drinking whiskey.

Alex Burns contributed reporting

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