How Kirsten Gillibrand's Presidential Dreams Unraveled

There were less than three weeks until the deadline to get into the fall presidential debates that she deemed crucial to keeping her campaign alive, and 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 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, Gillibrand dropped out.

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

How 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.

Gillibrand 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” and affordable child care, pioneered a new litmus test to select only judges who support Roe v. Wade and traveled to Republican-controlled states to protest new restrictions on abortion.

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

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

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 for Gillibrand.

Her kickoff event was overshadowed by the release of the first snippets of the Mueller report, a development she could not have planned for.

Yet she was also prone to self-inflicted wounds. At one fundraiser in Boston, Gillibrand, desperate for donors, 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 an attendee, who said she was repelled by the implication that the women gathered did not have professional circles of their own.

By early August, the downward trajectory was plain to see. Sen. 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.

Gillibrand’s campaign had commandeered a small RV 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 launch 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 from the U.S. Senate dogged her throughout the campaign, with voters and reporters periodically bringing it up on the campaign trail and some Democratic donors and social media posters denouncing her. And Gillibrand’s record included policy reversals that liberal cable hosts and others drew attention to, like her past support of gun rights and her opposition to “amnesty for illegal immigrants” — making her a hard sell for progressives who care about 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 Donald Trump’s nominees?

“There’s a false debate in the party right now,” Gillibrand said at a recent Washington Post event. “Either you have to be an uberprogressive 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.”

Gillibrand never achieved liftoff, and as her candidacy languished she began plunging ever more money into Facebook ads, prospecting for donors with money-losing offers like giving away T-shirts for one dollar. She spent $2.8 million on the site. That is double what she raised from all donors who gave her less than $200 through the end of June.

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

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

Forced to defend her record

Gillibrand’s candidacy did not get off to an auspicious start. She had secured a big booking on her first full day in the race, a spot on Rachel Maddow’s highly rated MSNBC show. The show is normally a friendly space for Democrats, but Maddow grilled Gillibrand about her “transformation.” “She had an A-rating from the NRA,” Maddow said as she outlined Gillibrand’s decade-old stances. “She said she wanted to make English the official language of the United States.”

It would be Gillibrand’s only campaign appearance on Maddow’s show. But 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 driving issues of Democratic primary — that she tried to turn that skill into an asset, comparing herself favorably to Trump’s signature lack of contrition. But she yielded no ground on Franken, saying he was not entitled to her “silence” after multiple, credible accusations of sexual misconduct were leveled against him.

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

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

Gillibrand’s campaign had made the early bet that she 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 first eight months of the 2020 race have showed the national narrative playing out on social media and on television. That dynamic began driving 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,” said L. Joy Williams, the president of the Brooklyn NAACP and a Democratic strategist. “I don’t know why to be honest with you.”

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

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

Money problems outweigh the bright spots

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

In May, 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. Few of those people became 2020 donors.

A few months into her bid 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 their run.

Rival campaigns took note. Privately, some began discussing how soon would be too soon to attempt to poach some of the talent that Gillibrand had assembled in her Troy, New York, headquarters.

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 early June Fox News town hall, she was dismissed by the moderator, Chris Wallace, as “not very polite” — a rare viral moment that led to a burst of attention.

“We want women to have a seat at the table,” Gillibrand said at the town hall. “What about men?” 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, as voters seemed to settle on a top tier of contenders that did not include her.

Gillibrand’s 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 and former vice president, Joe Biden: his opposition to a child tax credit in 1980.

But Gillibrand telegraphed the attack days before the debate. So Biden came prepared for her premeditated broadside, dismissing her questions about his record defending women as coming only because she was now running against him.

“By the time she tried to go on the offense in the second debate it was unfortunately too late to pop,” said Reinish, her former aide.

Gillibrand did receive her first 2% qualifying poll soon afterward, which helped inspire the ill-fated ad blitz. Her advisers had hoped more qualifying polls would inspire more savvy donors to chip in.

In recent weeks, her campaign filled inboxes with pleas for cash as often as three times a day. Gloria Steinem even signed emails to ask for money more than once. T-shirts were sold for $1.

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

It would be her last day on the trail. She took a spin class near San Francisco, canceled fundraising events in Southern California and then flew back to New York, where she huddled 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 Troy headquarters staff in person. They ended the night together at the bar, drinking whiskey.

This article originally appeared in

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