Tim Alberta is chief political correspondent for Politico Magazine.

HAMPTON, New Hampshire—Kirsten Gillibrand is only asking for a dollar.

It’s not that she couldn’t use more money. In the first quarter of 2019, the junior senator from New York raised just $3 million for her presidential campaign, the weakest haul of the six senators running at that time and arguably one of the most disappointing totals of anyone in the sprawling Democratic field. Given her anemic polling since entering the race, Gillibrand’s feeble fundraising performance fanned skepticism about her viability to earn a nomination that Democrats believe will require close to $100 million in hard money raised.


But at this point, Gillibrand isn’t focused on winning the primary. She’s worried about surviving the next few months.

Despite a soaring national profile in the U.S. Senate, Gillibrand has failed to achieve liftoff as a presidential prospect. She has not broken 2 percent in a single national poll since officially declaring her candidacy in mid-March, and her 0.4 percent average in the RealClearPolitics aggregate of surveys places her behind the likes of Julián Castro, Tulsi Gabbard and even geeky long shot Andrew Yang.

Her bigger problem is fundraising. To secure a spot in the first double-header of Democratic primary debates in late June, candidates must meet two thresholds: surpassing 1 percent in three recognized national polls and collecting 65,000 unique campaign contributions. Gillibrand has checked the first box, however unimpressively. Yet the second mission remains unaccomplished. With the debates closing in—and with even quixotic candidates such as self-help guru Marianne Williamson hitting the 65,000-donor mark—Gillibrand is under the gun. The Democratic National Committee is limiting the total number of participants to 20. She could (and likely will) qualify by meeting the polling threshold only. But given the late gusher of contenders entering the fray, her place on stage can be guaranteed only by growing her donor ranks—and quickly.

Melissa Lyttle for Politico Magazine

Which brings Gillibrand to the climax of her stump speech. It’s the second weekend of May, she’s addressing a standing room-only crowd at a micro-pub four miles inland from the Atlantic Ocean, and the senator has finally hit her stride. Whether it’s the booze flowing from the taps or some other environmental factor—OK, it’s the booze—this has been Gillibrand’s best event of the day. Her talking points are sharp. Her jokes are well executed. Her audience is energized and engaged. Candidates typically fade late in a long day on the campaign trail, but Gillibrand has gotten stronger. The voters are hanging on her every word—about reforming the EPA, battling the NRA, encouraging national service programs and confronting Russian aggression. Finally, Gillibrand decides, it’s time to make the ask.

“For anyone here, if you like what you’ve heard tonight, I want to earn my place on the debate stage. I can’t do it unless you send a dollar—literally, really,” Gillibrand says, shaking her head as though to acknowledge the oddity of this request. “The measure is for anyone who wants to be on the debate stage, you need to get 65,000 individual supporters. So please go to KirstenGillibrand.com and just send a dollar. It will help me get to the debate stage.”

The Friday Cover Sign up for POLITICO Magazine’s email of the week’s best, delivered to your inbox every Friday morning. Email Sign Up By signing up you agree to receive email newsletters or alerts from POLITICO. You can unsubscribe at any time. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Gillibrand isn’t the only 2020 hopeful who has resorted to this method. Tim Ryan’s website features pop-up advertisements asking for $1. And Michael Bennet’s spots on social media make an identical solicitation.

But that’s Tim Ryan and Michael Bennet—an obscure congressman and low-profile senator, respectively. Ryan’s chief claim to relevance is being slaughtered by Nancy Pelosi as the sacrificial lamb who challenged her in the speaker’s race on behalf of disgruntled House Democrats after the 2016 election. Bennet has done little to distinguish himself as a senator and won his Colorado seat in 2010 only because the GOP snatched defeat from the jaws of victory, nominating a self-destructive Tea Party candidate whom Bennet managed to defeat by some 30,000 votes.

Gillibrand plays in a different league—or at least, she was supposed to.



***

A Dartmouth-educated lawyer who worked in corporate law before clerking on the U.S. Court of Appeals, Gillibrand gained national attention upon entering the political arena for possessing a rare combination of big brains, telegenic looks and personal magnetism. Her storming of a conservative upstate New York congressional district in 2006 announced her arrival as a player in Washington, and it was little surprise when, a few years later, after Hillary Clinton’s appointment as secretary of state, Gillibrand was tapped to replace her in the Senate. After winning her own full term in 2012—racking up the largest statewide victory in the history of New York politics—Gillibrand set about overhauling her political brand.

It wouldn’t be easy to shed the image responsible for her House victories—that of a down-home, gun-friendly, anti-amnesty, culturally conservative Democrat who identified with her rural constituents more than with the party’s coastal elite. But slowly, methodically, Gillibrand did just that, smartly picking and choosing fights that would burnish her populist progressive bona fides while elevating her national stature. She co-directed the effort that banned insider trading among members of Congress. She was an integral part of the campaign to repeal the “Don’t Ask, Don’t Tell” policy that governed gays in the military. She introduced pioneering legislation aimed at ensuring paid family leave. And she became Washington’s leading voice on sexual assault, first by focusing on cases in the military and then broadening to harness the energy generated by the #MeToo movement.

All the while, she raised tens of millions of dollars, wrote a New York Times bestseller and was named one of Time’s 100 most influential people in the world.

As it became clear that Gillibrand was preparing to launch a campaign for the presidency in 2020, the only question seemed to be the height of the senator’s ceiling. Could she win the Democratic nomination? And if so, could she succeed where her friend and former mentor, Hillary Clinton, failed four years earlier?

Today, the question is whether Gillibrand can get off the floor.

Top: In New Hampshire, Gillibrand high-fives a young child being held in his mother’s arms. Bottom: While speaking with voters, Gillibrand holds a glass of beer in one hand while gesturing with the other. | Melissa Lyttle for Politico Magazine

In a conversation for POLITICO’s “Off Message” podcast, the New York senator vacillated between insinuating that she is being treated differently because of her gender and arguing that Americans are ready for a female president.

“Hillary won the election. She won the popular vote by 3 million votes, and you have to remember, she was definitely the most qualified candidate we’d ever had running for president,” Gillibrand says. “And, but for Russia, but for Comey, but for misogyny, but for a lot of things, she would have won. So, I believe that of course this country is ready to elect a woman president, but they need to know what we’re running on and what we’re for, and why we’re running and why we think we’re the best candidate.”

Yet Gillibrand has struggled to communicate this to voters. Things have gotten so grim for her that recently, a high-ranking campaign aide to Cory Booker—Gillibrand’s opponent for the Democratic nomination—tweeted that she had donated to the New York senator’s campaign and encouraged others to follow suit. This was done, the aide noted, to ensure that Gillibrand’s “important perspective is on the debate stage.” To other Democrats, this looked less like an act of short-term benevolence than one of long-term strategy: The historically large field will soon begin to be winnowed, and when it does, some of the surprising early exits will make for valuable endorsements. No name has surfaced in those conversations of late more frequently than Gillibrand.

How did it come to this? How did one of America’s best-financed senators come to rely on charity and presidential pan-handling, begging for a dollar at a time just to stay alive? How did one of Washington’s most recognizable women find herself buried in the polls beneath a number of less prominent men? And how does she breathe life into her campaign before it’s too late?

Gillibrand and I discussed this, and much more, while having lunch in Manchester, in the car while driving to Goffstown and over a beer during her final stop of the day in Hampton.

Gillibrand claims, like all candidates do, that she’s having the time of her life campaigning for the highest office in the land. And yet her cheerful demeanor cannot mask the annoyance she is feeling—with the media, with the gender dynamics central to the race, and with the Democratic Party itself.

Gillibrand clearly doesn’t think much of the DNC’s rules governing the debates. Even before the national party announced the stricter criteria candidates would need to meet to qualify for the third and fourth debates this fall—effectively putting an expiration date on more than half of the Democratic candidacies—Gillibrand took issue with the emphasis on early polling to shape a process that has commenced far earlier that it once did.

“The last couple of presidential candidates who were Democrats who won, or even are nominees, you had to look at where they were at this early stage. I think somebody looked up where Bill Clinton was at this stage. He had 1 percent in the polls and had 30 percent name recognition in Iowa. So, like, it takes time,” Gillibrand said. “And with 20 candidates, it might actually take longer … because for each one of us to have a chance to be heard it’s going to take time. I mean, even the debates alone, if we get more than five minutes each on that stage, that’ll be surprising. So, you’re really even not even going to have more than a few minutes to talk about what you’re for and why you’re running and what your views are for the country.”

Top: At the Velcro Companies plant in Manchester, New Hampshire, Gillibrand talks with a class of high school interns taking part in “Velcro University,” where participants will learn both business and technical skills. Bottom left: Gillibrand autographs a book. Bottom right: A “Gillibrand 2020” sign is pinned to a bulletin board above a table of coffee supplies. | Melissa Lyttle for Politico Magazine

Gillibrand argues that both of the debate thresholds, polling and unique contributions, “are related to name recognition.” But she certainly is better known than the likes of Yang, or Williamson, or Gabbard, or Washington Gov. Jay Inslee, the latest 2020 candidate to “double qualify” by reaching both qualification milestones. Working the referees this early isn’t a sign of strategic savvy; it’s a sign of desperation.

Asked about the pressure she’s feeling, Gillibrand said it’s “created because of the DNC’s framework that they’ve put the candidates under,” which she suggests isn’t the “natural” or “normal” role for a national party. Asked whether she disagrees with the DNC’s rules, she replied, “I’m not sure. I don’t know that they’re serving the public well.”

Meanwhile, compounding Gillibrand’s frustration is her fraught relationship with the political issue that has defined her ascent: gender.

When I asked whether it was problematic to have so many white men—Beto O’Rourke, Joe Biden, Bernie Sanders, Pete Buttigieg—soaking up the media spotlight, she replied, “Yeah, I think it’s problematic. …. We have amazing women candidates, amazing candidates of color, and hopefully through this process we will lift our voices up and be heard.”

The look on her face when I mentioned O’Rourke’s appearance on the cover of Vanity Fair was beyond description. “Unusual,” she finally mustered, biting her lip and her tongue at once, a litany of curse words no doubt suppressed underneath her smirk. “Never seen it before.”

And when I asked Gillibrand to name the worst part of running for president, she replied, “I don’t want to tell you.” She added that “it’s not an appropriate thing for me to say,” then promised to tell me later, off the record.

After hearing the off-the-record answer, I pressed for a sanitized version, which she offered in the most measured of tones. “The one thing that’s annoying to me is how many times reporters ask you about our male colleagues. Who cares? I’m running for president. I want to tell you what my vision is, why I’m running, and why I’m going to win,” she said. “I think reporters like yourself, who are super smart and super careful, will always ask me what I think about the male colleagues. Are you asking the male colleagues what they think about us? Probably not.”

The one thing that’s annoying to me is how many times reporters ask you about our male colleagues. Who cares? I’m running for president. I want to tell you what my vision is, why I’m running, and why I’m going to win,” Gillibrand said. “Are you asking the male colleagues what they think about us? Probably not.”

This is the hang-up of Gillibrand’s campaign. Never has the Democratic electorate been more exercised by issues of identity, and never has gender been more central to the national conversation—politically, culturally, socioeconomically and otherwise. And yet Gillibrand, despite having very little to lose at this point, remains cautious in interviews and on the stump—aiming for broad appeal instead of a niche brand, trying to draw in support from every cell of the party rather than cultivating a base and building out.

During a tour of the Velcro factory in Manchester, the senator learns about their hook-and-loop fasteners, and their deep roots in the community, where the company has been based for 60 years. | Melissa Lyttle for Politico Magazine

At every stop in New Hampshire, the senator was careful to modulate her answers and her tone in ways that would render her universally acceptable. She talks of how she dominated the blue boroughs of New York City—but also how she carried the state’s red, rural counties. She believes Trump is a “coward”—but she wants to calm the vitriolic nature of our politics. Gillibrand didn’t shy away from a single proposal—whether it was expanding the Supreme Court, increasing funding for indigenous groups or signing a breast cancer-related pledge—that voters asked her about.

Yet when it came to addressing the gender bias she believes is inherent to politics—a belief shared by many younger progressive women, a sizable chunk of the Democratic coalition—Gillibrand held back. Had her off-the-record answer been published, it would have gone viral overnight, racking up hundreds of thousands of clicks and instantly erasing any concerns about her small-donor disparity. But Gillibrand chose to be careful. Having won in a red district, having persuaded older, whiter, Republican audiences to support her in the past, she believes she can do so again.



***

The problem for Gillibrand is, the polls and the fundraising numbers show that this cautious approach isn’t getting her anywhere. The over-50 male demographic in Iowa and New Hampshire is likely to lean toward candidates such as Joe Biden, Bernie Sanders, or perhaps even Elizabeth Warren, whose paeans to economic populism resonate with the dwindling remnant of blue-collar Democrats. The market Gillibrand was poised to corner—after becoming Washington’s leading voice on women’s rights issues and embracing the risk of calling for Al Franken’s resignation from the Senate—was that of the young, female voters who have mobilized the backlash to Donald Trump’s presidency.

Instead, in an overflowing field with more than 20 candidates slicing and dicing the electorate every which way, Gillibrand seems to believe that she can’t afford to alienate any one bloc of voters.

If the recent controversies surrounding new state-based abortion laws are any indication, it’s a tactical misreading of the race. Gillibrand’s forceful denunciations, on social media and cable news programs, earned her more free media coverage than anything else since the launch of her campaign. It was a reminder that she is more comfortable than any of the other Democrats in speaking to women’s issues, having not only mastered the messaging but worked extensively on the policies regarding everything from pay equality to workplace discrimination.

In that instance, Gillibrand seized the opportunity to gain headlines and eyeballs—and most likely, campaign donations—by owning an issue of visceral importance to what should be her core base of supporters.

Still, she seems conscious of doing so infrequently, wary of being typecast as a single-issue candidate. In a vacuum, for a generic Democratic woman candidate hoping to defeat Trump in a November election, it’s not necessarily a bad idea to downplay the talk of glass ceilings. And yet, for a female Democratic candidate like Gillibrand, whose image is heavily colored by her fights for gender equality, winning the party’s nomination—and the right to challenge Trump—might require a greater reliance on her identity.

Gillibrand clasps her hands. | Melissa Lyttle for Politico Magazine

This is the paradox of Gillibrand’s candidacy. She believes, as do many of her Democratic rivals, that voters want “electability” in a nominee—someone who above all else will defeat Trump in 2020. And she does have a case to make in that regard: As a former upstate congresswoman, she does have a feel for the nonideological challenges facing rural and poor America. And at her core, layers beneath the questions about her political evolution, she is inherently relatable, someone who quotes Scripture as easily as she sips a beer or rocks a baby.

But Gillibrand’s emphasis on long-term electability may be coming at the expense of her short-term viability. She has chosen not to pursue with reckless abandon the demographic that should be her core constituency in the primary—women—believing it would limit her appeal to other portions of the electorate. And she has ignored suggestions that she change course and act with more urgency in this regard, telling me, “I need to be patient, and know that it’s going to take time and hard work. … Your poll numbers are irrelevant today. What matters is where you are a year from now.”

The problem facing Gillibrand is, poll numbers at this stage of a presidential primary have never been more relevant to the outcome—and if she doesn’t do something drastic to improve hers, she won’t be around a year from now.