Democrats are torn over whether Kirsten Gillibrand can be their savior from Trump

REUTERS/Scott Audette

U.S. Senator Kirsten Gillibrand (D-NY) speaks at the Democratic National Convention in Philadelphia, Pennsylvania, U.S. July 25, 2016.

• Sen. Kirsten Gillibrand has become one of the most talked-about potential 2020 candidates as she's led her party's response to the #MeToo movement and been attacked by the president for it.
• Supporters say Gillibrand checks lots of presidential candidate boxes: She has support from a broad swath of the party, a very liberal voting record, and she's young and a woman.
• But critics say her ideological shape-shifting on key issues, status as a career politician, and obvious ambition will sink a potential bid.

Sen. Kirsten Gillibrand has spent her career being underestimated.

The New York Post once called her Sen. Chuck Schumer's "hapless little poodle." Sen. Joe Lieberman has described her as "adorably persistent." Former New York City Mayor Michael Bloomberg refused to meet with her for months after she was appointed to fill Hillary Clinton's vacated Senate seat in 2009. And her former colleagues in the US House would call her "Tracy Flick," an unflattering reference to Reese Witherspoon's ruthless, overly-eager character in "Election."

So when President Donald Trump attacked Gillibrand on Twitter in early December, calling her a "lightweight" who "would do anything" for campaign contributions, it seemed the junior New York senator had prepared her entire political career for precisely this "sexist smear meant to silence" her, as she described Trump's attack.

Her response to Trump - "You cannot silence me or the millions of women who have gotten off the sidelines to speak out about the unfitness and shame you have brought to the Oval Office" - became her most retweeted message ever, elevating her status as a feminist hero of the anti-Trump resistance movement. And as her Democratic colleagues dutifully rushed to her defense, the media described Trump's tweet as a "political gift."

Amid all that, the ever-strategic former corporate lawyer remained on brand, subtly plugging her women-focused political action committee, Off the Sidelines and appearing on liberal comedian Samantha Bee's show. Bee said she hoped the incident would become Gillibrand's "superhero origin story and ignite her 2020 campaign."

Indeed, Trump's attack was the clearest indication that Gillibrand is no longer being underestimated.

'Woke to the moment'

While the senator and her aides won't confirm or deny Gillibrand's plans for a 2020 run, all signs, including her prodigious fundraising, outreach to young people and communities of color, and deeply anti-Trump voting record, point to the lawmaker's higher ambitions.

She led her caucus in pressuring Democratic Sen. Al Franken, a close friend and ally, to leave office amid mounting allegations of sexual misconduct. Critics and supporters alike say the national spotlight she's attracted for her leadership on sexual misconduct issues is well-deserved, given the years-long fight she's waged, often with little political support, against sexual assault in the military and on college campuses.

"There's a saying in show business that it took me 15 years to be an overnight success. In many ways, when it comes to attention and leading the party on one of the most important issues, it's taken her seven or eight years to be an overnight success," Stu Loeser, a Democratic strategist and former press secretary to Mayor Bloomberg, told Business Insider.

Mark Wilson/Getty Images

Democratic Sens. Al Franken and Kirsten Gillibrand

The senator shocked even some of her close allies when she told a New York Times reporter in November that President Bill Clinton - her longtime supporter - should have resigned over his affair with Monica Lewinsky.

A total of zero prominent elected Democrats backed Gillibrand up on this, but many agree it was a smart political move, winning her points from the party's anti-establishment base. Gillibrand's principled stance now differentiates her from her Democratic colleagues and has made clear that she will not be caught equivocating or apologizing on behalf of her allies on her signature issue.

"Gillibrand is trying to capitalize on the current political moment - kill your idols," wrote FiveThirtyEight political reporter Clare Malone in November. "This is smart, in my book, because frankly: (i) a lot of people hate the Clintons, (ii) it makes Gillibrand seem woke to the moment, (iii) it's a way to make her seem like a more appealing anti-establishment liberal to the younger folks."

An outspoken voice for the so-called "resistance," Gillibrand currently holds the most anti-Trump voting record in the Senate and a recent analysis published in The Washington Post found that Gillibrand is also voting to the left of her constituents.

Checking the boxes

Gillibrand checks a lot of politically helpful boxes: she has support from a broad swath of the Democratic Party - from Clinton-allied centrists to Bernie Sanders progressives, she's relatively young at 51, she's worked across the aisle while maintaining a very anti-Trump voting record, and she's a woman at a time when the party will likely seek a history-making nominee.

The senator's supporters argue that her appeal both among progressive New York City voters and conservative communities upstate could position her as a bridge over the gaping urban-rural divide.

Loeser, the Democratic strategist, says that Gillibrand "shows up" and "delivers" in the suburbs of Buffalo and exurbs of New York City - places where Hillary Clinton either lost or barely clinched a majority in the 2016 general election - while recognizing that satisfying those constituents "doesn't come at the expense of also caring about refugees, immigrants, and people stuck in the cycle of poverty" in urban areas.

"It's not an easy thing to understand and speak to the progressive side of the Democratic caucus and also internalize and understand how people think and what matters to them in areas of the country that are not strong Democratic bastions," he said. "That ability would be extraordinarily useful in putting together a majority vote in states like Ohio, Pennsylvania, Michigan, and even Florida."

Andrew Harnik/AP

Sen. Bernie Sanders and Gillibrand unveil their Medicare for All legislation at a press conference in September.

Her supporters say the mother of two represents a new crop of leaders, more relatable and accessible than ever before.

"She's a new generation. No pomp and circumstance, or pretense. Less baggage," Jon Reinish, a Democratic strategist and former aide to the senator, told Business Insider.

The fact that Gillibrand is a woman - and a powerful advocate for women in politics - could be an asset if the party decides it wants to break the glass ceiling in 2020. Matt McDermott, a Democratic pollster at Whitman Insight Strategies, said that Gillibrand's success may rest on that question.

"Do we feel as a party as if we need a history-making candidate, the most obvious being a woman candidate?" McDermott told Business Insider. "Is there a strong push to have a nominee of the Democratic Party that breaks conventional molds, that would be a first? And if there is that upswelling, it's hard to see how a candidate can push against that."

But Gillibrand's national prominence and new reputation as an anti-Trump crusader may come at the expense of her popularity across New York. Formerly one of the most conservative Democrats in the House, Gillibrand won reelection in 2012 with 72% of the vote. But just 49% of New York state voters surveyed in a September Siena College poll and an October Morning Consult poll viewed her favorably - compared with Schumer's respective 58% and 55% approval ratings.

"Consultants love candidates who check a lot of boxes," Bradley Tusk, a venture capitalist and former top adviser to Mayor Bloomberg, told Business Insider, questioning whether Gillibrand really has the broad appeal some credit her with. "The problem is, what appeals to someone on K Street seems to be extremely different from what appeals to voters on Main Streets in swing states."

Still, some Democrats point to career politicians like Sen. Bernie Sanders, a 30-year veteran of Washington who's celebrated by the party's left wing as the picture of authenticity.

"Bernie is a 40-year politician with 30 in DC and he felt fresh and authentic to his supporters," Marc La Vorgna, a political consultant and former press secretary to Mayor Bloomberg, told Business Insider. "It's about feel and voice. The point is years in office doesn't matter. You can be fresh and exciting via authenticity."

'Kirsten Gillibrand, champion for one woman'

Some argue Gillibrand's status as a Washington insider and career politician, history as Blue Dog Democrat, and accusations of shape-shifting will hurt her.

As one of the most conservative Democrats in the House, Gillibrand had an "A" rating from the National Rifle Association and was opposed to allowing illegal immigrants to obtain driver's licenses. But she very quickly moved left on gun control and immigration after former New York Gov. David Paterson appointed to her Senate seat, as she took up the fight against sexual assault in the military and the "Don't Ask Don't Tell" policy.

Like Hillary Clinton, who has long been accused of political opportunism, many predict Gillibrand would be hammered both in a Democratic primary and in a general election for her ideological evolution.

"The biggest hit on her is going to be her lack of core principles," one New York-based Democratic operative told Business Insider. "In New York, the biggest hit on her has always been that she's a creation of political consultants."

Ciro Scotti, a political commentator and contributing editor at the Fiscal Times, wrote in a Daily Beast column earlier this month that Gillibrand is "an especially egregious practitioner of the finger-in-the-wind politics that so many voters can no longer abide."

Jacquelyn Martin/AP

Gillibrand with her staff on Capitol Hill in December.

But Gillibrand is endlessly apologetic about positions she chalks up to her former ignorance.

In a December podcast interview with liberal organizer and activist DeRay Mckesson, Gillibrand said she was "embarrassed and ashamed" that she "didn't know enough" as a House member to inform her positions.

"I didn't work hard enough to be a kinder person, a more empathetic person, a person who could feel the challenges that families were facing in a very real sense," she said, adding that when she was appointed to her Senate seat she worked quickly to get up to speed on the issues that impacted her newly diverse constituency.

Some argue that this larger narrative about Gillibrand's lack of authenticity - the belief that she is "too transparently opportunistic to be a viable candidate," as Scotti put it - may be her death knell.

"The narrative about her isn't going to be Kirsten Gillibrand, champion for women," Scotti said. "It's going to be Kirsten Gillibrand, champion for one woman."