Until recently, Scott Stringer, New York City’s avuncular two-term comptroller, was widely viewed as the embodiment of a conventional Upper West Side liberal — a designation that once paid dividends for the city’s elected officials but now seems fairly antiquated in a political landscape populated by upstart progressives. The stereotype, to be sure, didn’t always hold. As the city’s chief accountant, he has savored the occasional quarrel with Mayor Bill de Blasio — and briefly flirted with a primary challenge against his fellow Democrat — while pushing to divest the city’s pension funds from the fossil fuel industry.

For the most part, though, the 60-year-old comptroller, who for nearly three decades has steadily ascended the traditional career ladder of New York City politics — from state assemblyman to Manhattan borough president to his current role — was more likely to give the impression of a “center-left, run-of-the-mill, incumbent New York City Democrat,” as Nicole Gelinas, a senior fellow at the Manhattan Institute, put it in a blunt assessment.

But with Gracie Mansion now in his sights, Stringer has undergone something of a makeover. As he mounts his first mayoral bid, the politically moderate insider has effectively rebranded himself as one of the leading progressive candidates in a packed primary — racking up endorsements from a growing faction of left-wing stalwarts like Rep. Jamaal Bowman (D-NY) and State Sen. Julia Salazar, both of whom unseated longtime incumbents with support from the Democratic Socialists of America.

“I’m very proud of the endorsements I’ve received,” Stringer said in a recent interview with Jewish Insider. “I have support in the progressive community and support throughout the city.”

Stringer’s newfound cachet, viewed from one angle, represents the product of an ongoing political courtship as progressives gain influence in the state. Over the past few years, Stringer has tacked leftward, having endorsed another DSA-backed candidate, Tiffany Cabán, in the recent Queens district attorney race, after throwing his support behind a group of insurgent state Senate candidates, some of whom have returned the favor as he runs for mayor.

“The way you become mayor is to build a multiracial, intergenerational coalition,” Stringer told JI. “The beauty about New York City is that there’s not one group that elects you. You have to build a broad coalition — and I’m happy that we’re doing that.”

While he has no doubt benefited from his new relationship with progressives, Stringer’s affiliation with the left-leaning flank of the Democratic Party has also come at a cost. Several of his traditional allies, including Jewish community members as well as pro-Israel advocates and real estate developers, are questioning the authenticity of Stringer’s approach as he pulls in support from progressives whose views, at least on some matters, do not seem to match his own. 

“As the old saying goes, he’s trying to dance at two weddings,” said a prominent Jewish leader who is active in New York City politics, speaking anonymously due to the sensitive nature of the discussion. “That’s going to be a real challenge for him.”

One hot topic is Stringer’s support for two prominent DSA-backed progressives, Cabán and Salazar, who are seen as aligned with the Boycott, Divestment and Sanctions movement — connections that do not sit well with many in the Jewish community. Orthodox Jews in Queens were said to be infuriated by Stringer’s decision to endorse Cabán over Melinda Katz in the highly competitive DA race two years ago. Stringer also endorsed Salazar, a vocal proponent of BDS, when she ran for state Senate in 2018. 

Cabán, who is now running for City Council after losing to Katz, hasn’t yet reciprocated as Stringer makes his bid for mayor. But with four months remaining until the June primary, Salazar has already offered her enthusiastic support. 

“He’s toxic at this point,” said a Jewish community leader in Queens who asked for anonymity to speak freely. “People don’t trust him anymore.”

Asked about those concerns in the interview, Stringer expressed surprise at his allies’ positions. “I don’t know if they’re pro-BDS,” he said. “I don’t know that.” As comptroller, Stringer, who is Jewish, led a delegation to Israel in 2016, and oversaw the city’s retirement funds, which are invested in Israel Bonds. He has previously denounced BDS as antisemitic and, over the summer, spoke out against a DSA questionnaire asking local candidates to pledge not to visit Israel if elected. Stringer reiterated to JI that he rejects the BDS movement, but he was reticent on the topic of his recent endorsements. “Let me just say,” he noted, “I’ve endorsed a wide range of people over the years.”

“I’m going to work with our community as I always have,” said Stringer, who adds that he is raising two Jewish sons with his wife, Elyse Buxbaum, an executive vice president at the Museum of Jewish Heritage. “When there have been upticks in hate crimes against Jews and non-Jews, I have always stood up,” he added. “I am very proud of that record, and I’m not going to get sidetracked by the politics of the moment.”

Matt Nosanchuk, president and co-founder of New York Jewish Agenda, a progressive advocacy group, defended Stringer’s newly forged political alliances in an interview with JI. “I think he’s made his position clear,” Nosanchuk said of the comptroller’s stance on BDS. “In order to work on issues that are of importance to all New Yorkers, we need to be in partnership with others who hold diverse views.”

On other issues of concern to the Jewish community, Stringer has been equally circumspect. Asked about his stance on yeshiva education, he spoke in broad strokes. “We have to work with yeshivas and make sure that we strike the right balance between education and making sure that every child gets a strong secular and Jewish education,” Stringer said. “All our students should get a quality education that prepares them for the future.” 

Andrew Yang, the former presidential candidate and another Democratic frontrunner in the race, has expressed perhaps the strongest support for the existing yeshiva model of any candidate, indicating that he won’t seek to impose more secular education in such schools. But Stringer was critical of Yang’s approach. “I don’t think he really understands what he’s talking about,” Stringer told JI. “I think there’s obviously going to be the balance between Jewish education and secular learning, and everyone has to work towards the same goals.”

Maury Litwack, executive director of Teach Coalition, an organization operating under the Orthodox Union umbrella, said that Stringer was a strong advocate for providing kosher and halal school lunches during his time as the city’s comptroller. “He has been someone who understands these issues and has communicated with schools throughout the five boroughs,” Litwack said. But now that Stringer is running for mayor, his positions appear somewhat more muddled. “He needs to articulate his stance on a whole variety of issues that are important to the community,” Litwack said, “including the fundamental issue, which is equitable and fair funding.”

As he moves to the left, Stringer has also alienated many in the real estate industry. His decision to abjure donations from developers, despite having benefited from their largesse earlier in the campaign, as a Politico analysis revealed, put him in line with progressive values but angered industry leaders who regard the move as disingenuous. “The impression from the industry is that he is saying to them, ‘Listen, this is what I gotta do to get elected, and when I am elected, then I will have to govern with everyone’s interests in mind,’ wink wink, nod nod,” Jay Martin, executive director of the Community Housing Improvement Program, said in an interview with JI. 

“I’ve made the decision not to take big developer money going forward, but I’ve made it very clear that we’ve taken real estate contributions in the past, and I’m totally comfortable with that,” Stringer clarified, adding: “I would like to be a mayor in City Hall that is unencumbered by contributions, because I think the voters want to see that.”

Still, Martin is incredulous. “Who are we to trust, the old Scott Stringer or the new Scott Stringer?” Martin asked. “That’s the question.”

But there may not be much of a difference between them after all. While Stringer called for defunding the police at a memorial service for George Floyd in Brooklyn last June, for instance, he has since tempered his enthusiasm for such measures — one indication that he might stick to the middle lane if elected. Jerry Skurnik, a Democratic political consultant in New York, told JI that Stringer is still the same politician he was before the progressive push. 

“By getting endorsed by them and by endorsing a number of them in their contests, he may have given the image that he’s more progessive than he was originally,” said Skurnik, who counts Stringer as a friend. “But in reality, on the issues, I don’t think he’s changed much at all.”

His observation underscores what appears to be a central tension in Stringer’s campaign, as he has jettisoned old allies to bring in the left. But despite endearing himself to a number of high-profile progressives, Stringer is struggling to emerge as the left’s preferred candidate, according to Susan Kang, an associate professor of political science at John Jay College of Criminal Justice and a steering committee member of the DSA’s Queens branch. 

“The main reason why Scott Stringer doesn’t completely occupy that progressive lane is because, I think, a lot of people want to support a more diverse candidate,” she told JI. “We really generally have white, male mayors, with very few exceptions, and with the Black Lives Matter movement, there’s been a lot of desire for a really progressive woman of color, or a woman, to run in the left lane.”

Not that Stringer isn’t a formidable candidate. “Scott Stringer can win, he definitely has a path to victory,” said Kang, suggesting that the city’s new ranked-choice voting system could give him an edge over other candidates because many voters will likely be familiar with his name and pick him as their second choice. “But he’s not necessarily a darling of the progressives in the way that, a couple of years ago, it looked like he could have been.”

Either way, Stringer is confident that he will prevail as he goes up against a number of big-name candidates, including Yang, Brooklyn Borough President Eric Adams, former Citigroup executive Ray McGuire and former de Blasio aide Maya Wiley. He boasts of the small-dollar donations that have helped buoy his imposing war chest, while claiming that his experience as a citywide official bolsters his appeal.

“Serving as comptroller has given me a unique understanding about the economy of the city, the budget of the city, the agencies that worked for the city,” he said. “I’ve been the auditor-in-chief, I’ve managed a $240 billion pension fund, which is the 14th largest in the world. I have looked at every single contract that the city enters into. I’ve refinanced $800 million in debt savings. And that’s just half my day.”

Stringer is unconcerned by recent polling suggesting that he is in third place with only 13% of the vote. “I’ve seen this movie before,” he countered, arguing that he was looking at similar odds when he ran for comptroller against Eliot Spitzer. “But I campaigned my heart out, I made the case, and I won the race,” he said. “I’m ready for the upset and the comeback. It’s what I’ve done in the races I’ve run.”

As the city faces an unprecedented financial crisis exacerbated by the pandemic, Stringer emphasizes that he will need to take bold measures if elected. “I look back at Mayor LaGuardia, who was so much about doing big important things,” he said, “and I hope that I bring my skills and vision to rebuild the city in an inclusive way.”

Rep. Jerry Nadler (D-NY), a mentor, seems to think Stringer is the right man for the job, having endorsed him in December. Stringer, who grew up in a politically connected family in Washington Heights, was in his early 20s when he started working as a volunteer in Nadler’s former State Assembly office. In a recent interview with JI, Nadler suggested that Stringer has always been a dependable leader. 

“At every stage of the game, he’s been, number one, courageous, number two, perceptive, understanding people,” Nadler said, pausing for a brief moment before tacking on a final descriptor: “Progressive.”