Scott Stringer’s deep experience in New York City politics has yet to translate into momentum in the mayor’s race. Could an endorsement from the Working Families Party help?

The New York City mayoral race is one of the most consequential political contests in a generation, with immense challenges awaiting the winner. This is the second in a series of profiles of the major candidates.

By Katie Glueck

On a late February morning in Tribeca, the most seasoned politician in the New York City mayor’s race was sitting outside, futzing with his fogging-up eyeglasses as he wrestled with an assessment of an election that appeared to be slipping from his grasp.

For Scott M. Stringer, every chapter of his steady ascent through New York politics — serving on a community planning board as a teenager; becoming a protégé of Representative Jerrold Nadler; moving from district leader to state assemblyman, Manhattan borough president and finally, city comptroller — has laid the groundwork for a long-expected mayoral bid.

He has deep experience, boasts a raft of endorsements and verges on jubilant when describing his passion for his hometown. For much of the mayoral campaign, none of that has been enough to generate a surge of enthusiasm around his candidacy, according to polling and interviews with more than 30 activists, lawmakers and other New York Democrats.

Mr. Stringer is working hard to change that.

“If I was a book, and you’re in a bookstore and you saw the cover of the book, you may say, ‘I’m not sure I want to read that,’” Mr. Stringer said, framing a picture of himself with his hands, reaching from his head to his midline.

“What my job is, is to get people of all different backgrounds to take that book off the shelf, open up the book, look at the different chapters of my career and the issues I’ve championed.”

Mr. Stringer, 60, would appear to have the resources, the résumé and the name recognition to do just that, trailing only Eric Adams, the Brooklyn borough president, in funds on hand so far.

He is hoping that his carefully cultivated political network and a mood of citywide emergency will help him attract voters motivated by both his progressive pitch and his pledges of steady managerial competence.

On Tuesday, Mr. Stringer was endorsed as the first choice of the Working Families Party, aiding his efforts to emerge as the race’s left-wing standard-bearer.

Still, in recent months, it is Andrew Yang — embraced as a celebrity from the 2020 presidential race — who has led polls and infused significant energy into the mayoral campaign. Mr. Stringer, who began the race as a top candidate, has scrambled to brand Mr. Yang as an unserious purveyor of “half-baked ideas” even as he dominates news media coverage.

Mr. Adams and Maya D. Wiley, a former counsel to Mayor Bill de Blasio, beat out Mr. Stringer for several major labor endorsements. Those candidates and others in the crowded field are also competing with Mr. Stringer for either the “government experience” mantle or the title of left-wing standard-bearer.

And for all of his prominent supporters, detailed policy plans and ambitious ideas on issues like climate and post-pandemic education, Mr. Stringer is also a white man who spent his career rising through traditional political institutions. New York Democrats in several recent races have preferred to elevate candidates of color and political outsiders.

Now he faces his most challenging balancing act to date, as he campaigns as a veteran government official while seeking to ally himself with the activist left.

“He’s trying to thread this needle between new and old supporters,” said Susan Kang, a member of the steering committee of the New York City Democratic Socialists, in an interview late last month. “You know how if you try to make everybody happy, you don’t make anybody happy? That is something that has given people pause.”

Yet with the Working Families Party’s endorsement, Mr. Stringer found new cause for optimism. It was a signal to deeply progressive voters that the group believes they should unite around supporting Mr. Stringer’s candidacy, at a time of growing left-wing concern about Mr. Yang.

Mr. Stringer remains in contention for other major endorsements, including one from the United Federation of Teachers. And he is aware that many voters have just begun to pay attention. Major debates do not begin until May, and the race to the June 22 primary may not crystallize until more candidates hit the airwaves with television advertising in the final weeks of the race.

Still, one supporter recently compared Mr. Stringer to Senator Elizabeth Warren of Massachusetts, Mr. Stringer’s choice in the 2020 presidential primary. Like Ms. Warren, Mr. Stringer has a long list of policy plans and is thoughtful about governance. But Ms. Warren, the ally noted, did not win.

Mr. Stringer said his campaign planned to be “very aggressive” in the coming weeks, “reminding people of my record and who I am and what I believe in and what I would do as mayor.”

“I need a message moment,” he said.

A political upbringing

Any book written about Mr. Stringer would have a common theme: He is a political animal.

Mr. Stringer, born to a politically active Jewish family, was raised in Washington Heights. His father was counsel to Mayor Abraham Beame, his mother was elected to the City Council, and his stepfather also worked in city government.

He made his campaign trail debut at age 12, volunteering for Representative Bella S. Abzug, his mother’s cousin, who went on to run for mayor.

At 16, he was tapped for a community planning board position. His appointment made the front page of The New York Times, and while on the board, he honed a version of at least one line that he still uses today: that the A train was his “lifeline.” Soon he was working for Mr. Nadler, serving on his assembly staff.

“He was a little cocky,” Mr. Nadler recalled. “He learned to restrain that and to work with people very carefully.”

Mr. Stringer, who did a stint as a tenant organizer, also served as a Democratic district leader in the 1980s, building a base on the Upper West Side, where the political culture reflects a vibrant Jewish community.

Longtime observers tend to reach for Yiddish phrases of affection and derision to describe him. Admirers call the affable Mr. Stringer, a married public-school father of two sons, a “mensch.” Detractors privately dismiss the nasal-voiced candidate as a “nebbish.”

New York City voters have often embraced politicians with more boldly distinctive personas.

Mr. Stringer, who once taught his parrot to say “Vote for Scott,” is working on it.

Asked in a campaign video to share something about himself that might surprise others, Mr. Stringer insisted, “I really am funny.” After a reporter asked him to tell a joke, Mr. Stringer spent the rest of an hourlong interview sprinkling his remarks with wisecracks.

“Scott, when he’s not doing his work politically, he’s actually quite funny, he’s got a great personality” said Michael Mulgrew, the president of the United Federation of Teachers. “But I guess because of his years of experience, he’s guarded when he’s doing his governmental work.”

Mr. Stringer was elected to the State Assembly in 1992, following failed efforts running bars. In Albany, he pressed for some reforms of the State Capitol’s insular political culture, including a requirement that lawmakers be present in order to cast their votes.

In 2005, he won a nine-way primary race for Manhattan borough president.

Over the years he forged a reputation as a liberal who supported marriage equality and tenants’ rights, was skeptical of stop-and-frisk policing tactics, and had strong relationships with labor leaders and some reform-minded candidates. And he sharpened his skills as a strong retail campaigner who delights in touring senior centers.

He mulled and abandoned several options for higher office, including a 2013 mayoral bid. Instead, he ran for city comptroller. In the greatest test of his career, he faced a late entry from Eliot Spitzer, the deep-pocketed and aggressive former governor who resigned after revelations of his involvement with a prostitution ring.

Many had expected Mr. Spitzer to steamroll Mr. Stringer. For awhile, he seemed on track to do so. But Mr. Stringer held his own in a brutally personal race and overcame a polling deficit, though Mr. Spitzer beat Mr. Stringer with Black voters by significant margins.

“We were not just behind early, we were behind at the end,” Mr. Stringer said. “I fought back through the debates, through the campaigning, and I won. So for me, this positioning is what I’m used to.”

There are key differences, though: In 2013, Mr. Stringer had overwhelming support from unions and the political establishment. Now, labor endorsements are more scattered.

And this race is unfolding in a pandemic. He had been cautious about in-person campaigning, after his mother died from Covid-related complications. Now vaccinated, he is seeking to match the more frenetic pace that some rivals, most notably Mr. Yang, have maintained for months.

As comptroller, Mr. Stringer handled issues from housing authority audits to promoting kosher and halal food in public schools.

He also supported closing Rikers Island and was a key part of the effort to divest $4 billion in city pension funds from fossil fuel companies; he cited that initiative when asked to name the proudest accomplishment of his career.

People who have watched Mr. Stringer in the role say that he has been active in issuing audits and reports on issues vital to the city’s well-being, while embracing a time-honored comptroller tradition of tangling with the mayor.

“Have there been contracts that have gone haywire? It doesn’t seem so,” said State Senator John C. Liu, who preceded Mr. Stringer as comptroller and has yet to endorse in the mayor’s race. “Has the office conducted audits that improved the performance of agencies? I believe there have been some.”

On the whole, Mr. Liu ruled, “He has done a fine job as comptroller.”

Kathryn S. Wylde, who heads the business-aligned Partnership for New York City, said that she believed Mr. Stringer had been “bold on corporate governance issues, he’s been bold in taking on the mayor.”

Mr. Stringer has pressed for more disclosures about board diversity, and he has sharply criticized the de Blasio administration over issues ranging from affordable housing to its handling of prekindergarten contracts.

“He’s done an aggressive job — and substantive — on all the key responsibilities of the comptroller,” Ms. Wylde said.

To many New Yorkers, Mr. Stringer retains a reputation of being a traditional Democrat. He supported Hillary Clinton over Senator Bernie Sanders in the 2016 presidential race, and served as a delegate for Mrs. Clinton. In 2018, he supported Gov. Andrew M. Cuomo over his progressive challenger, Cynthia Nixon.

Mr. Stringer has since called for Mr. Cuomo’s resignation amid accusations of sexual harassment.

A progressive wager

Last September, a group of New York’s leading left-leaning lawmakers, many of them women and people of color, gathered at Inwood Hill Park to cheer on Mr. Stringer’s announcement for mayor.

It was a scene years in the making.

In early 2018, Alessandra Biaggi and Jessica Ramos were political unknowns, seeking to topple powerful moderate members of the State Senate. Mr. Stringer heard out Ms. Biaggi over a side of pickles at the Riverdale Diner; Ms. Ramos of Queens sought his support at drinks in Albany.

He became an early champion of several insurgent progressives, cultivating genuine relationships over strategy sessions, phone calls and meals. Those endorsements were an uncertain political bet at the time.

By last fall, they appeared to have paid off: As he announced his mayoral campaign, he was flanked by a diverse group of progressive lawmakers — including State Senators Biaggi and Ramos — who, to their admirers, represent the future of the party.

It is less clear if their endorsements will translate into grass-roots enthusiasm for Mr. Stringer among voters who are skeptical of his left-wing bona fides.

In his 2005 borough president race, a rival ran an ad criticizing Mr. Stringer for taking real estate developer money at a time when the city’s traditional power donors were looking for receptive politicians (the mayor at the time, the billionaire Michael R. Bloomberg, accepted no donations). It wasn’t until much more recently that he said he would stop taking cash from big developers, as prominent progressives highlighted the issue.

He has become a sharp critic of segregated schools, saying definitively that he wants to eliminate the admissions exam that determines access to top city high schools, which some critics say perpetuates racial inequality. But he has not typically been associated with major integration efforts in past years.

And he appears uncomfortable discussing aspects of the policing debate.

Amid protests over the killing of George Floyd, Mr. Stringer declared that it was time to defund the police.

But Mr. Stringer no longer emphasizes calls to “defund,” a term associated with a specific movement — another reminder that he is not fully part of the activist left. Pressed on whether he believed the phrase was divisive, Mr. Stringer would not answer directly.

“I have used it,” he said. “I don’t think you should be judged based on, you know, one word or another word. And I do believe that when you’re going to talk about these issues, you have to be prepared to come forth with a plan.”

He has proposed reallocating $1.1 billion in police funds over four years and has been more specific on the matter than some of his rivals, though Dianne Morales, perhaps the race’s most left-wing candidate, has pushed for far more, urging $3 billion in cuts from the police budget.

No saga better illustrates Mr. Stringer’s political high-wire act than his 2019 endorsement in the Queens district attorney race. His embrace of Tiffany L. Cabán, the choice of the New York Democratic Socialists, over Melinda Katz, a colleague from his Assembly days who narrowly won, delighted progressive activists but stunned old allies.

Critics who spoke with him at the time say Mr. Stringer had privately described New Yorkers as moving to the left, and they sensed that he wanted to embrace that shift. Mr. Stringer has said he believed Ms. Cabán, who is now running for City Council, was the more qualified candidate, but he also sounded testy when pressed on his decision in an interview with a Jewish outlet, to the irritation of some activists.

“Scott, you know, seemed to have changed some of his positions over the years,” said Representative Gregory Meeks, the chairman of the Queens Democrats. “That has caused him, in Queens County at least, which I can speak to, to have some difficulty.”

Competence over ideology?

From Mr. Stringer’s earliest days in politics, he learned to think strategically about relationships.

He has maintained communication with business leaders, and his central message that he will be prepared from Day 1 to “manage the hell out of the city” is not ideological.

Ms. Wylde said that some business leaders “know him as a steady hand.”

“When I think he’s going totally off the deep end, we have a conversation,” she added.

Ranked-choice voting, which enables voters to support up to five candidates, will test Mr. Stringer’s political skills like never before.

Even if he is not the favorite of deeply progressive voters, he hopes to be their second choice. That could also work with moderates who see him as more of a manager than a firebrand. But first he must cement his standing as a leading candidate in the homestretch of the race.

Mr. Stringer knows that he has significant work to do.

In a campaign video he filmed to introduce himself to voters, he said that his favorite movie was “The Candidate,” a 1972 film that traced the arc of a dazzling young candidate, played by Robert Redford, who had little understanding of government process.

He has little in common with Mr. Redford’s character. But Mr. Stringer, too, must prove that he can win.