Scott Stringer in Brooklyn on March 3.
Photo: Andrew Lichtenstein/Corbis via Getty Images/2021 Andrew Lichtenstein

Last fall, Scott Stringer wasn’t just confident. “He was cocky,” said one person close to him. “He was very aggressive about it, like, ‘I am going to be the next mayor, and you need to decide if you are with me,’ ” said another.

Stringer had reason for optimism: The city comptroller was the only person in the mayoral field who had been elected to citywide office. He was maxing out in fund-raising, had relatively high name recognition with voters, and had collected a pile of chits from four decades in and around New York politics and government. And perhaps most important, he had shrewdly endorsed a number of far-left insurgents who had run against the political Establishment in 2018 and 2020. Nearly all of them won, then promptly lined up behind Stringer’s campaign, adding a youthful activist panache to his otherwise plodding persona.

Stringer has spent a lifetime slowly climbing the ranks of city politics. His mother, father, and stepfather were all part of the Democratic machine of the 1970s. His cousin was the feminist icon (and 1977 candidate for mayor) Bella Abzug. He first joined his local community board as a teenager, ran for City Council at 29, and hadn’t yet been sworn in as Manhattan borough president before he told a New York Times reporter he had his sights set on City Hall. He considered running in 2013 and again in 2017 before twice taking a pass.

But after climbing at last to the political precipice, Stringer has taken a tumble. Polls give former businessman Andrew Yang double the support of Stringer, who has dropped to third place, just behind Brooklyn borough president Eric Adams, and in some cases to fourth, behind civil-rights attorney Maya Wiley. In other words, after a lifetime of spending his evenings popping from one political event to the next, and his days tending to the flames of city government, Stringer is now getting his lunch eaten by a guy who has admitted that he never voted in a local election and whose recently passed kidney stone received more media coverage than the rest of the field combined.

“I could give a shit,” Stringer said at an outdoor café in Queens earlier this month when asked what Yang’s entry means for his strategy, as he took out a couple of the packets of Sweet’N Low he keeps folded in his wallet and dumped them into his coffee. “It didn’t alter one moment of the campaign. I’m not kidding. There was no emergency meeting, no nothing. I have been in this movie before.”

It is canon in Stringer world that he’s a campaign closer. In 2005, he came from behind to best the better-known Eva Moskowitz in the borough-president race. Then, in 2013, he cleared the field to run for comptroller only to see the race upended when Eliot Spitzer figured the public had forgiven him for his prostitution scandal and jumped into the contest. National news covered it as if Spitzer’s comeback were complete; the former Luv Guv was even invited on The Tonight Show With Jay Leno. Stringer, meanwhile, rallied the political class locally; got every labor union, elected official, editorial board, and political club to endorse him; and went sharply negative against Spitzer in the final weeks. He was down 19 points and came back to win.

There are rhythms to these local races, and the key is to not get too spun up about polling and Twitter engagements in early April. Mayoral campaigns tend to be won in the last five weeks. “Then,” Stringer predicted, “you will see a candidate plummet, and everybody’s shocked, and at the end, it is supposed to be some great upset. And I say, no, it wasn’t an upset. It was a false narrative going in that everyone bought into.” He continued, “Take a deep breath and let the campaign play out. It hasn’t even begun yet.”

Meet Thich Nhat Stringer urging everyone to slow down and simply concentrate on their breath. It’s a new posture for a man known to closely track who serves on the community boards and which electeds can actually move voters, along with who has slighted him lately or, worse, helped one of his rivals. Hank Sheinkopf, a longtime political consultant who worked for Moskowitz in the 2005 race, said, “Stringer never forgave me. He had this idea that if you weren’t with him, then there was something mentally deficient with you.”

It would be easy to imagine that this is all a show for the media — Look at me being so relaxed over here! — especially for someone who has spent decades building toward this moment. People close to Stringer say that some of the bravado he had last fall is gone now, that he speaks more about the work needed to carry the city to recovery and less about whether he will be the one to do it.

But with the primaries now little more than two months away, dozens of campaign staffers, advisers, surrogates, and supporters say Stringer is saying much the same privately. “I really get no sense from him that he is worried,” said one lawmaker supportive of Stringer who requested anonymity to speak for the campaign. “Maybe he should be, but if he is, he isn’t telling me.”

Aides told me that when a bad poll came out, they braced themselves for their call with the candidate, fearful that he would need bucking up or express frustration with the campaign. Instead, Stringer seemed barely to register the poll, mentioning his Spitzer race and telling his staffers simply, “We are fine.”

Some of this is owed to the nature of Yang and Adams, two candidates Stringer sees as having never been vetted on this kind of citywide scale.

“Scott really feels like they are both going to drop, that neither has run a real race before,” said another lawmaker supportive of Stringer. Back in 2018, when it looked as if Attorney General Letitia James were going to run for mayor, “Scott was obsessed with her. I mean obsessed. He was obsessed with Corey Johnson,” the City Council Speaker who dropped out of the race last year. “He is still kind of obsessed with Maya Wiley. But he is just not obsessed with Yang in the same way. He just thinks he is fundamentally flawed and likely to fade.”

When Yang walks around New York, people stop and ask for selfies and cheer for free money. Yang’s livestreams generate tens of thousands of views. How can Stringer compete with that?

“But I am famous too. They recognize me, too,” he said, and, indeed, as we talked, a candidate running for a City Council seat and a couple of locals who had spent the day volunteering on behalf of another City Council candidate stopped him. “Everybody loves you here,” the candidate, Alfonso Quiroz, said to him.

“Great! Did you know there is a reporter here? Say that again! I can go home now,” Stringer responded before turning back to me.

“How do I get 26,000 signatures and Yang gets 9,000? It’s the volunteers,” he said. “Who has enthusiasm? Well, how do you quantify it? Who has endorsements? Who has financial resources and labor support? Me. What does he have? I am in a pretty good place.”

This confidence has surprised Stringer’s rivals, who have expected him to reboot his campaign — to rip up his strategy, shake up his staff, and reposition himself as the underdog fighting like hell for every last vote. Instead, the Stringer campaign has been much like the steady mayoralty he promises. “Despite what my opponents want you to believe,” he told me, “do not get conned by people who would love to see me out of this race.”

Yet it’s undeniable that Stringer has a narrative problem. If the perception hardens that he is sinking, key parts of his coalition may start to slip away. In recent weeks, two powerful unions that Stringer has been courting for years (32BJ, which represents building workers, and DC 37, which represents municipal employees) announced they were going with Adams. Labor sources told me the decisions were in part about representation — both unions are majority people of color, and Adams would be only the second Black mayor of New York — and in part due to concerns that Stringer couldn’t beat Yang. If similar institutional players think he won’t make it and abandon him for Yang or Adams, the path to a Stringer victory narrows.

The endorsements highlighted an issue that has plagued the idea of a Stringer candidacy since it was first conceived: How does the Democratic electorate in this city, which has been convulsed over questions of racial justice, line up behind a middle-aged white guy for mayor yet again? A number of rival campaigns pointed out to me that some of the extremely online young electeds who support Stringer — and who used to dunk on every single one of Yang’s gaffes — have been noticeably quieter in recent weeks as Yang has shown few signs of fading.

Stringer bristles at the notion that he got religion and moved to the left in recent years as if he were simply riding the post-AOC wave. He was one of the most liberal members of the state assembly when he served in Albany two decades ago, where he was a thorn in the side of leadership, and was a tenant activist before that. He has been a consistent favorite of good-government groups and the Times editorial board.

But what happened in New York since Trump’s election was something new. The Zeitgeist became not so much liberal as leftist, not Upper West Side and The Nation but Bushwick and Jacobin. A rising crop of newly elected officials wasn’t so much hyperliberal as anti-political, skeptical of the Democratic Party and the rest of the Establishment. They were mostly Black and brown, mostly female, and mostly outside the political system. They were bartenders and public defenders and middle-school principals making their first run for office and railing about how the political class had betrayed New York.

Stringer was often the first, and sometimes the only, elected official to rally to their cause. The dynamic benefited both parties (for the upstarts, institutional support; for Stringer, inroads into communities that would have been suspicious of him otherwise), but it was never going to be an easy fit. He could join them in calls to defund the police, although he recently said in an interview that this was more about budgetary concerns from his position as city comptroller, but the political Establishment has been his home and helped raise him from boyhood.

“He took a big bet, and it paid off spectacularly,” said one person supportive of Stringer. “Is he a far-lefty? Obviously not. He does a lot of signaling without committing one way or the other on policy. It is a high-wire act, and we’ll have to see if he can pull it off.”

The move enraged his old allies in the Establishment and led his opponents to scoff at what they saw as mere opportunism, but it did win him support among the rising generation of elected leaders. “I am really impressed with his progressive bona fides. He has been working at this for years, and his platform is one of the most progressive in the race,” said Jabari Brisport, a 33-year-old newly elected state senator. He cited Stringer’s support for the “decommodification of housing” and his calls for defunding the police last year as the reasons he decided to support the comptroller.

Stringer didn’t endorse Brisport when he ran against an entrenched incumbent for his Central Brooklyn seat in 2020. Brisport said he hadn’t thought to ask, but he credited Stringer with paving the way for lawmakers like him by supporting fellow far-left challengers in 2018.

As for the fact that Stringer is a middle-aged white man and Brisport is a gay Black man, Brisport said, “I am a socialist. I am driven by policy first and foremost, and I see Stringer as someone who will break the iron grip of the real-estate industry in our neighborhoods and who will have policies on education and climate that will most benefit people of color.”

“I don’t think anyone ever expected him to be a high-voltage guy,” said Eric Phillips, a former top aide to Mayor de Blasio who frequently tangled with Stringer when he was city comptroller. (“Was he a pain in the ass? Yes. But that was sort of his job.”)

“But he is very good at politics,” Phillips added, “has a real sense of the political moment, and his play was always to get a bit of institutional support, get the support of the folks he backed early on and then play in as many lanes as possible. The polls show that it hasn’t borne out so far, but it wouldn’t surprise me if it ends up working out for him.”

Stringer has run a conventional campaign. He trumpets policy idea after policy idea, like putting two teachers in every K–5 classroom and creating a $1 billion recovery fund for small businesses and nonprofits. But those haven’t done much by way of making news or generating excitement outside the wonk class, nor has putting him behind a podium that says READY ON DAY ONE — efforts that remind some observers of Hillary Clinton’s and Elizabeth Warren’s campaigns and a slogan meant not so much to inspire as to reassure. Stringer pulls together “Bangladeshis for Stringer” and “Estamos Con Stringer” events in immigrant-heavy city neighborhoods, but they scarcely get covered by the press.

At a recent event in Harlem to lay out his small-business plan, Stringer was asked about Yang’s call for de Blasio not to spend all of the federal stimulus money this year, something that would be impossible to do anyway. The question was a softball over the plate, but Stringer struck out. He wiped his mouth on the sleeve of his overcoat, arched both eyebrows so his glasses rolled up his face, and said, “I guess he passed the smart test.” He muttered something about Yang’s MTA plans and then contradicted both himself and Yang: “That’s what stimulus money does — it gets applied over a couple of years. But it is good that he knows that stimulus money is applied over two years. That’s good.”

“Cringe, cringe, cringe, cringe,” said political operative Lis Smith after watching the press conference. “Yang is too likable; you can’t hit him like that. It’s like punching a baby.”

Stringer’s belief is that once voters truly tune in, they will line up the three current polling leaders and find that Stringer is the only one who can carry the city through this crisis. In 2013, de Blasio won because the mood of the city was anti-Bloomberg and concerned about police practices. He railed on front-runner Christine Quinn and staked out an early position against stop and frisk, and eventually the public came around.

This time, as Stringer sees it, if voters want a sober-minded technocrat, someone who has no designs on higher office but who gets the depths of the problems the city faces, and an unapologetic liberal who lost his mother to COVID, then Stringer is the next mayor.

For a political reporter, or for a politician, this theory of the race can be a little frustrating. You can cover the city for years, or lay the groundwork for a run for decades, but it all comes down to the final weeks in May or June.

“My man! Hate the game, not the player! Don’t punish me for it!” he told me. “There would be no Scott Stringer if the game ended when you wanted it to end. The cake isn’t baked yet.”

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