Spring of junior year was my last time on the ballot. I was running for student-council president at the fancy prep school on the Upper East Side of Manhattan that I attended on scholarship. I had staked my electoral hopes on witty posters, but a lot of my classmates gravitated toward a new kid with a simple promise: putting a Snapple machine in the cafeteria. Snapple was huge in the late ’90s, and this was the kind of rich private school where not having a chance to pay more for a drink with lunch was the biggest problem most of the student body faced.
These days, that other candidate is the campaign manager for Andrew Yang, whose mayoral bid is inspiring more New Yorkers than anyone would have guessed—and driving everyone else crazy. “It’s hard to defeat Snapple for everyone,” Yang joked when my former opponent and I recounted the story as the three of us sat down for dinner recently in Manhattan. “Universal basic Snapple would prevail.”
New York’s Democratic mayoral primary is less than a month away. The winner will likely be the next mayor of this deep-blue city. But no one has any clue who that winner will be. The polls have been all over the place, and how well the vote-counting will work is uncertain: New York is making its first-ever attempt at ranked-choice voting (each voter will be able to rank up to five choices), giving even the stragglers a sense that they may be able to pull out a win. The city’s famously incompetent Board of Elections will be administering the election and trying to figure out the results.
New York City’s municipal government is the biggest and most complicated one in the country, and the mayor has more unilateral power and a higher profile than nearly anyone else who doesn’t have access to nuclear codes. The race has been a special brew of post-Trump celebrity campaigning, racial politics, and progressive infighting. It’s arriving just as New Yorkers are starting to emerge from the pandemic, full of uncertainty about the city’s future. But Yang is part of every discussion, and in first or second place in nearly every poll so far.
Yang is the first celebrity candidate who’s famous for being a celebrity candidate, a sort of political Kardashian. I asked Yang if he’d be doing this well in the polls if not for his presidential campaign, which got a lot of attention but, in the end, only a few thousand votes. “Of course not,” he told me. A friend had urged him to run for mayor in 2017, when the current officeholder, Bill de Blasio, was unpopular heading into reelection but didn’t have a challenger. Flattering as it was, Yang said, “the thought of running against Bill de Blasio at that point seemed frankly unrealistic because I did not have, like, a great deal of name recognition.” As I report in my new book, Battle for the Soul, several aides on Michael Bloomberg’s presidential campaign tried to get Yang to endorse Bloomberg by saying they could help Yang with a mayoral campaign. Bloomberg’s team even considered Yang’s offer to back Bloomberg in exchange for the ex-mayor putting $1 billion into a universal-basic-income pilot program. (Yang turned down Bloomberg’s team’s counteroffer: He’d invest the money only if he won the White House.)
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Despite living in New York since graduating from Columbia Law School 20 years ago, Yang never cared about city government or politics; he barely paid attention to politics at all. He defends this apathy by making it out as relatable. “There’s a sense that New York politics is an insider’s game,” he said, before launching into a well-worn defense: When he was pursuing his career as a tech entrepreneur, he never thought of local politics as a way to make a difference. This is a good line, but it skips right past the fact that he’s voted in barely any election, for any office, during his years in New York.
So I asked Yang: What is the job you’re running for, as you conceive it? He recited a bunch of numbers and statistics, as he tends to do. He can tell you how many municipal agencies the mayor oversees, and how many people they employ. He offers a beautifully crafted bit of management consultant–speak about how much economic value could be generated if agencies worked just 10 percent better. He wants to get tourism back to pre-pandemic levels, which would probably include posting DIY “I Love New York” videos on Twitter from City Hall. He likes saying the words public-private partnerships so much that he tells me the phrase will be “one of the watchwords of my administration.” He wants to get business to come back to New York, and to have a generally warmer relationship with the private sector than de Blasio’s pointedly antagonistic one. “I’ve had conversations with multiple business leaders here in New York City where they said, ‘If you win and you call me, we are prepared to invest tens, even hundreds, of millions of dollars to solve problems that New Yorkers can all see around us,’” he told me. This, like the thumbs-up that Yang flashes whenever he takes photos with supporters, feels very Trumpy, and very little came of the former president’s similar claims. When I asked Yang for an example, he excitedly told me that he’d talked with the restaurateur Danny Meyer, and recounted a story of an engineer for Airbnb who created an app to search for vaccine appointments, which is heartwarming and innovative, but wasn’t the answer to my question. Then again, after JetBlue announced that it would be moving jobs out of the city, Yang was the only candidate to say publicly that he’d meet with the CEO, and he did indeed have a Zoom call with him. So far, the jobs haven’t left. A Yang aide told me that he’s talked with other CEOs, including one of “a familiar brand name” who would be ready to create tens of thousands of jobs in the city via a new headquarters, depending on who’s mayor.
“Some men see things as they are, and say, ‘Why?’” Robert F. Kennedy, another man who popped into a New York primary (for the U.S. Senate) and ran away with it, famously said. “I dream of things that never were, and say, ‘Why not?’” Yang’s whole essence is Why not? His bubbliness and charisma stand out in a city depressed by the pandemic, whether he’s dancing with a drum line or appearing in a rap video with MC Jin. He displayed the same contagious enthusiasm when he was running for president, whether he was screaming into a microphone like a pro wrestler at a candidate event in South Carolina or making awkward jokes about being “the Santa Claus of burgers” while flipping patties in a small town in Iowa. He was the comic relief of the race, eagerly participating in what he called the “candidate Olympics” and obviously having fun. He loved his Yang Gang internet superfans, and he loved how reporters would line up to tweet whatever his quirky mind and dorky sense of humor had come up with. But he had serious points to make too. He was sincerely worried about how automation was rapidly reshaping the economy, and I rarely saw audiences connect with any candidate as much as they did with him when he pointed out all the empty storefronts in their local strip malls and warned about how Amazon and driverless trucks could destroy even more jobs. His ideas had more impact on the national conversation than those of nearly every experienced politician who ran. And of course, his proposed solution was catchy: free cash for everyone!
Jessica ramos is unconvinced. The state senator from Queens had endorsed City Comptroller Scott Stringer, the longtime city pol who was emerging as the progressive alternative to Yang before a woman accused him of sexually assaulting her in 2001. Ramos pulled her support for Stringer after the allegations against him emerged in April. “Yang has no idea how government works,” she told me, “so how can we pretend he knows where government doesn’t work and needs to be fixed?” During Yang’s presidential campaign, he spoke to voters’ mistrust and desperation. But because he was extremely unlikely to win the Democratic nomination, few voters cared that he never explained how he was going to pay for his Yang Bucks. The closest I got to an answer was in January 2020, as we drove out of Des Moines, Iowa, when he told me something vague about reallocating money from existing social programs. (By the way: There’s no clear path for a mayor to start sending out monthly basic-income checks.) But institutional progressives’ main objection to Yang seems to be more about his late arrival on New York’s political scene than it is about policy.
When Yang entered the mayoral race, few of the supposedly serious observers took him seriously. In January, as he was being mocked on Twitter for blundering his way into inadvertently viral videos, Sally Goldenberg, one of the most experienced city political reporters and the City Hall bureau chief for Politico, dismissed the power of his name recognition. Other leading candidates had more important assets, she tweeted: “Scott Stringer has won citywide, Eric Adams has won borough-wide, Ray McGuire has long-standing ties in certain civic circles and Maya Wiley had a national TV platform.” Yang didn’t know what bodegas were; he says Times Square is his favorite subway station. He spent most of the pandemic at his house in the Hudson Valley, abandoning the city. Almost every bit of policy is new to him. His wide-eyed tweets come off more like Kermit the Frog than Ratso Rizzo.
But Yang has defined the race around him. De Blasio is determined to stop him, but has been trying to avoid making his efforts public. He convened a meeting of some of the city’s most powerful unions earlier this year to urge them to consolidate their endorsements behind Adams—the Brooklyn borough president, who is wrestling with Yang for the top spot in the polls—for the sake of stopping the upstart. De Blasio tried to get the Reverend Al Sharpton to endorse Adams too, but was refused. (De Blasio’s press secretary didn’t comment on these conversations.) Ramos told me that she and other established progressives agree they should all get behind a specific candidate, but they haven’t yet been able to agree on which one.
Yang is receiving the kind of résumé scrutiny he never got during the 2020 presidential race, but he has also spent months getting coverage just for being interesting. When he briefly went into the hospital with a kidney stone last month, his campaign counted 231 mentions in local media. He’s dismissed The New York Times to the point that a few weeks ago, three of the paper’s reporters came to a street where Yang was campaigning and called out to him, asking why he wouldn’t talk with them. “Yang is taking right after Donald Trump’s playbook—just do Twitter, create this false narrative, truth doesn’t matter,” Adams complained to me. “Media was making a mistake, turning this guy into a celebrity.”
Yang says he’s trying to use his celebrity to bust through calcified local politics in New York. I first met Adams in Brooklyn when he was running for state Senate 15 years ago, and by then the former police officer was already known for starting a group called 100 Blacks in Law Enforcement Who Care. In the time since, Adams has moved up in Albany and city politics, both of which tend to be filled with muck and compromise. To Yang, those sorts of decades-long political careers are part of the city’s problem. He uses his own life—he has two children (one who is autistic) in public school who have dealt with virtual learning during the pandemic—as an example: “If you’ve been in government for a long time, you can actually provide a very detailed explanation for why schools have not been open in a way that will not make sense to the vast majority of parents.”
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He believes that his understanding of how nonpoliticians think would help him in negotiations with the city’s famously powerful and demanding teachers’ union, its very left-tilting city council, and insistent alpha pols such as New York Governor Andrew Cuomo. (That last relationship is one Yang is eager to make work, even as Cuomo has become anathema to nearly every Democratic leader in the state after years of picking fights with progressives and now facing accusations of sexual misconduct. He told me that he’d be open to backing Cuomo for reelection, depending on the state of their working relationship and what would be best for the city.) Skeptics see a guy who’d be rope-a-doped or railroaded by any interest that put on a good show. After all, New York is a city where de Blasio was attacked for not changing Columbus Day to Indigenous People’s Day, then attacked when he did change it to Indigenous People’s Day, then attacked for compromising and calling it both. (Yang’s formulation on Christopher Columbus: “I must say, it’s struck me for a long time that it’s weird we’ve lionized him. Even as a kid, I was like, ‘What’s going on?’” But he also says he’s open to hearing what others have to say.)
“There’s no single human mind that knows the labyrinth of city government and the mechanics of every single agency,” Ritchie Torres, a former city councilman and a freshman U.S. representative who endorsed Yang at his campaign launch, argued to me. “The purpose of a mayor is to be an inspiring and inspirational visionary, a cheerleader for the city, and then surround yourself with specialists.”
De Blasio, who started out as a political operative, has shown a knack for combining his problems and ending up with even bigger ones. I asked to come by City Hall to talk with him about how much harder the job is than he had realized. He considered my request, but said no. When I asked his press secretary why he declined to comment, I was told it was because “he was busy leading New York City’s comeback.”
Trivia: the last elected mayor of New York who went on to another elected office was … John T. Hoffman, who was elected governor in 1868 (his mustache is an amazing example of the era). But because of the power of the office, the number of national journalists who have worked or live in New York (myself included), and the place the city holds in the American psyche, New York City mayors have an outsize role in national politics. That’s true within the mayors’ own minds too: Four of the past seven have run for president. And because it’s New York, candidates are expected to take stands on not just snow-plowing strategies, but also the rockets Hamas fires out of Gaza.
“Whoever becomes the next mayor of New York City is going to be, within a week, with the president and the vice president of the United States in the Oval Office, talking about the national economy and how New York has to lead in bringing that back,” Stringer, who worked his way up from district leader to assemblyman to Manhattan borough president to city comptroller (with a few runs for other offices thrown in along the way), told me. He’s trying to survive the primary by dismissing the institutional support he once was counting on and casting himself as an outsider. “And then what happens as you leave the meeting? Everybody exchanges their cellphone [numbers]. Because you’re mayor of New York City, and the day you’re elected mayor, whether you like it or not, you are the national spokesperson for cities around the country.” Adams told me he believes that within a few years, he’d be the type of mayor who would attract leaders from around the country to study how he reinvented city government.
Coming at the job with no experience means that Yang has no basis for knowing what would make for a good police commissioner or schools chancellor, and that has led him to make some strange comments, such as suggesting that Representative Val Demings of Florida, a former police chief, would be a good pick to run the NYPD. When Yang said this, he didn’t know that she was on the verge of launching a run for the Senate. He admitted to me that all he knew about Demings was that she’s a Black woman who used to be the Orlando police chief and was vetted for vice president. That kind of obliviousness is another supposed weakness Yang wants to turn into a strength: “Whether it’s education or the NYPD or parks, any of these roles could and should be filled by a world-class expert or one of the best people in our country.”
Yang’s support among wealthy New Yorkers and business lobbyists, including a number of prominent Bloomberg alumni, has bred suspicion among progressives, and led some to describe Yang as the second coming of the billionaire whom the left loathes. Bloomberg alumni who don’t support Yang are angry that he’d be compared to someone they revere, and have described him to me as a “fraud” or “in over his head.” Yang is so annoying to his rivals and detractors that when he shows he’s studied up on issues, he’s made fun of for knowing the answers. In truth, the only candidate in this race close to being a Bloomberg-style Brahmin of the city is Ray McGuire, a former Citigroup executive and the chairman of the Studio Museum of Harlem, whose fundraising for Barack Obama helped him enter the former president’s orbit; his campaign is co-chaired by Valerie Jarrett, the former president’s confidante. McGuire was urged into the race by a number of civic leaders, and he’s running commercials declaring himself the serious candidate—with serious underlined—but he’s struggled to make any impact at all.
Even though Yang’s presidential campaign was made possible by Twitter, he has become a piñata for extremely online progressives. “I’m a bit mystified by it,” he told me of the progressive pushback. Maybe, he said, it’s because he’s an “outsider.” In New York City, where even the Republicans are basically Democrats (just three of the city council’s 51 seats are held by the GOP), progressive has become a term that means whatever the person saying it wants it to mean. “We allowed people to hijack that term,” Adams told me a few hours after the Trump-friendly New York Post endorsed him. Adams, who was once a registered Republican, now considers himself a progressive; he describes progressivism as taking a holistic approach to city problems. New York City’s electorate isn’t as far left as the Democratic Socialists of America would like to believe, Adams said. The rapid collapse of progressive support for Stringer following allegations by one woman whose story has been questioned, and the left’s inability to settle on an alternative, seems to demonstrate how fragile the supposed power of progressives in the city is. Stringer allies have been calling reporters, insisting off the record that the sexual-assault accusation was a conspiracy by Yang supporters. “New York City voters are the most sophisticated voters at decision time,” Stringer told me plaintively.
The sense that the retreat from Stringer may have paved the way for Yang has settled in: U.S. Representative Jamaal Bowman, a left-leaning politician who ran a winning primary campaign against a longtime incumbent, said recently that he regrets pulling his endorsement from Stringer before interrogating the accuser’s story more. “I would say, and I’ll be very frank with you, I do not want Andrew Yang as mayor. So I hope that we’re able to get to a place where we’ll be able to figure something out so that doesn’t happen.” Then again, maybe the impossible-to-predict ranked-choice-voting process will keep Stringer, whose fundraising spiked this month, in the running.
Yang told me that he thought he’d be considered as to the left of Senator Bernie Sanders when he launched a presidential campaign all about universal basic income. Some of the same people who are now opposed to him, he said, praised him during his previous campaign. New York’s progressive establishment values long relationships. And on policy, progressives “see that there’s a certain degree of misalignment that I’m not even sure exists,” Yang said. Progressives’ dismissal of Yang seems particularly notable given that he could become one of the most prominent Americans of Chinese descent to hold political office. “I don’t think Asian Americans fit into the conventional progressive narrative. I’m not quite sure why that is,” Yang said, noting that the needs of the city’s Asian residents parallel those of other communities.
The morning after our dinner, we stood next to a giant vacant lot overrun with grass on the east side of Manhattan. Fiddling with the tax regulations, Yang argued, could produce up to $900 million in additional annual revenue from lots like that all over the city. Is that enough to plug the multibillion-dollar budget hole looming for the next mayor? Of course not. But if he’s right, that would be a start. Standing there with a Latino city-council member who had been running a long-shot progressive mayoral campaign of his own before he dropped out and endorsed Yang, I saw another piece of Yang’s jigsaw coalition falling into place. Over the previous 24 hours, he’d also been endorsed by an ultra-Orthodox Jewish assemblyman and an Orthodox city councilman in front of a Judaica store in Brooklyn, and by the national AAPI Victory Fund while standing in front of the Dim Sum Go Go restaurant in Chinatown.
I ran Yang through some scenarios. Would he have the police shut down the city after a terrorist attack? How would he respond if police officers turned their backs on him at a police funeral, as they did to de Blasio in 2014? His answers were vague. He wants to do something about NYPD morale and also something about crime and also something about making New Yorkers not feel like the police are targeting them.
“People are in a bad place, and you’re going to give them the snake-oil false promises to further hurt them and disappoint them,” Adams told me. Maya Wiley, the civil-rights attorney hoping that a coalition of Black voters, women, and the liberal intelligentsia (and an important endorsement from the local power broker U.S. Representative Hakeem Jeffries) will power her to victory, told me that she sees Yang as another politician making big promises that won’t go anywhere. New Yorkers, she said, want to know “it’s not going to be promises that aren’t met, that it’s [not] going to be the same type of leadership that failed to solve the deep problems that need to be fixed after every election.” She told me this after an event that attracted just three supporters who weren’t with her campaign, and just one other reporter.
The New York Times and the New York Daily News editorial boards and other demonstratively serious people have now landed on former Sanitation Commissioner Kathryn Garcia as the right choice to stop Yang. But Yang might need to be only the most popular first-, second-, or third-choice pick amid a clearly uninspiring field. “Winning any ranked-choice vote is all about being the most liked, not the best loved,” Ace Smith, who has run candidates in three ranked-choice mayoral elections in San Francisco and Oakland, California, told me. The other candidates are counting on most of Yang’s supporters being like the young man I saw run up to him after the vacant-lot event, asking for a selfie. “Remember to vote!” Yang told him. When the man said he didn’t know if he could, Yang told him he could register until May 28. The man said he would look into that. He didn’t seem likely to actually do it. Plus, how could Yang win this election when the city’s entire political establishment finds him annoying at best?
We won’t know the true extent of Yang’s support until June 22, when the primary happens. Really, we probably won’t know until at least several days later. (The Board of Elections took three weeks of counting to determine the winner of a sole city-council race in the Bronx earlier this year.) This seems like a relevant place to point out that I lost my high-school election. Not only did the Snapple guy win in a landslide; he brokered a deal with the principal to get the drink machine installed. All he had to do was agree to get the seniors to wear their dress-code jackets in the hallways. That’s a little less complicated than running a city with 8 million residents, 325,000 city employees, and an $88 billion annual budget. But the people got their Snapple.
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