Andrew Yang's Insider Campaign
New York magazine|May 10 - 23, 2021
How did a former CEO of 100 employees become the front-runner to govern a city of 8.5 million? Not simply by being a national celebrity and an excellent campaigner.
By Clare Malone. Photograph by Mark Peterson

From the moment Andrew Yang sat down in the back corner of a dark restaurant in the Bronx—brow knitted, wearing an overcoat and scarf that would stay on for the whole lunch—he was not the same cheerful New York City mayoral candidate of our popular conception, the one who cheeses for photos and tweets things like “It’s Friday!” when it’s Friday or shouts “Yankee Stadium!” while standing in front of Yankee Stadium. Politicians are always a little different behind the scenes, their ambition harder to conceal in close quarters, but the man sitting across from me was particularly unfamiliar. Since entering the race in January, Yang has pitched himself as the happy warrior for the Everyman, an energetic presence promising to lead New York out of its grim recent past. While other candidates have emphasized the city’s need for an experienced and empathic crisis manager, Yang has acted like a constant human joy machine.

But today, he was serious, even a little crabby. Gone was the man who wants to bring TikTok Hype Houses to New York; he was replaced by a bristly high achiever, albeit one who has a habit of punctuating somber statements with outbursts of giggles. I asked him, Did other people ever note this difference?

“I really appreciate the line of inquiry,” Yang said. (He actually seemed mildly offended by it.) “I think people underestimate what a disciplined operator I am.”

“Anyone who’s an operator sees me and this campaign and says, ‘Oh, I get it, Andrew Yang’s an operator,’” he continued. “And then if you put a businessperson next to me for ten minutes—or, I’m guessing, the vast majority of people who also are operators—they get it. Like, we speak the same language.” Yang, 46, seemed to be saying he wasn’t just the goofy, smart guy from the 2020 presidential debate stage who wore a math pin that made some fellow Asian Americans cringe. Yang—he of Phillips Exeter, Brown, Columbia, white-shoe law, start-up wealth, godfatherdom to Teddy Roosevelt’s direct descendant— could hang with the city’s power brokers.

He also appeared eager to reflect the value systems of those places of power: Yang, who calls himself the anti-poverty candidate based largely on his proposal for annual $2,000 direct payments to the poorest New Yorkers, said he envisioned himself spending his first six months in office luring back the city’s elite by calling the many Masters of the Universe who have recently decamped to Florida.

“‘Like, what are the issues that drove you out? What were the decisions?’ And then be like, okay, here are, like, the things that drove people away. If we resolve them, can we get them back?” he had told me previously. “It’s a pretty tight community, so if the mayor is calling people asking these questions and trying to get them back, I think there are a lot of people who would be thrilled about it.”

He slurped black spaghetti, continuing to sketch out his ambitions for the early days of his mayoralty. Aside from working the phones, his plans were vague. He was fuzzy about how exactly he would be able to wrest more control from Albany over the subways: “I haven’t had those conversations.” He said he thinks the MTA board should be altered to give the city more power, which sounds simple enough but, close up, is an incredibly complicated political proposition. One concrete move Yang knows he wants to make is to hire Kathryn Garcia, the former head of the Department of Sanitation and one of his rivals in the race. “What I appreciate about Kathryn is that she’s an operator,” he told me. He’s big on the idea that he would hire the right people to do the job, just like Michael Bloomberg did.

Yang said he calls Garcia at least once a week to say, “Hey, Kathryn, we’re gonna need you.” (It’s true he calls a lot, according to her campaign. “Makes her crazy,” said Christine Quinn of the implications that Garcia should be Yang’s No. 2. Quinn was the front-runner in the 2013 mayor’s race until Bill de Blasio overtook her in the final weeks.)

On June 22, New York City Democrats will nominate a mayoral candidate for what is widely expected to be an uncompetitive general election, and polling currently suggests a three-person race between Yang, Eric Adams, and Scott Stringer with Yang ahead in most polls. He has never worked in government, or voted in a New York City election, or started anything bigger than a hundred-person nonprofit, yet he’s convincing a not-insignificant number of people that he can run a bureaucracy of 325,000 municipal workers in a city of more than 8 million at one of the most challenging eras in its history.

Yang’s surprising dominance hasn’t just been luck. He has cannily deployed his fame, charisma, and hustle, bringing his very modern celebrity to a field otherwise low on name recognition and charm. But another part of his success, perhaps more central than most voters realize, must be credited to his team of advisers and close supporters. Many of the city’s most well-connected, savviest strategists have bet on Yang, and in less than two months, eight years after rejecting the legacy of Bloomberg for someone defiantly to his left, New York may very well elect an heir to the billionaire ex-mayor’s worldview. Yang is a couple of generations younger, with business ideas that are more tech inflected than Wall Street honed, but his vision for the city is fundamentally Bloombergian—not only appealing to the same privileged, progressive-to-a-point audience but shaped by some of its very same architects.

Yang’s mayoral candidacy started as a game of telephone. Although played out on Twitter and in the press, the dynamics were both personal and particular to a small group of former Bloomberg staffers. At 8:45 p.m. on February 11, 2020, Howard Wolfson, then a senior adviser on Bloomberg’s ill-fated presidential campaign, tweeted out a Politico piece about Yang dropping out of the Democratic primary: “@AndrewYang would make a very interesting candidate for NYC Mayor in 21.”

“I didn’t really give it a lot of thought. It was one of those tweets that went from the brain to fingers fairly quickly,” Wolfson told me. A few days earlier, the New York Times had run a story about Shaun Donovan, a former Obama administration and Bloomberg appointee, running for mayor. Chris Coffey, another Bloomberg alum and now one of Yang’s campaign managers noted that, at the time, Donovan was playing down his Bloomberg connections. That rubbed some people in the ex-mayor’s orbit the wrong way, and derisive quotes in the story made it clear that his set was still searching for a candidate.

Yang’s biography reflects Bloomberg’s New York: constant onward-and-upward strive room. He grew up in Schenectady and Westchester, the son of Taiwanese immigrants, and he has written about the regularity of the racist taunts he endured in school. Yang was a good student, scoring over 1500 on the SAT and a 178 on the LSAT, but he also focused on fitness. He has said that he worked out too much, naming his pecs Lex and Rex—“Probably my proudest achievement in college was that I could bench-press 225 pounds eight times in a row”—and always related to the underdog. He liked to find the awkward kids at parties and make them feel welcome.

Yang came to New York for law school, graduating from Columbia in 1999 and briefly taking a job at Davis Polk. By 2002, the first year of the Bloomberg mayoralty, he had made and lost money in the tech bubble. In 2006, he joined and soon became CEO of the test-prep company Manhattan GMAT, where he had worked as a tutor. Yang and his partners sold the company to Kaplan in 2009 at a price in the low tens of millions, he has said. In 2011, he started Venture for America, a nonprofit that aims to reinvigorate flagging American cities by injecting them with young entrepreneurs— sort of a business version of Teach for America. Yang has acknowledged it didn’t achieve all he had wanted; a recent Times report found that, despite its setting out to employ 100,000 people in those cities, only 150 of the jobs remain. Still, it generated a significant sense of personal accomplishment and professional acclaim; Yang likes to mention how President Obama named him a “champion of change.” He stayed at Venture until he entered the Democratic primary in 2017.

As the Wolfson tweet suggests, Yang quickly distinguished himself among the candidates as a bright, interesting young thing. He was never going to win, but, unlike Tulsi Gabbard, he seemed to know that: Yang was out to raise his profile and spread the good word about his ideas. Those ideas were easily digestible and not particularly new, but he managed to redirect the conversation toward them more than many Democratic insiders had expected. He called attention to the looming automation job crisis, and, in what became the centerpiece of his mayoral race, he introduced many Americans to the concept of a universal basic income.

Yang first fell in love with the idea of paying Americans direct economic relief— a policy once championed by Martin Luther King Jr.—while running Venture, where he realized that bringing new jobs to cities couldn’t offset the total wages lost to automation. On the presidential campaign trail, Yang was open about the fact that his Freedom Dividend of $12,000 a year was just a rebranding of an old policy proposal, but it was still a pretty radical one. “An economy where big tech and Wall Street are held accountable,” one Yang presidential TV spot proclaimed. Little did he know the federal government would soon be making $2 trillion in direct payments to Americans during a pandemic.

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