Andrew Yang is leaning into his outsider status as he campaigns to be New York City’s next mayor amid early questions over his qualifications and ties to the city he wants to govern.

Yang, a former Democratic presidential candidate who outlasted governors and senators in the nominating race despite sporting a thin political resume, is again running in a crowded primary field packed with candidates with beefier governing or business experience. And he’s again dogged by concerns that he has too little know-how to be running for office in such a time of crisis.

In this race, however, Yang is an early front-runner, a distinction that provides a broader profile but also forces him to address questions about his experience more forcefully than he ever had to in his long-shot presidential bid. 

“It's something new about being a front-runner, because as you know, I was never a front-runner of the presidential, and there wasn't much political upside to attacking Andrew Yang presidential candidate. But that seems to have changed in the mayoral,” he told The Hill.

Yang spent his career running startups before bursting onto the political scene with his presidential bid.

His competitors, meanwhile, have broad swaths of political and business experience. They include Eric Adams, the Brooklyn borough president and a former state senator; Shaun Donovan, the former director of the U.S. Office of Management and Budget; Scott Stringer, the city’s comptroller; and Kathryn Garcia, the former commissioner of the city’s Sanitation Department. 

But in an interview, Yang suggested that voters might look poorly upon involvement in a city government that has stumbled in its coronavirus recovery efforts, managed a nosediving economy and overseen a rise in crime.

“I have a healthy degree of respect for different forms of experience that other people might have. And I respectfully submit that if anyone thinks that our government bureaucracies have been functioning at a very high level in New York City throughout this crisis, most New Yorkers would disagree,” Yang said.

“I think a lot of New Yorkers would look around and say, ‘is that really like the approach we're going to take?’ It's going to be up to voters to decide, but I would put my experience up against anyone's.”

Yang was most known for running Manhattan Prep, a small test preparation company, and Venture for America, a program that helps place recent college graduates at startups.

After suspending his presidential campaign, Yang founded Humanity Forward, a nonprofit dedicated to furthering the policies he promoted on the stump like universal basic income and data privacy.

That resume is at the heart of concerns that he might not be up to the task of running New York City, particularly as it faces emergencies on multiple fronts.

“He talks a good game, I'll say that,” said Kathryn Wylde, who leads the Partnership for New York City and met Yang over Zoom last week. “He says he's running for mayor because he wants to lead the city's recovery. But there's no evidence that he really knows how to do that.” 

But Yang maintains that his outsider status sets him up well to serve as mayor.

“I think having an entrepreneur who does have relationships all over the country and in D.C. would be vital to trying to get our city back on its feet,” he said. “I think I can tap into resources that other candidates might not be able to.”

Beyond drawing fire over his experience, Yang’s also handed his opponents ammunition with early stumbles.

Perhaps the most viral blunder occurred when Yang drew a collective scoff over a video touting his passion for bodegas in a glitzy store few New Yorkers would characterize as one of the city’s iconic neighborhood shops.

Critics have said his ties to the city are thin after it was revealed that he did not vote in the 2000 and 2012 presidential elections or in every mayoral election in New York City between 2001 and 2017 — a criticism Yang defended by saying he was “one of a large number of New Yorkers who perhaps didn't have very strong allegiances” to a candidate.

And he was chastised as being out of touch after he fumbled a question over why he stayed in his suburban home during the pandemic rather than his apartment in Hell’s Kitchen, telling The New York Times, “Can you imagine trying to have two kids on virtual school in a two-bedroom apartment, and then trying to do work yourself?”

“Yes, actually I can,” Stringer fired back on Twitter.

“I spent all of 2020 in NYC, living with THREE generations under one roof, AND running a campaign from home,” added Dianne Morales, a former nonprofit executive and another mayoral candidate. 

Observers say the individual critiques may fade away with rapidly evolving news cycles, but the missteps feed a narrative that will continue to follow Yang. 

“It struck me as unprepared and perhaps even a little naive,” said Eric Phillips, a former spokesperson for Mayor Bill de Blasio (D), when asked about the early gaffes.

“They're evidence of a more meaningful critique, which is that he's kind of come out of nowhere and hasn't put much time into the civics of the city. And that's a meaningful critique that he's going to have to explain to voters.”

Yang has a limited runway to rebut those critiques. This year’s primary is in June instead of its usual timing in September, and while he has been holding some in-person events, the coronavirus has curtailed his ability to glad-hand city voters — and that was before he announced Tuesday that he contracted the virus. 

Through the criticism, Yang has leaned on his signature quirky vibe and stuck to a playbook of building on his name recognition and doubling down on policies, like boosting cash assistance and a universal basic income, that underscore the outsider nature of his candidacy.

While critics say his ideas are unrealistic, the strategy could particularly pay off in a ranked-choice primary. Should no candidate get 50 percent or more of the vote on the first round, voters’ subsequent picks are taken into account until one contender emerges with a majority of the vote.

The winner of the primary will essentially stamp a ticket to Gracie Mansion in a city where registered Democrats outnumber Republicans by a 7 to 1 ratio. 

“Given the breadth of both his name recognition and his appeal, and given his sheer likability, Andrew uniquely benefits from ranked choice voting. And the goal of ranked choice voting is to be everyone's second choice,” Rep. Ritchie Torres (D-N.Y.), an early Yang endorser who represents parts of the Bronx, told The Hill.

The strategy appears to be working, at least for now. An internal poll obtained by The Hill shows Yang leading the field and that just 22 percent of New York voters have never heard of him or don’t have an opinion of him — at least 10 points fewer than any other candidate in the survey.

It remains to be seen if those numbers hold in the face of the withering scrutiny that is characteristic of New York City’s politics. But observers indicate that broad frustration with City Hall’s handling of a host of the city’s issues combined with an unfamiliar election format could open the door to an outsider candidate who represents a divergence from business as usual.

“It's not the best of times, and it might very well be the worst of times. But what it also could be is a time for someone nobody knew to take the job that nobody really cares about anymore,” said Hank Sheinkopf, a longtime Democratic consultant. “Point is, anything is possible, including Andrew Yang.”