Shaun Donovan Has the Résumé and the Money. He Just Needs the Votes.

In operating for mayor of New York, Mr. Donovan is arguing that his management expertise provides what town wants in a time of disaster.

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

Five years ago, a powerful New York-based political strategist was rooting around for someone whom voters could envision as the city’s next mayor, someone with the right type of experience and gravitas to take on the weakened incumbent, Bill de Blasio.

The strategist, Bradley Tusk, believed he had found his candidate: Shaun Donovan, a veteran of the Obama administration and a former city commissioner under Mayor Michael R. Bloomberg. Mr. Tusk believed that Mr. Donovan’s credentials would be irresistible to voters, saying then that New Yorkers “want the competency of Bloomberg, but they want something that’s more progressive.”

Mr. Donovan recently recalled that moment with some wistfulness. He remembered thinking how he had missed so much time with his two sons because of his work for President Barack Obama, first as housing secretary and then budget director. He decided then that running for mayor would have to wait.

Mr. Tusk never found his candidate, and Mr. de Blasio went on to easily capture his second term.

Things have since changed significantly. Mr. de Blasio is in his final year as mayor, and Mr. Donovan is one of 15 Democrats and Republicans seeking to replace him. Mr. Tusk’s firm now manages the campaign of Andrew Yang, one of the race’s front-runners.

But Mr. Donovan, 55, has not been able to live up to Mr. Tusk’s initial ambition. He remains anchored among the second tier of mayoral contenders, despite the support from a super PAC — funded almost exclusively by his father — that has spent $5.5 million so far, much of it on ads trumpeting Mr. Donovan’s accomplishments.

He has tried attacking the record of Mr. de Blasio, decrying what he saw as the mayor’s poor management of everything from city parks to the census and even the food supply, and drawing a contrast to his time in the Bloomberg administration with its aura of efficiency.

Voters want change, Mr. Donovan says. “They’re sick of the political status quo in New York, but they also want experience,” he said after a news conference last month at Pelham Parkway Houses in the Bronx, where he criticized Mr. de Blasio’s management of public housing. “New Yorkers don’t want a rookie as mayor.”

Yet many of Mr. Donovan’s news conferences, where he lays out detailed plans to end homelessness or address gun violence, are sparsely attended. His broadside attacks on other candidates are mostly ignored. Viewers of the first official televised mayoral debate talked more about the expansive HGTV-ready kitchen in Mr. Donovan’s background than about his proposals.

Mr. Donovan entered the race confident that his track record of implementing his ideas about reducing inequality while working for the country’s first Black president would win voters, but instead he has faced criticism that his privileged background left him out of touch with middle-income New Yorkers. He has announced reams of technocratic plans that he considers among the most progressive in the race but has not secured support from the city’s progressive establishment.

Mitchell L. Moss, a professor of urban policy and planning at New York University who advised Mr. Bloomberg during his first campaign for mayor in 2001, said that Mr. Donovan had not taken off because “New Yorkers aren’t electing a résumé, we’re electing a person.”

Professor Moss effusively praised Mr. Donovan, saying he was one of the smartest people he knew, a common refrain. Mr. Donovan almost single-handedly put New York “back in the housing business” when he worked for Mr. Bloomberg, he added.

“Donovan has everything on paper,” Professor Moss said. “He may be the right candidate at the wrong time.”

The realization that he might run for mayor, Mr. Donovan said, came more than four years ago, on the final evening of the Obama administration.

He was among roughly 30 of the administration’s longest-tenured officials who gathered on the Truman Balcony of the White House with the president and the first lady, Michelle Obama, reflecting on their past and worrying about the nation’s future with Donald J. Trump as president.

“It was a look in the mirror moment,” Mr. Donovan said. “How could this have happened, and what are you going to do about it?”

Mr. Donovan grew up on the Upper East Side of Manhattan and attended the prestigious Dalton School. His parents divorced when he was 8 years old, a period that he recalled as difficult for him and his three siblings. He bounced between his parents’ apartments, and “there was lots of feeding ourselves,” Mr. Donovan said.

“The profound thing for me was being surrounded by people who were wealthy and not happy and not making a difference in the world,” Mr. Donovan said, recalling how that sense was compounded after he graduated from Harvard University and a friend from Dalton committed suicide.

By then, Mr. Donovan had begun interning for the National Coalition for the Homeless. Mr. Donovan said his father, Michael Donovan, who started a business that became one of the largest ad technology companies in the world, encouraged him to follow his heart in choosing a career, telling him that he could do anything “except come work for me.”

Mr. Donovan served as Mr. Obama’s funds director, led the response to Hurricane Sandy and was secretary of the Division of Housing and City Improvement, the place he helped scale back veteran homelessness by virtually 40 p.c and negotiated the $25 billion settlement with mortgage servicers after the foreclosures disaster.

Eric H. Holder Jr., who served as United States lawyer normal beneath Mr. Obama, mentioned Mr. Donovan had an “expansive view” of his positions in his quest to assist Individuals. “He’s a man who hasn’t forgotten why he wished to be concerned in authorities,” Mr. Holder mentioned in an interview.

Mr. Donovan additionally created the Rental Help Demonstration Program, which permits personal builders to renovate and handle public housing items. Tenants have nervous that this system would possibly result in displacement, an concept Mr. Donovan rejects.

Afua Atta-Mensah, government director of Group Voices Heard Energy, mentioned that many residents discovered Mr. Donovan to be “good, trustworthy and open” when he defended the rental help program throughout a gathering with mayoral candidates however that he did not see the hole between “doing a large plan from D.C.” and “lived expertise.”

The group endorsed Maya Wiley, Mr. de Blasio’s former counsel, for mayor, and ranked Dianne Morales, a former nonprofit government, as its second selection.

Mr. Donovan is fond of claiming that he’s operating a “marketing campaign of concepts” and is within the midst of unveiling 70 concepts in 70 days (Day 36: strengthening the regional meals system; Day 42: fast-tracking felony gun instances).

If elected, he has promised to supply poor kids with bonds to eradicate the racial wealth hole; create 15-minute neighborhoods the place an excellent faculty, recent meals, transit, a park and well being care are inside a brief stroll; take away the New York Police Division from metropolis faculties; and lower $three billion from the police and corrections funds by the top of his first time period and spend the cash on underserved neighborhoods.

Closing the racial wealth hole has been recognized as among the best methods to handle systemic racial inequality in America. Beneath Mr. Donovan’s fairness bonds proposal, each little one born in New York Metropolis would obtain an annual cost of $2,000, which might go into an account that may be accessible after they flip 18, and will have $50,000 ready to pay for school or begin a enterprise after they flip 18. Mr. Donovan proposes utilizing a mixture of personal, metropolis and federal cash to fund the pricey effort.

Slicing cash from each the police and corrections funds exhibits a willingness to dive beneath the floor on a nuanced concern reminiscent of defund the police and search for artistic options, Mr. Donovan mentioned.

On a latest go to to the Bronx that included a cease on the Futa Islamic Middle for Friday night prayer companies, Mr. Donovan talked in regards to the redevelopment of the South Bronx. The neighborhood was not removed from Charlotte Road, the burned-out stretch of vacant tons and rubble close to Boston Highway visited by President Jimmy Carter in 1977. It’s now stuffed with suburban model properties with lawns, a fabled story of city renewal.

Mr. Donovan recalled visiting the Bronx as an impressionable 11-year-old, watching from the Yankee Stadium stands as Reggie Jackson hit house runs in three consecutive at-bats to assist the Yankees win the 1977 World Sequence. He went from being elated and hugging strangers to seeing burned-out buildings after leaving the sport, he remembered.

“Individuals thought the American metropolis was dying,” Mr. Donovan mentioned. “And this was Exhibit A,” he added in reference to the South Bronx.

Many political observers agree that Mr. Donovan has the credentials of a prime mayoral candidate, however nonetheless has not been in a position to join with voters.

He’s a local New Yorker however doesn’t at all times sound like one. In an interview with The New York Instances editorial board, he advised that the median worth for a house in Brooklyn was $100,000. The right reply is definitely 9 occasions that quantity; Mr. Donovan, who, together with his spouse, Liza Gilbert, paid $2.three million in 2019 for his or her house in Boerum Hill, Brooklyn, later mentioned he had misunderstood the query.

The error drew derision on social media, and fed the notion that Mr. Donovan was out of contact with the issues of working-class New Yorkers in one of the crucial unequal cities within the nation.

That notion has additionally been fueled by the $6.eight million that his father, Michael Donovan, has contributed to New Begin N.Y.C., an excellent PAC supporting his son’s marketing campaign.

Mr. Donovan mentioned that a number of different candidates within the race have PACs and added that not like another donors, his father was not in search of something in return for his contributions. “I don’t suppose New Yorkers are involved that my dad’s intentions are to foyer me for extra time with the grandchildren,” he mentioned, whereas nonetheless acknowledging that his father’s assist bolstered the notion that he had benefits that different candidates lacked.

Mr. Donovan, conscious that his privilege had turn out to be a legal responsibility with some voters, has been attempting to handle that concern within the final weeks of the marketing campaign.

On the primary anniversary of George Floyd’s homicide, he was arrested with a small group of protesters who blocked the doorway to the Holland Tunnel in an act of civil disobedience. Mr. Donovan, sporting a Black Lives Matter T-shirt, talked about how he has not needed to fear about his 19- and 21-year-old sons going through discriminatory policing.

“I’m grateful,” he mentioned, “however I’m additionally offended.”

Jack Begg contributed analysis.

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