In running for mayor of New York, Mr. Donovan is arguing that his leadership experience offers what the city needs in a time of crisis.

The New York City 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.

May 31, 2021

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.”

A ‘look in the mirror moment’

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 went on to earn master’s degrees in public administration and architecture from Harvard. When he was at graduate school in Harvard, Mr. Donovan learned about the Nehemiah Housing Project, which used a community planning model to build thousands of homes in the neglected Brooklyn neighborhoods of Brownsville and East New York.

Bishop Johnny Ray Youngblood, who was then with East Brooklyn Congregations, spearheaded the project. Mr. Donovan read about the effort and sought Bishop Youngblood out.

“He was bright-eyed and bushy tailed,” said Bishop Youngblood, who recalled sending Mr. Donovan to California for training as a community organizer and saw his follow-through as proof that Mr. Donovan “was more serious than I thought he was.”

Bishop Youngblood connected Mr. Donovan with the Community Preservation Corporation, an affordable housing developer in New York. Mr. Donovan eventually landed a job with the Clinton administration in the Department of Housing and Urban Development, where he designed a program that helped to preserve moderate- and low-income units across the country.

In 2004, he became Mr. Bloomberg’s housing commissioner and worked to reduce homelessness by giving housing vouchers to people being released from Rikers Island. Homelessness declined while Mr. Donovan was in charge of housing.

Housing advocates credit Mr. Donovan with fighting the earliest wave of private equity firms who were buying multifamily properties and forcing out rent-stabilized tenants; they said he effectively worked with tenant groups to identify at-risk buildings and preserve their affordability.

In 2008, Mr. Donovan helped launch the Center for New York City Neighborhoods, which is dedicated to helping people avoid foreclosure and to promote homeownership, an idea that Mr. Donovan believes put him on Mr. Obama’s radar.

Craig Gurian of the Anti-Discrimination Center, a fair-housing group that is suing the city to end community preference in affordable housing lotteries, claiming it reinforces segregation, said Mr. Donovan missed opportunities as the city’s housing chief to address the problem. Later, when he joined the Obama administration, Mr. Donovan failed to vigorously enforce a similar suit against Westchester County, Mr. Gurian said.

“He’s a very smart guy. He knows about housing and he’s had the power to do stuff, yet he didn’t,” Mr. Gurian said. “It just doesn’t jibe with his current persona in the mayoral race.”

Mr. Donovan served as Mr. Obama’s budget director, led the response to Hurricane Sandy and was secretary of the Department of Housing and Urban Development, where he helped reduce veteran homelessness by almost 40 percent and negotiated the $25 billion settlement with mortgage servicers after the foreclosure crisis.

Eric H. Holder Jr., who served as United States attorney general under Mr. Obama, said Mr. Donovan had an “expansive view” of his positions in his quest to help Americans. “He’s a guy who hasn’t forgotten why he wanted to be involved in government,” Mr. Holder said in an interview.

Mr. Donovan also created the Rental Assistance Demonstration Program, which allows private developers to renovate and manage public housing units. Tenants have worried that the program might lead to displacement, an idea Mr. Donovan rejects.

Afua Atta-Mensah, executive director of Community Voices Heard Power, said that many residents found Mr. Donovan to be “smart, honest and open” when he defended the rental assistance program during a meeting with mayoral candidates but that he failed to see the gap between “doing a massive plan from D.C.” and “lived experience.”

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

A perception of privilege

Mr. Donovan is fond of saying that he’s running a “campaign of ideas” and is in the midst of unveiling 70 ideas in 70 days (Day 36: strengthening the regional food system; Day 42: fast-tracking felony gun cases).

His campaign mailed a 200-page book of ideas to the homes of journalists covering the race for mayor and to elected officials and other candidates. There are proposals for everything from how to alleviate public health disparities to how to fix the New York Jets, a parody plan he unveiled on April Fools’ Day. The more left-leaning of those ideas, he said, differentiated him from the more moderate candidates in the field.

If elected, he has promised to provide poor children with bonds to eliminate the racial wealth gap; create 15-minute neighborhoods where a good school, fresh food, transit, a park and health care are within a short walk; remove the New York Police Department from city schools; and cut $3 billion from the police and corrections budget by the end of his first term and spend the money on underserved neighborhoods.

Closing the racial wealth gap has been identified as one of the best ways to address systemic racial inequality in America. Under Mr. Donovan’s equity bonds proposal, every child born in New York City would receive an annual payment of $2,000, which would go into an account that would be accessible when they turn 18, and could have $50,000 waiting to pay for college or start a business when they turn 18. Mr. Donovan proposes using a combination of private, city and federal money to fund the costly effort.

Cutting money from both the police and corrections budget shows a willingness to dive below the surface on a nuanced issue such as defund the police and look for creative solutions, Mr. Donovan said.

On a recent visit to the Bronx that included a stop at the Futa Islamic Center for Friday evening prayer services, Mr. Donovan talked about the redevelopment of the South Bronx. The neighborhood was not far from Charlotte Street, the burned-out stretch of vacant lots and rubble near Boston Road visited by President Jimmy Carter in 1977. It is now filled with suburban style homes with lawns, a fabled tale of urban renewal.

A few blocks in the opposite direction was Via Verde, a mixed-income 222-unit development dedicated to healthy living where Mr. Donovan formally announced his campaign. As Mr. Bloomberg’s housing commissioner, he helped bring the building into existence by launching an architectural design contest for affordable housing.

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

“People thought the American city was dying,” Mr. Donovan said. “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 top mayoral candidate, but still has not been able to connect with voters.

He is a native New Yorker but does not always sound like one. In an interview with The New York Times editorial board, he suggested that the median price for a home in Brooklyn was $100,000. The correct answer is actually nine times that amount; Mr. Donovan, who, with his wife, Liza Gilbert, paid $2.3 million in 2019 for their home in Boerum Hill, Brooklyn, later said he had misunderstood the question.

The mistake drew derision on social media, and fed the perception that Mr. Donovan was out of touch with the concerns of working-class New Yorkers in one of the most unequal cities in the country.

That perception has also been fueled by the $6.8 million that his father, Michael Donovan, has contributed to New Start N.Y.C., a super PAC supporting his son’s campaign.

Mr. Donovan said that several other candidates in the race have PACs and added that unlike some other donors, his father was not seeking anything in return for his contributions. “I don’t think New Yorkers are concerned that my dad’s intentions are to lobby me for more time with the grandchildren,” he said, while still acknowledging that his father’s support reinforced the notion that he had advantages that other candidates lacked.

Mr. Donovan, aware that his privilege had become a liability with some voters, has been trying to address that concern in the last weeks of the campaign.

On the first anniversary of George Floyd’s murder, he was arrested with a small group of protesters who blocked the entrance to the Holland Tunnel in an act of civil disobedience. Mr. Donovan, wearing a Black Lives Matter T-shirt, talked about how he has not had to worry about his 19- and 21-year-old sons facing discriminatory policing.

“I am grateful,” he said, “but I am also angry.”

Jack Begg contributed research.