Raymond McGuire has lived a grand New York life, conquering Wall Street and kibitzing with Steve Martin. But in his campaign for mayor, he is eager to reach beyond his wealthy supporters.

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 first in a series of profiles of the major candidates.

Feb. 10, 2021

At last, Raymond J. McGuire was among friends.

“I see my crew from Citi!” he called out to his Zoom gathering, midway through a virtual fund-raiser for his mayoral campaign, its grid of video feeds looking like a chapter meeting of the 1 percent: grand libraries and fire-warmed living rooms, Steve Martin in a smart white button-down, a Tisch, a Seinfeld, a Knick.

“I see my crew from Citi!”

Mr. McGuire sounded almost giddy to be in such company. It had been an uneven couple of weeks for his candidacy, driven by an audacious if unproven idea: that the times demand a trailblazing Black businessman with nearly 40 years of experience on Wall Street and none in government, pledging to deploy his prolific contact list in service of his city.

While Mr. McGuire, 64, had raised more than $5 million in the three months since announcing his run, propelling him to the race’s upper tier, he also often looked the part of a first-time campaigner.

Opponents chafed at his repurposing the tagline of Shirley Chisholm (“unbought and unbossed!”), observing that the former congresswoman declared such independence because she lacked ruling-class connections, not because she had too much money to care. Reporters started asking about Mr. McGuire’s past business ties to the Koch brothers and to the government of Saudi Arabia while at Citigroup. And when pressed in public forums, Mr. McGuire occasionally wobbled, defaulting to the slight pique and projected self-assurance (“Let’s go! I’m good!”) of someone not used to being challenged.

But the fund-raiser, at least, was a safe space — for Mr. McGuire, yes, but also for a most devoted constituency: masters of the universe who feel like pariahs in the New York City of Mayor Bill de Blasio.

Mr. de Blasio is the first mayor in at least a generation who has not been openly solicitous of the city’s business elite, which was uniquely spoiled by 12 years with one of its own, Michael R. Bloomberg, at the controls. In Mr. McGuire’s bid, New York’s upper crust sees a prospective return to the civic influence and unquestioned relevance they long assumed. It just so happens that they are projecting these visions onto a man who rejects comparisons to Mr. Bloomberg as reductive and racially ignorant, no matter how many admirers call him “the Black Bloomberg” out of earshot.

Both Mr. McGuire and his most powerful supporters recognize that the path to City Hall runs through neighborhoods far from his duplex in the famed San Remo building on Central Park West. And so his team is working to stitch together an unusual Democratic coalition, crafting appeals to affluent Manhattanites — aggrieved by Mr. de Blasio’s snubs — and to lower-income, predominantly nonwhite voters in the other boroughs.

The cold math of off-year elections with an unwieldy, divided field makes this theory of the case more than plausible: The winner of the primary might need to persuade perhaps a few hundred thousand people — if that — a total slightly greater than the population of the Upper West Side.

For now, that is the slice of the city that probably knows Mr. McGuire best. Presiding over his fund-raiser from his home office, surrounded by leatherbound volumes of Shakespeare and Faulkner and an exhaustive collection of African and African-American art, Mr. McGuire gazed upon the pixelated faces of success.

In one virtual window, the academic Henry Louis Gates Jr. sipped a drink while muted. In another, Jessica Seinfeld, the cookbook author and wife of Jerry Seinfeld, sporadically replaced her video feed with an away-screen headshot of her regal-looking cat, Javier.

At one point, a businesswoman spoke up to assure Mr. McGuire that her husband, a financial news anchor, covertly supported the cause but was not attending “because of journalism.”

Others waited for Mr. McGuire to address them directly:

“Bewkes! My man!” (That would be Jeff Bewkes, the former chief executive of Time Warner.)

“Charles Oakley in the house!” (The retired Knicks great nodded from his rectangle.)

“Peter Malkin in the house!” (Mr. Malkin’s Zoom window was blank. His portfolio is not: The Malkin family controls the Empire State Building.)

This is the Mr. McGuire, loose but in command, whom friends hope the city will come to see: the world-straddling overachiever from Dayton, Ohio, studying his way out of trying financial circumstances in his youth; the savvy dealmaker who rose to vice chairman at Citi, after stints at Morgan Stanley and Merrill Lynch; the man who would be mayor, if only the city would start listening to its highest earners again.

“He’s very popular,” said William J. Bratton, the former police commissioner and veteran Manhattan schmoozer. “Even watching him at the Harvard Club, it took him a while to get to his seat, saying hello to people.”

While Mr. McGuire wears his high status openly, never known to lean on the faux modest “school in Cambridge” construction like some classmates, he has resisted analogies to Mr. Bloomberg, for reasons difficult to refute: Mr. Bloomberg did not grow up Black and scraping, across from paper mills so pungent that a blast from an open refrigerator door was sometimes the surest way to find fresh air. Mr. Bloomberg was never mistaken for the security guard or the bathroom attendant as he climbed. Mr. Bloomberg does not know what it means to be profiled still, no matter his assets, when he steps out from the comforts of his tony address.

It happened again just a few months ago, Mr. McGuire recalled: He joined a driver, also Black, in a waiting car, set to ferry him to a film shoot for his introductory campaign video, which was narrated by Spike Lee. Within a few blocks, police sirens howled.

“Driving while Black,” Mr. McGuire said in an interview. “There are occurrences like this that help shape how you think about the world, right?”

Yet in a signal of the disparate support bases that the campaign plans to court, Mr. McGuire declined twice to answer whether Mr. Bloomberg had been a good mayor. (A campaign spokeswoman, Lupe Todd-Medina, said Mr. McGuire “does not recall” ever voting for Mr. Bloomberg but remembers supporting his Democratic opponent, William C. Thompson Jr., in 2009.)

Mr. McGuire noted the damage that stop-and-frisk policing had inflicted upon nonwhite New Yorkers under Mr. Bloomberg but added that the former mayor had “managed the city the right way.” Mr. Bloomberg himself has stayed out of the race publicly but is said to have a fondness for Shaun Donovan, his former housing commissioner.

In some ways, Mr. McGuire seems to be moving against some of the city’s prevailing Democratic winds. He is a supercapitalist without apology, betting on the sort of center-leftism that ascendant progressives like Representative Alexandria Ocasio-Cortez shun.

Mr. McGuire has sought to position himself as the jobs-focused candidate, a budget-minded realist who laments inequality but questions some left-wing proposals for shrinking it, like a universal basic income program. He has called for wage subsidies at small businesses and a yearlong post-Covid “comeback festival” to boost tourism and nightlife, emphasizing the need for federal aid and speaking mostly euphemistically so far about any politically painful crisis remedies.

Possible cuts? Mr. McGuire says he would “review inefficiencies and spending levels.”

Tax hikes? He says leaders must “consider tax increases on those who can afford it,” as he can, and is quick to label himself a progressive despite any suggestion to the contrary.

“My definition,” he said, “is I have a life of progressing through the system as a Black person in a 99.9 percent majority world.”

Making his case on the mostly virtual campaign trail, Mr. McGuire describes his considerable means with a blunt accounting that can bear little resemblance to typical political messaging.

Absent governing credentials, he has argued that his philanthropy should count for something.

“Health care, long before Covid, I helped fix it — not too far away, at the nurses’ station, emergency room, NewYork-Presbyterian Hospital, 168th Street,” he said in Harlem last month. “You go there, look above that nurses’ station and see whose name is there.”

Questioned by activists at a recent forum about his commitment to social justice, Mr. McGuire said he had given money to the mother of a 1-year-old named Davell Gardner Jr. who was shot and killed in Brooklyn last summer.

“Who put furniture in that apartment?” Mr. McGuire demanded. “Who furnished it?”

The Rev. Al Sharpton, whose National Action Network has benefited from Mr. McGuire’s largess, said the candidate’s focus on his own wealth — and how he has used it — had a way of connecting with Black voters.

“There’s something that resonates, particularly in our community,” Mr. Sharpton said, “when you are who you are.”

Mr. McGuire’s commitment to candor is not absolute. He declined to discuss his wealth in detail or ballpark his starting salary in finance, characterizing it as “enough” and stressing that he grasps the realities of poverty because of his own humble origins.

For his more senior posts, like helping to lead Citigroup’s corporate and investment banking, those familiar with the industry said annual pay for managers in equivalent positions could generally range from the high single-digit millions to the teens.

Mr. McGuire’s most sustained relationship to the city’s civic life has come through the arts, with board or executive committee roles at the Whitney Museum of American Art and Lincoln Center, among other institutions.

His apartment has doubled as a museum unto itself through the years, shared with his wife, Crystal, an author and filmmaker; their two children from her prior marriage: Cole, 20, now a guard for the N.B.A.’s Orlando Magic, and Ella, 18; and the couple’s 8-year-old son, Leo.

The space’s front rooms greet guests with masterworks by Henry Ossawa Tanner, a renowned African-American painter; a sculpture by Elizabeth Catlett, an African-American and Mexican artist, of a reclining woman poised across a marble table; and an array of ancient African masks and other objects dating to 300 B.C.

“Kuba cup, man,” Mr. McGuire said, giving a tour recently, approaching a treasured piece. “That’s the cup of kings.”

Then there are the books of kings: the Bard (“you see the Shakespeare collection?”), the Romantics (“these are my guys here, Keats and Shelley!”), a memoir by Susan Rice (“good friend”).

Mr. McGuire, schooled in English literature, refers to his academic history as “the 4H club”: the Hotchkiss School in Connecticut; then three degrees from Harvard, for undergraduate, business and law.

David Paterson, the former New York governor who has known Mr. McGuire since the 1970s, marveled at the social circle his friend had built from Manhattan to Bridgehampton, N.Y., where the McGuires also own a home.

“I’ve run for a few things,” Mr. Paterson said. “Spike Lee never made a video for my campaign.”

Taking stock of his feats and contacts, Mr. McGuire can often sound enthralled by his own arc, wondering aloud if Hollywood could dream up anything quite so unlikely.

“Even with your big brain, you can’t imagine anything like that — you can’t imagine writing anything like that,” he said of his path. “Who else has got anything like that? Who else?”

During a recent afternoon at his home, Mr. McGuire handed over four stapled pages of accomplishments that included board leadership roles at Hotchkiss and the San Remo Tenants Corporation. (Residents over the years have included Dustin Hoffman, Diane Keaton and Mary Tyler Moore; Madonna was once rejected by the co-op board.)

He pulled out a book of art that featured “Springtime in Washington” by Alma Thomas, before revealing the work on the wall of his dining room: “You may see some similarities between this and that.”

Later, word came that the author Malcolm Gladwell had praised his candidacy during a talk, a surprise to the campaign. Mr. McGuire was asked if they knew each other.

“Malcolm?” he said, eyes flickering in semi-offense. Of course he knew him. He knows everyone.

And where he does not, Mr. McGuire is moving to catch up, convening with current and former officials in a crash course to find his municipal bearings.

Several people who spoke to Mr. McGuire as he considered a run this past year described him as a conspicuous novice in city policy and politics. He said he had filled stacks of notebooks beside his desk in the interim, with a particular focus on New York’s turbulent 1970s.

“Talked to Dick Ravitch,” Mr. McGuire volunteered, citing the former New York lieutenant governor with deep experience weathering fiscal calamity in government.

In an interview, Mr. Ravitch called the candidate a “fast learner” with a skill set to meet the moment. He added some caveats.

“He doesn’t know a thing about the city government,” Mr. Ravitch said, preceding “thing” with an expletive, before adding: “Do I think Ray would be the best of the candidates? Yes.”

Gale Brewer, the Manhattan borough president and another government long-timer with whom Mr. McGuire has spoken, said diplomatically that there was only so much she could convey in a phone call.

“It’s a hard city,” she said.

Mr. McGuire has said that voters should prize executive experience over government résumés. On this score, some former colleagues at Citi report mixed returns. In interviews, they appraised Mr. McGuire as an approachable leader and willing mentor, particularly to younger Black talent, but also as an image-conscious manager who could struggle with indecision if a looming choice seemed destined to upset someone.

Allies have framed such qualities as an instinct for defusing conflict, noting that the candidate even tried to play peacemaker between Mr. de Blasio and his wealthy antagonists: In 2015, Mr. McGuire hosted a reception for the mayor and his wife, Chirlane McCray, hoping they might grow closer to assorted business titans. (It didn’t take.)

Some competitors have moved quickly to attach the political stench of banking to Mr. McGuire, whose rivals include Eric Adams, the Brooklyn borough president; Scott M. Stringer, the city comptroller; and Andrew Yang, the former presidential candidate.

Operatives for other campaigns have focused especially on Mr. McGuire’s business dealings with figures unpalatable to Democrats, like the Koch brothers.

Friends say that this, too, speaks well of him.

“We are investment bankers!” said William M. Lewis Jr., a co-chairman of investment banking at Lazard who has known Mr. McGuire since their time at Harvard. “We get paid a lot of money to help bridge differences. People should view it as a compliment that somebody, who is as different at their core as Ray, would look to Ray to try to help them get something done.”

For those eager to hasten the cleanest break from the de Blasio era, the attraction to Mr. McGuire often seems as much about attention as ideology — about being seen, and heard, and seen being heard.

Mr. McGuire has been adamant that personal relationships would confer no special treatment at his City Hall. In fact, he has turned the implication on its head, accusing the current mayor of operating an “exclusive government, not an inclusive government.”

And don’t the successful care about the city, too?

“Let’s face it: Anybody that lives above 57th Street doesn’t feel that Mayor de Blasio has been attentive,” Mr. Bratton said. “The next person in, they want to be able to have access.”