Raymond McGuire, the longtime Wall Street investment banker who, on December 2, will formally announce his bid to become the next mayor of New York City, has friends in high places and lots going for him, such as raw intelligence, charisma, and a desire to rebuild a city—and a budget—ravaged by the coronavirus. “We are in a war for the survival of this great city,” he told CNBC when he admitted he was going to make the mayoral run. That’s for sure. Crime is up. Budget deficits are up, and real-estate occupancy rates are down, way down. But his well-heeled supporters hope his combination of gifts will make McGuire a formidable opponent in a crowded field, even though he has never before run for office.

McGuire, 63, has a killer backstory. And in many ways that’s part of his challenge. He’s the plutocracy’s fantasy of a populist candidate. The question is: will average New Yorkers relate to him? He was raised by a single mother and his grandparents in a Dayton, Ohio, neighborhood that he has referred to as “the other side of the tracks.” “My family had all of the essentials that money could buy: food, shelter and clothing,” he told BET in 2014. “But more importantly, we had all that money could not buy: love, honor, respect, integrity and, most importantly, faith.” He got bused to school, but only after he’d walked a mile and a half to get to the bus. He was on scholarships starting in the sixth grade.

Onstage at the Jackie Robinson Foundation Annual Awards Dinner at the Waldorf Astoria.

He capitalized on his educational opportunities. He went to Hotchkiss, the tony Connecticut prep school, and then graduated from Harvard College, Harvard Business School, and Harvard Law School. He married Crystal McCrary, a television producer and novelist. He has three stepchildren, including Cole Anthony, the University of North Carolina basketball superstar whom, on November 18, the Orlando Magic chose in the first round of the N.B.A. draft.

He began his 38-year Wall Street career in 1982 at what was then known as First Boston (since subsumed into Credit Suisse), one of the hottest firms at the time. For the past 15 years he’s been at Citigroup, most recently as a corporate vice-chairman and the chairman of the investment-banking division, where he advised Time Warner on its $85 billion sale to AT&T and Wyeth on its $68 billion sale to Pfizer. (I have known McGuire since 1997, when I worked for—and with—him in the mergers-and-acquisitions group at Merrill Lynch.)

McGuire, 63, has a killer backstory. He was raised by a single mother and his grandparents in a Dayton, Ohio, neighborhood that he has referred to as “the other side of the tracks.”

But his years in the elite worlds of private education and Wall Street has not exempted him from experiencing systemic racism firsthand. “If I go into a major department store, I’m one of three things: I’m security. I’m men’s room. I’m men’s suits,” he told the Economic Club of New York. “And that is if I’m dressed up. If I walk in any neighborhood … they see a six-four, 200-pound Black man.... I could easily be George Floyd, or Ahmaud Arbery, and the list goes on and on. Or Trayvon Martin. I could be Emmett Till. Just because I have those degrees and I have benefitted from all of the great education, greatest institutions that exist on the planet, I’m still Black.”

He seems especially beloved by the rich and powerful. He’s being advised by Charles Phillips, a former president of Oracle and Morgan Stanley banker, as well as Nicole Seligman, a former president of Sony Corporation of America and one of Bill Clinton’s attorneys during his impeachment. (Her husband is Joel Klein, the former New York City schools chancellor.) In addition, several of McGuire’s former Citigroup colleagues have told me they are informally advising him. Last month, The New York Times reported that McGuire has “close ties” to Valerie Jarrett, a longtime Obama confidante. As Michael Corbat, the C.E.O. of Citigroup, said, McGuire is “a path-breaking voice for the industry on diversity and inclusion.”

McGuire and his wife, Crystal, at the Gordon Parks Foundation Awards Dinner, in New York.

But all this financial and cultural firepower may not make McGuire’s path to Gracie Mansion any easier. “The idea of Ray is great,” a political consultant told the Financial Times. “The reality is yet to be seen.” McGuire is running as a Democrat. That means he has to win the Democratic primary, home to an increasingly vocal, cranky, and energized progressive faction. He’ll also have a tough row to hoe with the New York City teachers’ union—an important and powerful voting constituency—who may fear McGuire as a 2021 version of Bloomberg.

McGuire knows what he’s up against. In our November 20 conversation, he joked, sort of, that his 94-year-old mother thought he was nuts to quit his Wall Street job after 38 years to make an improbable run for mayor. “She prayed for me,” he says.

He’s running, he says, because he loves New York, and because he has the skills to try to solve its myriad problems. “When I came to this city, I had a great education and a lot of student debts. I had no money. And this city gave me the opportunity to use the education to compete on the biggest stage in the world.”

But can he prevail in the Democratic mayoral primary next June? He tells me his path is through the people. “You gotta go to the boroughs,” he says. “You’ve got to explain to the people: I am the people. I am the same. My journey is not dissimilar to their journey. I know what it’s like to struggle. I know what it’s like to have to debate whether or not you’re going to pay the telephone bill or do something else.... You have to be able to have that kind of conversation and talk to the people in a language that people understand.”

He may not be a politician yet, but McGuire has a politician’s gift of eloquence, and of evasiveness. “What about that Democratic primary?” I ask again. How are you going to win that? He pauses. “I’ve been a long shot all my life. I wouldn’t be talking to you if that long shot hadn’t prevailed.”

William D. Cohan is a Writer at Large for Air Mail, and the author of numerous books, most recently Four Friends: Promising Lives Cut Short