In 1980, Ray McGuire was on a Rotary fellowship in the south of France when he felt the urge to travel more. Then in his early 20s, the Dayton, Ohio, native had yet to embark on his distinguished Wall Street career, during which he would rise to become one of the country’s most prominent Black banking executives, managing budgets that he says were larger than those of most states.

Traveling between degrees at Harvard University and with extra time on his hands, McGuire extended his international pilgrimage to the Middle East, venturing first through Athens on his way to Cairo and then onto Israel. He sojourned for about 10 days in Jerusalem as a guest of a local theological seminary, walking the Via Dolorosa and praying at the Western Wall — experiences he describes as some of the most meaningful of his young adult life.

But the experience he remembers most was somewhat more familiar to him. “I’m sitting there during the new year, in the middle of Jerusalem, and they think I’m Aulcie Perry,” McGuire, now 63, recalled in a Zoom interview with Jewish Insider, referring to the African-American basketball star who played as a center for Maccabi Tel Aviv in the late 1970s and early 1980s. Though McGuire shot hoops in high school, he was six inches shorter than Perry and only bore a passing resemblance to his supposed doppelgänger. Still, the young itinerant, who doesn’t speak Hebrew, was hard-pressed to object to the comparison. “They think I’m Aulcie Perry,” McGuire repeated. “And I can’t tell them I’m not.”

McGuire is used to navigating life as an outsider, particularly during his decades-long tenure in an industry considered to be historically inhospitable to Black people. “You’ve got to bring your A-plus game every single day,” McGuire emphasized in the video call from his Central Park West apartment, casually dressed in a brown turtleneck rather than his usual suit-and-tie. “There’s no 6’4” Black person,” McGuire, who served as vice chairman at Citigroup until he announced his candidacy in October, said of the financial world. “Nobody else who woke up Black every day was doing this.”

Now that he is running for New York City mayor in the crowded race to succeed Bill de Blasio, who terms out of office this year, McGuire has in some ways found himself navigating similar terrain as he seeks the Democratic nomination in a city that has only elected one Black mayor in its history. Though McGuire had never previously run for public office, he hasn’t shied away from civic life, having served as a board member at a number of New York institutions including the New Museum, Lincoln Center, the De La Salle Academy and NewYork-Presbyterian Hospital — civic résumé boosters that have provided him with a wealth of connections he says will be necessary in order to cobble together a range of coalitions if he is elected.

Ray and his son, Leo, at National Action Network Grab n Go Meal Distribution on Thanksgiving Day 2020. (Margot Jordan)

As a relative neophyte to campaign politics, the former banking executive could be operating at a disadvantage against some of the more experienced candidates in the race, such as City Comptroller Scott Stringer, Brooklyn Borough President Eric Adams, former presidential contender Andrew Yang and former de Blasio aide Maya Wiley. Still, McGuire believes he is uniquely suited to lead a city deeply scarred by the ongoing coronavirus crisis, which has so far claimed more than 25,000 local lives, shuttered countless small businesses and left many public school students struggling to keep up with virtual learning. 

“I’m the only one who can bring all this together whose interests are solely what is in the best interest of New York,” said McGuire, who has opted out of participating in the city’s matching funds program, allowing him to raise and spend beyond a prescribed limit. “My judgment is going to be influenced by that and that alone, because I don’t have any allegiances.”

His pitch for the mayorship is a deeply personal one, and begins with his poor upbringing in the once-thriving Midwestern manufacturing town of Dayton — the loose details of which were described in a slickly produced campaign ad released last month, narrated by Spike Lee and featuring a soundtrack from Wynton Marsalis. “I grew up on the other side of the tracks,” said McGuire, who was raised by a single mother who often struggled to make ends meet on her social worker’s salary. “We lived across the street from Howard Paper Mills, which sometimes emitted fumes that were so strong that you had to open the refrigerator door in order to get some fresh air, or to get some air period.”

McGuire went on to overcome such adversity, earning business and law degrees at Harvard before he was recruited in 1984 by legendary investment bankers Joe Perella and Bruce Wasserstein to work in the mergers and acquisitions group at First Boston — his first financial job. (Perella later became the godfather of McGuire’s son, Leo.) McGuire’s trajectory would include stints at Morgan Stanley, Merrill Lynch and Citi, where he spent 13 years as global head of corporate and investment banking before ascending to vice chair. 

“I’ve said when I got there, if I wanted to have lunch with somebody who looked like me, it was, like, me at a table for two and I was the only person there,” McGuire said of the obstacles he was forced to clear on his way to the top. “In the corporate world, there was a close friend of mine who’d been an analyst, so he was probably two or three years ahead of me, but that’s it. I couldn’t call anybody, there were no references and no models out there where you could look and say, How do you do this? Because nobody had ever ever traveled that journey.”

During his time in corporate banking, McGuire earned a reputation as a mentor to younger corporate bankers, according to investor and businessman Mark Gerson, who is backing McGuire’s mayoral bid. “Ray has really mentored a whole generation, maybe two generations now, but at least a generation of really outstanding young people in and around New York business,” Gerson told JI in a phone interview. “This is a really wide network of people who are completely devoted to him. He earns trust, he commands respect and he makes friends so easily because he’s genuinely committed to other people and genuinely committed to their success.” 

“The network is especially true among young Black professionals,” said Walker Brumskine, a 34-year-old investment professional at Apollo Global Management who credits McGuire with helping him land his first summer associate job in banking. “Everyone has had coffee with Ray McGuire.”

As a candidate, McGuire makes clear that he remembers his roots as he appeals to voters who may not be interested in boardroom triumphs. “This morning, I went to get a coffee, and I was walking down the street and I saw three women with clear-through bags,” McGuire said in the late December interview with JI. “You know what they were doing? They were going from trash bin to trash bin collecting cans and bottles. So they go to the corner and cash them in at the machines. That’s the level to which we have reached, the deficit we’ve reached. And so I know what that’s like.”

Ray McGuire with his high school basketball team. (Courtesy)

“His personal story is definitely an inspiring one,” said Susan Kang, an associate professor of political science at John Jay College of Criminal Justice, adding that McGuire’s administrative experience may well qualify him for the mayorship because the city government is a giant and unwieldy operation. She speculated, however, that voters may look askance at the first-time candidate’s Wall Street background as the stock market booms but regular New Yorkers see few tangible benefits. “It’s unclear to what extent New Yorkers are ready to give a businessperson a try.”

McGuire rejects the notion that his Wall Street bona fides may be a liability. “I would say, if there’s ever a moment in time when you want me on that wall, it is now,” he said. “If ever there’s a moment in time you want somebody who’s got business experience, who can bring public and private partnerships together, who can change the narrative, who can change the reality — that’s me, that’s now. This is a change. This is very different.”

New York’s business community, for its part, seems to have rallied behind McGuire in the two-and-a-half months since he declared his candidacy. In interviews with JI, a number of prominent business and philanthropic leaders expressed their strong support for McGuire’s mayoral bid. 

“I have known Ray for many years and the combination of his financial acumen and lived experiences make him the best leader in my view to help bring New York City back as a powerhouse in the global socioeconomic sphere,” LionTree investment bank founder and CEO Aryeh Bourkoff said in an effusive email. 

Laurie Tisch, a philanthropist who sits on the board of the Whitney Museum of American Art, agreed with Bourkoff’s appraisal, noting that she has “deeply admired” McGuire for several decades. “We are in an unprecedented time in the city and we need a leader who can bring us back from one of the worst economic and health crises in generations,” she said. “I believe Ray is that man. He comes from humble beginnings and worked his way up the corporate ladder despite many obstacles, and he did it without losing his humanity and awareness of the lives of people who are struggling.”

“Ray is a brilliant and committed leader and a compassionate and courageous advocate for the most vulnerable among us,” said Brad Karp, chairman of the law firm Paul, Weiss, adding: “He loves New York and I believe he has the unique capacity and skillset to deal with the enormous challenges that lie ahead.”

Still, whether such support will earn him the Democratic nomination remains to be seen. “The hedge fund set appears to be aligning behind him, but that probably won’t be enough,” said veteran Democratic campaign strategist Hank Sheinkopf. “It’s hard to see a path for him today, but it’s early,” he added. “Anything is possible in New York.”

In conversation with JI, McGuire averred that New York is at a critical inflection point, comparing the current moment to the crucial negotiations in 1975 when the city pulled itself back from the brink of bankruptcy. “Remember, in the ’70s, we saw business, labor and government all coming together,” McGuire said. “Labor bought the bonds. We’re going to need those coalitions.”

But asked to name a former New York City mayor whose approach he might seek to emulate, McGuire instead cited the late Maynard Jackson, Atlanta’s first Black mayor, who assumed office in 1974 and served three terms. “There have been some other distinguished leaders here as well,” McGuire said. “But I think Maynard Jackson would be one that I’d look to. You just look at the growth in Atlanta, look at all of the businesses that were impacted — all the developers, all the suppliers, minority and majority, all benefited. One of the biggest economic growths that we’ve seen, where it was all-inclusive growth, and that’s what we’ve gotta do right now.”

His plan for the city is three-pronged, focusing on the economy, public safety and education. McGuire, who supported Amazon’s aborted decision to build its second headquarters in Long Island City, loosely outlined his economic vision for New York, entailing what he described as a “massive job program that includes the fundamentals” of “analog” and “digital infrastructure and everything in between.”

Ray McGuire at the ProScholars Athletics, Inc. 2019 Benefit Gala. (Margot Jordan)

McGuire has positioned himself as a supporter of the Black Lives Matter movement, but clarifies that he is not in favor of defunding the police. “I am for better policing,” he said, emphasizing his desire to foster partnerships between mental health agencies and the police and to invest in community-based organizations that can work with law enforcement. “What that does is it then establishes a bond, it establishes what we don’t have today, which is trust between the police and the community,” he said. “It can’t be that what gets highlighted in the community is Sean Bell or Tamir Rice or Eric Garner or George Floyd.”

McGuire was equally adamant that he would address the uptick in antisemitic violence New York has seen in recent years, noting that he has built strong relationships with Jewish community members. “Those allegiances are going to be important going forward. My risk tolerance, my tolerance for any of this is nonexistent,” he said, adding: “In any instance where we see this, we need to eliminate it. I got zero tolerance for it, zero. And so I would work with the police department and with the Jewish community to ensure that the Jewish population of New York is not only secure, but feels secure as well.”

Leon Goldenberg, an Orthodox Jewish real estate executive and talk radio host in Midwood who is active in Jewish causes, said that he had spoken with McGuire on a Zoom call in December and found him to be an “extremely bright person” who had “some very good ideas on policing” as well as a compelling personal story. 

“He comes from a poor family, he pulled himself out, but he understands fully the Black experience, the minority experience, and that’s so important in New York,” said Goldenberg, who made clear that he wasn’t making an endorsement and that the city’s 500,000-strong Orthodox community, segments of which often vote as blocs, had not yet coalesced around any one particular candidate. “He’s very strong on Israel and he seems to understand our issues also,” Goldenberg said of McGuire. “Does he need to learn more? Yes. Yes, he does.”

Since he quit his job in October and entered the race, McGuire has been busy engaging with voters, telling JI that he is planning an aggressive ad campaign that includes digital, radio, TV and mail — a strategy that won’t be hampered by spending limits and which will allow him to build up name recognition as he seeks to differentiate himself from the pack.

McGuire, whose campaign is co-chaired by Obama confidante Valerie Jarrett, declined to reveal how much money he had raised, though his campaign said in early December that it had pulled in more than $2.3 million. “I want to get out and talk to the people,” he said. “I want to listen to them. People have a very good handle on what the issues are, because the issues are prevalent and they are pervasive.”

“The well-being of this city is on the line,” McGuire added. “This may be the most important time in this city’s history. And so, this is not a time for people to get promoted into this or get termed out into this. You’ve got to have somebody who has the confidence of each of the communities.”

“My wife and our kids have all contributed to the conversation,” said McGuire, who is married to the producer and novelist Crystal McCrary and whose stepson, Cole Anthony, is a professional basketball player who was drafted in the first round of the 2020 NBA draft by the Orlando Magic. “We all say now is the time. If we don’t get it done now then I’m not convinced that it’s ever going to get done.”

Using a basketball analogy, McGuire — who was captain of his high school team and frequently plays ball with his son Leo in Central Park — emphasized that he was in the race to win. “Hard in the paint, man,” he said of his game plan ahead of the June Democratic primary. “I’m going hard in the paint.”