This past June—as the coronavirus continued to rage and anti-racism protests convulsed city streets—Robert Smith, the nation’s wealthiest Black man appeared on the cover of Town & Country magazine. A handsome, avuncular, self-made private-equity king worth $5 billion, Smith buzzed into mainstream-media prominence last summer when—midway through a Morehouse College commencement speech—he committed himself to assuming the student debt of the school’s entire graduating class.

Considering this was T&C’s philanthropy issue, Smith’s cover appearance (better-known altruists like Matthew McConaughey and Agnes Gund had covers as well) made sense. As the student-debt crisis threatens to trap young people—especially young people of color—in a cycle of downward mobility, Smith demonstrated that selfless gestures and bold ideas can actually make a difference.

Which is great. But the real significance of Smith fronting an issue of Town & Country—and the accompanying photo shoot at his Colorado ranch—is not that he’s a benefactor billionaire but that he’s Black. And not just Black but Black and rich and powerful at a moment when the majority of discussions about Black Americans center around poverty, pathology, and defeat.

Billionaire businessman Robert F. Smith receives the W. E. B. Du Bois Medal during ceremonies at Harvard University last year, for contributions to Black history and culture.

Often overlooked, and at times purposefully press-shy, America’s
“Black elite” stand as a powerful rebuke to the nefarious notion that Black Americans are fated to a life of fatherlessness, handouts, and failure. Which is why their fall from positions of power resonates, as it did this week when Jide Zeitlin, one of only five Black C.E.O.’s of a Fortune 500 company, resigned from Tapestry, the parent company of Kate Spade and Stewart Weitzman, after the board was made aware of a decade-old sexual-misconduct allegation. Perhaps the coverage of Zeitlin’s disgrace stings harder when you consider there is scant coverage of Black executives at the very top.

“The media doesn’t like to write stories about folks like us, successful Black businesspeople,” observes R. Donahue Peebles, C.E.O. of the Peebles Corporation, a real-estate-development firm prominent nationwide. “But we are at a very unique moment right now; America, corporate America, is finally paying attention.”

Often overlooked, and at times purposefully press-shy, America’s
“Black elite” stand as a powerful rebuke to the nefarious notion that Black Americans are fated to a life of fatherlessness, handouts, and failure.

It’s easy to think that Black men such as Peebles—estimated by Forbes to be worth more than $700 million in 2015—have little in common with Black men like George Floyd. But as America’s history of restricted country clubs and “no Jews/no Blacks” luxury co-ops demonstrates, it often doesn’t matter how wealthy you are if you are Black. Black people—successful, celebrated Black people such as Harvard professor Henry Louis Gates Jr.—still run the risk of being arrested (and, yes, killed) when partaking in the most quotidian of activities, such as relaxing in their own homes.

John Lewis and Henry Louis Gates Jr. in 2017.

Perhaps the most damning proof of America’s endemic injustice is that Blacks, even über-deci-one-percenter Blacks like Smith, are still bound by the forces that constrain all Blacks in America. As Harvard Law School professor Ronald S. Sullivan Jr. noted in a CNN article about wealth and racial profiling, “No matter how much money I have in my pocket, if I’m stopped by police … what they see first and foremost is my black skin.”

Yet as police forces consider much-needed reform—and industries from media to academia to banking initiate economic-empowerment programs—the rarest of rarefied worlds has also begun to tackle (or at least discuss) race and racism. Straddling two worlds, one of privilege and the other of prejudice, affluent Black Americans are uniquely positioned to bridge the gap between protest movements and polite society.

“There is finally a willingness, even a thirst, for these types of conversations [with white people], whether it’s on Zoom calls or philanthropic boards or private gatherings,” observes author, activist, and style figure Susan Fales-Hill. “There is still a contingent that doesn’t want to talk about these issues, but they’re pretty hard to avoid when even Mitt Romney is marching in a Black Lives Matter protest.”

As America’s history of restricted country clubs and “no Jews/no Blacks” luxury co-ops demonstrates, it often doesn’t matter how wealthy you are if you are Black.

But what exactly are these conversations about? Interior designer Corey Damen Jenkins says his clients—who are predominantly white and wealthy—are leaning on him to delicately navigate a new racial reality they don’t entirely understand. Mostly sincere, mostly well meaning, “they’re coming from a good place,” says Jenkins, who was recently named to Elle Decor’s A-List. “But they’re painfully aware that one misstep, particularly on social media, and they can be ‘canceled.’”

Real-estate entrepreneur R. Donahue Peebles: “The media doesn’t like to write stories about folks like us, successful Black businesspeople.”

For individuals like Peebles, who’s developing one of the tallest towers on the West Coast, the focus is on large-scale economic justice and opportunity. He sees this as a moment to be seized. “Suddenly those with capital, institutional investors want to work with us, are calling us back,” he says. “These are folks who think of themselves as progressive, who support African-Americans philanthropically,” he continued. “But very few actually do business with Black people, very few actually know any Black people.”

As Harvard Law School professor Ronald S. Sullivan Jr. noted in a CNN article about wealth and racial profiling, “No matter how much money I have in my pocket, if I’m stopped by police … what they see first and foremost is my black skin.”

Master sommelier Carlton McCoy, meanwhile, views this period (and his role in it) as a unique opportunity to foster and deepen a robust roster of future Black achievers. This is clearly a social-justice imperative: “We must dig deep to find and refocus our attention on successful African-Americans,” says McCoy. As C.E.O. of Heitz Cellar, in Napa Valley, California, he is the first Black American to lead a major winery, and he recently established the Roots Fund, which supports wine scholarships and industry-job placement for young Black Americans.

While Peebles, McCoy, Jenkins, and Fales-Hill understand the urgency of their efforts, this labor—like so much Black labor over the past 400 years—is neither compensated nor without consequence or complications, especially when it comes to the generation coming up behind them. “This adds a burden on those who are already burdened,” Jenkins says. It’s a burden younger upper-class Black Americans appear less inclined to shoulder amid the current activist-led climate.

Peebles, for instance, says his son—though raised amid wealth—has become far more “progressive and political” since joining the family business a few years back. “I was able to insulate him from many of the burdens I experienced while running my business,” Peebles says. “Now that he is in it, he views [institutional] unfairness quite differently; he wants to see dramatic changes.”

Affluent Black Americans are uniquely positioned to bridge the gap between protest movements and polite society.

Indeed, the burdens facing affluent Black Americans are real—and real in ways that similarly situated whites can barely imagine, let alone experience. And this, more than anything, shapes the fundamental differences between white and Black elites. For one thing, Black American money remains inherently insecure. “Most successful Black people are self-made. There’s very little generational wealth,” says Ralph Richard Banks, a law professor at Stanford University and the founding director of its new Center for Racial Justice. “Even at the highest levels, African-Americans lack the economic stability enjoyed by wealthy whites.”

Carlton McCoy, the only Black C.E.O. of an American winery: “We must dig deep to find and refocus our attention on successful African-Americans.”

Affluent Black Americans, adds Professor Banks, are also rarely immune from the structural legacies of inequality and racism—from health problems and shorter life expectancies to fatherlessness and random encounters with the criminal-justice system. This has been particularly true during the coronavirus pandemic, which has disproportionately impacted Black Americans.

Covid has been a wake-up call for the upper crust,” observes Sheila Bridges, another Elle Decor A-List interior designer, whose clients range from Bill Clinton to music impresario Andre Harrell. “Being affluent may provide better access to health care, but everyone knows someone who has died.”

The pandemic—along with the MAGA hats and Confederate flags near Bridges’s upstate home—is a constant reminder of the work still to be done. Work now made far harder by the economic instability caused by the coronavirus and, Bridges notes, by the “invisible glass ceilings” that even the highest-achieving Black Americans seem to always encounter.

Ultimately, however, prominent Black Americans will make their strongest impact only when the media finally understands that their stories—while clearly informed by access and privilege—are as varied and valid as those of Black strife. Indeed, in their attempts at diversity and inclusion, too often the media—particularly the progressive media—clamors for coverage of “Black excellence” that’s focused far more on the “Black” than actual “excellence.” Sure, representation has never mattered more. But considering their outsize burdens—activists, ambassadors, loners, leaders—America’s Black elite deserve to be reckoned with on their own terms.

“The media wants to show a type of Black person who isn’t going to compete for your spouse, who’s not a threat to your job,” says Fales-Hill. “There’s been an erasure of Black excellence,” she continues. “Because they’re a threat to the status quo; they’re revolutionaries in their own way, too.”

David Kaufman is a journalist based in New York City