WASHINGTON — In a sleepy southern town, an unexpectedly violent scene: a mob of angry whites chanted racially charged slogans on one side, while equally incensed counterprotesters advocated for civil rights on the other side. National headlines, decades-old grievances and the nation’s deepest racial wounds were on display. Talk of “the start of the white civil rights movement” filled the air as America’s liberals warily evaluated the appeal of a revanchist white supremacist movement that would bring the likes of David Duke to the national stage.
Thirty years before the clashes in Charlottesville, this was Forsyth County, Georgia, after a series of protests over the region’s long legacy of racist violence and de facto segregation that brought national media attention. And then, as today, an ascendant media figure inserted herself into that morass in an attempt to create understanding where there seemed to be laughably little hope of it — Oprah Winfrey.
Winfrey’s segment, filmed on location in Forsyth County, was more of a ratings success than a true healing moment. But that hasn’t dissuaded her, America’s premiere therapist, cultural interlocutor and spiritual guide (to name just a few of her distinctions), from turning her eye to our most politically sensitive topics time and again over her now four-decades-long career in broadcasting. Accepting the Golden Globe Cecil B. DeMille Award Sunday night for “outstanding contributions to the world of entertainment,” Winfrey placed herself at the center of the conversation again, offering a rousing defense of the press, touting its ability to expose “tyrants and victims, and secrets and lies,” and championing the #MeToo movement of women speaking out against “a culture broken by brutally powerful men.” It was a speech perfectly pitched to capture liberal imaginations — and it worked like magic, setting off a day of frenzied media speculation and earnest chatter on the left. Would Democrats really support a celebrity presidential candidate? Does Oprah have what it takes to knock out Donald Trump?
Oprah Winfrey accepts the 2018 Cecil B. DeMille Award during the 75th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 7, 2018 in Beverly Hills, California | Paul Drinkwater/NBCUniversal via Getty images
But just what, exactly, does Oprah believe? Noble and well-timed though they may be, Winfrey’s gestures in support of women’s rights and compassion in the public sphere do not a political platform make. From the start, the former talk show host has skilfully walked the tightrope between political advocacy (as a reliable Democratic donor and vocal Obama booster) and political engagement. But running for office would mean staking out political ground, and potentially alienating people on the other side of the fence, which is not exactly part of the universalist Oprah brand. Winfrey has consistently placed herself just close enough to the political fray to exert her gravity on it, but not close enough to be burned by its heat — a privileged status a presidential campaign would sorely test, not least of all a contest against a brawler like Trump. Squaring off against the president would call for an opponent with the confidence to wade into the muck of America’s racial discontent, but also the gracefulness to find the common ground Trump so frequently salts behind him — exactly the kind of high-wire act a young Oprah Winfrey attempted at the start of her broadcast career.
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The mid-1980s were a heady time for black politicians, especially in Chicago — Harold Washington, the city’s first black mayor, was elected in 1983, future U.S. Senator Carol Moseley Braun represented a portion of the city in the Illinois House of Representatives, and a young Barack Obama, fresh out of college, absorbed it all during his work as a community organizer on the city’s South Side. Winfrey was breaking barriers of her own, having overcome widespread skepticism on the part of stodgy white producers and executives to become not just a star broadcaster but an Academy Award nominee for her performance in Steven Spielberg’s “The Color Purple.” On Martin Luther King Jr. Day in 1985, Winfrey hosted then-Mayor Washington alongside musician Stevie Wonder on a star-studded episode of “A.M. Chicago,” an early incarnation of “The Oprah Winfrey Show.”
That appearance, however, would be a rarity — for her first decade-plus on the air, Oprah declined to book politicians as guests on the show, citing their conversational slipperiness as fundamentally at odds with her confessional interview style.
“I didn’t want to delve into the world of politics, because I felt that I lost control of any situation where I was seated with a skilled politician,” Winfrey said of her early years in an interview with WBEZ’s Jenn White last year. “I can’t get them to actually respond, because a skilled politician knows how to give the answer they want regardless of what question you ask.” She added: “When you’re dealing with someone who’s skilled in that way, it’s their game. They’re using you and you’re giving them the platform to be used.”
The heightened political environment, however, clearly energized her — for much of its early run, “The Oprah Winfrey Show” tackled flashpoint political topics like the Forsyth County case, and Winfrey donated $1,000 to Moseley Braun’s successful 1992 Senate campaign.
Over the years, Winfrey’s resistance to booking politicians softened, and not because of a sudden willingness to perform the conversational kabuki of the traditional stump-speech interview — she instead discovered that the world of politics had bent to her will. Echoing a common sentiment of late-nineties punditry, James Bennet of the New York Times noted in a 1997 column how “Bill Clinton has Oprah-fied American politics, turning it into a playground for inner children and a forum for feeling pain.”
By any conventional metric she’s a dream candidate. But for someone whose brand is built on their ubiquity, she may only be just that: a dream.
In other words, the political had become personal. And nobody did personal better than Oprah, who had by then gone national, made a fortune through syndication on the advice of her friend Roger Ebert, and established “live your best life” as the self-improvement mantra of a nation of loyal viewers, overwhelmingly women, searching for fulfillment in the relatively bucolic Clinton era.
Hence, in 2000, the exception to the rule: Winfrey invited both Al Gore and George W. Bush on the show to make their respective cases to millions of viewers, under the auspices of revealing “the real man” — allowing said viewers to decide “what feels like the right candidate for you.”
Gore’s appearance was predictably serviceable, but Bush made the real impression, bounding onto the set and planting a kiss on Winfrey’s cheek with impish Texan glee. Winfrey told WBEZ’s White that the gulf in appeal between the two candidates was obvious.
“George Bush was more comfortable in his own skin,” Winfrey said in an interview for the station’s “Making Oprah” podcast series. “That’s what everybody is looking for … who you decide to align yourself with is the person who feels most like the truth to you. Either you feel it or you don’t.”
The rest was history, with Bush narrowly eking out a presidential win — by a margin in Florida much, much smaller than the viewership for an average episode of “The Oprah Winfrey Show.” Most stopped short of ascribing Bush’s win to his appearance, but Oprah’s status as a media kingmaker was now undisputed.
Perhaps feeling sufficiently insulated from controversy, Winfrey made the uncharacteristic decision in the aftermath of the September 11 attacks to air a series of episodes directly tackling what was then the most hot-button issue imaginable — the debate over military intervention in the Middle East. Beginning with an episode titled “Is War the Only Answer?” Winfrey hosted a succession of guests like Thomas Friedman and Lebanese-American Middle East expert Fawaz Gerges, who debated the pros and cons of a potential invasion, with framing that was heavily skeptical of American interventionism, including clips from Michael Moore’s then-controversial “Bowling for Columbine.”
The backlash was swift. Winfrey described in her own O Magazine receiving hate mail that read “Go back to Africa,” and the follow-up to “Is War the Only Answer?” “What Does the World Think of Us?” was delayed until late November of the next year, although episodes on the history of Islam were aired in the interim.
Oprah Winfrey (center) attends a campaign event with Michelle Obama and Barack Obama in Manchester, New Hampshire, on December 9, 2007 | Darren McCollester/Getty Images
Since then, Winfrey has remained tight-lipped on most policy matters, although she was an ardent supporter of Barack Obama in both his 2008 and 2012 presidential bids (and a slightly more lukewarm ally of the 2016 Hillary Clinton campaign). She’s staked out safe liberal ground on topics like guns and immigration, and used her platform to humanize the LGBT community long before it was Democratic dogma, but for the most part avoided the side-taking and claim-staking that comprises much of public life for today’s political figures.
She now primarily serves as a reliable Democratic donor and a fixture of the liberal-philanthropic complex, donating tens of millions through her charity Oprah’s Angel Network. For the most part, she’s laughed off talk of pursuing office — joking that she would have “fallen off her treadmill” if she’d been watching when disgraced former Illinois Governor Rod Blagojevich floated her as a potential Senate appointee on a 2009 episode of “Good Morning America.”
Until, as these stories tend to go, Trump came along. The seemingly impermeable barrier between celebrity and the presidency now breached, rumblings of a 2020 bid by Winfrey started almost immediately, with voices like Michael Moore floating hers and Tom Hanks’ names on CNN just days after the 2016 election as “beloved celebrities” who could take down Trump. At the time, Winfrey didn’t mince words in response, saying unequivocally on the Hollywood Reporter’s “Awards Chatter” podcast that she would “never run for public office.”
But in September came a flip-flop. She noted pointedly during an interview with Bloomberg News that “it’s clear you don’t need government experience to be elected president of the United States,” and that “now [she’s] thinking, ‘Oh.’”
Which leads to this moment, with Winfrey the closest she’s ever been to casting in her lot with the politicians to whom she’s previously served as confessor and kingmaker, a chorus of supportive voices behind her and a fiery stump speech in her back pocket. Universally recognized, near-universally beloved — by any conventional metric she’s a dream candidate. But for someone whose brand is built on their ubiquity, she may only be just that: a dream.
Politics is comprised of moments where one must enter the fray, defending tough choices on drone warfare, taxation and the social safety net; does Oprah have the stomach to start making enemies? For someone whose motto is “live your best life,” the presidency doesn’t exactly sound appealing. Lyndon Johnson described it as “being like a jackass caught in a hailstorm.” Harry Truman said the job was like being “a glorified public relations man who spends his time flattering, kissing, and kicking people to get them to do what they are supposed to do anyway.”
Given her already-massive cultural imprint and the misery of the job, the likeliest case may be that Oprah hears her advisers out and ends up deciding she’s perfectly happy cutting checks, puttering around her estate with Stedman and offering a sympathetic ear to the next Obama-level celebrity seeking a high-profile cable interview.
But if she does run, perhaps it will be because, in the lament of another former president — William Howard Taft — she hears a call to action. “I’ll be damned if I am not getting tired of this,” Taft once reportedly said. “It seems to be the profession of a president simply to hear other people talk.”
Derek Robertson is an intern for POLITICO Magazine.