The cases for and against Oprah as the Democratic nominee are substantially similar: She’s a charismatic billionaire who has never run for office but has an enormous national profile and seems (though who knows) generally amenable to the party platform. Of course, it’s helpful that she’s a black woman in a party that depends heavily on African American and female voters, meaning she could be at once the Democratic Trump and also an anti-Trump.
The excitement, however fleeting, about an Oprah candidacy is a sign of the despair within some elements of the party. In 2016, Democrats nominated a deeply experienced person with a granular hold on policy. Everyone knows how that turned out. With a packed-but-shallow bench ahead of the 2020 election, it’s easy to see why some Democrats might be tempted by the siren song of a Democratic Trump. Though one cannot imagine Donald “What the Hell Do You Have to Lose?” Trump giving a speech about Recy Taylor, he and Winfrey have substantial similarities. Both floated around the edges of politics for years and were asked repeatedly about running, and neither has any experience in public office. Winfrey has her own corporate turnaround to brag about, just like Trump. Both have been known to brag ostentatiously about owning their own planes. (“It is really fantastic to have your own jet, and anybody who says it isn't is lying to you. That jet thing is really good,” Winfrey said at my college commencement. I am not making this up.)
The anti-Oprah faction is, if anything, even more despairing. A Democratic Trump? How can anyone hope for that, given today’s gridlock on domestic affairs, chaos on the international stage, and spectacle of the president’s own staffers ridiculing him to the press and treating him like a child? These all spring from Trump’s manifest unpreparedness and lack of interest in what it takes to govern. Any time John Podhoretz and Bill Kristol agree on something, progressives are likely best advised to head in the opposite direction. It seems preposterous for Democrats to respond to this by nominating an inexperienced mogul of their own.
Strangely enough, an Oprah candidacy might be the one thing that could heal the still-festering divide over the 2016 Democratic primary, uniting Hillary Clinton supporters appalled by Winfrey’s lack of expertise and dues-paying, and Bernie Sanders backers appalled by Winfrey’s neoliberalism. (The only Marx Winfrey gets anywhere near is Harpo.)
The cleavage here is partly a familiar divide between whether it’s more important to win elections or to govern once they’re over, but it’s also about what attack Democrats should use on Trump in 2020. Is the president an unhinged wild man, an utter anomaly? Or is he actually the worst possible Republican—a particularly extreme example of all the impulses Democrats have attributed to the GOP for decades? This debate plays out when some Democratic members of Congress talk about impeachment or 25th Amendment remedies, while others focus instead on how the benefits of the Republican tax plan flow to the wealthy and big corporations. Although Democrats as a whole will likely try some combination of the two attacks, these options are largely mutually exclusive: Either the president is different in type or he is different in degree.