And the next celebrity billionaire president may be ...

Hey, it could be worse. It could be Michael Bloomberg. After NY Post columnist John Podhoretz picked Oprah Winfrey as the Democrats’ best hope in 2020 for winning back the White House, the multimedia tycoon sent a personal note of thanks on Twitter for his, er, “vote” of confidence:

Before we get to J-Pod’s arguments in his essay, we have to ask: was Oprah serious in this tweet? It looks like she had her tongue firmly planted in her cheek, but the Washington Post’s Aaron Blake isn’t so sure. It’s not the first time that she’s raised the question, most recently in an interview with Bloomberg’s David Rubenstein, Blake notes, which gives the impression that Winfrey has it on her mind to some extent:

I don’t know if Oprah Winfrey is actually thinking about running for president in 2020. I do know that she really seems to want us to talk about it. …

Thursday night’s tweet is jokey enough — “VOTE of confidence!” — that it could perhaps be dismissed as another meaningless bit of Twitter banter. Maybe King or Winfrey will tell us exactly that in the hours or days ahead.

But Winfrey is such a savvy communicator — perhaps even the savviest of communicators — that she had to know what her tweet Thursday night would set off. And that’s especially given what happened back in March. Maybe she’s apprehensive about running and often thinks she won’t, and then it crosses her mind again. (People have been known to change their mind about such things — most notably Barack Obama, whom Winfrey endorsed back in 2008.) She may not want the full scrutiny of saying “I’m thinking about it,” but wants to stay in the conversation. That would be understandable.

Regardless of whether Oprah takes it seriously or not, John certainly did in his NY Post column. While noting that American politics have gone “through the looking glass” into celebrity and id-venting, John writes that Oprah has both the political and personal chops to leverage her celebrity and wealth against an incumbent who, well, trumped the establishment with both in 2016:

On Sunday night’s “60 Minutes,” a panel of Michigan voters spent 20 minutes discussing their political differences on screen. It was a moving segment and a powerful one, but it wasn’t all that novel if you’ve been paying attention to the political divide over the past year. The power came not really from what the panelists were saying but who the moderator was: Oprah Winfrey.

Listening, asking, speaking without judgment, trying to find common ground — it was a superb performance by Oprah, and I use the word “performance” advisedly. She was dazzling in exactly the way that Oprah could always be dazzling, finding a tone appropriate for the moment without being heavy-handed.

If any figure in the United States bears watching over the next couple of years as our political culture continues the radical transformation that led to the election of Donald Trump, it’s Oprah. I believe she’s uniquely positioned, should she wish to commit herself, to seek the Democratic nomination for president and challenge Trump in 2020.

It will take a celebrity to beat a celebrity, John argues, and Oprah’s uniquely positioned to take on Trump:

She is the mirror image of Trump, but more so. Of course, she’s female and he’s male; she’s America’s generous aunt and he’s America’s crazy uncle. And yes, she’s black and he’s white, she’s liberal and he’s whatever he is.

It goes beyond that. He’s rich and she’s rich, but she made her $3 billion herself and with no controversy. She is, in herself, the embodiment of the American Dream. He got famous from TV, and so did she, but she became vastly more famous and vastly more successful at it.

It’s a serious and compelling argument, but it’s not quite convincing. This calculus assumes the status quo of 2016, which may not hold in 2020. Trump was an anomaly in an electorate demanding disruption and change, which Trump’s qualities (and even his brand of celebrity) fit almost perfectly. By 2020, though, either Trump will have succeeded in making this celebrity-disruptor model work effectively, or he won’t. If he succeeds, he’ll get re-elected. If he fails, voters won’t want another four years of chaos — they’ll be looking for a traditional candidate to restore normalcy.

Besides, Winfrey would be 66 years old in 2020, part of an aging Baby Boomer generation — in fact, a woman who helped define the Baby Boomer generation. There may not be enough Boomers left to get another of their cohort across the finish line, and her new gig at 60 Minutes isn’t going to make Oprah any more trendy with millennials. Had she run in 2016, she may well have won — but then again, that’s true of nearly anyone from the Democratic Party not named Hillary Clinton or Bernie Sanders.

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