Oprah In 2020? The Serious Case For President Winfrey

This image released by NBC shows Oprah Winfrey accepting the Cecil B. DeMille Award at the 75th Annual Golden Globe Awards in Beverly Hills, Calif., on Sunday, Jan. 7, 2018. (Paul Drinkwater/NBC via AP)
This image released by NBC shows Oprah Winfrey accepting the Cecil B. DeMille Award at the 75th Annual Golden Globe Awards in Beverly Hills, Calif., on Sunday, Jan. 7, 2018. (Paul Drinkwater/NBC via AP)
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When the Hollywood Foreign Press Association announced that Oprah Winfrey would be receiving the 2018 Cecil B. DeMille Award, most viewers probably expected a regal compilation reel of Oprah’s cinematic journey and a nice speech.

Instead, we got a roof-shaking, blood-boiling and galvanizing call to arms against structural and cultural inequality. We got Oprah with tears in her eyes promising every marginalized American — particularly women -- that things around here are about to change. Big time. It might have been the most conspicuously presidential speech that a Hollywood award show winner has ever delivered on live television.

So let’s talk about that idea: President Oprah.

It actually makes a lot of sense.

The case for Oprah, in a traditional sense, is simple. She’s a highly successful businesswoman who hasn’t forgotten her impoverished roots — the embodiment of the American Dream. (That’s also a potential problem, but we’ll come back to that later.) She’s nationally beloved and has an enormous fan base that would be go berserk if Oprah declared her candidacy. Her forays into the “political” arena make her shoe-in for the Democratic Party, which is not only struggling to cultivate candidates capable of beating Donald Trump in 2020, but is also unlikely to unite behind Bernie Sanders, the only politician who appears capable of beating Trump.

This brings us to the most urgent and practical reason for Oprah to strongly consider running for president, and for likely Democratic voters to imagine how this scenario might play out.

As a candidate, Oprah could squash Trump like a rotten orange.

Think about it. What better way to fight to a man who defies any trace of political decorum than by forcing him to fight another (more popular!) denizen of the entertainment world? What better way for the Democratic Party to inject its base with a mega dose of excitement than by cutting the West Wing cosplaying crap and doing something bold and game-changing like putting Oprah at the top of the 2020 ticket? This idea is so crazy that in times like these, it might just work.

As a candidate, Oprah could squash Trump like a rotten orange.

Of course, like any wildcard strategy, the Oprah option carries considerable risks.

Since the 2016 election, we’ve seen the more Democratic lawmakers listening to frustrated voters and finally beginning to accept that to stay competitive, the party must move to the left on economics, the environment and foreign policy. There’s no empirical reason to assume that Oprah would oppose this leftward evolution, but her story — a literal rags-to-riches tale — does beg reasonable concern at a moment when inequality is turning America into a Dickensian world of haves and have-nots. The trouble with many folks who’ve achieved the American Dream is that they tend to believe in it too dogmatically. And even if Oprah took to the campaign trail and called for a new FDR-style bill of economic rights for every American, her candidacy might also feel unseemly and even dangerous to those who believe (justifiably) that politics in America is a game for the wealthy elites.

And of course, there’s the fact that Oprah has no experience in political office. Not that this has stopped others from becoming president, but for Democratic voters, who tend to fancy themselves as wonks and pragmatists, this would be a concern.

If Oprah were to run, she could assuage skepticism from both pragmatists and progressives by hitching her wagon with an experienced and proven leftist lawmaker like Elizabeth Warren or even Bernie himself. She could gain further credibility and foment progressive populist energy by assembling a team of policy advisors culled from greener pastures than Wall Street and K Street. Her campaign could reach beyond feel-good platitudes and introduce something major and tangible — a new New Deal, for the 21st Century — that voters could not only believe in but also hold President Oprah accountable to fulfilling.

Then, there’s the question of whether Trump will even make it to 2020, and it’s really this question that should determine Oprah’s big decision.

In the event that Trump quits or croaks from a clogged artery — if the man to beat in 2020 is Mike Pence or even Paul Ryan — the Oprah option doesn’t make sense. In that scenario, Democrats could run someone as milquetoast as Jon Tester and likely win. That advantage, if it appears, should be utilized to run a more politically experienced candidate who is essentially a stranger to the world of big money.

But in the likelier event that Trump somehow hangs on, propped up by the Republicans who are grateful to Trump for signing their plutocratic tax bill and wary of being primaried by Trump’s alt-right base (the voters who chose Roy Moore over Luther Strange in the Alabama special election), then the Democratic Party will have to approach 2020 with a resolve to put on a show for the ages.

Oprah knows a thing or two about doing that.


Miles Howard Twitter Cognoscenti contributor
Miles Howard is a freelance writer who covers culture, travel and transformational politics.