Political Betting: Will Oprah Winfrey Run for President?

by Taylor Smith
on January 17, 2018

The entire political landscape of the United States was turned onto its head on the night of November 8, 2016, when Donald Trump shockingly defeated Hillary Clinton in the presidential election. Rather than electing a career politician that has been building up to this job for years, America elected a billionaire reality TV star with zero prior political experience.

While the economy has continued its upward trend under Trump’s reign, the first year of his presidency has been marred by countless distractions. Numerous White House staffers and members of his cabinet didn’t even make it through a year. Trump has caused several other firestorms, most of which stem from his obsessive, relentless use of Twitter. There’s also the whole, uh, racism thing.

Trump’s approval ratings have been consistently hovering between 33 and 38 percent, which is, frankly, dreadful. There’s no telling where his popularity will be once campaigns for the 2020 election begin to ramp up, but the first year of his term indicates that there will be no shortage of opposition emerging.

At the Golden Globes in early January, Oprah Winfrey stirred the crowd with a rousing speech as she was awarded the Cecil B. DeMille Award for “outstanding contributions to the world of entertainment.” The inspirational tone of the speech clearly struck a chord with people, as things like #Oprah2020 immediately began trending on social media.

Considering the U.S. just elected a billionaire TV star in 2016, could it make sense for the Democratic Party to try and fight fire with fire using Oprah? Let’s break it down.

Betting Odds

The election is still three years away, but it’s never too early to start trying to project the field. It’s early, and we obviously don’t know who is actually going to enter the race. Any betting odds at this point are purely speculative. With all of those disclaimers out of the way, let’s take a look at some early odds on who will win the 2020 election.

  • Donald Trump +225
  • Oprah Winfrey +1000
  • Mike Pence +1400
  • Kamala Harris +1400
  • Bernie Sanders +1600
  • Joe Biden +1600

The full list is much longer, but these are the 6 people with the best odds to win. Prior to her speech, Winfrey was priced at +10000. Now, she’s got the second-best odds at +1000. That’s quite the leap.

Now that Trump is president, Winfrey is the only person without political experience among those 6 names.

Would Oprah Actually Run?

Of course, Oprah would actually have to enter the race in order to be elected president. Not 12 hours after Oprah’s speech ended, CNN’s Brian Stelter reported that sources close to Winfrey have said that Oprah is “actively thinking” about running for president in 2020.

Thinking about running is obviously different from actually going through with it. We hear all the time about people that consider running but ultimately decide against doing so. Former Vice President Joe Biden has admitted that he regrets his decision against running against Trump in ‘16, for example.

CNN’s report says that some close to Winfrey have been privately “urging” her to enter the race during the next election cycle. The conversations reportedly date back several months, so it isn’t as though Oprah just got the idea as a result of the reaction to her aforementioned speech. She still hasn’t made up her mind one way or the other.

It’s going to be a little while before we see candidates throw their respective hats into the ring. The campaign for president won’t begin in earnest until the 2018 midterm elections this November. That said, some Democrats potentially interested in challenging Trump have already started making trips to Iowa in an attempt to jump-start some momentum for the party.

Winfrey’s partner, Stedman Graham, told the Los Angeles Times after the speech, “ [Oprah] would absolutely do it. It’s up to the people.” Hmm.

While Winfrey has not held publicly elected political office herself, she has been active in politics. She campaigned for Barack Obama during his initial run for president in 2008 and endorsed Clinton in 2016. In endorsing Clinton, Winfrey said that “it’s time” for the United States to have a female president.

Considering Clinton came up short in that endeavor, it does make sense to assume that Winfrey would have some interest in trying to do so herself. Winfrey has publicly said in the past that she has no plans to run for office, but things change. If Oprah believes that she is capable of taking down Trump, one would imagine she’ll give it a shot.

Could She Win?

Donald Trump was not supposed to win the 2016 election. Hell, Donald Trump didn’t even think Donald Trump was going to win. Trump had toyed with the notion of running for president on numerous occasions in the past, and once he actually announced his candidacy in the summer of 2015, most pundits and the like laughed it off. Quite literally.

Nobody’s laughing now, are they? Celebrities entering the world of politics is nothing new. We’ve seen the likes of wrestler Jesse Ventura and comedian Al Franken successfully enter the political realm in the past. Ronald Reagan was an actor and a sports broadcaster before becoming governor of California and, eventually, president of the United States.

The notion that a celebrity with zero political experience could just run on a whim and win the presidency may have been laughable before, but now we know it’s doable. If Oprah does decide to run for the Democratic Party’s nomination, we have every reason to believe she’s capable of winning. If Donald Trump can get elected president, anyone can.

It will be fascinating to see what kind of effect Trump has had on the electorate moving forward. Perhaps more than ever, likability is now a hugely important trait for a candidate. Trump is obviously loathed by many, but those that voted for him often cited his unfiltered style as a favorable personality trait. They contended that his “tell it like it is” attitude showed that he’s honest.

Voters obviously want their elected officials to be honest, and that was a box Clinton struggled to check in ‘16. Trump comes up with catchy nicknames for all of his political rivals, most of which are, frankly, silly and immature. That said, his “Crooked Hillary” jab clearly stuck, and many voters were unable to overlook whatever baggage Clinton was dragging along during the campaign.

Clinton’s perceived lack of likability dogged her all the way into election night, and it’s what may have ultimately kept her out of the Oval Office.

Potential Holdups

The most noteworthy red flag regarding Winfrey’s potential candidacy would be her obvious lack of experience. Again, the American voters told us in the most recent election that experience isn’t necessary. Is Trump’s tumultuous tenure going to be enough to give voters pause on that notion next time around? Or is that the way it’s going to be moving forward?

Oprah has plenty of jobs keeping her busy as of now. She is the CEO of her own cable company (OWN), a correspondent on “60 Minutes” and she’s also an investor in companies like Weight Watchers. The “60 Minutes” gig could prove to be conflicting if she does one, but you’d have to believe she’ll resign that post if she decides to seek political office. She could also leave her position at OWN, even though her current contract runs through 2025.

Clinton was a flawed candidate, but for different reasons. Clinton had plenty of political experience, but a number of controversies ultimately caught up to her. “Opposition research” may dig up something on Winfrey if she elects to run, but, as of now, she doesn’t come with nearly the number of detractors Clinton did.

It’s too early to say whether Oprah will actually run when the time comes. At this point, electing a second consecutive television celebrity president is probably not what the majority of Americans would prefer. Sure, it’s fun to imagine Oprah debating Trump, etc., but at some point, it’s apparent that previous experience should matter.

Winfrey makes for an excellent value bet to win the 2020 presidency at +1000 as of now.

If she announces her plans to run later in 2018 or in early 2019, the profit potential will obviously be slashed. She’s worth a flier bet if you’re feeling frisky, but the smartest course of action is probably to wait and see how things unfold over the next year.

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