Could Donald Trump’s Success Mean More Wealthy Celebrity Presidential Candidates?


There’s no doubt that President-Elect Donald Trump’s celebrity and business success helped him stand out with voters who wanted something new in the 2016 election, but a major side-effect of his victory may well be that non-establishment types have a better shot at being taken seriously if they run for office. Whether that’s a positive or negative development remains to be seen, but for now, we decided to take a far-too-early look at a few celebrities and billionaires that might be a fit for 2020 or beyond.

Jon Stewart

Stewart seemingly quit The Daily Show because he had given enough of his soul to commenting on the political process so it’s hard to imagine that he’d want to hand over the rest of it by opening himself up to the effects of actually running for office or living through the arduous process of running the country. Still, the Rally To Restore Sanity And/Or Fear proves that Stewart can throw a good campaign event and that, along with his work for 9/11 first responders, shows that he has experience blurring the line between entertainer and activist.

Stewart will forever live in the hearts and minds of Gen Xers and senior Millennials as a voice of reason, authority, and hope for a bullsh*t free tomorrow — so there is built-in support. The question is, can that support overcome those that completely distrust liberal elites in the media? This election was many things and a repudiation of establishment media was high on the list. Stewart might be the antithesis of Trump (save for their shared affection for the WWE), but that might not be as much of an asset as it seems in this highly charged moment. – Jason Tabrys

Warren Buffett

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If we’re going to elect a Beltway outsider again based on his business experience, it might as well be the original billionaire himself, Warren Buffett. Buffett turned a textile firm into one of the greatest investment companies in the world, Berkshire Hathaway and might well be the single most successful capitalist in the history of the ideology. But he’s also been sharply critical of Wall Street, making him uniquely suited to deal with the economy and appealing to both sides of the aisle, and is a noted philanthropist. And since he lives off his salary from Hathaway and his outside investments, and is famously frugal, he can easily deal with the pay cut being president involves. – Dan Seitz

Kanye West

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Few are as ambitious or as accomplished when it comes to building up a brand and few understand and appreciate the power of celebrity and keeping it startlingly real like Kanye West. Add his social media IQ and reach (and that of his wife, Kim Kardashian) and you really have a younger (better, faster, stronger…) version of Donald Trump. And with West’s built-in following among teens and people in their twenties (and beyond, of course) whose interests extend past his music and into his thoughts on fashion and his overall philosophy, maybe we should all take Yeezy’s talk about running for president in 2020 for real.

“My Life Is Dope And I Do Dope Sh*t” would look pretty great on a red hat, no? – Jason Tabrys

Bill Gates

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Gates is arguably one of the best-equipped billionaires to take over the White House. After years running Microsoft, he retired and used his fortune to found the Bill and Melinda Gates Foundation. The BMGF is far more than just a rich man’s fancy, though: It’s the largest transparently operated charitable foundation in the world. Gates has spent billions fighting malaria, HIV, and tuberculosis, and has gone around the world working on projects to assist with extreme poverty and public health. He’s also invested billions to support businesses in the developing world. And since he’s familiar with computers, we’ll never have to hear about email servers ever again. – Dan Seitz

Charlie Sheen


Stop laughing. Donald Trump shattered years of precedent that said that candidates were doomed if they encountered allegations of sexual impropriety or offended large segments of the public with verbal gaffes. Charlie Sheen’s disqualifying past in both of those areas (and beyond) are seemingly disqualifying no more and the former Hot Shots star loves a publicity stunt.

Besides, Sheen’s already played the president before (Machete Kills) and his father, Martin, is our greatest fictional commander in chief (The West Wing), so it’s not like he doesn’t know the ins and the outs of the job. – Jason Tabrys

Jeff Bezos

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Bezos is best known for founding and running Amazon and owning the Washington Post, but he’s also been spending his fortune trying to push humanity into space. He recovered the original rocket engines from the Apollo moon mission and his company, Blue Origin, has been working with both NASA and the military for years to develop sub-orbital flight as a building block to exploring the stars. As a result, he’s got plenty of experience dealing with government, and besides, he runs a company that can get you a novelty pet costume, your groceries, and an obscure DVD to your house all on the same day. – Dan Seitz


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Like Stewart, Oprah is a left-leaning media star thanks to her iconic talk show, cable network, and magazine, but she’s less divisive in that her primary arena isn’t particularly political. That’s not to say that Oprah isn’t vocal about progressive causes, but she’s more known as a powerful tastemaker and the embodiment of celebrity worship culture. So basically, an old media Kanye (even though Oprah also has impressive social media reach), but Oprah’s popularity is somewhat centered on the maintenance of an aspirational middle-aged/upper middle-class lifestyle brand and the products that reinforce it, so there might be a relevancy gap with young voters and blue collar workers were she to run. – Jason Tabrys

Mark Zuckerberg

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Though Facebook is facing criticism for the spread of baseless news stories during the election, Zuckerberg has some points in his favor for his efforts to focus on curing disease with the billions he’s made from the social media giant and your addiction to Farmville. Still, it’s easy to envision town hall debates being a bit of a problem, especially when people come to complain about how their Facebook wall is laid out. If Zuck ever runs, it might mark the first time web design is a campaign issue. – Dan Seitz

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