5 Outsiders Most Likely to Run for President in 2020—And Their Chances of Winning

America is on the cusp of the permanent celebritization of politics

Like clockwork, every four years Americans have come to expect that a diverse coterie of aspiring presidential candidates will throw their hats in the proverbial ring in the hopes of becoming the nation’s next President. Since 1992, with Ross Perot’s high-profile presidential bid, every four years the media begins speculating about potential “outsiders” from the business world or Hollywood that might enter the race and upend the political landscape. In 2016, speculation turned to reality in the form of Donald J. Trump, an outsider as much from the world of business as he is a product of Hollywood. Although polls indicate that America’s first bold experiment with a political outsider in the White House hasn’t gotten off to a great start, Trump’s election has finally put to rest the debate about whether political outsiders can actually win an election for America’s highest office.

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Many members of the political establishment, like Congressman Ro Khanna, believe that Trump’s initial missteps may have ruined it for future celebrity presidential candidates. They reason that America will want its next president to be the exact opposite of Trump: an established politician with a long and distinguished career of public service. “Folks will turn to someone with a record of service and depth on the substance,” observed Khanna.

While the current polls may sound the alarm against an outsider, Bradley Tusk, a former Illinois deputy governor, political aide to New York City Mayor Mike Bloomberg and now consultant to a host of prominent Silicon Valley companies, doesn’t see it that way at all. “Trump’s historic implosion doesn’t make the voters like Democrats more,” remarked Tusk. “It just makes them want change more.”

For America’s political class, the controversies and political divisiveness of the Trump presidency should not be misinterpreted as a call for a return of the traditional politician; the election of ‘the Donald’ has already emboldened an increasing number of media and business superstars to think about seeking the Oval Office in 2020. America is about to enter an era that will come to be known as the “Permanent Celebritization of Politics”—a trend that will shake up the political establishment like never before.

Although Trump—or Pence, depending how the cookie crumbles—might face a stiff primary challenge in 2020, America should brace itself for another race with at least one brand-name political outsider running as a Democrat or, particularly if they are self-funding, as an independent candidate. Here are five potential business and celebrity candidates who might be running in 2020:

#5 Mark Zuckerberg

Net Worth: $63 Billion

Claim to Fame: Co-Founder and CEO, Facebook

It’s no secret that Mark Zuckerberg has been looking for a new gig. Despite open denials that he harbors political aspirations, the mere fact that the Facebook billionaire has been devoting a lot of time and energy into crisscrossing the country, engaging on a “listening tour” with disaffected voters, and posting his experiences on his Facebook page has left ample room for speculation about his end-game. The New York Times’ Mike Isaac wrote “Mr. Zuckerberg’s road trip … has taken on the trappings of a political campaign. His every pit stop—eating with a farming family in Ohio; feeding a baby calf at a farm in Wisconsin—has been artfully photographed and managed, and then posted to Mr. Zuckerberg’s Facebook page.” Perhaps even more telling is Zuckerberg’s recent Harvard commencement address, which had a definite political ring to it.

As a candidate, Zuckerberg’s immense wealth would be a tremendous advantage, but it would be far from his only one. “The amount of reach, intelligence and insights that candidate Zuckerberg would have access to via Facebook would be without precedent,” said Oz Sultan, a big data strategist and former Trump campaign surrogate. “It would give him an advantage that would be hard to counter and that would be before he even spends a dollar on the campaign. He would pose a formidable challenge to Trump on the trail.”

The power of the Facebook platform as a political tool is not at all lost on its wunderkind founder. “In recent campaigns around the world—from India and Indonesia across Europe to the United States—we’ve seen the candidate with the largest and most engaged following on Facebook usually wins,” Zuckerberg wrote in a recent Facebook post.

And then there’s the famous carve-out in Zuckerberg’s deal with Facebook, in which it is explicitly stated in Facebook’s bylaws that he will be allowed to retain control of the company should he serve at any level of government. Although a Zuckerberg run might still be unlikely in 2020 (by then he will just barely meet the Constitution’s minimum age requirement of 35), it’s a name to watch in the future.

Probability of Running: Low (in 2020)

Probability of Winning: Medium

#4 Oprah Winfrey

Net Worth: $3.1 Billion

Claim to Fame: Talk Show Host and Media Mogul

Although she has a surname, the woman the world knows simply as “Oprah” is another outsider often bandied about as a contender for the White House in 2020. For a woman who needs no introduction, the idea of an “Oprah Winfrey for President” campaign would certainly shake up the race no matter who else is in it.

Winfrey has been a fixture in American living rooms since 1986 when The Oprah Winfrey Show began its national syndication run. Of all the potential candidates—including both outsiders and traditional politicians—Winfrey is the one candidate able to connect with a vast cross-section of the country and has already effectively won the hearts and minds of Americans. To a generation of voters, she is the conscience of America.

“From the Bronx to Youngstown to La Jolla, everyone trusts Oprah,” says Patrick McKenna, a Silicon Valley entrepreneur and political organizer. “Oprah has the advantage of instant name and face recognition as well as very high likability. Once she announces she is seeking the presidency, she could immediately dive into her proposed policies and solutions for the heart-aches of the country,” continued McKenna.

In a conversation with billionaire David Rubenstein on Bloomberg’s The David Rubenstein Show: Peer-to-Peer Conversations shortly after Trump was elected, Winfrey seemed to dance around the issue of her running in 2020, forgoing the standard “Never!” that she had regularly delivered prior to Trump’s unexpected victory.

Although she could certainly self-fund, why would she? Oprah is a one-woman marketing juggernaut and with the slew of endorsements she would get from everyone from Beyoncé to the Obamas, she could easily break all previous presidential campaign fundraising records. Her campaign materials would become required reading for book clubs across the country.

As a female candidate, almost universally admired, one could expect to see the “first female president” movement broadly coalesce around Winfrey in a way that never really happened with Hillary Clinton. Winfrey’s celebrity and familiarity would catapult her beyond the traditional trenches of racial identity politics in America to garner universal support from men and women of all ages and backgrounds. She could build a truly diverse coalition that goes beyond party.

Although an Oprah for President run is still highly improbable, were she to enter the race, she would almost immediately be considered the front-runner.

Probability of Running: Low

Probability of Winning: High

#3 Dwayne Johnson (aka “The Rock”)

Net Worth: $185 Million

Claim to Fame: Hollywood’s Go-To Action Hero

“Johnson is the juggernaut to watch in 2020. His star power is only exceeded by his brilliant smile and bulge in his biceps,” remarked CNN and Fox News commentator and West Coast Talk Radio Host Ethan Bearman. “Football champ, wrestling icon, hollywood box office hero—it seems that the presidency is in his destiny. I know people across the political spectrum who’d love to vote for The Rock.’”

It may have started off as something of a joke, but more and more, Dwayne “The Rock” Johnson seems to be moving towards a presidential run in 2020. “The man has so much charisma and ambition he can do anything,” wrote Caity Weaver in a recent GQ profile.

Like a steady drum beat, the talk of a Johnson presidential bid has been building for the better part of a year—even before Trump was elected. Weaver writes, “So, after all that consideration, Johnson doesn’t hesitate when I ask him whether he honestly might one day give up his life as the highest-paid movie star on earth—which is unquestionably easier, more fun, and more lucrative than being president of the United States—in order to run for office. ‘I think that it’s a real possibility,’ he says solemnly.”

So far, it’s been mostly more fun speculation than serious political planning. Johnson has often used his frequent SNL hosting gigs to satire his own political aspirations, most recently on the 2017 season finale in which he jokingly announced his candidacy alongside his supposed running mate, Tom Hanks.

Johnson is a registered independent, but that doesn’t mean he would necessarily run as one.

“The Democrats would love to have Johnson on their team, but the DNC wouldn’t just hand the nomination to him; however, if he studies the issues and ends up holding his own on the debate stage with the Elizabeth Warrens and Corey Bookers of the world, he could actually emerge as the Democratic front-runner,” added Bearman.

As for a campaign slogan, the possibilities are endless, but “Vote The Rock” already seems to be gaining steam on social media. He certainly knows how to battle on a live stage and put on a good show. While Tom Hanks will not be his real-life running mate, The Rock, paired with a running mate with some political gravitas, would be a formidable force.

Probability of Running: Medium

Probability of Winning: Medium

#2 Howard Schultz

Net Worth: $3.3 Billion

Claim to Fame: Founder and Executive Chairman, Starbucks

Howard Schultz is the undisputed king of the five-dollar cup of coffee, yet his recent move to step back from running the day-to-day operations of Starbucks was seen by many as an indication of bigger plans. As he mentioned in his last annual meeting in March, he aims to concentrate on issues such as, “’rising nationalism’, the need for ‘shared values’ and a call to build ‘a great and enduring America.’” Talk like that from a retiring CEO of a major U.S. company—particularly one with such massive retail penetration as Starbucks—will almost certainly get the media to speculate that you are considering making a run for political office.

“Howard Schultz has not to date demonstrated enough political prescience; he and Starbucks have made a few unforced errors,” said independent political consultant Bill Hillsman, the engineer behind outsider Minnesota Governor Jesse Ventura’s election. “But Mr. Schultz’s motivations all stem from a good heart and a genuine desire to help people, and that’s a great starting point. He’s not afraid of big ideas. He went to college in Michigan’s Upper Peninsula—so we know he’s plenty tough enough—and he has a helluva personal story to tell.”

Schultz has been contemplating a future in politics for quite a while. He has been known to call up his friend Mike Bloomberg and talk about the transition from business to government. Like Bloomberg did in 2001 in his first mayoral race, Schultz will have to spend a lot of money and time introducing himself to Americans; the man behind the Starbucks empire is a relative unknown across large swaths of the country. Unlike Bloomberg, who initially struggled to get a knack for the impromptu stump speech, those who know Schultz personally compare his raw communications skills and ability to connect with “average Joes” to be more Bill Clinton-esque than stuffy boardroom type.

“Schultz would not start out as a top contender, but his potential upside is formidable. And working hard to earn his success has always been a part of his makeup. That’s attractive to most voters,” added Hillsman. Although a Schultz run is much more likely than several other names on this list, he will also have the steepest hill to climb.

Probability of Running: High

Probability of Winning: Medium

#1 Mark Cuban

Net Worth: $3.4 Billion

Claim to Fame: Entrepreneur, Investor and Owner, Dallas Mavericks

Of all the names of outsiders on this list, the one that comes up most regularly is that of Mark Cuban, the internet pioneer, billionaire, Shark Tank personality, and outspoken owner of the Dallas Mavericks NBA franchise. Although Cuban has been an ally of Trump at times, recently he has been a very vocal critic, often sparring with Trump on Twitter. Now it appears he is serious about a potential presidential bid of his own in 2020. “We will see,” Cuban told Business Insider when he was asked if he would run for president.

Even if Cuban is still undecided, the White House is not; Steve Bannon has purportedly already placed Cuban on a short-list of potential 2020 foes, alongside names like New York Gov. Andrew Cuomo and Colorado Gov. John Hickenlooper, according to the New York Post, which added that “…the White House’s ‘biggest fear’ is that Cuban, a billionaire businessman, would run because he can appeal to Republicans and independents.”

Like Trump, Cuban found success early in life, but has also become more and more recognizable due to his success on reality television. He also has experience on the campaign trail; he was a frequent surrogate for Democratic presidential candidate Hillary Clinton throughout 2016.

Perhaps most telling is that Cuban has apparently broached the idea of his running with his family. “We discussed how much of a threat I believe Trump to be,” said Cuban according to a Business Insider story. “We discussed why it was important to me to get involved—that if I could have an impact and didn’t try, it would have left me guessing forever.”

“Of all the political outsiders on the list, Cuban is one that would have smart money betting on him running in 2020 and one that also carries an incredible relevant connection to the leadership of our generation,” said Sergio Fernandez de Córdova, the chairman of PVBLIC and a global political activist. “No other ‘non-political’ has been so outspoken about his or her plan as Cuban.”

Probability of Running: High

Probability of Winning: Medium

Two popular outsider names that are definitely not in 2020 are Mike Bloomberg and Elon Musk.

Although not technically an outsider, it is tempting to suggest that Michael Bloomberg, who has eschewed both parties in recent years and has self-funded all three of his campaigns for mayor of New York, might have it in him to make another presidential run. A billionaire some 45 times over with 12 years of experience running America’s largest and most complex city is a powerful combination, but for Bloomberg, who will be 78 years-old on election day in 2020, the opportunity to run may have most likely come and gone. “I can’t see a scenario in any way, shape or form where Mike runs,” said Tusk, who ran Bloomberg’s 2009 mayoral campaign. “But a highly credible independent who can be free of donors and special interests and bring new ideas to the system could be very appealing—someone like Mark Cuban or Howard Schultz. It just won’t be Mike.”

The idea of the guy behind Tesla, Space X, and hundreds of other bold ideas running for president might make for a media-friendly story-arc, but barring a constitutional amendment, Musk is ineligible from running (he was born in South Africa to a Canadian mother and South African father).

America is only five months into a Trump’s presidency, but already there is ample talk about 2020, a race that might be not only upended by one of these powerful outsider candidates, but a point in history that marks beginning of the permanent ‘celebritization’ of presidential politics. Washington insiders often quip that “politics is show business for ugly people.” Presidential politics is about to get a lot more Hollywood and a lot less ugly.

Arick Wierson is a former political and communications adviser to New York City Michael Bloomberg where he was responsible for managing the City’s multiple television, radio and digital platforms. Currently, Wierson is a political and branding consultant to the Government of Angola, advising the country’s efforts to attract foreign investment and promote trade.

Richard Hecker is the CEO of Traction + Scale, an investment holding company that builds companies transform their industries. He is also the co-founder of SeedingX.org. You can follow him on twitter @RichieBlueEyes

5 Outsiders Most Likely to Run for President in 2020—And Their Chances of Winning