Republican presidential candidate Donald Trump
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When Donald Trump announced his plan to run for president in June, few Republican strategists and cable-news media personalities gave him a serious chance to secure the party’s nomination. Many people believed that early missteps, especially controversial statements he made about Mexicans and Sen. John McCain, would sink his campaign before it could really get going. Fast-forward two months, and he continues to lead the GOP field by a wide margin. Recent polls even indicate he would be competitive in a general election matchup against presumptive Democratic nominee Hillary Clinton.

Political pundits have spent a good deal of ink and airtime trying to figure out why Republicans have flocked to Trump. Most conclude that his name recognition, immense wealth and willingness to say things that would doom a more conventional candidate have all resonated with GOP voters. Trump is by far the most famous political outsider vying for a major-party nomination in the last two election cycles. Since 2012, he is one of four Republicans without previous political experience to appear in major national polls.


That got me thinking: Is there someone on the Democratic side who could be Trump’s outsider equal?

Obviously, the candidate would need to have ties to the Democratic Party or a history of supporting progressive causes. The person would also need to be someone so rich, he or she wouldn’t be beholden to special interest groups or big-money donors. Like Trump, this person would also need to be famous enough to draw in the casual voter and have the type of instant name recognition and personal appeal most candidates spend millions to attain. That combination of personal wealth, fame, charisma and outsider status left me thinking about only one person: Oprah Winfrey.

Don’t get me wrong, I’m not saying Oprah should run for president. She’s just the only person I believe who could match Trump’s unique set of qualifications on the Democratic side. She’s the first black female billionaire in history, and her rags-to-riches life story would inspire many casual voters. She’s also one of the most famous people in the world, and the trust she’s built with her audience over decades helps her influence public opinion and consumer choices on everything from books to spirituality. In fact, Trump himself seemed to recognize Oprah’s political potential when he recently said she would make a good running mate.

What would a Winfrey-for-president campaign look like? It’s hard to say for sure, but I assume that her personal views, philanthropic endeavors and business dealings reveal something about Oprah’s passions and priorities. I could easily see Oprah delivering campaign speeches on closing the gender pay gap or expanding legal protections for the lesbian, gay, bisexual and transgender community. I could also see her being a passionate advocate for urban-education reform in the U.S., as well as having a foreign policy focus on countries where girls and women are denied equal access to education and economic opportunity.


OK, back to reality.

Thinking about Oprah as a presidential candidate makes for a lighthearted game of “what if,” but true outsider candidates have never come close to winning the presidency. Every single U.S. president has had a record of public service, either through elected office or military service.


Aside from Trump, the current crop of Republican nominees for 2016 also includes former CEO of Hewlett-Packard Co. Carly Fiorina and former world-renowned neurosurgeon Ben Carson. While they both trail Trump by significant margins in the polls, all three have used their outsider status to tap into voter frustration with career politicians. This phenomenon isn’t new. Herman Cain led Mitt Romney by 8 points in a major national poll in October 2011. By year’s end, however, Cain’s lack of depth on foreign policy issues and allegations of sexual misconduct and extramarital affairs effectively sank his campaign.

Politicians receive a great deal of criticism from the public, and much of it is well-deserved. That said, running for and winning elected office is something that requires specific personality traits and professional experiences. One advantage that individuals who’ve held elected office have is an actual record reflecting their personal and political views that can be used to appeal to prospective voters and party leaders. Those new to politics typically lack that ability.


Some people have made the transition from outsider to elected official on the local level by parlaying success in business, sports or entertainment into political success as mayors, governors and senators. Running for president is something totally different. You can play on the anger and fear of voters for a while, but eventually your lack of substance and inability to communicate a vision that appeals to a broad coalition of voters will hurt you.

Basically, you can’t win your party’s nomination—let alone become president—if your best quality is a willingness to say crazy things. This is something Cain, Carson and Trump have had to learn. Unfortunately, unless she runs for president one day, we’ll never know how the “Queen of All Media” would do on the national stage.


Delano Squires is the creator of Truth, No Chaser, where he explores the intersections of race, politics, faith, culture and relationships. Follow him on Twitter