Photos via Flickr (Eric Bridiers / JD Lasica)

2020 Preview: Could One of These Wild Cards Jumble the Field?


More Democrats have announced bids for president in 2020, with Sen. Kirsten Gillibrand of New York, former HUD Secretary Julian Castro, and Rep. Tulsi Gabbard of Hawaii joining the fray. In the first three parts of our 2020 preview series, we looked at the front runners, middle-tier, and bottom-of-the-barrel candidates. Today we’re looking at the outsiders and wild cards who could shake everything up if they decide to run.

Tom Steyer — the billionaire hedge fund manager who has spent millions of his own dollars funding Democrat candidates and running ads urging the impeachment of President Trump — would have been on this list, but he recently announced he will not be entering the race.

Howard Schultz

The former CEO of Starbucks, Schultz oversaw a massive expansion of the coffee chain. He also helped turn it into a liberal icon, attaching the chain’s name to every hot new leftist cause from same-sex marriage to gun control. He has become increasingly involved in politics and recently stepped down from Starbucks, fueling speculation that he is preparing a presidential bid.

Early prognosis: Schultz would be another billionaire itching to take on Trump, and his history at a hedge fund would agitate many voters who have spent years railing against the one percent. But billionaires can buy credibility, and thus he would garner real attention. He could position himself as the Democrat version of Trump — the outsider candidate with no political experience who changes everything.

John Kerry

Kerry has been in the public eye for decades, beginning with his involvement in Vietnam Veterans Against the War. After being elected lieutenant governor of Massachusetts in 1982, he successfully ran for U.S. Senate in 1984. In 2004, he won the Democrat nomination for president but lost to President George W. Bush in a general election campaign focused on the Iraq War. He returned to the Senate and declined to run again in 2008. In 2013, President Barack Obama appointed him to succeed Hillary Clinton as Secretary of State.

After 2016, Kerry seemed to be done in public life until saying last November that he was thinking about running in 2020. He would be yet another Democrat candidate who would break the record for oldest president on election day at 76 years old.

Early prognosis: Kerry would be a well-known commodity to Democrat voters, but the impact of his entry would be hard to gauge. Most early polling has not even asked about him. His most natural constituency is the same as Joe Biden’s — people who aren’t paying attention and gravitate to the most familiar name. If he jumped in, it would not be surprising if he became an immediate front runner in the polls.

Mark Cuban

This is probably the longest shot of all. The billionaire sports and reality TV figure is popular and well-known, and Cuban has publicly flirted with the idea of running for president in the past — though he isn’t quite sure which party he belongs in. He is pro-abortion but at least somewhat fiscally conservative, and he has been a frequent critic of Trump but doesn’t identify as a Democrat. If he decided to run, it would probably be as an independent.

Early prognosis: Cuban is likable and, like every other billionaire who wants to run for president, could easily buy credibility in the race. But he seems unlikely to run as a Democrat. He could become a Ross Perot type of candidate who pulls votes away from both sides.

Oprah Winfrey

Sure, I’ll mention her here because she’s been talked about so much, but Oprah running for president seems to be a fantasy at this point. She’s certainly taken a higher profile in liberal politics, supporting Democrats around the country. But she has repeatedly declined to run for president, not wanting to give up her empire as one of the most well-liked personalities in America to expose herself to the messiness of a presidential race.

Early prognosis: Sorry Democrats, but it’s not going to happen.

The Other Celebrities and Billionaires

The Trump phenomenon has caused virtually every billionaire and celebrity to delude themselves with the idea that they too could be president. There’s Disney CEO Bob Iger, actor Dwayne Johnson, actress Angelina Jolie, Facebook CEO Mark Zuckerberg, and many others. But none of these seem serious about or interested in running. 

That’s it for our 2020 candidate preview series. It’s not out of the question that we could see 20 or 30 Democrats run for president, and the Democratic National Committee is already trying to plan out how to accommodate a massive number of candidates in the debates. Over the next few months, we’ll be taking a closer look at the process ahead — from debates to early voting states and the polls as the race takes shape. At this point, anything could happen. But if you thought the 2016 race was wild, one thing’s for sure: You ain’t seen nothing yet.

Photos via Flickr (Eric Bridiers / JD Lasica)

Thomas Valentine

Thomas Valentine is a columnist for

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