Oprah 2020? Hollywood Holds Out Hope for Candidacy

Paul Drinkwater/NBC

Handicapping a tantalizing possibility that might never happen for a mogul who has spent her life outside the political arena.

Will she actually run? Post-Trump, nothing can be ruled out as Oprah Winfrey’s emotional Cecil B. DeMille Award acceptance speech at The Beverly Hilton on Sunday electrified both Hollywood and the Beltway at the prospect of a presidential candidacy.

Whether she intended to or not, the 63-year-old mogul set off a frenzy after a nine-minute speech during which she spoke of meeting with and portraying those with the “ability to maintain hope for a brighter morning, even during our darkest nights.”

An outsized response seems to have taken her aback, say sources close to Winfrey. On Tuesday, her longtime best friend, CBS This Morning co-host Gayle King, said on air that Winfrey is “intrigued” but that “I don’t think at this point she is actively considering it.”

For Democratic strategists, however, she sounds like a new hope. “It absolutely could happen, and if she runs, there is little the Democratic Party can do to stop her from being a top-class contender, even if they wanted to,” says veteran Democratic strategist Joe Trippi, who is fresh off beating Roy Moore in the Alabama Senate contest in December.

“It’s not as simple as, ‘Oh, that was a great speech, she should be president.’ I think that there’s been some signaling on her side as well,” CNN anchor Chris Cuomo says. (Cuomo’s brother, New York Gov. Andrew Cuomo, is on an early list of potential Democratic candidates for 2020 that so far is light on star power.)

A Winfrey candidacy has obvious strengths: She’s admired, has near-universal name recognition and a personal fortune in the billions that could help fund a professional state-by-state campaign. “If Oprah goes anywhere near Iowa or New Hampshire, it becomes more likely she is making moves to actually run,” notes CNN contributor and former Bernie Sanders campaign aide Symone Sanders.

Sanders said Winfrey could signal her interest in running by getting involved in the 2018 midterm elections, either by raising money or contributing to candidates.

As a television star turned president, Donald Trump charted a path that Winfrey potentially could follow. “Like Donald Trump, she is a master communicator,” Christopher Ruddy, a friend of the president who runs the conservative television network Newsmax, says of Winfrey. “Where she falls short is on perception. She’s viewed simply as a talk show host and a conversationalist.”

Also like Trump, Trippi says that Winfrey would attract voters who never before had been motivated enough to vote in a primary election. “Turnout is so low in both party primaries that anyone with an ability to excite or turn out people who don’t usually vote in primaries can swamp the insiders and win,” he explains.

"There is a lot of running room, even in a crowded Democratic primary field, for a candidate whose message is rooted in a genuine sense of optimism about the future," said Barack Obama's last White House press secretary, Josh Earnest. "That was the part of Obama's message that resonated so deeply in 2008. It is not hard to imagine that the same theme would resonate again — particularly when matched up against the 'American carnage' president."

While "President Oprah" is a fun possibility, the national Democratic Party might prefer to counter Trump with someone in 2020 who has deep experience running a government or serving in Congress — a senator like Elizabeth Warren or a governor like New York’s Cuomo.

"I think that the ability to do the job, because of what we're experiencing right now, will be in so much sharper focus if somebody from outside the discipline of government service enters the fray again," Chris Cuomo says. 

Another non-politician, Disney CEO Bob Iger, also was bandied about as a potential 2020 candidate, but that possibility went down the tubes when he agreed to remain with the company through 2021 as part of the 21st Century Fox transaction. (Iger seemingly endorsed Winfrey in a tweet saying “AMEN” to her speech.)

FiveThirtyEight statistics guru Nate Silver, however, notes that Winfrey shouldn’t be treated as a typical star candidate. “People may be making a mistake by lumping Oprah in with other ‘celebrities,’” he wrote Monday on Twitter. “She’s not Mark Zuckerberg or George Clooney. She has much broader and deeper appeal among everyday Americans.”

President Trump, asked on Tuesday by reporters in the White House Cabinet Room about the prospect of a Winfrey challenge, replied, “Yeah, I’ll beat Oprah.” He also guessed she wouldn’t run.

That challenge for Republicans could be even steeper than in 2016. “Demographics significantly favor the Democrats in 2020,” says conservative exec Ruddy. “The president will need to think up an outside-the-box strategy against any Democrat he faces.” 

This story first appeared in the Jan. 10 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

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