Rapper Kanye West shows President Trump a photo of a hydrogen-powered airplane in the Oval Office on Oct. 11. (Calla Kessler/The Washington Post)

On Sunday, Taylor Swift endorsed two Tennessee Democratic candidates for Congress — one for the Senate, the other for the House — and urged her millions of followers to register to vote. On Thursday, Kanye West joined President Trump for a lunch visit at the White House, capped by a choice expletive in the Oval Office. And this weekend, Alec Baldwin, known for spoofing Trump on NBC’s “Saturday Night Live,” is headed to New Hampshire to speak at a fundraising dinner for Democrats.

Live from the campaign trail, it’s the Celebrification of Politics, 2020 Edition.

The election of Trump — a reality TV star turned novice politician turned president — represented the latest and most potent fusion of politics with the nation’s celebrity fascination. Now, as the 2020 presidential campaign ramps up, a new cast of celebrities and famous-for-politics personalities are taking the stage as some Democrats ponder — with a mix of enthusiasm and horror — whether they need to put up their own celebrity nominee against Trump. 

Within the expanding but unofficial Democratic field, the definition of who constitutes a celebrity remains amorphous — and who will actually run largely a subject of speculation. But Trump’s presidency has created both an urgency and appetite among Democrats eager to defeat him in 2020, with some believing that a progressive candidate in Trump’s mold might hold the party’s best chance.

Lawyer Michael Avenatti, a potential 2020 candidate who represents adult-film star Stormy Daniels in her lawsuit against the president, said Democrats should not necessarily nominate the candidate most qualified to be president, but the one best equipped to take on Trump.


Michael Avenatti speaks at the Vanity Fair New Establishment Summit on Oct. 10 in Beverly Hills, Calif. (Matt Winkelmeyer/Getty Images)

“They’re not going to want someone as reckless or as extreme as Donald Trump, but they are going to want someone that is charismatic and can hold the stage, that is successful in navigating the media landscape and that has an entertainment factor to them,” Avenatti said. “No policy wonk is going to beat Donald Trump. And we’ve seen what he has done with your traditional politicians.” 

Potential hopefuls such as Avenatti are a direct response to Trump and the current political climate. Others, like Baldwin, Dallas Mavericks owner Mark Cuban and JPMorgan Chase executive Jamie Dimon — who recently said and then retracted remarks that he could beat Trump because he is “smarter” — seem to fall into the Why Not Me camp. 

Still others are famous for being political outsiders, such as Facebook CEO Mark Zuckerberg and former Starbucks CEO Howard Schultz, dismissed by one Trump ally as “what’s-his-name the Starbucks guy.” And then there are the perennial dabblers in presidential politics such as former New York mayor Michael R. Bloomberg.

Few, in other words, are actually A-listers in their own right like Oprah Winfrey, who is a regular focus of Democratic interest despite her repeated demurrals.

Democrats, however, remain torn about what sort of nominee could succeed. Among the many debates roiling the party is whether the best choice is a candidate — celebrity or otherwise — who embodies Trump’s combative tactics — like Avenatti or Sen. Elizabeth Warren (D-Mass.) — or a more temperate messenger, like Winfrey or Rep. Beto O’Rourke (D-Tex.), who is challenging Sen. Ted Cruz (R-Tex.) and drew more than 50,000 people for a September rally featuring Willie Nelson in Austin. 


Alec Baldwin, portraying President Trump on “Saturday Night Live” on Sept. 23, is set to appear this weekend in the primary battleground state of New Hampshire. (Will Heath/NBC/AP)

“Do I think Alec Baldwin is likely to be the nominee? No. But will he run? He may. Will Avenatti run? He probably will,” said Robert Shrum, a veteran Democratic campaign strategist. “Some of these contenders could have a big season, but it’ll come down to the question that voters are asking. Is it: Who’s the purest progressive? Who’s the meanest against Trump? Or who’s able to beat Trump?”

Ron Brownstein, author of “The Power and the Glitter: The Hollywood-Washington Connection,” said Democrats might be taking the wrong lesson if they think Trump’s celebrity alone powered him to the presidency, calling that “an understandable but shallow interpretation” of the president’s appeal.

“The key to Trump is much less his celebrity than his racial nationalism,” said Brownstein, senior editor of the Atlantic and senior political analyst at CNN. “He has more in common with Pat Buchanan than he does with Alec Baldwin.”

For Democrats trying to win back white working-class voters, he said, “You can’t imagine anything worse than a celebrity because Republicans have spent 40 years portraying celebrities as these kind of Hollywood liberals who look down from their mansions on Mulholland Drive with scorn on these working-class people who have dirt under their fingernails.”

Trump, for his part, understands how to manipulate the levers of fame and has often spoken with aides about how he believes both parties have misunderstood celebrity in politics. During the 2008 campaign, for instance, when Republican nominee John McCain attacked his then-rival, Barack Obama, in an ad for being too much of a celebrity, Trump criticized McCain’s approach. 

“He’d say to us: ‘That makes no sense. Who doesn’t want to be a celebrity?’ ” said former Trump adviser Sam Nunberg. “He’d talk about how Obama used Oprah to beat Hillary and how he helped to get Romney across the finish line,” Nunberg added, referring to Hillary Clinton, whom Obama defeated in the 2008 Democratic primary, and Mitt Romney, the 2012 Republican presidential nominee. 


Democratic presidential candidate Barack Obama, his wife, Michelle, and talk-show host Oprah Winfrey wave to the crowd at a campaign rally in Manchester, N.H., in December 2007. (Brian Snyder/Reuters)

Privately, those close to Trump say the Democrat who most worries the president and his team is former vice president Joe Biden, who they fear could cut into his working-class white support in such states as Michigan, Ohio, Pennsylvania and Wisconsin. 

“The only candidate that’d worry me is a candidate who could also appeal to the blue-collar Democrat and Republican,” said Rudolph W. Giuliani, the president’s lead lawyer on the Russia investigation. “But celebrities these days are usually seen as wacky, left-wing crazies who treat Trump voters as deplorables.”

Nonetheless, the president is attuned to the machinations of his potential rivals, especially those who exhibit the power of celebrity. Former White House chief strategist Stephen K. Bannon said Trump is well aware that both he and his possible challengers are operating within what Bannon calls the “modern McLuhan-esque presidency,” a reference to the late media theorist Marshall McLuhan, who forecast a political future in which images and mass communications would be critical — and in which “the medium is the message.”

“McLuhan was all about the overwhelming power of the media and mass communications, and both Obama and Trump understood that,” Bannon said. “It’s about impressions and brand and mass communications. And as I’ve said from Day One, Oprah, Avenatti, Cuban — people like that who speak to a broader, aspirational lifestyle is where politics is going.”

Those close to the president say the only long-shot celebrity challenger who has raised any concern within Trump’s orbit is Winfrey. In January, Winfrey entered the 2020 sweepstakes with her rousing remarks at the Golden Globes ceremony reminiscing about her impoverished girlhood and ending in a call to action in the #MeToo era.

“Oprah is the only person who would make me sit up and take notice,” said David Bossie, a Trump adviser and former deputy campaign manager. 


From left, Willie Nelson, Lukas Nelson and Rep. Beto O'Rourke (D-Tex.) perform “On the Road Again” during a rally for O’Rourke’s Senate campaign in September that drew more than 50,000 people in Austin. (Laura Roberts/Invision/AP)

Richard Sher, a Winfrey friend and former broadcasting partner in Baltimore, said that based on his conversations with her, Winfrey was “blown away by the reaction to the Golden Globes” but has little interest in running for president. 

“I just don’t think it’s something she wants to do,” Sher said. “She loves her life — and she has the best life possible.”

Later, Sher called back and said he had spoken by phone with Winfrey on Wednesday and told her about The Washington Post’s inquiry. Winfrey told him: “ ‘No, I’m not running for president. That’s not how I can best serve,’ ” Sher recounted. “That was it, verbatim.” 

So, which challengers might match up well against Trump?

“I’d certainly put myself near the top of the list at this unique point in our history,” Avenatti said with a chuckle.

Another wild card is megastar Dwayne Johnson — also known as the Rock — who has nonpartisan appeal to a diverse swath of demographic and economic groups. Johnson said in July that “due to my schedule,” he doesn’t plan to run in 2020, but Giuliani said Johnson could be formidable if he were to change his mind.

And what about West, who set social media aflame Thursday with a long, somewhat profane soliloquy praising Trump? Is he a future presidential candidate?

“Could very well be,” Trump said in response to the question from a reporter in the Oval Office.

“Only after 2024,” West chimed in, adding: “Let’s stop worrying about the future. All we have is today.”