The Washington PostDemocracy Dies in Darkness

The battle in your ear buds: The bros of political podcasting and their quest to reinvent punditry

LEFT: Ben Shapiro during a break of the filming of his podcast, “The Ben Shapiro Show.” RIGHT: Jon Favreau of Crooked Media, in foreground, with “Pod Save America” colleagues (seated from left) Dan Pfeiffer and Tommy Vietor, guest Alyssa Mastromonaco. (Jessica Pons/For The Washington Post)

LOS ANGELES — In a drab office building across from a used-car lot in the San Fernando Valley, the host of the nation’s most popular conservative podcast was preparing to interpret reality for his listeners.

“These are one of those days where you think, ‘Maybe I should’ve gone on Wall Street,’ ” joked Ben Shapiro, glaring at a torrent of tweets on his laptop in a cramped, windowless studio. “This news cycle is — ”

“ — the wildest thing since Trump winning,” said Jon Favreau. The former speechwriter for Barack Obama was just a few miles away from Shapiro, in an airy, sunlit Hollywood office, as he, too, processed the day’s news into analysis and talking points for his own podcast listeners, on the liberal end of the spectrum.

It was Thursday, Sept. 27, and 2,500 miles away, Washington was stricken by the unprecedented spectacle of a Supreme Court nominee answering to a decades-old allegation of attempted rape. Sen. Lindsey O. Graham (R-S.C.) was on the flat-screen TVs in Los Angeles, sputtering “This is hell!

“I can’t believe this is happening,” muttered Tommy Vietor, Favreau’s colleague, formerly at the White House and now at their new venture Crooked Media. Meanwhile, Shapiro — who had just published a 673-word piece on “How Republicans Blew The Christine Blasey Ford Hearing” — saw his side regaining the upper hand.

“Good for Lindsey Graham,” he tweeted.

The hearing was drawing to a close, but it was barely past lunchtime in Los Angeles, and for these two offices — major hubs for a rising new breed of punditry — there was work to do, messages to craft, content to shovel.

“What time are you guys recording?” Crooked Media’s Dan Pfeiffer, another Obama alumnus, asked Jon Lovett, another former White House speechwriter. On the TV, Brett M. Kavanaugh and Sen. Amy Klobuchar (D-Minn.) jousted over whether they’d ever blacked out from drinking alcohol.

“Four,” Lovett said, as his goldendoodle Pundit licked empty takeout containers. “We’re running out of time.”

“DID YOU HAVE A FART JOKE IN YOUR YEARBOOK? DO YOU, SIR?” Shapiro tweeted, mocking Democratic Sen. Sheldon Whitehouse’s line of questioning. He would soon write another piece, this one for Newsweek, and appear that night on Laura Ingraham’s Fox show to lament the assassination of Kavanaugh’s character. The guys at Crooked would record two podcasts, including one titled “We believe Christine Blasey Ford,” and prepare for a dress rehearsal for their new HBO special.

The Republicans are “incapable of acting with seriousness, compassion and empathy,” said Pfeiffer on their “Pod Save America” podcast.

“I hope you bring all your friends to vote,” Shapiro said the next morning on his show, “because [Democrats] cannot have power.”

Of the Crooked Media guys, Ben Shapiro says: "I disagree with everything they say, but I think they're good at what they do."

Told that a visiting journalist is seeing Shapiro first, Tommy Vietor says: “Please tell Baby Steve Bannon I say hello.”

Their operations, methods and goals are different, and yet both have leveraged podcasting into niche stardom, becoming powerful brands, with franchises and spinoffs and corporate sponsors (including, for both, a brand of tailored men’s underwear that bills itself as “life-changing”). Their shared business model is no-nonsense political analysis and a commitment to “intellectual honesty” — a term they use to distance themselves from their stodgy elders.

“On cable news, you have talking-point machine A versus talking-point machine B, or greenroom fixture A versus Bill Kristol, who lives in a green room,” says Vietor, 38. “And they playact politics. They say their stilted bulls--- talking points, and then David Gergen comes in with his ‘both sides’ broom to mop up when they’re done.”

Now, both Crooked and Shapiro are expanding beyond their new-media platforms into the establishment world of television, with the goal of influencing the midterm elections. Shapiro is wrapping up a four-show special on Fox News just as “Pod Save America” begins its own temporary run on HBO Friday.

Each is “emblematic of an astounding level of political polarization in the United States right now,” says Dannagal G. Young, an associate professor of communication at the University of Delaware. They are united, though, by the ingratiating powers of their increasingly popular medium. The percentage of Americans listening to a podcast every week has more than doubled in the past five years, according to Edison Research.

“Podcasts have become this really viable and popular form of intimate, discursive experience,” Young says. “People are in their cars or at the gym, and listening, and you feel like it’s them talking to you.”

Fans wearing “Friend of the Pod” T-shirts crowd the front rows at live events with the Crooked guys, who are greeted like rock stars instead of the political nerds they are. On liberal college campuses, lonely conservatives draw strength from YouTube clips of Shapiro dismantling progressive arguments like a hunter field-dressing an elk.

On his show, Shapiro reads ads from a sponsor that sells a three-month emergency food supply, plus seed packets, for when things finally go south. “Pod Save America” shills for a company that delivers fresh ingredients to your doorstep so that you can cook yourself a single, healthy meal — lentils and quinoa dressed in tahini, perhaps — as the world burns.

America through the Crooked lens is a grand experiment, ever more perfect and expansive, but endangered by ancient prejudices, persistent injustices and a despotic dunce in the White House.

Crooked Media’s headquarters has the look of a start-up and the feel of a small-town newsroom. A George Washington silhouette, rendered in yellow neon, hangs in the reception area. Conference rooms are named LIL MARCO and COLLUSION. The 25 employees are within earshot of one another but chat on various Slack channels, including one labeled “newsnewsnews.” The junior staff is majority female, but its nucleus is three men in their 30s: co-founders and officemates Vietor, Lovett and Favreau, with an assist from 42-year-old Pfeiffer, a “Pod Save America” co-host who lives in San Francisco.

They’ve created a company with “media” in its name, and its main product is a suite of podcasts. But it’s more of a rolling campaign than a reinvention of journalism.

“We’re not traditional reporters. We’re storytellers,” says Tanya Somanader, Crooked’s chief content officer. “What we’re trying to do is have a no-bulls--- conversation about what’s happening in the world and what people can do to shape it.”

Since its January 2017 debut, “Pod Save America” has been downloaded more than 320 million times. What began as a hobby for Obama alumni has morphed into a thriving business that is also a crusade to save a teetering republic.

“If [Trump] left the White House tomorrow, democracy would still be threatened in a whole bunch of ways,” says Favreau, 37. “Politics is not transactional. It is not about you handing your vote to a politician, and a politician fixing all your problems, and you going back to your life.”

Alongside their media ventures, they have launched Vote Save America, an online portal for voter registration and civic engagement. In 2016, millennial and Gen X voters surpassed older generations at the polls for the first time; Crooked wants to harness that trend to rebuild the liberal coalition that elected Obama twice, as the Democratic establishment failed to do that year. The establishment seems happy to have them.

“Talk radio just reminds you that you are outraged,” says Democratic National Committee Chair Tom Perez. “Crooked Media reminds you to take action.”

To be fair, outrage fuels Crooked, too. Typical episode titles include “An orgy of corruption” and “A potpourri of stupid.” GOP leaders are referred to as “scummy” and “depraved.”

Do they ever worry about behaving like the smug partisan hacks they professed to hate?

“Yes,” Pfeiffer says. “Every day.”

America through the Shapiro lens is civilization's greatest triumph, a beacon of liberty and opportunity that is under assault from an evil, self-victimizing cabal of leftist baby killers.

Shapiro’s headquarters has the look of a think tank and the feel of a refurbished doctor’s office. A reproduction of “Washington Crossing the Delaware” hangs in the waiting area; an issue of Cigar Aficionado sits on a coffee table. About 55 employees work for him under the banner of Forward Publishing, producing his Daily Wire website and three other podcasts, all hosted by conservative men.

A “Never Trumper” who in early 2016 resigned from Breitbart, partly over objections to Stephen K. Bannon’s leadership, Shapiro has become a “Sometimes Trumper” who was surprised to see Trump govern conservatively. A Harvard Law grad, Shapiro is 34, has two children under 5, writes over a dozen articles a week, and produces at least one podcast every weekday (his show gets around 20 million downloads a month).

In April, Westwood One began syndicating his podcast on the radio; now it’s aired by 60 affiliates. He speaks regularly on college campuses, where he’s greeted by long lines of fans and groups of animated protesters who accuse him of racism, sexism and transphobia. In January, he will start doing two additional hours of live radio a day, on top of the podcasting.

“It’s his intellect. He commands the audience,” says Suzanne Grimes, president of Westwood One, who also praises “the rapidity with which he speaks. You feel as if you’re swept along in the conversation in a very moving way.”

Whereas the Crooked podcasts are playful, pondering conversations, Shapiro lectures sternly, with sermons that paint the world as black and white, good vs. evil. His prevailing on-air tone is one of scorn and disgust. Jim Acosta of CNN is a “garbage human being.” Barbara Boxer was “the stupidest woman in the Senate,” and Obama was a “racist” and “lawless” president.

It’s working for him. His podcast was No. 8 overall for August. “Pod Save America,” while the second most-downloaded new show on Apple Podcasts in 2017, didn’t rank in the top 20 that month.

Shapiro melds the tactics of two previous generations of conservatives, according to Reece Peck, an assistant professor in the department of media culture at CUNY’s College of Staten Island — the calculated, Ivy League debate style of a William F. Buckley Jr., and the pugilistic drive for a humiliating knockout, a la Rush Limbaugh. If streaming is the platform of choice for a new generation of conservative activists, Peck says, “I think Ben Shapiro is the brightest star.”

The second episode of Fox’s “Ben Shapiro Election Special” was the highest-rated show on cable news in its time slot, and the second-highest cable show overall on Sept. 30, according to Nielsen Media Research. “I’m just hungry to put out the message to the broadest population as I can,” Shapiro says.

Last year, he invited the Crooked guys for a civil dialogue on his weekly Sunday show. Lovett said he’d think about it, Shapiro says, but then didn’t reply to a follow-up. (Lovett says that his tendency to drop the ball on replying to people “is incredibly bipartisan.”)

George Washington, again — this time a giant, scarred bust looming over the stage at the Alex Theatre in Glendale, Calif., where the Crooked guys were taping a rehearsal for their HBO show. Five chairs were surrounded by cracked Styrofoam made to look like marble ruins.

“Get the subtle message?” Vietor said during the soundcheck. “Our democracy is dying.”

The HBO show will be an extension of their podcasts — a casserole of rant, humor, interviews and impassioned pleas to vote. They will tape each episode in a different city — Miami, Austin, Philadelphia and Irvine, Calif. — and hope to help strengthen the anticipated blue wave.

“They’re reminding people that the work of politics doesn’t just happen around elections or at the presidential level,” said Adina Brin, 25, an L.A. activist who arrived to watch the rehearsal. “Politics is every day.”

The show had an extemporaneous feel, though many of the arguments and punchlines had been refined over 36 hours of tweeting, chatting and podcasting at Crooked headquarters. The chaos of the Kavanaugh hearings had, by showtime, been repurposed into precision entertainment: a narrative about a “raving lunatic” in the Oval Office, an unfit nominee to the Supreme Court and the merry band of voters who — with an assist from Vote Save America — would call them to account in November.

“Donald Trump can perform this circus, and make everyone feel cynical about politics, and if a bunch of people don’t vote or a bunch of people don’t trust government anymore, then that’s okay for the Republican Party, because that’s their ideology,” Favreau said backstage. “Democrats have a different challenge, which is: We have to make people pay attention, but not make it so much of a circus that people are turned off by politics and government.”

Meanwhile, over in the Valley, Shapiro powered down for the Jewish Sabbath — perhaps the kind of break everybody needs — and waited to emerge Sunday to tape his second Fox show, on which he would try to frighten viewers with visions of a Democrat-controlled Congress.

“I literally have no clue what is going on in the world until I turn on the phone Saturday night,” he says. “There’s always a feeling of trepidation, half an hour before the end of the Sabbath because, oh God, I’m going to turn on the phone — and it’s just going to be garbage.”