In the Keswick Theater's lobby, Crooked Media’s staff set up a merchandise stand featuring T–shirts and $5 beer can koozies. As the lights come up, four guys sit backstage. All of them used to work for President Obama. 

Jon Favreau, Jon Lovett, and Tommy Vietor founded Crooked after the 2016 election; Dan Pfeiffer has been on board since the beginning. These guys have been in the room where it happens; the audience is clamoring for just a peek in the door. After a clip reminiscent of a concert opening, the four men spill onto the stage, two guests in tow, and plop down in armchairs with the air of having done this hundreds of times before (they have). Welcome to Pod Tours America. 

It’s masterful political branding. These are guys you not only, in the spirit of the political cliché, “could have a beer with,” they’re also guys you can’t help but picture yourself having a beer with. Theirs is a radio show for the 21st century, laden with expletives and pop culture references. It’s akin to fireside chat for punditry. (Pundit is, incidentally, the name of Jon Lovett’s goldendoodle. Favreau’s is called Leo.)

Crooked employs a digital strategy reminiscent of Obama, colonizing social networks and gaining incredible Twitter traction. Favreau (@jonfavs) wins the Twitter race with 826,000 followers, while the others hover between 200k and 500k. And, appropriately for the Trump age, they tweet a lot

Let’s get this out of the way: Crooked is run by four white liberal dudes. And it attracts a good subset of white liberal dudes in turn. A gangly 20–something behind me wearing a “Friend of the Pod” T–shirt turns to his friend, asking wide–eyed and earnestly, “What’s your favorite Pod?” Some fans border on hero–worship. But Crooked is actively working to employ and attract diverse people. 

Photo: Ilana Wurman

Onstage at the Keswick, for instance, they’re joined by Deray McKesson and Brittany Packnett. Deray and Brittany host Pod Save the People, which focuses on political organizing. Both are black activists. You may know Deray by his signature blue Patagonia vest, or remember his run for Baltimore mayor. 

Favreau’s response to the question of diversity at Crooked is heartfelt. “It seems unlikely that any of the four of us will stop being liberal white dudes, but, the network is not just going to have us in front, it’s going to have a lot of different and interesting people.”

Crooked Media started out as a two–man operation. Backstage, Tommy Vietor explains that Keepin’ it 1600, the podcast that Jon Favreau and Dan Pfeiffer created during the 2016 election season, “started out as a hobby for Dan and Jon.” But soon, he and Jon Lovett “glommed on." And, staring down the barrel of a Trump presidency, Crooked Media was born.

If presidential politics now veers towards xenophobic Veep territory, the four guys present an image of an updated West Wing. They speak in reverent terms of their former boss, President Obama. 

Photo: Ilana Wurman

When asked to tell something few people know about Obama, they seem genuinely stumped. “Everything sounds kissass–y.” They speak of their time on the campaign in similarly nostalgic terms. Tommy’s advice to college students interested in politics? “Move to Iowa, work on a presidential and it’ll be the most fun you’ve ever had in your entire life, I promise you.” 

Obama, too, once seemed like an upstart. Something in Tommy’s voice belies a sense of continued awe that Obama came back from a 2008 loss in Iowa to win the nomination and eventually the presidency. But he did. And he brought along Jon Favreau and Lovett as speechwriters, Tommy as a foreign policy advisor, Dan as Deputy and then Head Communications Director. They know their shit.

But whatever you do, don’t push these four on 2020 presidential picks. They’re (rightly) indignant that they get asked this question so often this far out. Their joking responses range from Hillary Clinton (“no baggage!”) to Sheriff Joe Arpaio (“clean record!”).

During the show and backstage, there’s quite a bit of talk about Twitter, Facebook, and Russia, particularly in the wake of Mueller’s recent charges. The guys are equal parts disgusted and incredulous at the Trump campaign’s ties with Russia. They launch into a bit imitating Donald Trump Jr.’s emails to Russian officials—"Let’s collude! When are you free to do the collusion?” Their assessment of former campaign chair Paul Manafort is simple. Favreau protests that “he laundered $75 million fucking dollars... unbelievable.” 

“He is a criminal.” Lovett responds. And that’s that. 

Photo: Ilana Wurman

Chrissy Houlahan, US House candidate for PA’s 6th, talks to Dan and Brittany during an interlude during which I imagine the other hosts were backstage finishing their beers. Pennsylvania’s 6th congressional is heavily gerrymandered and currently held by Rep. Costello, a Republican. She stresses that Pennsylvania is one of the only US states with zero women in Congress or the Senate. 

The tour is regionally specific for a few reasons. First, it’s easier to draw local candidates when you’re setting up a talk show in their backyard. And second, instead of studio–producing content during the tour period, Pod Save America is releasing the live shows as part of the normal podcast feed. It's a way to push out a consistent batch of content, while connecting in person to the listeners themselves.

Lovett is the jokester of the four. When talking about Al–Qaeda/ISIS propaganda magazines, he quips, “Don’t they know print is dying?” His show, too, relies on humor as much as it does on partisanship. He’s gained a fandom within the group unrivaled by any except perhaps Favreau.

Photo: Ilana Wurman

But Lovett’s joking front comes down a bit as he talks. In a few sentences, he uses “animus,” “stratition,” “accruing,” and “echelons.” But as soon as the esotericism threatens to overwhelm, he’s back to his (hilariously atrocious) Russian impersonation. After the break, he gleefully informs the audience that @realDonaldTrump was suspended from Twitter. It’s revelatory. Until he explains that Twitter called it an accident. And it only lasted 11 minutes. Gotcha!

More so than the others, Tommy seems comfortable with specificity. Midway through the show, he fiddles with some shiny object in his hand. It’s easy to wonder if, after all these tours and all these shows, these men still get nervous. But Tommy, who dropped by Perry World House earlier in the day, soon launches into a flurry of town names and Middle East–specific regional terms. It’s easy to see why he excels as the host of the foreign policy podcast Pod Save the World

Photo: Ilana Wurman

Another fun fact about Tommy: he holds the record for most congressional Republicans on a Crooked pod. Two—Will Hurd and Adam Kinzinger. “You’re one away from making me uncomfortable,” Lovett mutters backstage. 

Favreau is the facilitator. He’s smooth–talking in a way that none of the rest of the guys can quite approximate. During the show, he asks the questions, leaning forward in his chair or slouched comfortably. Backstage, he and Lovett prove the most talkative. And it’s Favreau who responds to the question of keeping Crooked from becoming an “echo chamber.” He says, “a partisan echo chamber is problematic when it is based on nothing but spin and lies and conspiracy and stuff like that... Partisan sites that give people facts...are quite useful.” Alternative facts jokes ensue.

Dan is the oldest and was the most senior to President Obama. The other three defer to him when asked about their old boss. ”You travelled with him more than any of us.” He’s also the only non–founder on the pod. His current gig is a much–derided correspondent post on CNN. 

The guys have an uncanny ability to make the audience feel in on the joke. Even on their website, Favreau’s founder bio insists that he held “a role that was more senior and influential than Jon Lovett’s” in the Obama White House. Their ads for BlueApron, MeUndies, and, once skippable podcast standbys, are funny.

And that’s what’s so comforting about Crooked Media. It’s so easy to imagine yourself sitting down with these guys and chatting. Backstage, sitting at a table surrounded by four men I used to know as disembodied voices, I found myself joking, laughing, trying to convince them that Wharton was its own Ivy, quipping about Arrested Development. 

And as I walked out of the Keswick, the line for merchandise stretched almost out the door. I bought a shirt anyway.