How the GOP Operatives Behind ‘Ruthless’ Turned a Niche Podcast Into a Right-Wing Media Sensation

They would have you believe it was destiny.

About five years ago, Shashank Tripathi, better known by his social media moniker, Comfortably Smug, instantly hit it off with GOP operatives Josh Holmes, John Ashbrook, and Michael Duncan at an off-the-record happy hour he hosted in Washington, D.C. — “The guest list remains confidential,” he told Mediaite — and in short order approached them with an idea.

“I’ve got a deck about an idea of  a podcast that uses satire to skewer the left. And a media company that really focuses on that idea. Because debating the left is absurd when they have absurd ideas, they should be mocked. And I put it down on Holmes’s desk and he’s like, ‘Huh, so here’s what we were thinking.’ He puts down a deck, slides it across the table to me — it’s the exact idea,” recalled Smug. “I’m telling you, I got chills, I was like, this is destiny.”

And maybe it was. Duncan credited the Covid pandemic with giving the quartet the chance to flesh out and test drive the idea that became the Ruthless podcast in bourbon-fueled 5 p.m. Zoom meetings during lockdown. The result: a cheerfully mischievous, lib-triggering show that has become a destination for prominent Republicans, including Vice President JD Vance, who has appeared on multiple occasions.

“I’m sure every friend group is like, ‘Bro, this would be a great podcast,'” he conceded. “But I mean, the reality is it kind of was…  And so that allowed us, I think, to home in on what the actual content of the show would be.”

But the show’s success in the years since its 2020 launch — Fox News announced last month that it had reached a licensing agreement with the “variety program,” as its hosts call it —  has to do with much more than fate.

“I mean, it became very clear in the era of Trump that authenticity is the only thing that matters, right? And you’ve got four people who genuinely became close friends who, with or without a microphone in our face, we’d be doing this exact same thing,” suggested Holmes. “And, you know, maybe a little bit more structure from a podcast standpoint, but the topics are all the same, and the laughter is all the same.”

“And part of the reason for that hole in the marketplace is the way that the left captured legacy media, and there were zero normal people working at and driving stories for other normal people out in the country,” offered Ashbrook. “And so other normal people in the country are looking for alternate forms of information where they can actually be told the truth. And they also are interested in a couple of laughs here and there, and we don’t take ourselves too seriously on our show.”

He added: “If I say something stupid, everybody laughs at me. And that’ what friends do to each other. And, you don’t get any of that in the legacy media. You certainly don’t get it in the broadcast news networks. You don’t get it at The New York Times, you don’t get it at The Washington Post. They all take themselves way, way too seriously.”

This author was not immune to the friendly banter. Before the end of our Zoom interview, Smug inquired why I was “recording from a CIA black site,” i.e. an unfinished guest bedroom.

The content being churned out by Ruthless, they argued, doesn’t exist on the left, although Holmes outed Duncan as a former fan of the pugnacious, far-left Chapo Trap House podcast.

“You loved those crazy dudes on the left for a while,” he observed.

“They’ve sort of lost their way,” lamented Duncan, who said that “our show is far more diverse in opinions on the Republican Party than you would ever see on Pod Save America, or any of these left-wing shows. You know what I mean? And our audience loves that because that also reflects them. There is not a monoculture in the Republican Party, even for people who love Donald Trump, or people who loved Mitch McConnell. They like parts of things, and they’re people, right? So much of our political media thinks there’s one lane that you run towards, and that’s the entire thing. And that’ not authentic, that’s not real, that’s not the way people process information.”

The value of the product, though, is attributable to more than just its casual, irreverent tone and “big tent” approach.

“I think the second component, other than authenticity that we had brought to it is we’d spent a lifetime being in the center of the conversation. So we actually knew what that was. And we also had spent not an inconsiderable amount of time with some frustration, listening to people with absolutely no idea what it was that they were talking about giving definitive views of what was happening when we were there, right!? I mean, we knew the real story,” said Holmes. “It’s at some point sort of cathartic to get to a point where you could not only have some yucks with your fellas, but then be like, ‘No, here’s, because I was in that situation, I’ll tell you exactly the situation that they were dealing with at the time and what they’re trying to accomplish.'”

They dole out “candy and vegetables” in equal measure,” he explained. “There’s candy in that we’re all laughing, we’re bringing up cultural stories that we get a kick out of. And then there’s a vegetable component that we feel like you’re not going to really get anywhere else because we’ve done it before.”

Sometimes, that means taking the liberal mainstream media to task, as the Ruthless crew did after CBS’s vice presidential debate last fall. “We broke down every single trick that these moderators were using to try to steamroll Vance and lift up [Tim] Walz,” recalled Ashbrook.

And sometimes, that means telling hard truths to their largely conservative audience — including about early and mail-in voting.

“This was a huge conversation in the Republican Party in 2020, and ahead of ’22 and ’24,” said Duncan. “I mean, it’s like banging your head against the wall to help, you know, guide people to, I think, the best conclusion on that, which was: we got to do our best to get these votes in.”

“I look at a place like Arizona. We have a permanent early voter list, and Republican victories in Arizona were built for 20 years on performance on the permanent early voter list, where a voter has mailed that ballot, and then you’re just chasing them all summer to get them to turn the thing in,” he went on. “And so to see people in the conservative movement be like, ‘All of this is fraudulent forever.’ And it’s like, ‘Dude, what are you doing?'”

In an age in which audiences are demanding both ideological credibility and independence — informality and expertise — Ruthless is uniquely positioned to provide theirs with all of the above. And now, they’ll have a company with a uniquely impressive record of drawing, developing, and maintaining audiences behind them.

“The future of the business of media is that, it’s the relationship with the audience,” posited Duncan. “And Fox understands this, I think, innately.”