‘Know Your Enemy’ podcast gets why Taylor Swift drives conservatives crazy

If Democrats want to understand why President-elect Donald Trump is returning to the White House, a good place to start might be the “Know Your Enemy” podcast, hosted by two self-described leftist bros who, without mockery or tongue-in-cheek elitism, explore the complicated past and feverish present of the American conservative movement.

It’s a sort of anti-Joe Rogan program for a perplexed and dismayed left-wing set curious about William F. Buckley Jr., Ronald Reagan, the rise of the tea party movement, conservative fans of the Grateful Dead and why so many right-wing commentators suffer from “Taylor Swift derangement syndrome.” The show’s interrogation of conservative history is rigorous and occasionally peppered with expletives, but the exchanges with guests are nuanced and civil.

“Know Your Enemy” was started in 2019 by Matthew Sitman, the son of a factory worker raised in a Christian fundamentalist home in central Pennsylvania, and Sam Adler-Bell, a Jew who grew up in a left-leaning family, listening to union leaders and visiting picket lines with his labor-lawyer father. They met when Sitman, then an editor at Commonweal Magazine, asked Adler-Bell to write book reviews. The two shared a fascination for country music and right-wing politics, believing the best way to oppose conservatives is not to berate or ridicule but to respect and understand.

“Even if I come to find the [conservative] ideas unpersuasive, there might be some kernel or core there” — such as understanding the costs and consequences of social change — “that’s worth treating seriously and exploring,” said Sitman, 43, a onetime conservative disciple turned Bernie Sanders fan.

“The left has to think really hard about why we’re right [in our beliefs],” Adler-Bell, 34, said in one episode, adding that conservatives are not “self-consciously evil,” but rather rooted in their convictions.

Such equanimity is rare in the age of podcasts and politics of recrimination. The driving forces of the moment are fixated less on enlightenment than on attacking, distorting and vanquishing. Disdain and division reverberate across a vast and partisan social media landscape that includes X, TikTok and YouTube. A recent poll by the Pew Research Center found that 37% of Americans under 30 regularly get news from social media influencers, the large majority of whom have no background with or ties to news organizations.

“Know Your Enemy,” which the two record in their New York apartments, has a modest audience — about 30,000 listeners an episode and 8,000 subscribers who bring in $39,000 a month. The show is smaller than more prominent podcasts with similarly progressive temperaments. “Pod Save America,” hosted by Jon Favreau and other former aides to President Barack Obama, has a reported 20 million monthly downloads; and Tim Miller, host of “The Bulwark Podcast,” which is described as providing an “unabashed defense of liberal democracy,” has nearly 400,000 followers on X. Sitman has 31,300 followers on the platform, and Adler-Bell has 46,300.

But “Know Your Enemy” appeals to socialists, Democrats and more than a few conservatives — some who have been guests — interested in right-wing thought including that of neoconservatives, so-called reformicons and a species known as the paleoconservative. The show, as it wades into what Adler-Bell calls a “swampy morass” of conservative history that touches on free markets and American interventionism, is heavy on reading lists.

“It’s an innovative and important podcast,” said Curt Mills, executive director of the American Conservative magazine, who appeared on the show in November to discuss foreign policy and Trump’s picks for his national security team. “It doesn’t have an enormous audience, but it’s an extremely important audience.”

He added that the show’s willingness to dissect center-right ideas at a time when the left often demonizes Republicans implies “a level of curiosity that I think was often lacking for the last eight years. … They’re essentially honest brokers.”

Other podcasts that focus on right-wing politics include “5-4,” which analyzes Supreme Court cases, and “In Bed with the Right,” which studies conservative ideas on sexuality and gender. But few are as comprehensive as “Know Your Enemy.”

The show’s liberal followers are loyal but don’t hesitate to take Sitman and Adler-Bell to task when they sense a whiff of politesse toward the right.

An interview with rising young conservative Nate Hochman, who was later fired as a speechwriter for Florida Gov. Ron DeSantis for posting Nazi-adopted imagery online, drew backlash. And after the Mills episode, a listener wrote: “Completely ridiculous how you let him get away with talking about [Pete] Hegseth and the intelligence scandals around Tulsi [Gabbard]. If that’s your approach to having conservatives on – no thanks.”

Another wrote, “Stop giving Trump apologists a platform.”

“We’re really not debaters,” Adler-Bell said. “I think other podcasts on the left, if they had a conservative or a person they disagreed with, the goal would be victory. To embarrass or humiliate the guests. We just don’t do that.”

Listening to Sitman and Adler-Bell is like wandering the basement stacks of a library with two grad students jazzed on coffee and shuffling index cards. Nothing is too obscure, no tidbit too arcane. In an episode that discussed Buckley, founder of the National Review and widely considered the godfather of modern conservatism, the hosts examined extremist and racist elements in the conservative movement half a century ago that persist today.

In another show, they discussed global right-wing populism and a class realignment that foreshadowed Trump’s victory in November.

“Know Your enemy” also delves into right-wing influences on film, music and literature. It examined how conservatism played into the careers of celebrated authors such as Joan Didion — “why she loved Barry Goldwater and hated Ronald Reagan” — and Tom Wolfe, he of the vanilla suits and quicksilver prose, who navigated how post-World War II prosperity led to American subcultures.

Sitman and Adler-Bell spent more than an hour in March on an episode about Taylor Swift.

“Why does she make the right so crazy? Why does she sometimes make the left so crazy? What does her celebrity mean?” Adler-Bell asked at the beginning of the show. “What can she tell us about the nature of American culture today? It turns out, listeners, Taylor Swift is a great lens into making sense of some of the American berserk.”

The podcast offers possible solutions for how liberals and Democrats can appeal to working-class voters they have lost. In an episode called “Organizing in Rural America,” the hosts spoke with Luke Mayville of Reclaim Idaho, a grassroots group that mobilized voters to expand Medicaid in a deep-red state.

“Know Your Enemy” has criticized Democrats for hubris and elitism as the party has shifted toward identity politics and urban college-educated voters. That occurred in the years Trump was breaking taboos within the Republican Party by opposing the war in Afghanistan and global trade, and, according to Sitman, tapping into a “vicious and nativist” anti-immigration sentiment that was embraced by his working-class base even as it left the GOP establishment initially uneasy.

“I can’t really remember when a candidate had shown up in the place where I grew up and told people they were being ripped off and they were right to be angry,” said Sitman, who is on the editorial board of the leftist magazine Dissent, which partners with his podcast. “The nature of Trump’s transgressions mattered less than their anger at the system.”

Sitman knows something about that anger. Growing up in a blue-collar, deeply Christian home, he was shaped by the Bible and the conservative politics of self-reliance. Those who fail in life, he once thought, bring it on themselves. He carried those views into young adulthood as he met prominent conservative thinkers while interning at the Heritage Foundation and attending graduate school at Georgetown University.

“I was at my most conservative,” he said, “when I experienced the least of the world — when I was at my most naive.”

His sentiments shifted after he experienced severe depression and reflected on the struggles of others and how the economic class one is born into affects the trajectory of their future.

“The reason I moved from right to left is not because my fundamental values changed,” said Sitman, who has converted to Roman Catholicism. Rather, it was because he came to realize he wasn’t empathetic enough to class differences and the privations of others.

Sitman — who as a boy saw his father pull out one of his teeth over the kitchen sink because he lacked dental insurance — wrote in a 2016 essay for Dissent: “The failure of conservatives to attend to the world as it actually exists, the world in its suffering and hardship, drove me from their ranks.”

Adler-Bell’s upbringing was more secular, tailored by labor struggles and watching movies like “Matewan,” about union organizing in the coalfields of West Virginia in the 1920s. This background taught him, he said, the power of solidarity: “We are all vulnerable, frail and broken and flawed, and the only way we can overcome atomized suffering is through recognizing [this] in others.”

At which point, Sitman, the more understated of the two, chimed in during an interview: “Your diaper was pink, if not red.”

They laughed, then pressed on.

The conservative right, said Adler-Bell, who writes for Jewish Currents, the New Republic and other publications, is less empathetic to shared vulnerability.

“Trump represents,” he added, “more explicitly than any politician I think maybe in American history, … the message of the racketeer, of the mafioso who says, ‘I will protect you, and you can get yours, and everyone else, f— ‘em.’ The world is a war of all against all.”

Both hosts wonder who will rise as key players in the new Trump administration. Elon Musk, who spent more than $250 million to help get Trump elected, is in the ascent and supports the president-elect’s pro-business agenda. But Trump’s eldest son, Donald Jr., is also a force. He is close to Vice President-elect JD Vance, whose brand of economic populism leans more toward the working class of Trump’s base than corporate America.

They are also watching how Trump, who has threatened to arrest his political enemies, will oversee the FBI and the Justice Department, and how much of a hawk Sen. Marco Rubio might be if he becomes secretary of State.

“We’re very much in Versailles, French monarch territory,” said Sitman. “Observing the courtiers around the king and trying to decipher who wins favor.”