David Frum thinks I should smoke less weed. “If you start it early, it will have an effect on your IQ, and it does seem to have strong effects on motivations and ambition,” he told me. We were sitting in a Georgetown Starbucks on an unseasonably beautiful Saturday morning in January, the federal government had been shut down mere hours ago, and Frum was happily chattering away about his favorite topic—the slow demise of the American republic.

We met atop Washington DC’s Exorcist Steps , one of the steepest and scariest staircases in America, famed for its appearance in the iconic horror film that it’s named for. Immediately I was in trouble: I feared if I attempted to do Frum’s biweekly routine—three sets of five flights with a two-minute rest in between—I would actually die. “I’m not joking when I advise not to be a hero about it if you haven’t done something like it before,” Frum had ominously warned me before we met.

Instead, he proposed an alternative that was effectively the opposite of smoking weed—would I care to join him for a workout? Exercising with a former Bush administration speechwriter who helped coin the now-iconic term “axis of evil” was an offer that was simply too weird for me to refuse.

Though Frum spends his days decrying Donald Trump and working as an editor for the liberal Atlantic, he’s still a sort of stereotypical Bush-era Republican, a pundit who has penned multiple articles on the dangers on legalizing pot. So naturally, I thought it would be fun to split a joint with him to convince him weed wasn’t actually that bad. I’d tweeted at him a bunch of times about the prospect of getting high together, but he (sensibly) ignored my smug trolling. So when his book editor reached out to me about covering Trumpocracy: The Corruption of an American Republic , his latest polemic on the country’s slow collapse, I once again found myself begging Frum to get high with me.

“I’ve seen accidents here. I’ve gotten into altercations once or twice,” he told me, explaining a feud he got into with a personal trainer who frequents the Exorcist Steps with his clients, and often blocks the way of others. Frum, clearly, is a man who believes in and enforces the rules.

Frum is a fundamentally serious man, and his particular brand of seriousness manifested itself as he briefed me on the rules of the Exorcist Steps, which are usually crowded both with tourists looking to get the perfect picture at the cinematic landmark and athletes who simply want to work out. Frum compared the conflict between two types of visitors the narrow stairway attracts to the Israel/Palestine conflict, in that both groups were entirely unwilling to even recognize, never mind accommodate, each other’s interests. He emphasized that when we got to the bottom of the steps, I was not to immediately turn around to climb back up, but instead walk a couple feet forward before turning around. This was important for safety reasons, he explained.

Although he has consistently been an anti-Trump conservative voice, lefties despise him for fairly understandable reasons. He’s an Iraq War-defending Zionist who is “sad” about the trend of legal cannabis in the US; a George W. Bush–lovin’ Republican who isn’t so sure we should be letting more Syrian refugees into the country. He’s also been welcomed on NPR, CNN, and MSNBC; Trumpocracy has elicited praise from the anti-Trump right but also at least one former Hillary Clinton advisor, the actor Robert de Niro , and Democratic Senator Sheldon Whitehouse . In other words, he’s exactly the sort of establishment figure who drives the revolutionary-minded insane.

As I tried to regain my breath at the top of the steps, unable to wrap my mind around anything aside from taking my next breath, a worry gnawed at me. Am I being too chummy with David Frum? I wondered. In the Trumpian political scene, condemnation is always in the air, and the left is quick to judge anyone deemed problematic. And from a leftist perspective, Frum is certifiably problematic.

My anxiety about death on the Exorcist Steps proved entirely rational. As we descended down the stairs for the first set, I psyched myself into thinking I could do it. Even though I’m not in peak physical condition, I live on a third-floor walkup and generally use stairs in my daily life. But on the steep, steep journey back to the top—after walking a couple feet forward, of course—my breath grew heavier and louder, and I knew I was going to heed Frum’s advice and drop out. “I should really quit smoking,” I said insincerely.

Frum’s critiques of the president echo alarms sounded by political veterans on the center, center-left, and center-right. “Trump is much more of a constitutional problem than he is a political problem,” Frum told me. “It’s about American leadership in the world. The problem with Trump is not just that he has bad manners. The fact that he’s so terribly cruel is obviously a huge disgrace, and makes him a bad person and a bad leader. American institutions were in trouble anyway. This was a moment of vulnerability that would’ve taken a lot of effort by a very wise president to prevent those problems from getting worse.”

Frum is unconcerned with this sort of criticism, and doesn’t think that his status as a right-winger has much to do with his opposition to Trump. “People sometimes say, ‘Well I don’t like your view on the Iraq War, why should I listen to you?’ I say, ‘You don’t have to listen to me.’ I put it on the internet, I put it between covers. Read it or don’t. Don’t ask me why you should,” he told me after our workout.

“Frum is nothing more than a mediocre man with bad opinions, which makes it all the more puzzling how much personal history his benefactors are willing to overlook,” wrote Alex Nichols on the reliably leftist website, The Outline. “Listen to your conscience and not David Frum,” Judd Legum of ThinkProgress suggested on Twitter in September. “There's a particular grotesquerie to welcoming David Frum into the Resistance but the worst part might be that the ‘normal’ right fueled the alt-right,” a Twitter leftist mused .

But despite his strange new existence as a conservative voice of reason among the anti-Trump Resistance, Frum is not a fan of the term, telling me, “I don’t think you get to call yourself ‘the resistance’ unless you’re risking torture [if] you get caught.”

That post about the ACA marked a major break from his conservative allies, and since then Frum, though still a Republican, has come to believe that much of the policies his party champion are obsolete. In Trumpocracy, he wonders, “By August 2017, what was left of the philosophy formerly known as conservatism beyond ‘fuck you, leftists?’”

“Through the debate over Obamacare, I thought the principle of universal coverage was welcome and that Republicans should work on that and offer their own proposals and counter-proposals through the process,” Frum told me. “I’ve written an article [about that] that's caused an outcry. The next morning, I get summoned by the president of AEI, and two days later, I’m out on the street. So I tell people about this, I was just sacked by AEI. And AEI tells people that’s not true, he’s lying, he wasn’t fired. I think I was! 'No you weren’t, we just took away your office and salary. But you weren’t fired.'” (“David Frum resigned,” an AEI spokesperson told the Daily Beast in 2010. The think tank did not immediately respond to my request for comment.)

What sets Frum apart from many anti-Trump conservatives is that he’s been speaking out against his party’s descent into extremism since long before Donald Trump appeared on the political scene. After leaving the Bush administration in 2002—he says he never much liked the work of being a speechwriter—Frum became a scholar at the conservative American Enterprise Institute. In 2010, he left that gig after writing a blog post in which he criticized the Republican Party for not compromising on the Affordable Care Act, a remarkable bit of heresy widely covered at the time in both the mainstream media and blogs.

His main insight is that “the philosophy formerly known as conservatism” was in trouble long before Trump entered the scene. In 2011, he railed against the Tea Party in a post on his now defunct blog, Frum Forum, which he poured his energy into after leaving AEI. “[The Tea Party is] looking for an explanation of the [economic] catastrophe—and a villain to blame,” he argued. “They are finding it in the same place that [Michele] Bachmann and her co-religionists located it 30 years ago: a deeply hostile national government controlled by alien and suspect forces, with Barack Obama as their leader and symbol.”

Liberals may have cheered his bashing of the Tea Party just as they cheer his anti-Trumpism now, but he remains deeply concerned with rescuing, not defeating, the GOP. Over coffee, Frum told me, “I’m very angry with the Republican rule right now, but it remains my world. It’s my world in that I helped to make it the way it is, or at least, I was there, so I feel some obligation to clean up. I’m very worried that the Republican Party has become a party that has lost faith that it can achieve its policy goals by democratic means.”