The "What Would Hunter S. Thompson Say?" Trap

Over 50 years ago, in his 10,000+ word Playboy interview, Hunter warned us that Nixon was a symptom, not an accident. It’s time to stop looking for ghosts to save us and start looking in the mirror.

I usually try to stray away from writing about politics, mostly because it’s not a lane the organization I represent online tends to be particularly proficient in these days. But it’s a subject I, like any patriotic citizen, care deeply about, if only because it frames so much of the reality we have to wade through in our day-to-day republic.

I actually had two other drafts ready to go for this week, but I can’t bring myself to publish them. One is on internet business stuff, like I usually write about here on Substack, and the other is about a grand travel adventure I went on when I was 20 years old, back in the spring of 2006, when the world felt a little lighter. I think they’re both pretty clever, but I’ll publish them later. To run them now would be to ignore the reality of the moment, and we have a terrifying talent for returning to business as usual in this country; it’s the only way we know how to survive the things we refuse to fix.

But on Saturday morning, the news out of Minnesota made looking away impossible: the state-sanctioned murder of Alex Pretti. He was a VA nurse who witnessed federal agents shove a woman to the pavement. He didn’t attack them; he just held his phone up, stepped forward, and asked the woman, “Are you okay?” For that act of basic humanity, after seeing a holstered gun he was lawfully carrying, an ICE agent put six rounds in him. All on the heels of the murder of Renee Good.

Lately, being clever feels like a “cheap parlor trick”, in the parlance of Thompson, from what’s really on my mind. To do so would be a profound inability to read the room or address its ten-ton elephants.

So I’m writing this instead; mostly just to think out loud, trying to process the fact that absolutely none of this makes sense. All of it: Alex Pretti. Renee Good. Charlie Kirk. I think a lot of us feel that way right now about political violence, and the air in the national climate is too heavy for witticisms about the online content business and travel stories. I’m mad as hell about how we even found ourselves in this mess where so many lives are being recklessly ended, and I suspect a lot of you are too.

In times like this, when the machinery of the state grinds up a human being, someone we look at and think, “Wow, Alex looked like me; he seemed to act honorably, he was patriotic, he acted the way I hope I would act in the moment,” on a frigid Saturday morning in front of a donut shop, and then asks us to applaud the efficiency, I inevitably see the same question bubbling up on Hunter S. Thompson subreddits and other corners of the internet where his name is invoked. It’s a question that haunts the discourse, well-intentioned but ultimately futile:

“What would Hunter S. Thompson say about this?”

This is an honest and well-intended question. It is completely benign.

But…

Hunter has been gone for two decades now, and many still treat him like a counter-culture Magic 8-Ball. Shake him up, look into the aviator shades, and hope for a distinct, acid-soaked revelation that makes sense of the senseless.

Here is the hard truth: We have no fucking clue what he would say. And frankly, I’m not sure we’d want to know. It is an exercise in futility to try to channel the dead to explain the sins of the living.

However, while we can’t know what he would say, we know exactly what he did say about the machinery of American power. There are countless texts to go deep on, some more obscure than others, and I really encourage people to mine what Hunter said about the political stakes of another generation to form a framework for the present.

I take great comfort in that wisdom. But to find it, you have to stop looking for pithy insults or the caricature of the drug-addled outlaw. Having read more Hunter S. Thompson interviews than is probably healthy (a requirement of a job I once had), I can tell you that watching journalists try to “out-cool” him by fixating on his vices is exhausting. It’s a boring and distracting performance art. When you strip that away and engage with his actual analysis of power in the United States, the picture gets a lot darker. And a lot more useful for the present.

The Man Who Watched the Resignation

To understand the present, I keep going back to November 1974.

I spent a lot of time with this specific era while working on a book called Ancient Gonzo Wisdom when I was in college in 2007-2008, and afterwards at Owl Farm in Woody Creek, Colorado, working with Hunter’s widow, Anita Thompson.

I was Anita’s research assistant on the project. I threw everything I had at it. It was the very beginning of my career, and I was desperate to prove myself—not just to Anita, but to the legacy of a man whose work I believed needed to be preserved in academic libraries for future scholars and American literary nerds, like myself.

One thing that stands out from that time was trying to secure the rights to Hunter’s Playboy interview with Craig Vetter, a brilliant Chicago journalist who I believe was actually with Hunter in Washington, D.C., the day Nixon resigned.

Craig died in his sleep back in 2017, and I think it’s important we remember him a little bit here, because he was a hell of a writer and interesting person in his own right. To a fault, we often don’t give enough credit to hard-working writers like Craig, who documented larger-than-life personalities like Hunter Thompson and, in a way, contributed to the public persona and myth-making.

Craig was noted as a “constant motion machine,” an erudite, quick-witted man who was a risk-taker par extraordinaire. He cut his teeth at the University of San Francisco in the 1960s, where he famously tried to abolish student government by plebiscite, earning him the eternal animosity of the Jesuits, and went on to be the first Staff Writer for Playboy. He earned his adventure credentials doing a series of dares: wing walking on a biplane, climbing ice falls, and surviving an Acapulco cliff dive that made him view his own mortality in a different light.

I can’t really say I knew him other than a handful of emails, but his obituary remembers him as a “complicated guy, “an enigma wrapped in a riddle,” born Peter Simmons but renamed after his father was lost on the USS Longshaw in WWII. When I asked Craig for a brief bio for Ancient Gonzo Wisdom back in 2009, he included that he was working on a memoir about his father. I’m not sure if he ever finished it.

According to his obit, he fueled his work on a “writer’s diet” of cigarettes, coffee, and scotch, and even typed his daredevil manuscripts on Hunter’s old typewriter, the same one used for Hell’s Angels. You can understand why he and Hunter ran around with each other, I believe going back to when Hunter was working on Hell’s Angels in the late 1960s about the infamous Bay Area motorcycle gang.

Craig’s obit notes he was the kind of guy who could write about anything—from oil rig roughnecking in Wyoming to the death of Dean Potter—with a voice that made biting criticisms palatable through humor and sarcasm. He and Hunter had a 35-year friendship, and when Hunter died, Craig penned a unique eulogy called “Surviving Hunter S. Thompson.” He was a “marrying man” who finally found serenity late in life with his wife Barbara, and if you want to tweak him one last time in the heavens, have a Catholic Mass said for him by a Jesuit—the entertainment value alone would be priceless.

Back when we were working on the book, Craig was, shall we say, “stubborn” about the rights to that 1974 interview. He held onto them like a man protecting a rare isotope, presumably because he knew it was a brilliant framing of the post-Watergate moment. I believe he knew he had captured Hunter’s brilliance in observing a system in decay after a period of brilliant writing. I believe he understood the weight of those words in the context of history. The interview in Playboy was a brilliant secondary text to understanding the intent behind Hunter’s work.

Craig ultimately came around, wanting to be part of the anthology after speaking with Anita, but that friction stayed with me. It reminded me that these weren’t just tossed-off rants; they were hard-won observations from two men who lived on the edge of the American century. The result is a deep, contentous, and collaborative conversation between friends, though that context is largely missing from the Playboy interview itself.

In fact, speaking of context, the circumstances of that interview were manic. I recall reading somewhere (it might have been in Rolling Stone founder Jann Wenner’s memoir, though my memory is fuzzy) that Craig and Hunter were actually together in D.C. on the day Nixon finally quit. I really liked that tidbit when I first heard it: A lot of interviewers asked Hunter about where he was and what he was thinking when Nixon resigned, but the guy that got the most out of him was the fellow journalist he happened to be with.

What is certain is what happened nine days later. In his intro to the piece, Craig describes a scene of absolute desperation: the two of them locked in a penthouse full of mirrors on the 20th floor of an Astor Street high-rise in Chicago, with tornado warnings screaming outside. Craig sets the scene, writing that Hunter had snapped the neck off a lamp and was bent over a coffee table, cursing, mumbling that the motor control in his pen hand was failing. Nixon’s resignation had, in Craig’s words, “torched the entire second half” of the manuscript they’d spent seven months working on.

I don’t believe that “manuscript”, at least if it was in the form of a book, has ever seen the light of day, and I really hope it does some day. It is wild to think about how much unpublished Hunter S. Thompson writing might be out there from an era when we didn’t have the cloud to save things on.

“When this is over,” Hunter told him, “I’m going back to Colorado and sleep like an animal.”

It was from that wreckage, tired, drunk, weak, and seeing ghosts, that they finalized the text for a legendary 10,000+ word Playboy interview. The country was exhaling, but they were suffocating. Against the weary, jaded delirium that comes from too much time inside the Beltway, Vetter asked the question that everyone asks in 2026, deep in the second Trump presidency:

“Is politics going to get any better?”

This is the meat of it.

This is the part that stops being a history lesson and starts being a prophecy. Hunter’s answer was devastatingly precise, and it explains exactly why we are where we are today.

HST: Well, it can’t get much worse. Nixon was so bad, so obviously guilty and corrupt, that we’re already beginning to write him off as a political mutant, some kind of bad and unexplainable accident. The danger in that is that it’s like saying, “Thank God! We’ve cut the cancer out... you see it?... It’s lying there... just sew up the wound... cauterize it... No, no, don’t bother to look for anything else... just throw the tumor away, burn it,” and then a few months later the poor bastard dies, his whole body rotten with cancer.

Read that again. “Just throw the tumor away, burn it.”

We made this mistake. We looked at the first Trump term, and when it ended, we treated it like an aberration. We treated him like a “political mutant,” a bad accident that we had survived. We thought that because the man was gone from the White House, the cancer was gone from the body politic. We sewed up the wound without looking for anything else, despite the many ways that cancer had spread from January 6th onward.

But as Hunter warned us fifty years ago, the presidency is never an accident.

HST: I don’t think purging Nixon is going to do much to the system except make people more careful. Even if we accept the idea that Nixon himself was a malignant mutant, his Presidency was no accident. Hell, Ford is our accident. He’s never been elected to anything but Congress... But Richard Nixon has been elected to every national office a shrewd mutant could aspire to: Congressman, Senator, Vice President, President. He should have been impeached, convicted and jailed, if only as a voter-education project.

If only as a voter-education project.

We failed that class, and we failed it spectacularly. And because we didn’t learn, because we treated the symptom rather than the disease, the “poor bastard”—the entire American experiment—is now visibly rotting with heated rhetoric and a post-truth cancer that clouds our aspirations. And it’s immorally taken lives, all in the name of some grander, greater agenda that most of us can’t make a lick of sense of.

History is always messy, but it feels like we are seeing the results of that rot in real-time. The murders of Alex Pretti and Renee Good, and the entire ICE occupation of Minneapolis, are a horrifying echo of Kent State, when the Ohio National Guard fired 67 rounds into a crowd of unarmed college students protesting the invasion of Cambodia, killing four and wounding nine.

We are living in a moment where, once again, to our horror, the abstract violence of policy becomes the physical violence of the state against its own citizens, executed on a sidewalk in front of a donut shop. And just like in 1970, the powers that be reacted nearly instantaneously. Instead of pausing to examine the facts of the incident or taking a beat for self-reflection, there was a near-instantaneous justification to spin a horrible situation into a narrative. The propaganda machine screamed an arc that demanded we reject the evidence of our own eyes, gaslighting us all despite the clear bystander videos from the murder scene. It moved with the cold, mechanical indifference of a system that knows it is immune to consequences because we, the voters, keep signing the permission slips.

Fellow Substack writer Kevin Driscoll recently dug up a term Hunter used back in the chaos of the 2000 election that fits this moment with terrifying precision: “The New Dumb.” What Hunter means here is worse than ignorance. It’s pure cockiness and contempt for common decency. It is a certainty that feels no obligation to explain itself.

The Nation of Used Car Salesmen

This “New Dumb” is enabled by the people who consume it. The mistake people make is thinking Hunter was only obsessed with the power-hungry villains of the American political system—the Nixons, the Trumps, the Hoovers. He didn’t fear the man in the White House half as much as he feared the people who put him there.

In Fear and Loathing: On the Campaign Trail ‘72, specifically in the entry for September, while reflecting on the electorate as it became clear Nixon was going to crush McGovern, Hunter wrote something that chills me more than any horror movie. This was later excerpted in The Great Shark Hunt because of its brilliance about Nixon 2.0:

“This maybe the year when we finally come face to face with ourselves; finally just lay back and say it—that we are really just a nation of 220 million used car salesmen with all the money we need to buy guns, and no qualms at all about killing anybody else in the world who tries to make us uncomfortable.”

I used to think about that quote all the time 20 years ago when I first encountered it, in the context of what I believe was America’s Imperialist agenda and quest for oil in the George W. Bush era, during the Iraq and Afghanistan wars that took so many lives of enlisted millennials from the post-9/11 era.

Crazy how that quote applies to 2026 too.

Hunter was just trying to say, I think, that we aren’t victims of a political accident. We are looking in the mirror, warts and all, and a lot of us don’t like what we see. The “main characters” of our Republic are just projections of the American psyche. It is grim and ugly. Often, it’s hopeful and beautiful, but right now, looking at the news, it is mostly ugly. It leaves too many friends and families of fallen heroes asking “for what?” as they try to make sense of their loss.

Alex Pretti didn’t die just because of a rogue policy; he died because we are a nation that has decided, collectively, that our comfort and our leader’s posturing for power over us is worth more than human life.

Voices of Now

So, stop asking what Hunter would say. The question itself is a flimsy, projecting thought exercise; a ghost story or fantasy at best.

The lesson from that 1974 interview isn’t that we need a new Gonzo journalist to save us. Personally, I cringe when I hear someone being lauded as “the next Hunter S. Thompson,” because it’s usually just shorthand for “someone who performs the vices without doing the homework.” It mistakes the substance abuse for the substance, and misses the relentless, grinding work ethic that actually made his prose sing.

The lesson is that waiting for the “system” to self-correct is a suicide pact. The only people who fix anything are the ones working the “lonely outside edges.”

But if I’m being honest, I don’t entirely know what that work looks like right now, besides showing up at the polls. The rot is deep, the complications are endless, and the feeling of helplessness is often suffocating. I don’t have a roadmap for fixing a nation of used car salesmen. I don’t have a simple three-step plan to dismantle the ‘New Dumb.’

All I know is that we don’t need ghosts or a cover band to figure it out. We can miss his voice, but we also need to be the voices of now. We start by refusing to let mental gymnastics, whataboutisms, and official gaslighting pour more diesel on the flames. We start by collectively acknowledging that what happened on that sidewalk was ghastly, and refusing to look away.

If we don’t, and if we surrender to the helplessness, we know exactly what the epitaph will say: Here lies a nation of quitters.

---