Welcome back to the Deep Dive. Today, we are
focusing our lens on a writer who, well, who
basically believed the only way to get to the
truth was to ditch objectivity completely. Hunter
S. Thompson. That's right. This is our deep dive
into the American journalist, the author, who
really transformed himself, didn't he? From,
you know, a journeyman writer into this huge
literary phenomenon. His career ran from the
late 50s right up until he died in 2005. Yeah.
And Thompson, he's really more than just a writer,
isn't he? He's like an explosion in the history
of reporting. He often gets grouped with those
pioneers of the new journalism movement. Right.
The 60s and 70s crew. Exactly. People like Gay
Talese, Truman Capote, Norman Mailer, Joan Didion,
Tom Wolfe. They all started using, you know,
novelistic techniques, dialogue, getting really
deep into the story in ways that, well, newspapers
just hadn't done before. It was all very dry,
very objective back then. New journalism itself
was a huge shift, wasn't it? Treating factual
reporting like it could be high literature. But
Thompson, he didn't just join that movement.
He sort of detonated it from within. Totally.
He replaced that idea of the neutral, detached
reporter with this figure he called the raving
beast. And that really brings us to our mission
today, doesn't it? We want to unpack that journey.
How did he get from standard journalism, relatively
speaking, to creating this massive gonzo myth?
Exactly. That's what we're digging into. We're
looking at how his writing style evolved, that
iconic style. We'll trace his pretty ferocious
political activism, too. And maybe most importantly,
analyze that constant tension in his life. The
blurring line, which eventually just got erased,
between Hunter S. Thompson, the man, and his
chaotic alter ego, Roald Duke. Okay, and right
at the heart of all this, you have to talk about
gonzo journalism. So if new journalism meant
getting closer, getting more literary, what was
gonzo? Gonzo is. It's radical subjectivity cranked
up to 11. If you think about new journalism,
say, Tom Wolfe, right? He was all about being
the meticulous fly on the wall, observing, documenting,
reconstructing things with incredible detail,
like a novelist. Okay. Thompson, though, he specialized
in being, as he put it, the fly in the ointment.
The gonzo journalist doesn't just watch the chaos
unfold. They dive right into the middle of it.
They become a central participant, often fueling
the story through, well, their own chemical intake,
their emotional state, their deliberate interference,
frankly. So the writer isn't just shaping the
story anymore. The writer is the story. Precisely.
The whole idea behind Gonzo is that you can only
truly understand a really chaotic situation by
embracing that chaos completely. And Thompson's
work, it defined this, especially those two big
ones that sort of bookend his peak Gonzo period,
Hell's Angels in 67. Which showed how far he'd
go, right? Risking his own safety. Absolutely.
Total immersion. And then, of course, the big
one, Fear and Loathing in Las Vegas in 1972.
That's the book that really codified the style,
solidified the whole myth. OK, let's unpack that
then. How did Thompson, the journalist, the guy
we know was studying Fitzgerald's sentence structure,
how did he morph into this iconoclast, this old
Duke figure? Let's start back in Louisville,
Kentucky, where the chaos began, maybe? Hashtag
two to five. The formative years and the apprenticeship
of chaos. Well, he was born there in 1937, came
from a middle class family initially. His father,
Jack Thompson, was a public insurance adjuster,
a World War I veteran. So a pretty solid conventional
background to start with. But that stability
didn't last long, did it? The sources really
highlight how his father's death affected him.
Thompson was only 14. Yeah, his father passed
away at 58 from myasthenia gravis. It's a neuromuscular
disease. And that loss, you can see how it just
fractured the stability of his youth. His mother,
Virginia, she was the head librarian at the Louisville
Free Public Library. And the sources mentioned
she became a, quote, heavy drinker after her
husband died. So you have this picture of a stable
kid suddenly thrown into instability. He has
to grow up fast, maybe looks for structure elsewhere.
And then immediately, dramatically rejects that
structure. Yeah, that pattern seems to define
his whole early relationship with authority,
doesn't it? You see it right away with his education.
He went to Louisville Male High School. And,
you know, despite everything that came later,
he was actually quite literary. He was in the
Athenian Literary Association, which was apparently
quite elite. But that didn't end well either.
No, it ended pretty violently in 1955. Yeah,
this was a huge turning point. He got kicked
out of the Athenian for criminal activity. Specifically,
he was charged as an accessory to robbery. He
was in the getaway car, got a 60 -day sentence,
served about 31 days in the county jail. And
that conviction meant he couldn't graduate high
school. You can't really overstate how much that
first real run -in with the legal system must
have fueled his later, you know, absolute contempt
for the establishment. And losing those academic
credentials, that directly pushes him towards
his next big institution, the military. He enlists
in the Air Force right after getting out of jail.
Served from 55 to 58. And even there, inside
the strict military structure, the chaos, it
finds him or he finds it. He lands his first
proper writing gig by basically lying about his
experience. Bluffed his way into being the sports
editor for the command courier newspaper at Eglin
Air Force Base. Just made up his qualifications.
Amazing. And the Air Force cottoned on pretty
quickly, it seems, based on his discharge papers.
Oh, yeah. They recommended him for an early honorable
discharge. And the reasons are just pure Thompson
because he, quote, will not be guided by policy.
OK. And even better, his, quote, rebel and superior
attitude seems to rub off on other airmen. It's
like they saw the future coming. That document
basically predicts his entire career as this
radical troublemaker. So after the military,
does he settle down, find a steady job? And really,
the pattern continues. He gets a job as a copy
boy for Time magazine in New York. Fired. Insubordination.
Of course. Then he lands a reporting job at the
Middletown Daily Record in New York State. Fired
again. This time for damaging a candy machine
during an argument. A candy machine? Yeah, and
then arguing with a local advertiser who paid
the bills. He just couldn't hold down a conventional
job. But... And this is crucial, isn't it? During
all this chaos, this getting fired, he's actually
building the foundations. We focus on the drugs
and the drama later, but gonzo journalism doesn't
come from nowhere. It's built on serious literary
craft. You mentioned he was typing out Fitzgerald
and Hemingway. Yes, this is so important and
often gets overlooked. While he was at time,
getting fired, he was literally retyping pages
from The Great Gatsby and A Farewell to Arms.
Why? Just to feel it. Exactly. He wasn't just
reading them. He was physically copying the prose
to absorb their rhythms, their sentence structures.
Fitzgerald, you could argue, taught him about
that big, sweeping, sort of melancholic narrative
you need to tackle something like the failure
of the American dream, which becomes central
to fear and loathing. And Hemingway. Hemingway
taught him the opposite, maybe. Economy, precision,
using those hard, concrete details, which, ironically,
Thompson would later use brilliantly to anchor
his wildest, most subjective flights of fancy.
So it's this weird apprenticeship, learning grand
narrative structure from one and clipped precision
from the other. A real mix. Yeah. And all this
time, he's moving around constantly, right? Gathering
experiences, avoiding being pinned down. He goes
to San Juan, Puerto Rico in 1960 for a magazine
job that folds almost immediately. He ends up
stringing for different papers. Then California.
Then 1961, Big Sur. works for about eight months
as a security guard and caretaker at a place
called Slate's Hot Springs. This was just before
it became the famous Eastland Institute. It was
a real B -generation hangout. Henry Miller lived
nearby. Thompson's soaking up that whole bohemian
counterculture vibe. And he starts getting published
a bit. Yeah, his first published fiction, a story
called Burial at Sea, appears in Rogue magazine
around this time. And then there's that classic
anecdote that shows his unique blend of tribute
and sheer audacity. The 1964 trip to Ketchum,
Idaho. To Hemingway's place. Exactly. He went
there supposedly to write about Hemingway's suicide.
And while he's there, as this sort of morbid
souvenir, or maybe it was an act of aggressive
homage to the writer he'd studied so intensely,
he steals a pair of elk antlers right off the
wall above the front door of Hemingway's cabin.
Wow. He didn't just write about his hero's death.
He took a physical piece of the legacy. Pretty
much sums him up, doesn't it? That kind of appropriation.
But the real breakthrough, the first proper deep
dive that set the course for his career, that
was the Hells Angels. Right. The nation commissions
him in 65. Yeah, to write about the Hells Angels
motorcycle club. And this is where the immersion
really kicks in. He doesn't just interview them
politely. He lives with them, rides with them
for a whole year. He's living near Haight -Ashbury
in San Francisco, literally across the street
from the Grateful Dead's house, right in the
thick of the emerging counterculture. And that
level of getting inside must have fundamentally
changed how he saw journalism. But the sources
say the relationship didn't end well. No, it
was built on a kind of shaky truce, wasn't it?
Mutual exploitation, maybe. The biker started
feeling like he was going to make a fortune off
them and demanded a cut of the book profits.
And it got violent. It's extremely violent. The
whole thing ended with Thompson getting what
he called a savage beating, basically a stomping.
It happened when he apparently tried to step
in and stop a biker from beating his dog and
then his wife or girlfriend. So his commitment
to the story ended when his own maybe warped
moral code clashed directly with his subjects.
He didn't just report the violence. He experienced
it. Yeah, it confirmed the risks of that extreme
immersion. But the book that came out of it,
Hell's Angels, published in 1967, was a huge
success, critically and commercially. The New
York Times loved it. Called it angry, knowledgeable,
fascinating, and excitedly written, said the
prose, crackles like motorcycle exhaust. So he'd
proven he could deliver this immersive, high
-stakes journalism. But the experience itself,
the beating, maybe convinced him that the reporter
couldn't pretend to be separate anymore. Their
perspective had to be central. Hashtag tech three,
the peak Gonzo years, 1970, 1973. Exactly. And
the money from Hells Angels, especially the paperback
rights, that's what allowed him to buy Owl Farm,
his place in Woody Creek, Colorado, that famous
fortified compound. His base of operations. Right.
And moving there coincided with his real acceleration
in his political views. The late 60s, the chaos
of that era, really radicalized him. The 1968
Democratic National Convention in Chicago seems
key here. He was there, saw the police riots,
the clashes with protesters. Oh, absolutely.
He claimed that experience fundamentally changed
how he saw authority, politics, everything. He
put it very bluntly. I went to the Democratic
Convention as a journalist, he said, and returned
a raving beast. The idea of being impartial just
seemed ridiculous after that. Impossible, yeah.
The system to him was clearly rigged, violent,
and he felt only an equally beastly response
in journalism could actually capture that reality.
Which leads us straight into 1970 and his run
for sheriff of Pitkin County, Colorado. The Freak
Power Campaign. This wasn't just a stunt, was
it? It was serious political theater. Totally
serious, yeah. It was a genuine attempt to take
power locally and expose the hypocrisy he saw
in Aspen, the gentrification of the establishment.
And the platform itself was, well, it was pure
Thompson. What were some of the planks? Okay,
so you had drug decriminalization, but only for
personal use, not trafficking. which was incredibly
progressive for 1970. Then there were these really
specific, almost bizarre, local ideas. Yeah.
Tear up the paved streets in Aspen and replace
them with grassy pedestrian malls. Seriously?
Yeah. Ban tall buildings that block the mountain
views. Disarm the police force. Give them mace
instead of guns. And the kicker, rename Aspen
Fat City. to actively discourage developers and
unwanted wealth from coming in. It was this amazing
fusion of counterculture ideals with really pragmatic,
if radical, local policy. And he played the image
game brilliantly, too, didn't he? The bald head.
Oh, classic Gonzo move. He shaved his head completely
bald white so he could constantly refer to the
Republican incumbent who had a traditional crew
cut as my long -haired opponent. Yeah. Just flipping
the script, messing with expectations. Did he
come close to winning? He actually won the vote
within the city of Aspen itself. but lost the
wider county vote. He later felt that the article
he wrote about it for Rolling Stone, the Battle
of Aspen, actually backfired. It gave the opposition
too much notice, allowed them to mobilize against
him. So the campaign itself created the perfect
storm for his style to really crystallize. And
the definition arrived almost immediately after,
also in 1970. With the piece, the Kentucky Derby
is decadent and depraved, published in a magazine
called Scanlon's Monthly. And the story behind
this one is legendary, right? Deadline pressure.
Extreme deadline pressure. He was apparently
completely blocked, couldn't write a conventional
piece about the race. So in total desperation,
he just started tearing pages out of his notebook,
raw notes, observations, fragments, and sent
those to the editor. And that desperation turned
into innovation. Completely. The finished article,
it barely mentions the horse race. Instead, it's
all about the scene around the race. Yeah. The
grotesque drunken revelry, the sheer decadence
of the wealthy spectators. And he juxtaposes
all that with a political background of the time,
the Nixon bombing Cambodia, the Kent State shootings
just happening. Sounds like a lightning strike.
It was. Another journalist, Bill Cardoso, read
it and immediately wrote to Thompson. He said,
this is it. This is pure gonzo. If this is a
start, keep rolling. And the name just stuck.
It meant journalism that wasn't about objective
facts, but about the reporter's internal reality,
their psychic experience of the event. And crucially,
that piece also marked the beginning of his long
collaboration with the illustrator Ralph Steadman.
Yes. Steadman's art was the perfect visual match
for Thompson's prose. That wild, expressionistic,
sometimes really savage style. He used lipstick,
eyeliner, splattered ink. It just captured the
manic energy, the visual chaos that Thompson
was describing. And that partnership leads directly
into his most famous work, Fear and Loathing
in Las Vegas, which incredibly started as a tiny
assignment. Almost unbelievable, isn't it? Sports
Illustrated asked him for a 250 -word photo caption
to go with pictures of the Mint 400 motorcycle
race in the desert outside Vegas. And he sent
them. He sent him 2 ,500 words of pure hallucinatory
chaos. Sports Illustrated unsurprisingly aggressively
rejected it. I bet they did. But Jan Wenner at
Rolling Stern, he saw the genius in what Thompson
called the jangled pages. He ran it in two parts,
serialized it. And that book just exploded Thompson
into the mainstream consciousness. It follows
these two trips to Vegas with his lawyer, Oscar
Zeta -Acosta. The basis for Dr. Gonzo. Right,
his 300 -pound Samoan attorney. But underneath
all the drug -fueled mayhem, the book's actually
doing something quite serious, isn't it? It's
not just a drug memoir. Not at all. It's Thompson
wrestling with the failure of the whole 1960s
counterculture dream. Vegas becomes this symbol
of where that dream went to die, replaced by
crass commercialism and, well... fear and loathing.
He's searching for the high watermark of the
60s, realizing it's long gone. The New York Times
got it. They called it the best book yet written
on the decade of dope. But maybe his greatest
journalistic achievement using this gonzo method
came right after that. Fear and loathing on the
campaign trail 72, taking on a presidential election.
Yeah, this was Winner's idea, really. The voting
age had just been lowered to 18, and Rolling
Stone wanted to, as Winner put it, politicize
our generation. They wanted an inside account
of the 72 election, something like those popular
Making of the President books by Theodore H.
White. But Thompson delivered something completely
different from White's respectful insider view.
Oh, totally different. Instead of White's careful,
objective... Thompson gave them a narrator full
of contempt, paranoia, and fueled by God knows
what chemicals. The literary critic Morris Dickstein
had a great line about it. He said Thompson had
learned to approximate the effect of mind -blasting
drugs in his prose style. The writing itself
felt like the frantic, wired energy of the campaign.
And this is where we get that famous description
of the book, right? The ultimate gonzo paradox.
Exactly. Thompson covered the Democratic primaries.
McGovern, Muskie. Humphrey all vying to take
on Nixon. And Frank Mankiewicz, who was George
McGovern's campaign director, described Thompson's
collected Rolling Stone dispatches as the most
accurate and least factual account of the campaign.
Let's dig into that. Most accurate and least
factual. How can it be both? He was making stuff
up, wasn't he? Like the Muskie drug rumor. He
absolutely was. He floated this rumor that Ed
Muskie, who was a leading Democratic contender
at the time, was secretly addicted to Ibogaine,
this obscure psychedelic drug. There was zero
evidence for it. It was a fabrication. So why
do it if it wasn't true? Because. In Thompson's
view, the factual reporting coming from the mainstream
press was failing miserably to capture the real
atmosphere of that campaign. The paranoia, the
dirty tricks, the sheer desperation felt by those
trying to stop Nixon. He felt the so -called
objective truth that Muskie was probably a decent,
if maybe slightly boring guy, was actually misleading.
It didn't convey the emotional reality of politics
in 72. So the lie about Ibogaine, bizarre as
it was, somehow felt truer to the insane spirit
of the times than the actual facts did. That's
a Gonzo argument, yeah. He believed that conventional
facts, especially those presented by the establishment
media, were often the biggest lies of all because
they sanitized reality. Gonzo With its strategic
use of invention and hyperbole was his antidote.
It aimed for a deeper, visceral truth, even if
it meant bending the literal facts. It's an incredible
tight rip walk. And that period, roughly 1970
to 73, it's just an explosion of creativity.
But that kind of intensity. It can't last, can
it? Let's talk about what happened next. The
decline when the persona started to take over.
Hashtag, hashtag, bye. The consequences of fame
and the blurred persona. Yeah, the years right
after campaign trail 72, they mark a pretty clear
downturn. A tragic one, really. His actual literary
output, the new stuff, it just drops off a cliff.
And pretty much everyone, friends, editors, the
sources we have, they point to one major factor.
His escalating drug use. Particularly cocaine.
He started using cocaine around 1973. Around
then, yeah. And people close to him, like Jan
Wenner, his editor at Rolling Stone, they noticed
a devastating impact on his discipline, his ability
to focus, his actual creativity. Wenner said
something quite stark about it, didn't he? About
Africa. He did. He said, after Africa, he just
couldn't write. And Africa refers to that 1974
assignment Thompson had to cover the rumble in
the jungle. The huge heavyweight fight in Zaire
between Jordan Foreman and Muhammad Ali. And
what happened there? Well, it's almost a perfect
sad illustration of how the Gonzo model collapsed
on itself. The whole point of Gonzo is immersion
participation, right? Being there. But Thompson.
He got so messed up, so intoxicated back at his
hotel that he completely missed the fight itself.
He missed the rumble in the jungle. Missed the
whole thing and never filed a story. The persona,
the lifestyle required to be gonzo combined with
the drug dependency, it just overwhelmed his
ability to actually do the journalism anymore.
The chaos consumed the reporting. And that wasn't
an isolated incident, was it? Vietnam the next
year. Same pattern. 1975, Rolling Stone sends
him to cover the fall of South Vietnam, an absolutely
monumental historical event. And as Saigon is
collapsing, Thompson basically flees the country.
Refuses to file a proper dispatch. Another huge
assignment. Another failure to deliver. Winter
mentioned he sent something back. Yeah, Winter
later clarified Thompson did send an unfinished
dispatch, but said he spent most of his time
in Saigon completely obsessed with his own evacuation
plans, not actually reporting on the fall of
the city. The irony is just painful. His main
souvenir from covering the end of the Vietnam
War was apparently this custom -made brass door
plaque he'd ordered for his hotel room. What'd
it say? Rolling Stone, Global Affairs Suite,
Dr. Hunter S. Thompson. It's like the symbol
of his importance, the artifact, became more
real, more tangible than the journalism itself.
And that plaque kind of perfectly symbolizes
the whole problem, doesn't it? This persona he
created, Raoul Duke, this wild, drug -addled,
self -destructive journalist, it was now completely
out there in the public mind. It was starting
to overshadow the actual man, Hunter Thompson.
Oh, completely. He deliberately created Raoul
Duke, but the creation definitely started running
the show. Thompson himself knew it, too. He talked
about it quite openly in interviews. What did
he say? There's a BBC interview from 1978 where
he says, I'm never sure which one people expect
me to be. Very often they conflict. I'm leading
a normal life and right alongside me there is
this myth and it is growing and mushrooming and
getting more and more warped. The public wanted
the caricature right and the caricature needed
constant fuel. Which links back to the substance
abuse. Wenner tried to help him, didn't he? Offered
to pay for rehab. He did. Wenner was genuinely
worried, both for Thompson as a friend and for
his career, but Thompson refused the help. Why?
Did he think he didn't have a problem? Worse
than that, really. His reasoning was this kind
of dark, artistic fatalism. He honestly seemed
to believe that the drugs, the chaos, were essential
to his talent. He said it was a key to his talent,
and that without it, he'd just have the mind
of an accountant. He saw the dysfunction not
as a bug, but as a necessary feature of his genius.
That's tragic. So heading into the 80s and 90s,
the major new works dry up. Pretty much. A lot
of what got published in that era were collections
of earlier pieces compiled into those gonzo papers
volumes, like The Great Shark Hunt or Songs of
the Doomed. Good stuff, but mostly retrospective.
Did he attempt big new projects? He did. He spent
a lot of time researching a book about feminist
pornography. For Playboy, of all places. It was
supposed to become a novel called The Night Manager,
but it never got finished. He was still drawn
to extreme subjects, but maybe the focus, the
discipline to see a huge project through just
wasn't there anymore. He did have that newspaper
column, though, for the San Francisco Examiner.
Yeah, a weekly media column. And his editor there
had a fantastic description of Thompson's late
period output. He said the column swung wildly
between acid -soaked jubberish with a charm of
its own and... incisive political analysis of
the highest order. You just never knew what you
were going to get. The signal to noise ratio
was unpredictable. So let's circle back to the
actual style of Gonzo writing. You mentioned
he wasn't like the other new journalists, meticulously
reconstructing scenes. Right. He said he almost
never tried to reconstruct things after the fact,
unlike, say, Tom Wolfe or Gay Talese, who were
obsessed with getting dialogue and timelines
exactly right. Thompson's goal was different.
Tom Wolfe had a good take on it, didn't he? Yeah,
Wolfe described Thompson's style as part journalism
and part personal memoir and mixed with powers
of wild invention and wolverine rhetoric. It
was this hybrid thing. Narrative reliability
wasn't the point. Emotional impact, rhetorical
velocity, that was the goal. Which must have
been an absolute nightmare for his editor. Oh,
you bet. Fact -checking Thompson. One editor
called it a trip through a journalistic funhouse.
They constantly had to figure out, OK, where
does reality end and where does the riff, as
they called it, begin? So how did they publish
anything under the banner of journalism? What
stopped it from just being fiction? This is the
last really fascinating piece of the puzzle,
the final paradox of his method. While the overall
story, the sequence of events, might be completely
embellished or even fabricated, the concrete
physical details within that fabrication were
often meticulously accurate. He was apparently
a total stickler for numbers. for details like
gross weight and model numbers, for lyrics and
caliber. So he'd get the make and model of the
car exactly right, or the specific type of gun,
or the lyrics to a song playing on the radio.
Even if the entire scene happening around those
details was completely invented. Exactly. He'd
anchor these wild, sprawling, chemically fueled
narratives to these little islands of hard, verifiable
fact. He gives the whole thing this weird, unsettling
feeling of authority, of journalistic credibility,
even when you suspect it's mostly bullshit. It's
a really clever, subversive technique. Hashtag
tag V, political legacy, final days, and spectacle
funeral. And underpinning so much of that writing,
especially the best stuff, was his politics,
that fierce, lifelong iconoclasm. Absolutely.
And central to that, always, was Richard Nixon.
Thompson's hatred for Nixon was just monumental.
He saw Nixon as representing, quote, that dark,
venal, and incurably violent side of the American
character. That obituary he wrote for Nixon in
94. Oh, he was a crook. Published in Rolling
Stone, it's still one of the most savage, vitriolic
pieces of political writing you'll ever read
in a mainstream publication. It's brutal. But
his politics weren't simple left -wing, were
they? They were more complex, rooted in this
deep sense of individual liberty, like his stance
on guns. That's a key point, and it confuses
people who only see the druggie counterculture
image. Thompson was a lifelong firearms enthusiast,
owned a lot of guns, loved explosives, and he
was a fierce defender of the Second Amendment.
He believed it was crucial against government
power. Exactly. He saw the right to bear arms
as a fundamental check on state tyranny. This
might surprise a lot of people. He was actually
a member of the National Rifle Association, the
NRA. Wow. So how do you square that? The guy
railing against the white power structure and
hanging out with the counterculture, but also
an NRA member? I think it all stems from this
bedrock distrust. of any centralized authority,
whether it's the government trying to take your
guns or the police conducting illegal searches
or corporations polluting. It was all part of
the same oppressive system to him. Which explains
his work on the Fourth Amendment, too. Precisely.
His support for the Second Amendment came from
the same place as his passion for the Fourth
Amendment protection against unreasonable search
and seizure. He even co -founded an organization,
the Fourth Amendment Foundation, specifically
to help people who had been victims of illegal
searches or police abuse. He saw it all as connected.
Protect yourself from the state. And he put that
belief into action later in his life, didn't
he? With the Lizzle Amman case in Colorado? Yes.
That was a really significant late career intervention.
Lisa Laman was this woman in Colorado who got
sentenced to life for felony murder, even though
she wasn't even present when her accomplice shot
a police officer. It's based on these really
extreme accomplice liability laws. And Thompson
got involved. He took up her cause passionately,
wrote about it, organized public support, helped
raise money for illegal defense. It showed he
still had that power to mobilize people, to focus
attention on injustice. Did it work? It did.
Although Thompson died before the final ruling,
her sentence was eventually overturned not long
after his death. And many people directly credit
the pressure and the spotlight he put on the
case for that outcome. So guns, privacy. And
drugs, of course. He was always a huge advocate
for legalization. Oh, yeah. Served on the advisory
board for NORMLNL, the National Organization
for the Reform of Marijuana Laws, for over 30
years. And his argument wasn't just let people
get high. It was pragmatic, anti -authority.
He said legalize drugs across the board. He drew
the comparison to alcohol prohibition. Saying
it just makes criminals rich. Exactly. Criminalization,
he argued, just empowers illegal markets and
gives the state more power to interfere in people's
lives. You also see hints of other influences
in his politics, Marxist ideas. Yeah, he definitely
criticized white power structures. He expressed
real affection for the old radical labor union,
the industrial workers of the world, the IWW
or Wobblies. He even said he agreed with Karl
Marx on certain things. It's this unique blend,
isn't it? Hard left social critique mixed with
this almost extreme right libertarian focus on
individual freedom and distress to the state.
Very hard to pigeonhole. And that skepticism
never waned, did it? Even after 9 -11? Not at
all. He was actually one of the first prominent
voices to publicly express doubts about the official
story of 9 -11. He speculated in interviews that
the U .S. government might have been involved
somehow, though he admitted he didn't have concrete
proof. For Thompson, the default setting was
always deep suspicion of power no matter what.
Living life at that pitch, with that level of
intensity, paranoia, chemical intake, it takes
a toll. His final years sound like they were
marked by a real decline. They were. He was dealing
with chronic health problems, had a painful hip
replacement. He often talked about feeling old,
bored, told friends things like, this kid is
getting old. There was a sense of obsolescence,
maybe. And his death itself, February 20th, 2005,
age 67, self -inflicted gunshot wound at Owl
Farm. The details are just bleak. Incredibly
bleak. His wife, Anita, whom he'd married just
a couple of years earlier, she was actually on
the phone with him when it happened. She said
later she heard him cock the gun, but thought
it was the sound of his typewriter keys. Oh,
God. And his grandson and daughter -in -law were
apparently in the next room. They heard the shot
but thought it was just a book falling off a
shelf. The sheer, terrible banality of the end
is such a stark contrast to the spectacle of
his life. He left a note, didn't he? Football
season is over. Yeah. It's short, brutal, and
gives a pretty clear window into his mindset.
It read, No more games. No more bombs. No more
walking. No more fun. No more swimming. 67. That
is 17 years past 50. You are getting greedy.
Act your old age. Relax. This won't hurt. It
sounds like an artist just finally rejecting
an existence that wasn't giving him the intensity,
the fun he felt he needed. But even in death,
Thompson couldn't resist one last massive gonzo
performance. The funeral. Oh, the funeral was
pure Thompson. The $3 million spectacle, apparently
paid for entirely by his friend Johnny Depp,
who'd played him, well, Raoul Bouc, on screen.
And the main event. The ashes. His ashes were
loaded into fireworks and fired from a giant
cannon at a private ceremony at Owl Farm, August
20th, 2005. And the cannon wasn't just any cannon,
was it? It was on top of that tower. Exactly.
A 153 -foot tower shaped like that iconic Gonzo
symbol, the double -thumbed fist clutching a
peyote button. The same symbol he'd used for
his freak power sheriff campaign back in 1970.
It was literally building a monument to the persona.
So it wasn't just a funeral. It was a final piece
of performance art. Totally. Complete with fireworks
red, white, blue, and green exploding to the
soundtrack of Norman Greenbaum's Spirit in the
Sky and Bob Dylan's Mr. Tambourine Man. And the
guest list was pure Thompson, too. Politicians
like Senators John Kerry and George McGovern
rubbing shoulders with actors like Jack Nicholson
and Bill Murray. It was the perfectly choreographed
final act, transforming his suicide into spectacle,
ensuring his last dispatch was pure, 100 % gonzo.
And the legacy, it definitely lives on. People
still talk about him, still read him. Absolutely.
Tom Wolfe, who was stylistically very different,
still called Thompson the greatest American comic
writer of the 20th century. And that Raoul Duke
persona, it's echoed in characters like Uncle
Duke in the Doonesbury comic strip. or Hunter
Gathers in the animated show The Venture Bros.
And there are scholarships now, too, right? In
his name. Yeah, his widow, Anita, set them up.
One supports U .S. military veterans studying
at Columbia University, which feels fitting given
his own military background. And another helps
journalism students at the University of Kentucky.
So his legacy is also about supporting future
writers, especially maybe those coming from conventional
paths, like Thompson himself did. Hashtag TagsEP.
Outro and final thought for the listener. So
wrapping this up, what's the big takeaway from
this deep dive into Hunter S. Thompson? For me,
it really throws that central tension of his
life into sharp relief. On one hand, you have
this incredibly successful revolutionary effort
to make journalism subjective, artistic, that
most accurate and least factual approach. But
on the other hand, there's the constant. ultimately
fatal struggle to keep any distance between the
journalist doing the work and the extreme self
-destructive persona he seemed to need to create
that work. Yeah, I think that's exactly it. Thompson's
work, it really forces you to think about deep
immersion, about skepticism towards authority.
His legacy, maybe, is showing us that the reporter
Their biases, their feelings, their own chaos
isn't just part of the story. It's unavoidable.
Yeah. Especially when you're covering times like
his of huge political and cultural upheaval.
He basically turned the writer's perspective
into a weapon. OK, so we'll leave you, our listener,
with a final thought to chew on. We've talked
about Thompson, the iconoclast, the fierce defender
of the Second Amendment gun rights, the co -founder
of the Fourth Amendment Foundation fighting illegal
searches. He had this deep. almost paranoid hatred
of centralized power and surveillance. Right.
So how would Hunter S. Thompson, the man who
demanded absolute personal privacy and freedom
from the state, how would he view our world today?
This hyper digitalized age with constant tracking,
facial recognition, data harvesting, the balance
between freedom, technology and privacy now?
Yeah, that's a great question. Would the guy
who stole Hemingway's antlers be out there championing
encryption, waging war on big tech surveillance,
seeing it as the ultimate big brother nightmare?
Or would the sheer complexity and sort of overwhelming
nature of modern digital control just paralyze
the raving beast? Would he find himself unable
to even file a dispatch on a world that's maybe
become too weird, too controlled, even for Gonzo?
Something to think about as you navigate the
modern noise. That's all for this deep dive.
We'll see you next time.