Imagine, um, imagine pouring your absolute soul
into a novel, you know, putting all your deepest,
most painful insecurities into every single page.
Right. It's a very vulnerable thing. Exactly.
And you publish it and you're completely convinced
you've just written like the great American masterpiece
and then crickets. Just total silence. Yeah.
It barely sells 20 ,000 copies. The critics completely
missed the point. And then, uh, a few years later,
the Great Depression hits. Which really changed
the public's appetite. Oh, completely. The public
actually resents your book because it's all about
rich people drinking champagne. Yeah, they actively
hated it. Right. So you spend your final years
writing these terrible Hollywood scripts just
to pay off debts, drinking yourself to death,
and you die at 44. It's just so sad. It is. You
die entirely convinced you're a monumental failure
and that history is going to... Like, completely
forget your greatest work. It's a profoundly
tragic trajectory, especially when you consider
what actually happened next. Yes, the massive
plot twist, because history had this huge surprise
waiting. Fast forward to World War II. Right?
That same supposedly forgotten book gets printed
on, like this really cheap paper, and handed
out to over 150 ,000 American soldiers. Just
huddled in foxholes across Europe and the Pacific.
Yeah. And the troops absolutely devour it. And
from the ashes of that war, the book rises to
become, I mean, arguably the most famous, most
assigned piece of American literature ever. It's
wild. Today, we're tearing into the glorious,
messy, and frankly, deeply misunderstood tragedy
of the great Gatsby. It's such a crazy phenomenon.
And if you're joining us for this deep dive,
there's a really strong chance you're exploring
this text for a high school or a college literature
class right now. Which is great, but it is incredibly
easy to get distracted by the surface level aesthetics
of the novel. Oh, for sure. The flapper dresses,
the Art Deco fonts. The jazz music, the lavish
parties. It's like the ultimate 1920s mood board.
Precisely. But our mission today is to serve
as your intellectual companion to help you look
past that glittering facade. Because there is
so much more going on. There really is. We're
pulling from a very robust stack of sources today.
Comprehensive historical texts on the 1920s,
really deep biographical accounts of the author
F. Scott Fitzgerald. Right. And of course, some
of the most rigorous literary analysis of the
text itself. So we're really going to deconstruct
the major themes, right? Like the American dream
and social class. Exactly. And we want to ground
this fictional narrative in the very real and
honestly often brutal history of the Jazz Age
and Prohibition. Yeah, we really want to move
way beyond just a simple plot summary here. Right,
we need to dissect the mechanics of why this
tragedy unfolds the way it does and what it reveals
about social hierarchies that frankly still operate
today. Okay, let's unpack this because I want
you the listener to imagine stepping out of a
time machine into 1922. I love this mental image.
Right. So you're standing on the sweeping lawn
of this massive Long Island estate. The champagne
is flowing. The orchestra is roaring. Everyone
looks just completely carefree. But it's an illusion.
Totally. Yeah. Because what you don't realize
is that you are walking through a literal minefield
of invisible social rules, deep resentments,
and like vicious class warfare. Which is the
true core of the book. Exactly. To understand
the tragedy of Jay Gatsby, we can't just look
at the fictional world. We have to look at the
very real world that birthed him. And that means
starting with the man who built the time machine
in the first place, F. Scott Fitzgerald. Yeah,
you really cannot separate the great Gatsby from
the era it was written in. No, you can't. Nor
can you separate it from the psychological baggage
of its author. I mean, we are talking about the
1920s, a decade inextricably linked to the phrase
the Jazz Age. And Fitzgerald actually popularized
that term, didn't he? He did. He published a
short story collection in 1922 literally titled
Tales of the Jazz Age. He was like the ultimate
branding expert for his own generation. He really
was. But let's set the stage historically for
a second. What is actually happening in the American
psyche right now? Like, why is everyone partying
so hard? Well, to understand the manic energy
of the 1920s, you really have to look at the
trauma of the decade prior. Right. World War
I. Exactly. Think about the psychological whiplash
of this era. You have an entire generation of
adolescents and young adults who just witnessed
the old world. literally tear itself apart. Yeah,
the mechanized slaughter in the trenches. Right.
And for decades, they had been told by their
parents, by their institutions, that if they
just followed the traditional rules, you know,
duty, honor, strict Victorian morality society
would progress. And where did those rules actually
lead them? To millions of young men dying in
muddy trenches in Europe. So the prevailing mood
among the youth is basically like, your rules
got our older brothers killed. Why on earth should
we listen to you? That is the exact sentiment.
There is this profound systemic disillusionment.
The younger demographic actively rejected the
prevailing social norms because they just viewed
those norms as morally bankrupt. Makes total
sense when you put it that way. So they turn
to rebellion, self -gratification, hedonism,
and you couple that psychological rebellion with
a massive post -war economic boom. And the sudden
widespread availability of the automobile. Exactly.
Cars changed everything. Plus the explosion of
jazz music. You suddenly have a culture obsessed
with living entirely in the present moment because
the past is traumatic and the future is totally
uncertain. It's a culture running entirely on
adrenaline and borrowed money. And Fitzgerald
is right in the center of it. Oh, he's the epicenter.
But he isn't just taking notes from the corner
of the room. Right. He is living it. His own
life is essentially the rough draft for the great
Gatsby. It absolutely is. So let's look at his
background because it heavily influenced the
DNA of the novel. Fitzgerald is a midwesterner.
Right. Born in St. Paul, Minnesota. Yeah, to
a family that has some social standing, but they're
constantly struggling financially. And that financial
anxiety, that is the absolute bedrock of his
worldview. He always felt like the poor boy in
the rich kid's school. Always the outsider. Exactly.
And he eventually attends Princeton University,
which is, I mean, the ultimate bastion of the
East Coast elite. Which perfectly mirrors the
narrator of the novel, Nick Carraway. Yes. Nick
is also a midwesterner who travels East to attend
an Ivy League school Yale, in Nick's case. Right.
So Fitzgerald is at Princeton. surrounded by
the scions of American industry. The heirs to
massive, massive fortunes. And he desperately
wants to belong, doesn't he? Like, to be in their
exclusive eating clubs and be accepted as an
equal. He does. But he was always acutely aware
that he didn't have their money. He's just pressing
his face against the glass. Yeah. And that feeling
of inadequacy... goes from just a dull ache to
a sharp agonizing stab when it comes to his romantic
life. Oh, his romantic life is pivotal here.
The parallels between his real life and the plot
of Gatsby are almost uncomfortable to look at.
So he's an 18 -year -old student, and he meets
this 16 -year -old girl named Geneva King. Geneva
King is an absolutely crucial historical figure
if you want to understand the psychological engine
of this novel. Tell us about her. Well, she was
a prominent Chicago debutante. We are talking
about the absolute pinnacle of upper class Midwestern
society. Like old money royalty. Exactly. She
was wealthy, sought after, and moved in these
exclusive circles that Fitzgerald could really
only dream of. And he falls completely obsessively
in love with her. I mean, they write these intense,
passionate letters back and forth to each other.
They do. And for a brief moment, it really seems
like she reciprocates his feelings. But then
the reality - of the American class system just
steps right in. It always does. Her family looks
at this kid from St. Paul with no real money,
no concrete prospects, and they just shut it
down. And the sources point to a very specific,
devastating piece of advice that Genevra's father
supposedly delivered to Fitzgerald. Yes. He purportedly
told him poor boys shouldn't think of marrying
rich girls. Ouch. I mean, core boys shouldn't
think of marrying rich girls. You really have
to pause and consider the sheer destructive power
of a sentence like that. Especially on the psyche
of an ambitious, deeply insecure young man. It
completely rewrites his understanding of his
own worth. It does. And Geneva ultimately ends
the courtship and very quickly marries a wealthy,
established Chicago businessman. You know, a
man from her own social stratum. And that rejection
doesn't just hurt. It... permanently damages
him. It lodges like a splinter in his brain.
It's the wound that never heals. Right. And Genevra
King essentially becomes the blueprint for Daisy
Buchanan in the novel. Yeah. She's the golden
girl safe up in her palace, completely inaccessible
to the poor boy who loves her. Exactly. But the
story gets even crazier because Fitzgerald leaves
school. goes to the military during World War
I, gets stationed in Alabama, and lightning literally
strikes twice. He meets Zelda Sayre. Ah, Zelda.
She was a vivacious 17 -year -old Southern belle,
the daughter of an Alabama Supreme Court justice.
Again, very prominent in her local society. Very
prominent and fiercely independent. Fitzgerald
is entirely captivated by her, so he proposes
marriage. And her response is incredibly revealing
about... the pragmatic nature of romance in this
era. It really is. She basically says, I love
you, but no. Or more accurately, she postpones
the engagement specifically because he does not
have enough money to support the lifestyle she
expects. She puts him on layaway, essentially.
Yeah. Until he can prove his financial viability.
It is a highly conditional love. She only agrees
to actually marry him after he proves he can
generate substantial wealth. Watch your ex pulls
off. He does. In 1920, his first novel, This
Side of Paradise, becomes a massive overnight
commercial success. He gets the money and immediately
Zelda says, okay, let's get married. Just like
that. I really want you to think about what that
does to a person's soul. Like, how do you function
in a marriage? How do you look at your spouse
every morning, knowing with absolute certainty
that she only said, I do, because your royalty
check cleared? It's a dark thought. You got the
girl, but you literally had to buy her. And that
creates a profound agonizing ambivalence in him.
On one hand, Fitzgerald achieves the sudden fame
and fortune. He and Zelda become national celebrities
practically overnight. They move into the Biltmore
Hotel in New York City and just start acting
completely wild. Completely. The press follows
them everywhere. They are doing handstands in
hotel lobbies, jumping into public fountains,
riding on the roofs of taxis. Yes. They become
the very embodiment, the living avatars of the
jazz age hedonism they are famous for writing
about. They are basically the 1920s equivalent
of mega influencers. But instead of Instagram,
They're all over the society papers. That's a
great comparison. But this is where I really
need to drill down into something. Because on
the surface, this makes absolutely no sense.
Fitzgerald is the poster boy for the era. He
has the fame, he has the money, he has the beautiful
wife. He won the game. Green won the game. So
how does a guy who is living the ultimate American
fantasy sit down and write a novel that so viciously,
surgically criticizes and dismantles that exact
world? Because he never actually felt like he
belonged. Really? Even with all the money? Even
with all the money, he felt like he was just
renting his status while the people he was partying
with actually owned theirs. The historical texts
are very clear on this point. Fitzgerald deeply
admired the rich. He desperately strived to emulate
their lifestyle. But simultaneously, he found
their behavior, their entitlement, and their
carelessness just morally repulsive. It's a massive
contradiction. It is. He possessed what one of
his biographers famously described as the smoldering
resentment of a peasant toward the elite. Oh,
I love that quote. The smoldering resentment
of a peasant. It's so evocative, he could never
forgive the rich for being rich. It perfectly
captures that feeling of like wanting to burn
down the country club because they wouldn't let
you in. Exactly. And this exact duality, this
consuming desire to possess something that you
simultaneously despise, that is the psychological
foundation of the great Gatsby. It's all starting
to make sense now. Right. Jay Gatsby is driven
to acquire immense, impossible wealth purely
to win back his former fiance, Daisy, who rejected
him because he was poor. It's a mirror image
of his own life. Gatsby's five -year obsessive
quest completely mirrors Fitzgerald's own desperate
need to prove his financial worth to Zelda and,
before her, to Geneva's father. It really makes
you wonder about the... You have the green lights
we chase in our own lives today. Oh, absolutely.
Like the Ivy League acceptance letter, the Tech
Bro startup millions, the perfectly curated aesthetic
on social media. Fitzgerald is essentially warning
us from a century ago. Look, I got everything
I thought I wanted and it felt completely hollow.
The pressure to prove your worth through material
success is a trap. It's a total psychological
trap. But to understand the physical mechanics
of the novel, we have to look at the environment
that allows Gatsby to actually build his fortune.
Right, the economics of the 1920s. Because we
know the parties at Gatsby's mansion are legendary.
Hundreds of people, massive jazz orchestras,
and just endless free -flowing alcohol. Yes,
the alcohol is key here. Right, and here is where
the historical timeline gets very messy. The
novel takes place in the spring and summer of
1922. Now, anyone who knows basic American history
knows that the 18th Amendment went into effect
in 1920. Prohibition. Prohibition. The manufacture,
sale, and transportation of alcoholic beverages
is federally banned. It is the law of the land.
It is. So I have to ask, if alcohol is illegal
everywhere, How on earth is a guy like Gatsby
moving enough liquor to throw a 300 person carnival
every single weekend without the federal government
kicking his door down? There has to be systemic,
massive corruption at play. There has to be.
And there is. That is the great hypocrisy of
the 1920s. Prohibition did not stop America from
drinking. It simply transferred the incredibly
lucrative alcohol industry from legitimate businesses
into the hands of organized crime. It birthed
the speakeasy. Speakeasy culture and a massive
violent underground economy. And this is the
dark underbelly of the novel. Gatsby's mysterious,
seemingly limitless wealth is not inherited from
some noble family. Right, he's not old money.
Not at all. It is derived entirely from bootlegging
and his deep association with the criminal underworld.
So he is a gangster. I mean, a very polite, well
-dressed gangster in a pink suit, but a gangster
nonetheless. Precisely. And Fitzgerald didn't
just pull this out of thin air. He didn't. No,
he based Gatsby's operations on the very real
criminal ecosystem that surrounded him when he
moved to Great Neck, Long Island in late 1922.
Okay, tell me about this because this is fascinating.
The biographical sources highlight a specific
neighbor of Fitzgerald's named Max Gerlach. Max
Gerlach? Yes. Gerlach was a very enigmatic figure.
He purportedly served as an officer in the American
Expeditionary Forces during World War I. And
upon returning, he became a gentleman bootlegger.
A gentleman bootlegger? Yes. He lived like an
absolute millionaire in New York. He threw incredibly
lavish parties, fostered these grand myths about
his own background. What kind of myths? including
a rumor that he was related to the German Kaiser.
Oh, just like the rumor about Gatsby in the book.
Exactly. And he frequently addressed people with
the phrase, Old Sport. Wait, wait, wait. He literally
said Old Sport in real life. He did. Fitzgerald
essentially lifted his neighbor's entire persona
and just dropped it into the manuscript. That
is wild. I had no idea Old Sport was a real guy's
catchphrase. But Gerlach isn't the only real
-life figure smuggled into the book, right? We
have to talk about Meyer Wolfsheim. Yes, Wolfsheim
is crucial. In the novel, Wolfsheim is the shadowy
figure who basically mentors Gatsby. He's the
one who helps him build his illegal empire. And
Fitzgerald explicitly bases Wolfsheim on a real
man named Arnold Rothstein. Arnold Rothstein
was the notorious kingpin of the New York Jewish
mob. A seriously dangerous guy. Very. He was
a pioneer of organized crime, really turning
it from street -level thuggery into a massive
corporate enterprise. And in the novel Gatsby
casually mentions to Nick that Wolfsheim is the
man who fixed the 1919 World Series. Which is
exactly what Rothstein was accused of doing in
real life. Exactly. The famous Black Sox scandal
where members of the Chicago White Sox were actually
paid to intentionally lose the championship.
Let's just pause on that for a second because
fixing the World Series in 1919 isn't just like
regular sports crime. No, it was a cultural earthquake.
Baseball was the ultimate symbol of American
purity and fair play. To rig the World Series
was to fundamentally corrupt the American ideal.
It basically proved that everything, even the
most sacred institutions, was up for sale. It
was a huge loss of innocence for the public.
Right. So Gatsby is surrounded by and entirely
dependent on this massive, corrupt, criminal
enterprise. Which brings up a huge contradiction.
What's that? Gatsby is a bootlegger. He associates
with men who ruin the integrity of the country.
Yet, Nick Caraway... who's supposed to be our
moral compass, and by extension, you know, the
reader, completely falls in love with him. We
do root for him. We totally root for him. Why?
Why do we root for the criminal? Because of his
motivation. Fitzgerald uses Gatsby's criminality
to highlight the deeper moral decay of the so
-called legitimate upper class. OK, how so? Well,
the era was racing along, generating this unprecedented
wealth, but it was utterly lacking a moral center.
Yes, Gatsby is a criminal, he breaks federal
laws, but you have to examine why he breaks them.
His crimes are committed in the singular, obsessive
pursuit of love. He builds an empire of dirty
money for pure reason, to reach Daisy. Contrast
that with the legal wealth of the other characters,
right? Like Tom Buchanan. Exactly. Tom Buchanan's
wealth is inherited. It is entirely legal. But
what does he do with it? Nothing good. He hoards
it out of pure selfishness. He uses it to dominate
others, to buy mistresses, to insulate himself
from the consequences of his own cruel actions.
So the legal money is actually the dirty money
in a moral sense. In Fitzgerald's moral universe,
yes. Gatsby's illegal pursuit of a pure romantic
dream makes him strange. Great. Even compared
to the legal, but morally bankrupt elite who
surround him. It's an incredible paradox. Like,
does the end justify the means? Gatsby clearly
thought that illegal wealth was a perfectly valid
tool if the dream was pure enough. He was a romantic.
A deeply flawed one, but a romantic. He literally
built an illicit empire just to buy a mansion
directly across the bay from the woman he loved
so he could just stare at her dock. It's track.
It is. And that intense tragic yearning brings
us to the beating heart of this entire narrative,
the concept of the American dream and how it
gets warped, corrupted, and eventually destroyed.
The American dream is a massive philosophical
concept with roots tracing all the way back to
the founding of the nation. Right. Life. liberty,
and the pursuit of happiness. At its core, it
is the fundamental belief that anyone, regardless
of their origins, their class, or their station
of birth, can achieve upward mobility and success
through hard work and determination. The ultimate
meritocracy. Yes. It is the promise of the frontier,
the idea that the future can always be forged
into something better than the past. And in The
Great Gatsby, Fitzgerald takes this massive centuries
-old national ethos and condenses it into one
single haunting image, the green light. It's
brilliant symbolism. In the opening chapter,
Nick sees Gatsby standing on his lawn alone in
the dark, physically trembling, reaching his
arms out toward a tiny green light at the end
of Daisy's dock across the bay. It's such a famous
scene. On a literal level, the light represents
Daisy. But symbolically, it represents that ultimate
achievable future. The promise that if you just
stretch your arms a little further, you can grasp
your destiny. But Fitzgerald does something revolutionary
here. In earlier American literature, the dream
was largely optimistic. It was all about pioneers
and self -made men. Rags to riches stories. Exactly.
But Fitzgerald strips the optimism completely
away. He makes Jay Gatsby a false prophet of
the dream. A false prophet. Yes. Gatsby believes
that because he has amassed the wealth, he is
entitled to the reward. But his pursuit results
only in deep existential dissatisfaction because
the goal he is chasing Daisy and the complete
societal acceptance she represents is an illusion.
It's like chasing the horizon. You get in your
car, you see the horizon line out there in the
distance, and you hit the gas. You drive a hundred
miles an hour toward it. But you never reach
it. Never. No matter how fast you drive, no matter
how much ground you cover, the horizon always
stays the exact same distance away. You can never
actually catch it. That's a perfect analogy for
Gatsby's struggle. Gatsby has all the money in
the world, the custom yellow Rolls Royce, the
biggest house, the wildest parties, but he is
still just a man standing in the dark, reaching
out toward a light he can never touch. It forces
us to ask a really difficult question. What happens
when you tie your entire identity, your entire
reason for existing to a goal that is inherently
unachievable? You break down. You do. Gatsby's
ultimate tragedy is his refusal to accept the
passage of time. He is so steadfastly committed
to a youthful, idealized concept of himself and
his memory of loving Daisy five years ago that
he completely rejects reality. Yeah, when Nick
tells him you can't repeat the past, Gatsby genuinely
replies, why, of course you can. He really believes
it. He thinks he can just buy a reset button.
He does. He cannot see the reality of the deeply
flawed, superficial woman Daisy has actually
become, nor can he accept the reality of the
brutal, rigid society she inhabits. He's blinded
by his own dream entirely. The text is saturated
with rampant adultery, broken promises and deceit.
These aren't just scandalous plot devices. They
symbolically represent the total corruption and
loss of faith in the American dream itself. The
dream rotted from the inside out. Exactly. The
1920s took a pursuit of self -improvement and
liberty and mutated it into a shallow, cynical
worship of sheer materialism. It makes you look
at your own goals differently. You know, we all
have a green light, maybe it's a specific career
milestone, a financial number in your bank account,
or like an idealized relationship you're obsessing
over. But Fitzgerald is warning us. Be careful
what you sacrifice to reach it, because the moment
you achieve the fantasy, it instantly turns back
into mundane reality. The chase is literally
the only thing keeping Gatsby alive. That existential
dread is the philosophical core, but we also
have to address the structural reality of the
novel. Right. Because there is a very specific
sociological reason why Gatsby could never achieve
his dream, regardless of his wealth. Oh, the
money was never going to be enough. Never. His
pursuit of the American dream crashes headfirst
into the unbreakable iron wall of social class.
Right, because the mythology of the American
dream tells us that class doesn't matter. It
tells us that meritocracy is real. If you work
hard and get rich, you win the game. You're at
the top. That's the myth. But Fitzgerald says
absolutely not. In this world, getting rich is
only half the battle, and it's the easy half.
The novel maps out this class division geographically.
Which is such a clever literary device. It is.
Long Island is split into two distinct areas
separated by a bay. You have East Egg and you
have West Egg. And this geography is crucial.
East Egg represents old money. These are the
families with inherited wealth, fortunes that
have been established for generations, people
like Tom and Daisy Buchanan. They don't have
to work. No, they don't even talk about money
because they've never had to worry about earning
it. West Egg, on the other hand, represents new
money. The nouveau riche. Exactly. These are
the self -made millionaires, the actors, the
industrialists, and the bootleggers like Gatsby.
They have massive wealth, but they severely lack
the social pedigree. And again, Fitzgerald grounds
this completely in reality. When he and Zelda
moved to Long Island in 1922, they lived in Great
Neck, which was the real life hub for the newly
wealthy Broadway stars, writers, the flashy crowd.
Right. That became West Egg. Directly across
the bay was Port Washington, specifically an
area called Sands Point, which was home to New
York's wealthiest, oldest aristocratic families.
That became East Egg. Art imitating life. Exactly.
So you have these two massive concentrations
of wealth just glaring at each other across the
water. But we cannot forget the third location,
which is arguably the most visually striking
in the entire book. The Valley of Ashes. The
Valley of Ashes. It's so dark. The Valley of
Ashes is the stark, brutal counterpoint to all
the glittering wealth of the eggs. Nick describes
it as a literal refuse dump, a desolate area
where ashes are dumped from the city's coal burning
furnaces. It's an actual place, right? It is.
Historically, this area corresponds to the Corona
ash dumps in Flushing Meadows, Queens. It's where
the working class characters, George and Myrtle
Wilson, live and run a failing garage. And the
imagery is just apocalyptic. Gray men shoveling
gray dirt. It is an environmental and moral wasteland.
The Valley of Ashes represents the devastating
human cost of the wealthy's industrial excesses.
It's the fallout. It is the by -product of the
booming capitalism that makes Gatsby's parties
and Tom's polo ponies possible. It is a physical
manifestation of the working class being ground
into dust to fuel the lifestyles of the elite.
And the elites simply drive right through it
on their way to the city, completely ignoring
the suffering. They literally look right past
it. Which brings us to the architect of that
suffering, the ultimate representative of the
elite. Tom Buchanan. Tom is just awful. He's
the worst. Tom doesn't just ignore the Valley
of Ashes, his entire lifestyle requires it to
exist. Tom is the embodiment of the worst traits
of the old money class. He went to Yale, he's
physically imposing, he is casually cruel, and
he's deeply fundamentally insecure about his
position at the top of the food chain. And that
insecurity manifests in a very dark, historically
accurate way. Tell me more about that. Tom is
explicitly portrayed as a white supremacist.
Early in the novel, he goes on a tangent about
a book he's reading called The Rise of the Colored
Empires by a man named Goddard. Right, at the
dinner party. Yes. He frantically warns the other
characters that the white race will be utterly
submerged if they aren't careful. I want to dig
into this because this isn't just Fitzgerald
making Tom look like a jerk for the sake of it.
This is grounded in a very real, very terrifying
historical movement in the 1920s. Absolutely.
The book Tom references is a direct parody of
a real widely read book from 1920 called The
Rising Tide of Color Against White World Supremacy
by Lothrop Stoddard. Oh, wow. So it was a real
bestseller. Sadly, yes. The 1920s saw a massive
resurgence of nativism, the rise of the Ku Klux
Klan to millions of members, and the popularization
of eugenics. It was a very xenophobic time. It
was. The old money elite, who consider themselves
old stock Americans of Nordic descent, were terrified.
They were terrified of the massive influx of
Eastern and Southern European immigrants, and
they were terrified of the new wealth being generated
by people they considered socially and racially
inferior. They felt their grip slipping. Exactly.
This anxiety culminated in the Real World Immigration
Act of 1924, which severely restricted immigration.
Tom Buchanan's racism is the defensive mechanism
of a ruling class terrified of losing its monopoly
on power. So this fundamentally changes the dynamic
between Tom and Gatsby. I always used to wonder.
Gatsby has a literal palace. He drives a custom
car. He throws parties that the mayor of New
York probably attends. Why does it matter so
much to Tom and Daisy that his money is new?
Because it threatens their entire worldview.
Right. I mean, money spends exactly the same
whether you made it yesterday into Speakeasy
or your great -grandfather made it 50 years ago
in railroads, right? In a pure capitalist system,
yes. But Fitzgerald is illustrating the concept
of class permanence. Class prominence. Yes. In
America, class transcends mere wealth. You cannot
simply buy your way into the upper echelon. Tom
actively belittles Gatsby by calling him a Mr.
Nobody from nowhere. It's like a country club.
Gatsby bought the multi -million dollar house
next to the golf course. He bought the most expensive
custom -made clubs in the world. But Tom and
Daisy are on the membership board, and they are
changing the locks. That is an excellent analogy.
You can buy the gear, but you cannot buy the
bloodline. Exactly. Gatsby's origins are obscure.
His ethno -religious identity is vague. His real
name is James Gatz, implying recent German, perhaps
Jewish immigrant roots. Which Tom would despise.
Exactly. And his money is illicit. He completely
lacks the pedigree of the established elite.
So no matter how astronomically wealthy Gatsby
becomes, he is trapped. He hits a glass ceiling.
He is locked out of the inner sanctum. The American
class system will never ever truly accept him
as an equal. It's an iron wall. And it's a sobering
thought that a century later, that invisible
wall is still standing. It definitely is. Think
about how hidden class systems operate today.
How often are people judged, not by their actual
output, or how hard they worked, or the brilliant
ideas they have, but by where they came from?
By their parents' know. Exactly. What zip code
they grew up in, or whether they have the right
degree from the right university. The game is
rigged from the start. And in the novel, the
pressure of that rigged system is building to
a breaking point. You have a highly volatile
mix. Yeah. Massive amounts of illegal wealth,
a deeply corrupted American dream, and an unyielding
prejudiced class system desperately trying to
maintain its borders. It's the powder keg. It
is a sociological powder keg. And in the novel's
climax, it finally detonates. And what a detonation
it is. The entire narrative collides in a suite
at the Plaza Hotel in New York City. It's the
famous hotel scene. It is a sweltering, unbearably
hot summer day. Fitzgerald uses the oppressive
heat to mirror the suffocating tension in the
room. This isn't just two men fighting over a
woman. This is a literal class war. It is. Tom
finally corners Gatsby, and he doesn't use romance
to win Daisy back. He uses opposition research.
He plays dirty. Very dirty. He brutally, surgically
exposes Gatsby's bootlegging operations to Daisy.
Notice how Tom wins this confrontation. He doesn't
appeal to Daisy's heart. He appeals to her ingrained
need for class security. He scares her. He does.
By exposing Gatsby as a common criminal, a bootlegger,
Tom violently strips away the glamorous facade
Gatsby has spent five years building. He reminds
Daisy that Gatsby is not and never will be one
of them. And Daisy shatters. She completely folds.
Forced to actually choose between the romantic,
deeply unstable fantasy of Gatsby and the cold,
hard, socially acceptable reality of Tom. She
chooses this She retreats to the financial and
social security of her marriage. The dream basically
dies right there in that hotel room. Yeah. But
the tragedy is just getting started. Because
the emotional destruction of the hotel room immediately
spills out into physical destruction in the Valley
of Ashes. Right. Fleeing the city, Daisy is driving
Gatsby's yellow car back to Long Island. Gatsby
is in the passenger seat. They're speeding through
the Valley of Ashes in the dark. It's a lesiped
for disaster. Myrtle Wilson. Tom's mistress who
lives in the ashes has just had a violent fight
with her husband. She sees the yellow car, thinks
it's Tom coming to save her, and runs out into
the road. And Daisy hits her. The description
of the book is brutal. And then Daisy just keeps
driving. She hits a woman and flees the scene.
A hit and run. And Gatsby, still tragically clinging
to his delusion of noble love, decides he will
take the blame to protect Daisy. Which sets off
a horrific chain reaction. Tom arrives at the
scene shortly after. He finds out Myrtle is dead,
and he knows exactly whose yellow car hit her.
He recognizes the car. Yes. But Tom, protecting
his wife and himself, deliberately misdirects
George Wilson, Myrtle's grieving, unstable husband.
Tom points the finger directly at Gatsby. Tom
essentially loads the gun and hands it to George.
He does. George Wilson, a working class man who
has been ground down by the system his entire
life, assumes Gatsby is the man who was sleeping
with his wife and who killed her. So he seeks
revenge. He sneaks onto Gatsby's West Egg estate.
He finds Gatsby floating in his extravagant swimming
pool, waiting for a phone call from Daisy that
is never going to come. George shoots Gatsby,
killing him and then turns the gun on himself.
It is the ultimate searing critique of the wealthy
elite. The tragedy is entirely orchestrated by
class dynamics. Look at who ends up dead on the
lawn. Exactly. The new money upstart Gatsby and
the working class mechanic George Wilson. The
two men desperately trying to climb the ladder
literally destroy each other based on lies and
manipulations fed to them by the established
elite. It's extraction. The old money class extracts
what it wants and disposes of the rest. They
leave everyone else to bleed. Nick Carraway says
it best at the very end of the book. He realizes
that Tom and Daisy are careless people. They
smash up things and creatures and then they retreat
back into their money or their vast carelessness
and they let other people clean up the mess they
made. They are completely insulated. They are
metaphorical hit -and -run drivers through life.
They leave a trail of bodies, pack their bags,
and go on vacation. They walk away completely
unscathed. The system is designed to protect
them at all costs. And the injustice of it is
hammered home at Gatsby's funeral. For an entire
summer, Gatsby's lawn was packed with hundreds
of people. Senators, Broadway stars, mobsters,
socialites. They all wanted a piece of him. They
drank his liquor, ate his food, used his boats,
and when he dies, nobody shows up. It's incredibly
bleak. It's just his elderly father who travels
from the Midwest, Nick, and a few servants standing
in the rain. It is absolutely heartbreaking.
It forces you to look right at the rig system.
It really does. It makes you reevaluate a comment
Daisy makes in the very first chapter. She has
a baby daughter, and she said she hopes the girl
will be a beautiful little fool because that's
the best thing a girl can be in this world. When
you first read that line, it sounds incredibly
cynical, perhaps just the lament of a bored socialite.
Yeah, just rich girl angst. Exactly. But by the
end of the novel, you realize it is a deeply
pragmatic survival strategy. How so? In a world
completely dominated by ruthless, powerful, and
careless men like Tom Buchanan, intelligence
and sensitivity are liabilities. They will only
cause you pain. Ignorance is bliss. Playing the
beautiful little fool is the only way a woman
in Daisy's precarious position, completely dependent
on her husband's wealth and status, can survive
the crushing reality of her own life. It's a
remarkable. bleak assessment of the American
social contract. Fitzgerald is basically saying,
the game is rigged, the dream is dead, and the
people in charge are monsters. It's a very dark
book. It is. And given the sheer depth and brilliance
of this critique, you would naturally assume
that when the book hit the shelves, the world
stopped and applauded. One would assume. You
would think The Great Gatsby was instantly recognized
as a literary masterpiece. But the actual reality
of the novel's publication is almost as surprising
and tragic as the plot itself. Like we mentioned
at the start. Right. When Charles Scribner's
Sons published the book in April 1925, it was
a massive commercial disappointment. It completely
belly flopped. It did. The critics were highly
divided. While some praised Fitzgerald's elegant
poetic prose style, many prominent reviewers
completely missed the thematic depth. They just
didn't get it. H .L. Mencken, one of the most
influential critics of the era, famously dismissed
the book as a glorified anecdote, finding the
plot highly improbable. A glorified anecdote.
That's harsh. And the public agreed with the
critics. By October of 1925, the book had sold
fewer than 20 ,000 copies. To put that in perspective,
his earlier works had sold tens of thousands
of copies almost immediately. Fitzgerald must
have been devastated. He put his entire soul
into this text. The archival letters between
Fitzgerald and his editor, Maxwell Perkins, are
genuinely difficult to read. Fitzgerald was deeply
dispirited. I can imagine. He complained bitterly
that of all the reviews, not a single critic
had the slightest idea what the book was actually
about. They just thought it was about parties.
Right. He hadn't intended it to be a realistic,
journalistic documentary of the jazz age. He
wrote it as a scenic, symbolic romance. He wanted
it to be an artistic triumph, a tragedy. But
the 1920s public who were currently living in
that excess just saw a somewhat implausible,
depressing story about a bootlegger. They were
too close to it. You can't see the hurricane
when you're standing in the eye of it. And then
it goes from bad to worse, because a few years
later, the stock market crashes. The Great Depression
hits. The mood of the country shifts overnight.
Millions of people are out of work, starving
in bread lines. The absolute last thing anyone
in the 1930s wants to read is a book about extremely
wealthy, entitled people drinking champagne on
Long Island and complaining about their lives.
Exactly. The book was totally dismissed as a
nostalgic, irrelevant piece of fluff about a
decadent and irresponsible time that the country
was actively trying to forget. It became a symbol
of the problem. And as the book faded into obscurity,
Fitzgerald's own life mirrored Gatsby's tragic
descent. His career spiraled. His wife Zelda
suffered a series of severe mental breakdowns
and was institutionalized. That is so sad. Fitzgerald
struggled with crippling alcoholism, at times
drinking massive quantities of gin and beer daily
just to function. He ends up moving to Hollywood
to be a script doctor, a job he considered intellectually
beneath him and absolute hated. Yeah. And in
1940, at the incredibly young age of 44, he dies
of a heart attack. So young. And he dies genuinely
believing he is a total failure. He thinks his
legacy is a joke and his greatest book is out
of print and forgotten. I mean, at his funeral,
Dorothy Parker, another famous writer of the
era, looked at his casket and quoted the book
saying, the poor son of a bitch. A tragic end
that Jay Gatsby himself would deeply recognize.
Oh, without a doubt. But as we discussed at the
very beginning, history had a completely different
plan for the novel. The resurrection of the great
Gatsby is one of the most extraordinary events
in publishing history. It really is. And it begins
during World War II. This is the part that absolutely
blows my mind. So we're in the middle of a global
war. The U .S. military and a group called the
Council on Books and Wartime launch an initiative
to boost morale. Right. They decide they need
to boost the morale of the troops overseas. So
they create the Armed Services editions, these
small, cheap paperback versions of various books
designed to fit exactly into the cargo pocket
of a standard military uniform. It was a huge
logistical effort. And out of total obscurity,
the Great Gatsby is selected for the program.
Between 1942 and 1945, the government printed
and distributed roughly 155 ,000 copies of the
novel. A hundred and fifty -five thousand. Yes.
Handed out to soldiers in foxholes, on battleships,
and in field hospitals across Europe and the
Pacific. A book that couldn't sell 20 ,000 copies
to the civilian public is suddenly dropped into
the laps of all these young men facing death.
And the crazy thing is the troops resonated with
it. on a molecular level. It makes perfect psychological
sense when you analyze the demographics. Why
is that? Think about who is reading the book.
Young men who had been pulled from their homes,
sent to a foreign land, fighting for a profound,
idealized concept of America. They were fighting
for a dream. And they read a story about Jay
Gatsby, a young soldier in the previous war who
went off to fight, fell in love, and spent the
rest of his life fighting to get back to the
dream and the girl he left behind. Oh, wow. The
GIs deeply, intimately understood Gatsby's yearning.
Gatsby was one of them. He was a veteran trying
to find his place in a world that had moved on
without him. The novel literally had to outlive
its own era to be fully understood. It needed
distance. In the roaring 20s, it was too close
to reality. In the depressed 30s, it was resented.
It took the crucible of World War II and the
distance of a few decades for the dust to settle.
The veterans returned home, bringing their appreciation
of the novel with them. This groundswell of popularity
coincided with a massive critical reevaluation
in the 1950s and 60s, led by prominent literary
critics like Edmund Wilson. So the critics finally
woke up. They did. They revisited the text without
the prejudice of the 1920s and realized that
Fitzgerald had not written a party manual. He
had written a timeless surgical social document
dissecting the American psyche. It changed everything.
This realization propelled the book into high
school and university curricula across the country,
turning Fitzgerald posthumously into a legendary
figure in the American literary canon. It is
the ultimate vindication, even if he wasn't around
to see it. It really makes you think about how
art or any work really is consumed in its own
time versus how history judges it. Success is
almost never immediate. Sometimes true greatness
requires the context of time to be recognized.
Indeed. The journey of the novel from a discarded
misunderstood manuscript to the great American
novel is a testament to the enduring universal
power of its themes. Absolutely. But as we wrap
up our analysis today, there is one final almost
surreal piece of the book's production history
that perfectly encapsulates everything we've
discussed about illusion and reality. Yes. Okay.
This is my favorite piece of trivia about the
book. Long before the book was published, Fitzgerald
really struggled with the title. He was very
indecisive. He hated the title The Great Gatsby.
He was throwing around crazy titles like Tremolchio
and West Egg, which is a super obscure reference
to a crude, wealthy upstart from ancient Roman
literature and under the red, white and blue.
Both terrible titles, frankly. Awful. His publisher
finally had to force him to stick with The Great
Gatsby. But the title isn't the craziest part.
It is the iconic dust jacket art of the very
first edition. If you have ever seen an original
copy or even a modern reprint of the first edition,
you know the image immediately. It's unforgettable.
It is a painting titled Celestial Eyes, created
by a Barcelona artist named Frances Cugat. It
features a flapper's disembodied, profound Losat
eyes and bright red lips hovering in a dark blue,
almost bruised looking sky. And below the eyes
is a glittering neon carnival landscape that
looks like Coney Island. It is haunting. It is
arguably the most famous celebrated book cover
in American literature. But what makes it truly
unique isn't just the aesthetic. It is the timeline
of its creation. Cugit designed, painted and
finished this cover. before Fitzgerald had actually
finished writing the novel. Which is highly unusual
in the publishing industry. Usually the art department
waits for the final manuscript to interpret the
author's vision. Right. But here, the art came
first. Fitzgerald was shown Cugat's early sketches
for the cover before he sailed to France to write
the final chapters of the manuscript. And he
loved it. He was utterly blown away by the imagery.
These massive, floating, melancholic eyes staring
down over a wasteland. He wrote a panicked letter
to his editor, Maxwell Perkins. He explicitly
demanded that Perkins not give the cover art
to any other author because, as Fitzgerald wrote,
for Christ's sake, don't give anyone that jacket
you're saving for me. I've written it into the
book. It is a brilliant, undeniable instance
of art imitating art. It really is. The famous,
haunting eyes of Dr. T .J. Eckelberg, the faded
optometrist's billboard that watches over the
Valley of Ashes like an uncaring, commercialized
god, were not originally in the plot. That is
just crazy to me. They were likely inspired directly
by the book's own promotional cover art. The
physical imagery of the object became a central,
highly symbolic element of the narrative itself.
I want you to really sit with that mind -bending
reality for a second. The image used to sell
the book literally created the substance of the
story inside the book. It's a perfect metaphor.
In a novel that is entirely 100 % about the dangers
of projecting false images and chasing illusions.
From Gatsby's completely fake, meticulously constructed
background to Daisy's hollow projection of perfection
to the entire facade of the American dream, the
book itself was fundamentally shaped by a projected
image. It perfectly blurs the line between the
reality we live in and the reality we construct
for others to see. Exactly. So as you close your
textbook or pull into your driveway or go about
the rest of your day, We'll leave you with a
challenge. A final thought. Think about Francis
Kugit's painting. Think about Gatsby staring
at the green light. And ask yourself, how much
of your reality is being shaped by the images
you were trying to project to the world? Are
your goals actually yours? Right. Are you living
your truth? Or are you just exhausting yourself
trying to match the cover art of the life you
think you were supposed to have? It is a profound
psychological question. It is the question that
Fitzgerald grappled with his entire agonizing
life, and it is the question that Jay Gatsby
died trying to answer. Because those invisible
rules of that 1922 Long Island party, the desperate
need for status, the illusions we build to survive,
they are perhaps not so invisible or so ancient
after all. They are right here with us. Thank
you for stepping into the time machine and joining
us on this deep dive. We hope this exploration
into the history of the author and the brutal
realities of the Jazz Age gives you a completely
new lens through which to view this classic.
Keep reading and keep questioning the systems
around you. And remember, don't let the green
light blind you to what is actually right in
front of you.