You know, when we talk about a historical tragedy,
usually we mean a bad ending, a dream that gets
crushed, maybe a lost war, a premature death.
Right. Something that stops the story before
it's finished. Exactly. But with the figure we're
looking at today, Simon Bolivar, the tragedy
isn't that he failed. The tragedy is that he
completely succeeded. He did exactly what he
set out to do. He broke an empire. He liberated
an entire continent. And then he had to just
sit there and watch it all fall apart. It's the
ultimate be careful what you wish for story.
I mean, we're looking at sources today that paint
this picture of a man who is, you know, arguably
the most successful military leader of the entire
19th century. The scale is just staggering. It
is. He liberated a territory five times the size
of Europe. And yet, if you read his final letters,
they read like the diary of a man who believes
he just wasted his entire life. That one line
from his last days, it just haunts me from all
the reading. He said, All who have served the
revolution have plowed the sea. Plowed the sea.
Yeah. I mean, just imagine that. It suggests
total, absolute futility. It's a devastating
image. And to understand how someone goes from
being hailed as the liberator to feeling like
he's just plowing the ocean, we have to kind
of dismantle the caricature. Right. Because in
the English speaking world, we love to call him
the George Washington of Latin America. Which
as soon as you look at the details, that comparison
just falls apart, doesn't it? It completely does.
I mean, Washington went home to his farm. He
left behind a pretty stable country, all things
considered. Believer died basically in exile,
hated by half the people he freed with his grand
project, this united continent just burning to
the ground. His path was so much more. Volatile.
Volatile, authoritarian, romantic, and tragic.
All at once, we're talking about the man responsible
for the independence of, what, six countries
today? Bolivia, Colombia, Ecuador, Panama, Peru,
and Venezuela. An incredible list. But our mission
today isn't just to list the battles. We really
need to figure out how a wealthy orphan becomes
a revolutionary general and why that dream of
a united South America collapsed. And honestly,
we have to grapple with the darkness in his character,
the ruthlessness. OK, so let's start with that
wealthy orphan part, because the economic scale
here is it's just mind blowing. This isn't your,
you know. gentry class of the 1700s. Oh, no,
not even close. Simon Bolivar was born in Caracas
in 1783, and he was born into what they called
the Mantuano class. Okay. The Bolivars were one
of the richest families in the entire Spanish
Americas. They owned copper mines, vast cacao
plantations, huge herds of cattle. He was a Criollo.
which means he was of Spanish descent but born
in the Americas. Right. But in terms of actual
resources, he probably had more money than most
European princes. But all that money, it doesn't
buy you a childhood. I mean, the timeline of
loss here is just brutal. His father dies of
tuberculosis when Simon is only two. And then
his mother dies of the same disease when he's
nine. So before he even hits his 10th birthday,
he's the master of this massive fortune. And
for all intents and purposes, he's completely
alone in the world. He really is. And this is
where we have to look at who actually raised
him. It wasn't his uncles who were more interested
in the inheritance. It was the enslaved people
of the household. Specifically, a woman named
Hippolyta. Exactly. Hippolyta. He called her
mother and father, didn't he? He did. He later
wrote that she was the only parent he truly knew.
And I think we have to keep that in our back
pocket for later. Because when Bolivar eventually
turns against slavery, and it's an imperfect
turn, but he does, it's not just some abstract
Enlightenment idea he read in a book. It's personal.
It's a polita. Okay, but he's still a rich, unruly
kid in this rigid colonial society. His legal
guardian, his uncle Carlos, he basically doesn't
know what to do with him. Right. He finds him
completely unmanageable. So he hands him off
to a tutor. And this isn't just some guy who
comes to teach him math and Latin. This is Simon
Rodriguez. And Rodriguez is a key figure in this
whole story. One of the most important. He was
a radical, a total eccentric. He was a devotee
of Jean -Jacques Rousseau, the French philosopher.
And Rousseau had this idea from his book, Camille,
that you shouldn't lock kids in classrooms. You
should teach them through nature, through exercise,
you know, through the real world. So you have
this scene, this incredibly wealthy heir and
his radical tutor just, what, running through
the Venezuelan countryside? That's literally
it. Swimming in rivers, climbing mountains, sleeping
under the stars. And all the while, Rodriguez
just... pumping this kid's head full of ideas
about liberty, the rights of man, the corruption
of European society. He's basically building
a revolutionary from the ground up, whether he
knows it or not. But then the script sort of
flips back to the more traditional rich kid path.
At 16, Bolivar is sent off to Europe to finish
his education, rub elbows with the Spanish aristocracy.
And this leads to what might be the biggest what
if moment of his entire life. The romance in
Madrid. He meets Maria Teresa Rodriguez del Toro.
And she is, by all accounts, the girl of his
dreams. She's aristocratic. She's beautiful.
She connects him to the Spanish court. He's totally
smitten. They fall madly in love. He's 18. She's
20. They get married in 1802. And if the story
stops there. Simon Bolivar is just a footnote
in a history book. He's a wealthy planter who
lives out a comfortable life in Caracas. He actually
said that himself later, didn't he? He did. He
said if he hadn't been widowed, he might have
been, you know, the mayor of his local town.
But tragedy strikes again. They move back to
Venezuela. And within eight months, Maria Teresa
contracts yellow fever. Eight months. She dies
in January 1803. And he's just 19 years old.
He's already lost his father, his mother, and
now the love of his life. The grief is just.
Total. He swears an oath on her grave never to
remarry. It's a promise he actually keeps, despite
having many, many lovers later on. But more importantly,
her death just creates this massive, agonizing
void in his soul. He has all this energy, all
this passion, all this pain, and now there's
nowhere for it to go. So he runs. He goes back
to Europe, not to study this time, but just to
escape. And this is where he runs smack into
history. He's in Paris, 1804. And he's living
the high life, spending money like water, sleeping
around, just trying to numb the pain. But he's
also watching the rise of Napoleon Bonaparte.
The man of the hour. The obsession of the age.
And Bolivar sees him as this fascinating paradox.
On the one hand, he just admires the glory, the
power. He's physically there in Milan when Napoleon
is crowned king of Italy. He sees the crowds,
the energy, the sheer capacity of one man to
change the entire map of Europe. But he hates
the crown. He hates the crown. He sees Napoleon
as a traitor to the French Revolution. Napoleon
took the ideals of liberty, fraternity, and equality
and turned them back into a monarchy. So Bolivar
is wrestling with this huge contradiction. How
do you get the power to change the world without
becoming a tyrant yourself? And this all culminates
in that famous scene, the oath on Montesacro.
It feels like something out of a movie, but it
really happened. It did. He's in Rome with his
old tutor, Rodriguez, who finds him there. They
climb the Montsacro, the Holy Mountain. It's
a hot day. And Bolivar, apparently just overcome
with emotion, he falls to his knees. And he swears
the oath. He swears, I will not rest body or
soul until I have broken the chains binding us
to the will of Spanish might. It's pure melodrama,
but it's real. And it sets the trajectory for
the rest of his life. The timing couldn't have
been more perfect either, because just a few
years later, Europe completely implodes. Napoleon
invades Spain in 1808. He kidnaps the Spanish
king, Ferdinand VII, and he puts his own brother,
Joseph Bonaparte, on the throne. The catalyst.
This is the catalyst. Because suddenly, all the
Spanish colonies in America are asking themselves
a very dangerous question. Who are we loyal to?
Right. And this is a really nuanced point in
the sources. The Criollos in Venezuela, they
form a junta in 1810, but they don't say, down
with Spain. No, not at all. They say, we are
ruling in the name of our beloved King Ferdinand
VII. The Mast of Ferdinand. It was a brilliant
political move. They claimed they were just protecting
the colony for the rightful king against the
French usurper. But in reality, it was the first
taste of self -rule. And once they had that taste
of autonomy, there was no going back. So Bolivar
dives in. He goes on a diplomatic mission to
London to try to get British support. And on
his way back, he picks up the old guard revolutionary
Francisco de Miranda. Oh, Miranda is a legend,
a total legend. He'd fought in the American Revolution,
the French Revolution. He knew Catherine the
Great in Russia. He was the precursor. And Bolivar
convinces him to come back to Venezuela and lead
the army. But this first attempt at independence,
what they call the First Republic, it's a complete
disaster. A total failure. And it's not just
because of the army. It's nature itself. The
earthquake of 1812. You honestly could not write
this in fiction. People would say it's too heavy
handed. On Maundy Thursday, the holiest week
of the Christian year, a massive earthquake just
flattens Caracas. And the really unbelievable
part is that it only destroyed the cities held
by the Republicans. Exactly. It left the royalist
cities almost untouched. I mean, that is a theological
weapon for the royalist priests. It was everything.
They stood in the rubble and preached that this
was God punishing the people for rebelling against.
their divinely appointed king it just broke the
psychological back of the revolution troops deserted
the whole thing crumbled and this leads us to
what is for me the most controversial moment
in bolivar's early career the betrayal of miranda
the simple version of the story is that miranda
surrendered and bolivar was disgusted but when
you look at the timeline it's It's much darker
than that. It is much darker. Miranda, seeing
the chaos and the bloodshed, signs a capitulation
with the Spanish to end the fighting. Bolivar
and his young officers see this as treason. But
when Miranda goes to the port of La Guardia to
get on a ship and escape. Bolivar arrests him.
He and his associates arrest their own commander
in chief. They lock him in a fort. And then they
hand him over to the Spanish. They do. Miranda
ends up dying in a dungeon in Cádiz, Spain, years
later. But here's a crucial detail that often
gets left out. The Spanish commander, Monteverde,
granted Bolívar a passport to leave the country
only after he handed Miranda over. So it looks
like a transaction, a quid pro quo. He traded
his commander's life for his own safe passage.
It's the moment the romantic idealist dies and
the pragmatic, ruthless politician is born. Historians
still debate it, you know, was it justice against
a traitor or was it a young officer saving his
own skin so he could live to fight another day?
Probably a bit of both. It's almost certainly
both. So Bolivar escapes to Cartagena in what
is now Colombia. He's exiled, he's defeated,
he's broke, but he doesn't quit. He writes the
Cartagena Manifesto, he analyzes all his failures,
he gets a new army, and he invades Venezuela
all over again in 1813. The admirable campaign.
And this is where the violence really shifts
gears. We have to talk about the decree of war
to the death. Guerra Muerte. I've read the text
of this, and it is just chilling. He basically
says to the Spaniards, even if you are neutral,
you will be put to the sword. Only if you actively
work for our independence will you live. And
on the flip side, to the Americans, the South
Americans, he says, you will be spared even if
you are a traitor. He is drawing a hard, bloody
line in the sand. What is the strategy there?
I mean, on the surface, it just sounds like pure
bloodlust. It wasn't bloodlust. It was psychological
warfare. He realized that most people were just
sitting on the fence. They didn't see themselves
as Venezuelans or Spaniards. They were just subjects
of a distant king. So he needed to force an identity
on them. He had to create a national identity
by force. He had to make it impossible to be
neutral. You were either a patriot or you were
dead. It was destroying that middle ground to
try and build the nation. And it worked. At first,
he retakes Caracas. He's given the title El Libertador.
But the Second Republic falls apart just as quickly
as the first. And this time, is because of the
Llaneros. The Llaneros. These are the cowboys
of the Orinoco Plains. Incredibly tough, mixed
-race horsemen who basically lived in the saddle.
And they were fighting for the Spanish. They
were. They were led by a royalist warlord named
José Tomás Boves, who was, by all accounts, a
clinical sadist. Boves convinced the Llaneros
that the independence movement was just a rich,
white, Criollo conspiracy to take power for themselves.
Which, to be fair, at that point, it kind of
was. It absolutely was. So the poor plainsmen
fought for the king against the rich Republicans,
and they just decimated Bolívar's forces. The
stories of Boves' cruelty are... They're horrific.
So Bolivar is forced to flee again. This time
he ends up in Jamaica in 1815. And he has absolutely
nothing. No army, no money, no country. This
is his lowest point, but it's also his most intellectual
moment. He sits down and writes the Jamaica letter.
And we really need to slow down here because
his analysis in this letter basically dictates
the next 15 years of South American history.
He compares Latin America to the United States,
right? He does. And he argues that the U .S.
federal system, where you have strong states
and a relatively weak central government, would
be a death sentence for South America. Why? He
argues that because the Spanish Empire kept the
people in total ignorance and tyranny for 300
years, they lacked the civic virtues needed to
handle pure democracy. That sounds incredibly
elitist. The people aren't ready for freedom.
Oh, it's hugely elitist. But he would argue it's
realistic. He believed that if you gave absolute
freedom to a fractured, uneducated populace that's
used to being ruled, you wouldn't get a republic.
You'd just get anarchy. So he wants a strong
hand. He wants a strong, centralized executive.
A benevolent dictator, in a sense, to hold the
chaos together until the people are ready for
the responsibilities of freedom. So he's got
the theory, but he needs money. He needs guns.
And the only country in the world willing to
help him is the one everyone else is terrified
of. Haiti. The Republic of Haiti. the first free
black republic in the world, born from a slave
revolt. A pariah state at the time. A total pariah.
Bolivar travels there and meets President Alexandre
Pechon. And this is just a beautiful historical
transaction. Pechon agrees to give Bolivar ships,
money, and weapons. But there's a price tag.
Not money. Pechon's condition is simple. He says,
I will give you all this, but you must promise
me one thing. You will abolish slavery in all
the lands you liberate. And Bolivar agrees. He
agrees. And, you know, realistically, he had
to. He had finally understood that he couldn't
win this revolution if the majority of the population,
the enslaved people, the mixed race Pardos, had
no stake in it. He realized he had to make the
war about freedom for everyone, not just for
the rich Creoles. So he returns to the mainland,
1817. He sets up a new base in the Orinoco jungle,
a town called Angostura. He finally convinces
the Llaneras to join his side this time. But
this new diverse coalition brings its own tensions.
And this brings us to General Manuel Pierre.
Pierre was one of his best generals. One of his
absolute best. He was mixed race, very charismatic,
hugely popular with the troops. And he started
challenging Bolivar's authority, basically claiming
that Bolivar was still just serving the white
elite. And Bolivar's response is extreme. He
has Pierre arrested. court -martialed for insubordination,
and executed by firing squad. Wow. Why? Why kill
one of your best commanders? It was a message.
A brutal message. Bolivar was terrified of a
race war. He saw what happened in Haiti, and
he feared that the revolution would fracture
along racial lines which would destroy everything.
So this was about control. It was about absolute
control. By executing Pierre, he was telling
everyone in his army, there is one leader here.
I don't care if you're white, black, or mixed.
If you break the chain of command, you die. It
consolidated his power, but it was another dark
stain on his conscience. So with the army now
united by this combination of fear and loyalty,
he makes his craziest move yet, the crossing
of the Andes in 1819. And, you know, we hear
crossing mountains and we might think of a tough
hike. We need to really paint the picture of
what this actually looked like. It's almost unimaginable.
First, it's the middle of the rainy season. So
the plains leading to the mountains are flooded.
The army marches for weeks through waist -deep,
leech -infested swamps. Before they even get
to the mountains. Before they even see a mountain.
Then they start to climb. And you have to remember,
these are men from the tropical plains of Venezuela.
They're wearing light cotton shirts, maybe some
sandals. They have no winter gear. And they're
going up to 13 ,000 feet. Over 4 ,000 meters.
The wind is freezing. The air is so thin you
can't breathe. The sources describe men just
sitting down to rest for a moment and never getting
up. The cold just stopped their hearts. They
had to kill and eat their horses or the horses
just froze to death and fell off the cliffs.
So a skeleton army is what comes out the other
side. A skeleton army. But why did he do it?
Why take that insane risk? Because no one thought
it was possible. Exactly. The Spanish commander
in New Granada, modern Colombia, he knew that
no sane general would try to cross the Andes
in the middle of winter. He didn't even bother
to guard the pass. So when Bolivar's half -dead
army came down the other side, it was like aliens
had just dropped from the sky. The surprise was
total. And that leads directly to the Battle
of Boyaca. A decisive victory. He crushes the
Spanish. He marches into Bogota. And just like
that, the entire map of South America changes.
He creates Gran Colombia. This was the dream.
This was the dream. A massive super state uniting
Venezuela, New Granada, and eventually Ecuador.
He wanted to create a nation that could look
the United States or Great Britain in the eye
as an equal. He's made president, but he can't
sit behind a desk. That's not who he is. So he
leaves the governing to his vice president, Santander.
And he heads south. He still has more liberating
to do. He marches toward Ecuador, and this is
where his personal life flares up again in a
big way. Enter Manuela Saenz. Ah, Manuela. She
is a fantastic character. We really shouldn't
just think of her as his mistress. She was a
revolutionary in her own right. Right. She had
left her boring English husband. She was fierce,
intelligent, deeply political. They meet in Quito
in 1822. There's a story that she threw a wreath
at him from a balcony as he rode into the city.
She did. And apparently it hit him square in
the chest. They met that night at a victory ball.
And they were basically inseparable in spirit.
if not always in the same location, for the rest
of his life. She wore a colonel's uniform. She
rode with his military staff. She organized his
archives. She was his equal in fire and passion.
But there's another huge personality he meets
in Ecuador who is very different. Jose de San
Martin, the Guayaquil Conference. This is the
great mystery of South American independence.
You have these two giants, Bolivar coming down
from the north, and Jose de San Martin, the liberator
of Argentina and Chile, coming up from the south,
and they meet in the middle. In Guayaquil. Two
alphas in one room. Two very different alphas.
San Martin was stoic, professional, a brilliant
strategist. And he believed the new nations of
South America should be constitutional monarchies.
He thought a king was necessary for stability.
And Bolivar was the flamboyant authoritarian
republican. Exactly. They meet in private. No
scribes, no minutes taken, just two days behind
closed doors. And when the doors open. San Martin
leaves. San Martin leaves. He resigns his command,
goes into self -imposed exile in Europe, and
never returns to South America. He basically
hands the entire continent and the glory of finishing
the job to Bolivar. That is just mind -boggling.
I mean, what could Bolivar have said to him?
No one knows for sure. But I think San Martin,
the pragmatist, just realized that South America
wasn't big enough for both of them and that a
civil war between the liberators would destroy
the cause. So he sacrificed his own ambition
for the sake of unity, leaving Bolivar as the
sole commander. So Bolivar takes the reins. He
goes into Peru. The battles of Junin and Ayacucho
follow in 1824. And that's basically the end
of the Spanish Empire in South America. It's
done. After 300 years, the Spanish are out. The
people are so grateful they create a new country
in Upper Peru and they name it after him. Bolivia.
There's that quote from the delegates. If from
Romulus Rome, then from Bolivar Bolivia. He's
at the absolute peak. The apex of his life. He
is president of Gran Colombia, he is the dictator
of Peru, and he is the namesake of Bolivia. He
rules a territory larger than the Roman Empire
at its height. And this is where the tragedy
really begins, because winning the war, it turns
out, was the easy part. Building the peace was
impossible. Okay, let's talk about the unraveling.
Why did it all fall apart so fast? Well, the
first enemy is just geography. These new nations
are separated by massive jungles, impassable
mountains. Trying to govern Caracas, Bogota,
and Quito from one central capital was a logistical
nightmare. It could take weeks, even months,
for a letter to travel. So you have these regional
identities already starting to form. Exactly.
And then you have the ideology. Remember Santander,
the vice president back in Bogota? The man of
laws. The man of laws. While Bolivar was off
fighting in Peru for years, Santander was actually
building a government, a liberal federalist republic.
He wanted limited executive power, rule of law,
a constitution. And then Bolivar comes riding
back from Peru. And Bolivar is now convinced
more than ever that the continent needs a dictator.
And he's got a blueprint for it, the Bolivian
constitution that he drafted. It's a shocking
document for a so -called Republican. It calls
for a president for life. A president for life.
Who has the power to choose his own successor.
That's just a king with a different hat. That's
exactly what Santander and the liberals said.
A monarchy in disguise. They were horrified.
They felt they had fought a 15 -year war just
to trade a king in Spain for a king in Colombia.
The entire political class in Bogota turned against
him. They started calling him a tyrant. And the
tension gets so high that they literally try
to kill them. The Septemberan conspiracy, September
1828. It's another one of those movie scenes
from his life. It's midnight in Bogota. A group
of conspirators. break into the presidential
palace. They kill the guards with knives. They're
heading for Bolivar's bedroom to assassinate
him. And Manuela Sions is there with him. She
is. She wakes him up. He grabs his pistol and
his sword, ready to go out and fight them. And
she realizes he'll be slaughtered. She physically
forces him toward the window. A second story
drop. She basically pushes the liberator out
the window to save his life. Incredible. And
then, and this is the real bravery, she opens
the bedroom door. and confronts the assassins
herself. She lies to them. She sends them on
a wild goose chase through the palace. She stalls
them just long enough for Boulevard to scramble
down the dark street and hide under a bridge
for hours in the cold river water. Just picture
that image. The man who crossed the Andes, the
liberator of six nations, shivering in the mud
under a bridge while his own countrymen hunt
for him with daggers. It broke him. Psychologically,
I think he never recovered. He survived, but
the dream of a united Gran Colombia was dead.
The political center just could not hold after
that. And the map starts to fracture. It shatters.
Venezuela, led by General Paez, his old Llanero
ally, secedes. And they pass a law banning Bolivar
from ever returning to his homeland. Peru invades
Ecuador. Gran Colombia dissolves into the countries
we more or less know today. So in 1830... He
resigns. He's sick. He's broke because he spent
his entire personal fortune funding the wars.
Every last cent. And he's effectively homeless.
He tries to go into exile in Europe, but he's
too weak to make the sea journey. He has tuberculosis,
the same disease that killed his parents and
his wife. It's like the cycle of tragedy that
started his life is now closing it. He ends up
at a hacienda near Santa Marta on the Colombian
coast. And the final irony is that the hacienda
belonged to a Spaniard. He dies in the guest
room of a Spaniard. There's a detail in one of
the sources that says when he died, his own clothes
were so tattered and worn out that they couldn't
bury him in them. The Spanish host had to provide
a clean white shirt for his burial. The richest
man in Venezuela, the liberator of a continent,
buried in a borrowed shirt. And that's when he
wrote those final devastating letters. America
is ungovernable. We have plowed the sea. He died
believing that by destroying the Spanish order,
he had just unleashed a chaos that would last
for centuries. He predicted that petty tyrants
would rise up and consume the entire region.
And if you look at the history of Latin America
in the 19th century, the era of the caudillos,
the military warlords, he wasn't wrong. He wasn't.
But his legacy is so incredibly complex. Because
almost as soon as he died, the cult of Bolivar
began. The very same people who had exiled him
and called him a tyrant started building statues
of him. He became the symbol of sovereignty,
of anti -imperialism. It's fascinating how he's
claimed by everyone on the political spectrum
today. You have Hugo Chavez and the socialist
left claiming him as a proto -socialist revolutionary.
But you also have right -wing authoritarians
who claim him as the model of the strongman who
brings order out of chaos. He's a mirror. People
see what they want to see in him. But I think
the core tension of his life, and maybe the question
we should leave you, the listener, with, is that
eternal battle between liberty and order. That's
the big takeaway for me. Bolivar came to believe
that you couldn't have true liberty without first
imposing order. And he was willing to sacrifice
democratic principles to maintain that order.
And the question is, was he right? Was the region
truly ungovernable at that time without a strong
authoritarian hand? Or was his own turn toward
dictatorship the very thing that prevented strong
democratic institutions from ever taking root?
Did he prevent the chaos? Or did he accidentally
create the model for all the dictators that followed
him? It's a question without an easy answer,
but what a life. From the peaks of the Andes
to the mud under that bridge. Simon Blivar. Truly
one of the giants of history. Thanks for diving
deep with us. We'll see you on the next one.