Episode 3 Simón Bolívar: Liberator and traitor to his class?

Born into immense wealth, he devoted his life to ending Spanish control across large parts of South America, enduring exile, repeated military defeat, assassination attempts, and physical collapse. His campaign reshaped entire nations, yet left him penniless and politically sidelined at the end of his life. The story raises deeper questions about leadership, sacrifice, moral contradictions, and what it takes to change the course of history.

Episode Show Notes:

• Bolívar’s upbringing in one of the wealthiest families in Venezuela
• The social and racial caste system of colonial Spanish America
• Personal tragedy and its influence on Bolívar’s life direction
• The decision to oppose Spanish rule and its long-term consequences
• Military campaigns, exile, and assassination attempts
• Moral contradictions, including slavery and emancipation
• Bolívar’s refusal of lasting political power
• His final years, illness, and legacy

Episode Timestamps:

• 00:00 Introduction and episode setup
• 01:20 The call to adventure and historical heroes
• 02:00 Introducing Simón Bolívar
• 04:00 Wealth, sacrifice, and dying broke
• 06:16 Bolívar family origins and land ownership
• 08:00 Orphaned youth and inherited fortune
• 09:00 Colonial caste system and criollo identity
• 10:28 Education in Spain and personal loss
• 11:17 Commitment to ending Spanish rule
• 12:00 Freemasonry and elite social structures
• 13:08 Early failures, exile, and assassination attempts
• 14:44 Military campaigns and endurance
• 16:00 Moral flaws and historical accountability
• 17:00 The Admirable Campaign and harsh tactics
• 18:00 Conflict with Spanish monarchy and leadership
• 19:00 Defiance of political authority
• 21:00 Emancipation of enslaved people
• 22:45 Nations shaped by Bolívar’s campaigns
• 23:00 Final years, illness, and death
• 24:38 Reflections on ambition and legacy

About the Podcast:
Hosted by Kevin Carney and Emanuel Petrescu, two curious minds exploring ideas, culture, and everything in between. Curious Pundits is a conversational podcast where each episode starts with a topic that caught our attention and unfolds into thoughtful, unscripted discussion. We follow curiosity wherever it leads, across disciplines, opinions, and perspectives, without pretending to have all the answers.

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People (Historical / Public Figures)

Simón Bolívar
Joan of Arc
Joseph Campbell
George Washington
Thomas Jefferson
Benjamin Franklin
Franklin Delano Roosevelt
John Fitzgerald Kennedy
Martin Luther King Jr.
Che Guevara
Edgar Ramírez
Ferdinand VII
Nelson Mandela
Winston Churchill
Karl Marx
Muhammad Ali
John A. Macdonald

Places (Countries, Regions, Cities)

Venezuela
Colombia
Peru
Bolivia
Ecuador
Uruguay
Spain
Italy
Haiti
Jamaica
Rome
Bogotá
New Granada
Tierra del Fuego
New Amsterdam
New York

Organizations / Institutions / Groups

Spanish Empire
Catholic Church
Freemasonry
National Public Radio

Concepts / Events / Works Referenced

Hero’s Journey
Hundred Years’ War

Transcript
[00:00:00] Emanuel: Everyone, and welcome yet to another episode of The Curious Pundits podcast.
My name is Emanuel
[00:00:06] Kevin: my name is Kevin.
[00:00:08] Emanuel: And together we’re two curious pundits that started a podcast about essentially everything.
As Kevin used to say a little bit about everything. We know a little bit about everything.
And each episode will have a certain topic that we’ll explore together.
Today’s episode will actually be led by Kevin, who come up with a topic.
He’ll be leading this, and I’ll just simply listen and enjoy the conversation as much as I can, and perhaps play the devil’s advocate every now and then.
It depends on the topic, right? And I wouldn’t wanna defend someone I truly, truly disagree with.
Fundamentally, again, depending on the topic.
That being said, thank you for listening to us. Thank you for watching us. Thank you for being here. And the website is [00:01:00] curiouspundits.com. That’s where you’ll find all the episodes. That’s where you’ll find links to like, share, subscribe to our newsletter to help us grow.
And I, we hope that you’ll enjoy listening to this as much as we like producing it.
That being said, Kevin, what’s today’s topic? What’s in the menu? On the menu today?
[00:01:20] Kevin: So I have an interest in what I’m gonna call stories from history, and to make a reference to the Hero’s Journey, which we mentioned in the original episode, every once in a while, someone receives the call to adventure, which is the way that Joseph Campbell describes it, and the call to adventure is just ridiculously audacious.
Like there is no way that that objective can be achieved and yet they set out to achieve it and in some cases, they do.
Now I want to open… So, [00:02:00] let me back up a little.
There’s two particular people that I’m going to talk about in this episode. One is Simón Bolívar, and the other is Joan of Arc.
I realize that they’re incredibly different people, they lived in different places and times, but the common thread is they were so committed their cause, it’s almost difficult for most people to comprehend.
They…
[00:02:27] Emanuel: Before I let you dive right in, I would like to make two comments.
First of all, I’m familiar with the characters.
I was not aware, so I’m very interested because I’ve research and read about  Simón Bolívar and he’s essentially the architect of what we call today, South America more or less.
And Joan of Arc is…
[00:02:45] Kevin: The northern part, there were a couple other guys in the far south.
[00:02:47] Emanuel: Yes , and also John of Arc.
She’s a saint in the Catholic, and has influenced the Western history a lot.
What I wrote here is someone, every now and then [00:03:00] receives the call to adventure. You put it nicely and perhaps the author put it nicely. Most of the time, I would say 99% of the time, the call to adventure is they are forced.
It’s either oppression, either something catastrophic is happening and they are forced, the heroes are forced to go into that specific adventure.
But that being said, back to you, Kevin.
[00:03:25] Kevin: Joan of Arc may well have felt forced, but Bolivar did it fully, willingly, and in fact, he…
We have this notion that people who lead rebellions and win made some kind of an ultimate sacrifice, but it’s rarely true.
Well, first they lived through it, so they didn’t make the ultimate, ultimate sacrifice.
But second, when you lead a rebellion and win like George Washington, Thomas Jefferson, Benjamin Franklin, et cetera, et cetera, you become a [00:04:00] economic and political elite of the new community.
So it’s rare for any of those guys to die broke.
Simón Bolívar died broke, and he died broke after having been born into one of the richest families in Venezuela.
But anyway, I wanna open with something that I heard on a radio program many years ago, and this is potentially a controversial statement, but I hope not.
It was on National Public Radio, and I don’t remember the name of the show.
But the opening teaser before the commercial break is, which of these people do you think suffered from mental illness?
Then they played an audio clip of Franklin Delano Roosevelt, John Fitzgerald Kennedy, and the Reverend Dr. Martin Luther King Jr.
So while they’re on commercial, I’m like really racking my brain. It’s like, you know, I don’t know which one.
The punchline was… all of them.
And the basic [00:05:00] premise is, and it’s kind of a catch 22, right?
If you think that you can be so influential that you can fundamentally change the course of human events, you must be crazy.
On the other hand, the people who do change the course of human events are people who believed that they had the ability to do so.
And that’s true of both of today’s people. Yeah.
It’s this weird, you know, there’s no way out of this trap, if you will.
[00:05:30] Emanuel: Which one do you want to start with?
But before you start I wanted to say about Simon Bolivar being born in, into wealth… I’ve heard some people kind of like associate Che Guevara with the… with the Simon Bolivar figure as well.
I don’t think it’s fair. I don’t think… again, I haven’t experienced South America in that sense myself, but I don’t think it’s fair.
And the last thing is, there’s a really good movie about Simon Bolivars life with Edgar Ramirez. I just remembered it, so I [00:06:00] didn’t want to, you know, not mention it because Edgar  Ramirez is a great actor. I believe he’s from Venezuela.
It’s an important figure and he is the right actor to portray it.
And now, which one do you want to start with?
Kevin? Now I’m curious about.
[00:06:16] Kevin: We’re going to start with Bolivar.
And I just want to say that there are very few families in history who were as rich as the  Bolivars are. And they became rich in…
What during colonial times was the usual way. Somebody would show up somewhere where it was basically empty wilderness, would acquire vast tracks of worthless land for like nothing.
And then over time over time a whole bunch of other people would arrive. A city, society, civilization would kind of like grow up around them, and that would give their landholdings enormous value.
Well, the first Bolivars…
[00:06:53] Emanuel: I’m going to play the devil’s advocate. Sorry to interrupt, but I said, I’m gonna play the devil’s advocate here.
And you said, [00:07:00] acquire some piece of lands.
You might imply that there’s a transaction somewhere, whereas unfortunately, historically, this acquired of piece of land was simply go there, kill everything that was around, and whoever lived in there and then, hey, it’s mine at a very modest, modest price.
[00:07:19] Kevin: Oh, absolutely. Absolutely.
So anyway, the Bolivar who showed up, as you you so accurately say, claimed ownership of that land was seven or eight generations before Simon and his siblings were born.
So by the time he was born, they owned extensive land holdings. They owned indigo plantations.
They just owned a lot. So he was just born into this.
Now he became orphaned… he was the youngest of four siblings, actually there were five of them, but one died in infancy.
So he’s the youngest of four siblings and he became orphaned at the [00:08:00] age of nine. And when he became orphaned, he’s also the youngest, so he has three older siblings.
They kind of roughly divided the Bolivar estate up into four equal parts.
And they were each still individually among the richest people in Venezuela. Like that’s how rich the Bolivar family was.
[00:08:19] Emanuel: Like the Walton family, the Walmart.
[00:08:23] Kevin: Kind of, but the closest real parallel I know of in the United States is actually the Roosevelt family.
A lot of people don’t realize, but the Roosevelt family had been in New York since it was New Amsterdam. Like they’ve just been there for forever and that’s why they own so much real estate that later became incredibly valuable.
[00:08:45] Emanuel: Back to the Bolivar and the youngest…
[00:08:47] Kevin: So Simon Bolivar, at the age of nine is kind of cut loose from any kind of parental authority. So he lives with an uncle, he lives with an older sister, but he’s kind of hard to control.[00:09:00]
He must know he’s incredibly wealthy and that probably gives him some sense of entitlement, but over time he kind time he kind of calms down.
Oh, and there’s another aspect of this I think is important… and I didn’t fully appreciate the nuances of South American racial caste system, as compared to the North American racial caste system…
But there’s more layers, if you will. They seem to have taken it more seriously.
Simon Bolivar and his siblings themselves, they were of a caste, I’m probably going to butcher the pronunciation and I apologize, but they were criollos, which means that they were born in Venezuela, but there were no ancestors in their past who were either African or indigenous.
A criollos was, pure blood of Spaniard ancestry, but his family had stayed  criollos for like eight or nine generations, maybe [00:10:00] seven.
So they really took this concept of Spanish purity pretty seriously.
[00:10:07] Emanuel: And it’s important to know that the land in modern day Venezuela, but by that time the Spanish empire was controlling the majority of America, I believe.
[00:10:17] Kevin: Well, from Mexico down to Tierra del Fuego, I mean, it was all… well and I’m not sure when Florida stopped being under Spanish control.
[00:10:27] Emanuel: Yeah.
[00:10:28] Kevin: So he’s off doing his thing and, and, and he mellows out a little earlier than we do now in Anglo America at least.
So by the time he’s 17, he’s kinda like calming down a bit and he does what the  criollos do, which is he goes back to Spain to be educated.
In Spain, he happens to meet the love of his life, and I forget her name, but they were very enthralled with each other.
They got married, they go back to Venezuela, she contracted a tropical disease, I think it was yellow fever, and died.
[00:11:00] This like, was a devastating proposition for him. So he goes back to Europe just to like hang out and stuff travel around and kind of like, not really do much, but deal with the fact that like his wife died.
And while he is in Italy, okay…
[00:11:17] Emanuel: Go ahead, maybe you’ll going to answer my question.
[00:11:20] Kevin: And while he is in Italy, he decides for some reason, his mission in life is stop Spanish control of the Spanish American colonies.
Like this is the call to adventure.
He’s apparently, he’s on a hill in Rome and he comes to this conclusion and he basically commits himself that he’s going to do it or die trying.
And the part I find most interesting is that he meant it.
[00:11:50] Emanuel: He kind of like did it. The question is, at one of these European visits, he was also introduced, initiated in Freemasonry as well. Is that [00:12:00] correct?
[00:12:00] Kevin: Yes. but based on what I’ve read, a lot of people seem to place a lot of significance on Masonry. If you look at George Washington’s first inauguration, it looks like a  Masons ritual.
Masons were just… everywhere. I don’t know that it’s quite as significant, like in that day and time saying that someone was a Mason might be equivalent to saying that someone is a Christian today.
Like there were just a lot of them and they were like everywhere.
[00:12:35] Emanuel: The upper class and the ones that made the ruling caste, so to say.
[00:12:41] Kevin: Yeah. I’m just not convinced that…
[00:12:43] Emanuel: Yeah.
[00:12:43] Kevin: …. Being a Mason was a significant part of their worldview. It may have been more of a social thing than a let’s rule the world thing.
It’s just that the upper elites kind of socialized with each other.
[00:12:57] Emanuel: It’s like wearing a badge or a…
[00:12:59] Kevin: Yeah[00:13:00]
[00:13:00] Emanuel: …private, which, which in a sense it is, but yeah, it was fairly common for a person of his stature at the end of the day.
[00:13:08] Kevin: So anyway, just to give like broad strokes from there.
So he goes back to Venezuela, and it does not go well.
I don’t have all of the details in mind, but he had to leave in exile. You know, he gathered an army, they fought a battle. He lost, he had to leave in exile. He’s spending time in Jamaica, he’s spending time in Haiti.
And this happened like three or four times where he’s being pushed out in defeat and has to leave in order to prevent him being assassinated.
And there were not a whole lot, but there were attempts to assassinate him. There was one, I think even might have even happened in Jamaica. Like they sent someone, I think it was Jamaica, maybe it was Haiti, to kill him.
And when they went to where he was living, somebody who he knew from the past who had been [00:14:00] looking for him, who basically showed up as like, okay, so this is his stuff, he must live here, but I’ve had a long day.
So he lays in Bolivars hammock to get some sleep, and when the assassin shows up, they kill the guy in the hammock thinking it’s Boliar.
Like he has some closed calls, right?
Just the broad brush was in the course of leading rebellions he traveled approximately a hundred thousand miles on horseback.
To put some perspective on this, that’s like traveling from New York to Los Angeles and back 15 or 16 times.
Now this is over the course of like 15 years, but still that’s a lot…
[00:14:44] Emanuel: His miles, he would have gotten a nice card from an airplane company.
[00:14:50] Kevin: Oh yeah. Frequent horseback miles or whatever it’s called.
He kept… as they gained momentum, and I think [00:15:00] the first country in northern South America to fully throw off the Spaniards was Columbia.
It used to be called New Granada, which I think was Columbia and Venezuela, but Columbia becomes free first.
He gets an army and they’re going to head east into Venezuela to free them.
So… One thing that I find kind of refreshing, so… here in the United States, we have a habit apparently, of not knowing that our founders had faults.
We like to pretend that George Washington and Thomas Jefferson established the seeds of the anti-slavery movement in America when there is little to no evidence to suggest that’s true.
I know from having lived in Canada for many years that Canadians don’t do that, and apparently in South America they don’t do that as well.
So the [00:16:00] flaws are fully acknowledged.
From Columbia…
[00:16:03] Emanuel: Recently, at least in Canada for the past couple of years, yes. We started to acknowledge, yeah, in Canada?
I mean recently we started to acknowledge publicly the flaws of many people.
[00:16:15] Kevin: That’s good. John A MacDonald definitely had some serious flaws.
[00:16:18] Emanuel: Yeah, there was this university called Ryerson University. Now it’s called Metropolitan University. Due to some not so… and this wasn’t happening when I came to Canada 10 years ago, so it was still not, not spoken. So this has happened recently, which is a positive thing and embrace it.
[00:16:33] Kevin: So Bolivars got this army, he’s heading east, and for some ridiculous reason and I am curious to dig into why, this became known as the admirable campaign.
And the reason I say ridiculous reason is, he went full George W. Bush. If you’re not with us you’re against us.
They actually issued a proclamation…
If you oppose us, you will be killed. If you are [00:17:00] neutral, you will be killed.
He’s leading the army, so he himself is not killing people who are neutral, but it was happening, on his watch, if you will. He was aware of it and he was like, well it may be cruel, but strategically it’s kind of important.
And it worked. They would show up at places, now nobody’s neutral.
[00:17:26] Emanuel: Also Nelson Mandela and more recent examples as well.
[00:17:28] Kevin: Yeah.
[00:17:29] Emanuel: Of the similar tactics and any other major political leader.
[00:17:34] Kevin: So as he’s going about his stuff… now he had extensive holdings in Venezuela… the Royalist forces, the people who were loyal to the King…
And I want to add another detail that I thought was fascinating, is… as Spain had a new King, a guy named Ferdinand, the royalist loyalists in South America are all rallying around this guy [00:18:00] Ferdinand, because he’s the King.
Well, of all the people in Venezuela, the only person who had actually met Ferdinand was Simon Bolivar.
And that’s because he was in Europe, he’s a South American criollo, he’s on the upper echelon of society, and he met the King.
And let’s just say he was not impressed. He’s like, you don’t understand. He’s not that bright, he is gonna make some bad decisions, we need to be free of him.
[00:18:30] Emanuel: Was also from the same family?
[00:18:32] Kevin: What’s that?
[00:18:33] Emanuel: Was also from the same family that was inbred, right? The King. They did a study recently… that the Spanish monarchy was the most inbred.
[00:18:43] Kevin: Yeah. So, Bolivar just keeps traveling around with his army as best he can taking over royalist positions until Spain just basically gives up.
And then there’s a point where Columbia is [00:19:00] now an independent nation. There’s some kind of problem in the south of Columbia, so the Columbian government gives Bolivar an army, it’s like, go down there and solve that problem.
So he does, and when the problem is solved, there was basically a disagreement between the government in Bogota and Bolivar as to what to do next.
The government in Columbia is like, this is a Colombian problem. We’re spending money for a Colombian army to solve a Colombian problem.
And Bolivar is like no, you don’t understand. There are still parts of South America that are under Spanish control. So he keeps going, in direct defiance of the government that funded and provided the army.
[00:19:46] Emanuel: Reality check.
[00:19:47] Kevin: Right? And then probably the extreme highlights…
and I love this particular detail… at some point in his adventure, he [00:20:00] realized that a free nation of criollo rule was just not going to work. The vast majority of the population had African and indigenous ancestry, and you can’t just like cut them out of all the political decisions.
So at some point Venezuela is now independent. He rides in in a conquering hero. They want him to be the president of Venezuela, which for whatever reason, he didn’t want to do the political stuff. He wanted to like take the Army and keep driving Spaniards out.
In fact, think during the Columbian incident I spoke of, Bolivar was officially the President of Columbia, but that wasn’t something he had interest in.
So the Vice President actually ran Columbia.
Technically this disagreement of what to do with the army was between the President who outranked the Vice President, which may have been why Bolivar felt comfortable taking them farther south.
But he [00:21:00] is back in Venezuela, as is typical in these kind of situations, it would’ve been within the norms of socially accepted behavior and within the rules of the New Republic for him to reclaim the properties that had been confiscated him.
So he rides out to an estate that used to be his, and I don’t know if they made sugar or indigo or what, but it used to be his.
And apparently there was his expectation he was going to declare that it was his, and instead he emancipates the slaves and then leaves.
He didn’t take it back. He apparently didn’t want it back. And then finally…
[00:21:45] Emanuel: Before Karl Marx, right?
[00:21:48] Kevin: Well, I don’t know that it was, Karl Marx class warfare kind of thing, especially because he was from the upper classes.
He just at some point came [00:22:00] to the belief that slavery was fundamentally wrong, and the fact that he personally had benefited enormously from the institution of slavery should not change that belief.
So he just declared what we’re… they weren’t technically his slaves at that point in time because his property had been confiscated. But rather than take it and them back, he just declared them to be free.
And then he goes also it’s Venezuela, Columbia,
Uruguay [this was an error, I meant Equador], Bolivia, and Peru. Like these are the five nations that he is credited with having founded.
And at the end of his life, the wars are over, the active fighting lasted about 15 years, from 1810 to 1825.
The wars are over.
Nobody really has much use for him anymore because the wars are over. And this is something [00:23:00] similar that happened to Winston Churchill. You know, the war’s over dude, we’re going vote you out.
By this time time he was in his mid to late forties and he’s kind of broken from a hundred thousand miles on horseback and all that rough living that he did over the course of his life, and he’s flat broke.
Like he has no property, he has no income. I think the government of Columbia gave him a one time payment as a pension.
And then, the forces of nature take over, if you will. And he gets sick. I think it was tuberculosis, and he dies.
His memory is significantly stronger than the way he was treated in the last year or two of his life.
It is kind of a classic of we really appreciate what you’ve done for us, but that’s over, we have work to do. [00:24:00] Enjoy whatever it is that you’re going to do with the rest of your life.
But the significant thing is that his degree of commitment to driving the Spanish out of South America is almost difficult for modern people to comprehend.
It was literally a do or die trying, and apparently he meant it, which I think is most illustrated by that disagreement between him and the Vice President of Columbia about what to do with the army.
That’s the highlights of Simon Bolivar and primarily why I find him so fascinating.
[00:24:38] Emanuel: Y ou mentioned mental illness. Is there any particular twist to his story?
[00:24:46] Kevin: He just had these, what we would ordinarily call delusions of grandeur, except in his particular situation, they weren’t really delusions. He [00:25:00] pulled it off.
I forget who this quote is attributed to, but I think they were talking about Muhammad Ali. And the basic quote is, “It’s not bragging if you can do it”.
[00:25:12] Emanuel: Good one. Given a man of in his position, you get probably tempted here and there, when you have many victories, when you have so many people in awe of you and you know, reporting to you and willing to kill for the idea, not necessarily for you, but the idea that you believe in which is remarkable of course, may, potentially tempt you to think about yourself more than you really are, but life and people around you have their own way of keeping you in, what’s it called? The short leash.
As we just said that after deliberation, okay, you’ve done [00:26:00] your part. Now move on so we can install our corrupt government and our corrupt system and do whatever we think it’s best without for you.
[00:26:11] Kevin: What it’s worth, he was not kept on a short leash. He was given a very long leash by the various countries that he was considered to be the founder of. And he kind of rejected it.
He was offered and actually officially appointed to dictatorships more than once in his life, and he basically turned the role of governing over to somebody else who wanted to govern, and then he left with the army to go do something else.
There were more Spaniards to be dealt with, so off he goes.
[00:26:44] Emanuel: He was on a mission and his mission was clear.
[00:26:47] Kevin: Yeah, and he did not waiver from his mission.
[00:26:54] Emanuel: Well, definitely I’ve took some notes, as you have seen me. I’m gonna revisit to [00:27:00] our listeners and our followers.
Kevin and I are trying to resist as much as we can not Googling stuff, although we’re doing this on a computer, and we can easily jump online and try to verify the facts, the accuracy, or if they exist correctly.
We highly rely on our memory, but we will edit this recording and we’ll, if anything was wrong or links to further support our claims, we’ll be added in the show notes, in the transcript and in the description.
So from wherever you’re listening to just make sure you follow us and you know, curiouspundit s.com is the website where you’ll find links to all of our profiles.
Kevin, you mentioned also Joan of Arc, but I believe that’s a topic for a full episodes in itself.
[00:27:52] Kevin: I agree.
[00:27:54] Emanuel: Because it’s such a important historical figure. [00:28:00] She is a saint currently. She was executed by the church that sanctified her couple hundred years later, and she influenced the history of the, whatever you might call, modern or western society.
That I believe there’s a… it’s worth an episode just for herself and I’ll be doing some research myself as well and bring some some points to this one.
[00:28:29] Kevin: Absolutely, can I just mention one little detail about Jon of Arc that I think is really fascinating?
[00:28:34] Emanuel: You have my permission.
[00:28:36] Kevin: She was born about 70 years into what’s called the hundred year war. At a time when what we view as France was occupied by three competing political forces. So there were the French, which she was born into, the Burgundians, which were also French, but opposed to the French and the English.
The story as I understand it, is she’s the [00:29:00] first person who articulated the idea that there was that there was such as France.
[00:29:09] Emanuel: We’ll do some research and we’ll find out in the next episode.
So whereever you’re tuning in from, make sure you like, follow and subscribe so that you don’t miss the next episode.
Until the next time. My name is Emanuel.
[00:29:22] Kevin: My name is Kevin.
[00:29:24] Emanuel: And see you and hear from us next time. Bye for now.
[00:29:29] Kevin: Bye for now.