Founders: #319 Winston Churchill (the Making of Winston Churchill)

Winston Churchill may be the most self-confident young man that I've ever studied on the podcast,

and that's saying a lot because the people that we study on the podcast,

their self-confidence levels are through the roof. Just wait until you hear

the way Churchill talked about himself when he was younger. Before we get into that,

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highly recommend that you do so. Members can email me questions directly. You actually get a

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So, come check that out if you want to see me live. I will leave a link to both the episode

and to get your tickets. That's everything I need to tell you about. Let's jump into this incredible

story of Winston Churchill's capture and his thrilling escape. Although he was still a very

young man, Churchill was no stranger to situations of great personal peril. He had already taken part

in four wars on three different continents and had come close to death in each one. He had felt

bullets whistling by his head in Cuba and saw his friends hack to death in British India.

Although he had tried again and again in war after war to win glory, Churchill had returned home

every time without the medals that mattered. No more distinguished or famous than he had been

when he set out. The Boer War, he believed, was his best chance to change that, to prove that he

was not just the son of a famous man. He was special, even extraordinary, and he was meant not

just to fight for his country, but one day to lead it. Although he believed this without question,

he still had to convince everyone else. The one scenario that Churchill had not envisioned was

crossing enemy territory alone without companions or provisions of any kind. He didn't have a weapon,

a map, a compass, or even any food. He didn't speak the language. Beyond the Vegas of outlines,

he didn't even have a plan, just the unshakable conviction that he was destined for greatness.

That was an excerpt from the book I'm going to talk to you about today, which is Hero of the

Empire, The Boer War, A Daring Escape, and the Making of Winston Churchill, and it was written

by Candice Millard. So about a year and a half ago, I read one of my favorite biographies of Winston

Churchill. It's written by Paul Johnson. It's only like 170 or 180 pages long. I thought it was

excellent. It's episode 225 if you haven't listened to it. But what's fascinating is the cover of that

book made me think of something. All the pictures in my mind and things that I've ever seen of

Winston Churchill were like the Winston Churchill that fought the Nazis. And yet the cover of Paul

Johnson's book has four different pictures. Two of them are of a young Winston Churchill. So after

that, I realized, hey, I should really read, I mean, what's the subtitle? The Making of Winston

Churchill. So I'm always fascinated by these biographies. And I've read a couple of them,

where they cover like the first like, you know, 2030, maybe 40 years of somebody's life.

And so I ordered two books that I could find on Winston Churchill. One is called A Young Tycoon,

and I ordered the book that I'm holding in my hand. I will leave both linked below in case you

want to get them. But the reason I started, I wanted to start with this one, is because

the author of this book, Candice Millard, also wrote my, I've read a bunch of books on Teddy

Roosevelt, he'll appear in this book as well. But my favorite book so far that I've read on Teddy

Roosevelt, this book called The River of Doubt, and Candice Millard was the was the author of that

book as well. So if I'm reading to understand what Winston Churchill was like, I might as well

start with the author that I already love her work. This book is only going to cover this is

incredible. It's an incredible story. This book is only going to cover the first 25 to 26 years

of Winston Churchill's life, and then it ends. There's a maxim that I repeat over and over again

that became really obvious and really apparent the more you study history's greatest founders,

and that is belief comes before ability. This book, if you had to summarize this book, that's

how you would summarize it. By the time Winston Churchill is 24, he is utterly convinced that

it is his destiny to become Prime Minister of England. And so let's jump into his personality

and some of the things that were motivating him to make the decisions he made when he was a young

man. Since his earliest childhood memory, Churchill had been fascinated by war. There is no ambition

I cherish so keenly, he said, as to gain a reputation for personal courage. And the important part of,

or one of the important parts I should say, of having this ambition for personal courage to

being interested in war and then using like being a hero and being coming famous as a

like an entry or gateway into politics, is he's doing this at the time when the British

Empire is at its apex or at zenith. At this point, it was the British Empire covered more than a fifth

of the world's land surface. The British Empire had come to rule about a quarter of the human race.

It was the largest empire ever known. It was five times the size of the Roman Empire.

By the time Churchill reached adulthood, the greatest threat to the empire no longer came from

other major powers, but from the ever expanding burden of ruling its own colony. So we are

going to be an 1899 and 1900 for most of this book. Now this is why Churchill took an early

interest in this. To Churchill, such far flung conflicts offered an irresistible opportunity

for personal glory and advancement. This book has a bunch of excerpts from letters that he wrote,

books that he wrote, there's a lot of correspondence between him and his mother,

and he tells her exactly what he wants. He wants a chance to prove himself.

Churchill was born into the highest ranks of British aristocracy, and what I respect about him

is, you know, he could have lived a life of privilege and a life of leisure, and very much

like Teddy Roosevelt, he desired to test himself into live a full life and not just rest on the

laurels of the family that came before him. For a member of Churchill's high social class,

such bold, unabashed ambition was a novelty. This is actually really important because it's

going to come up over and over again. He did not really act British or he did not act as he was

supposed to act. And so one thing that Churchill had from a very young age is this like, I don't

even know how to describe it, like unbelievable, relentless self-belief, almost like this God

complex. And usually with that, you have an indifference to the opinions of other people in

regards to how you should behave or what you should be doing. So it says, in his open pursuit of fame

and popular favor, Churchill seemed far less Victorian, as he was expected to act, right?

Then Rooseveltian, they mean Theodore Roosevelt. There's going to be a lot of parallels between

a young Theodore Roosevelt and a young Winston Churchill. In fact, there'll be a direct comparison

a little later on. This is some of the complaints that other people, he's like, you're not being

Victorian, you're not acting like you're an aristocrat. What are you doing? Winston advertises

himself as simply and as unconsciously as he breathes. Churchill was widely criticized for being

a self advertiser. And he did not care at all about this criticism. He thought, hey,

if I can actually seek fame, if I can win glory in these wars, and I can act, that's like the way

I'm going to break into political life. He says this explicitly, he says distinction in turn

could be parlayed into political clout, the kind of public life that he longed for,

in which he believed was his destiny. For that, he was willing to risk anything, even his life.

And that's the important thing. He was willing to risk his life on things that he believed in.

You know, they said that he could have stayed, he could have spent his time playing polo or

fox hunting or anything else. Instead, he goes to Cuba as a military observer. I think he's

like 21 years old at the time. And this is the first time that he gets up close with death.

He's actually, there's a bullet that goes right over his head, and strikes and kills the horse

that is standing next to him. When he doesn't get the glory that he wants in Cuba, he's like,

okay, well, then I'll just go and fight in India. And he'll use this is another thing,

or I guess two things. One, he never waits for an invitation. And two, he's completely fine

pulling every single string and using every single relationship that he has to get what

he wants. Churchill had never had any qualms about pulling every string he had. I am certainly not

one of those who needs to be prodded, he said. In fact, if anything, I am a prod.

And this is a great description of him at this time. Churchill did not need encouragement. He

only needed a chance. And so he goes to India to help the British fight the pastions. Now,

in his description of the enemy, we see the traits that he admires in other people.

And then based on his actions, this is what I mean, I don't even know how to describe it.

Megalomania might be the way you describe it, like his, you'll see, you'll only see what I'm

talking about in a minute. In his actions, it just tells you the level of self belief in this,

his complete belief that he's like destined for greatness. He can't be killed, because there's

no way he's too important. And fate wouldn't have him just have like this normal ending. The

descriptions of Churchill's like self belief in this book are my biggest takeaway from it,

because it just happens, you know, page after page after page. So let me just get into this and

hopefully you'll see why just I'm at a loss for words. Like, it's incredible the way this guy

thought about himself. So he says, the passions fought hand to hand and face to face, they seem

terrifyingly heedless of their own safety or even survival. And then Churchill, you can, his behavior,

you can say the same thing about him. They fought when they had no chance of winning,

when they were alone on the battlefield, when they had been shot and speared and bayoneted.

Careless of what injury they may receive, Churchill observed in awe, they devote themselves to the

destruction of their opponent. And so this is what I mean about this like megalomaniacal self

belief. Churchill understood that he could very easily be killed in the battle that lay before

him. But he did not for a moment believe that he would be. I have faith in my star, he said,

that I am intended to do something in the world. In fact, soon after arriving in India,

he had told a fellow officer that he expected to be prime minister one day. And so he does

something. The note I left myself on this page is like, I don't understand this, this I don't

understand. He, he's not trying to blend in on the battlefield, he literally wants to stand out,

so he gets this gray pony. And his entire point is to stand out to the enemy. This is crazy.

Churchill took great satisfaction and knowledge that he would be impossible to miss.

I wrote on my great pony all along the front of the line of the skirmish line,

where everyone else was lying down in cover. He would later confess, foolish, perhaps,

but given an audience, there is no act too daring or too noble. This mentality continues. This is

after the battle, he winds up shooting. This is the first time he's ever killed a person,

says he would never know how many men he killed that day before help came. But even as he looked

down on the mutilated bodies all around him, the bodies of men he knew men very much like him,

he knew that he would not share their fate. He was meant to live, of that he was certain,

more than that he was meant to do something great with his life. I do not, this is, check out this

quote, I do not believe the gods would create so potent a being as myself for so prosaic and ending.

So I think I should actually pause and back up like why, why am I doing so many, this is the

third podcast I've done on Churchill, I think I've done two on Napoleon, I'm going to do a ton,

you know, over the next few decades, I hope I do 10 or 15 or 20 different episodes on both

of these people. And the reason is, is because if you study the history of entrepreneurship,

two people that are not like, didn't start companies, they're not typical like entrepreneurs,

are mentioned over and over again by history's greatest entrepreneurs. So if you're studying the

history of history's greatest founders before World War II, they all say the same thing,

they're motivated and inspired by Napoleon. After World War II, Napoleon is still there,

but then they bring up Churchill a lot. And so I want to know why some of the people that built

the world's most successful companies ever were inspired by people like Churchill and Napoleon.

And there's so many times where Churchill is talking and writing and giving speeches where

I'm like, this just sounds like Napoleon. And so this is the first time in the book where I got,

I'm reading this where it's like, I don't believe the gods would create so potent a being as myself

for so prosaic and ending. I have no idea why, but when I read that line, I thought of something I

learned in the book, The Mind of Napoleon, that I did on episode 302. And Napoleon said,

if I have any ambition, it is so natural to me, so innate, so intimately linked with my existence,

that it is like the blood that circulates in my veins, like the air that I breathe.

This innateness, this self belief is innate in Churchill. Everything that happens to him,

he reads as an affirmation that he should believe what he believes about himself. As sobering as

Churchill had found the carnage that he'd witnessed, his faith in himself in the future

had not for a moment been shaken. On the contrary, he was acutely aware of the fact that the men all

around him were killed and he emerged not just alive, but whole, nothing touched me. He wrote,

I destroyed those who molested me and so passed without any disturbance of body or mind.

But just because he has this level of belief doesn't mean he's always right. He thought he

could leave the army. He's like, okay, I think I've done enough. I want to run. His whole goal is

like get glory in war and then parlay that into public office, then get elected to basic level

and then eventually work my way up and become Prime Minister one day. And so this is his first

mistake where he does this. He leaves the army. He says, I shall not be a soldier. He's going to

run for elected office and lose. I like how he described this though. He knew he could believe

that he was destined to do this, but it wasn't guaranteed. It is not without some misgivings

that I let go of my toe rope, he said, and commit myself unaided to the waves of life's oceans,

propelled only by my own machinery. He's saying, I will take the risk of not being a soldier anymore.

For my true goal, I want to be in public office. I want to be Prime Minister one day. This reminds

me a lot when I got to the section of, if you've read any of Robert Caro's books, his multiple

port biography on Lyndon Johnson, so LBJ, he had a plan to be president and it started with getting

elected to Congress. If I'm remembering correctly, he even turned down the ability to run for the

governor of Texas because that's not my goal. My goal is federal office. My goal is the presidency.

I'll have a better chance of getting there, going to Congress first. And so he has a lucky

turn of events for him. Unfortunately, one of the representatives dies unexpectedly of pneumonia,

so that opens up the opportunity for Churchill to run, but this is where his relentless self-belief

is going to be proven wrong temporarily. So it says he was stricken down with pneumonia.

This was less than a month before the election. Churchill was got himself on the ticket,

whether he was ready or not. In his own mind, of course, he was more than ready. There is no doubt,

he wrote, that if anyone can win this seat, I can. And so as you can guess, we know that he

is going to lose the selection because this entire book is about his time in the Boer War,

and specifically the fact that he becomes a, he becomes a, he's a POW, he gets captured,

and then he has this daring, successful escape that makes him world famous.

What I did admire about his approach to running for office, even a young age though,

is just how much he would practice. He has this relentless combination of practice and

self-confidence. Obviously, the public praises people for what they practice in private,

Churchill's known, his give some of the best speeches. Well, this is how he actually did it.

For Churchill, few things in life could compete with the thrill of climbing onto a stage,

stepping behind a podium and commanding the attention of every man in the room.

As much as he loved public speaking, it did not come naturally to him.

He overcame this problem with practice and perseverance, that is his quote.

Although he would become famous for his sharp wit, Churchill was also uncomfortable addressing an

audience unless he had carefully written and exhaustively rehearsed every line of his speech.

Winston spent hours preparing for every formal lecture and even his brief remarks,

and would do so throughout his life. A friend would later joke that Winston had spent the best

years of his life composing his impromptu speeches. And then in typical Churchill fashion, he

starts to get slightly good at something and he's like, oh, I'm going to be the best in the world,

best in the world at this. It was clear to them that he had the potential to become a great one,

perhaps even the greatest. And so even with the self-belief, even with the practice,

it's not good enough. He loses his first election. He is 24 years old at this point.

And so other politicians are making fun of him. They say stuff like this. I thought he was a young

man of promise, but it appears he's a young man of promises. This searing assessment only hardened

Churchill's resolve. He had no money, no occupation, and it appeared no one who believed in him quite as

much as he believed in himself. The only thing he knew with any certainty was that in the end,

whatever it took, he would succeed or quite literally die trying. There's a quote, an image

of a quote that I keep on my phone from this author, Steve Rinella, who also makes podcasts

and shows on Netflix. And he says, you're often driven by the hatred of the version of yourself

that would quit. And so he goes away to recover, to scheme, to plot, to figure out what his next

move is. Now here's the crazy thing. His family, they have a family history that goes back like

hundreds of years. His family had a palace. You got to Google image search this thing. This is

incredible. So his family's palace is called Blenheim. And this is where he's going to go.

Churchill had always believed that Blenheim, its history, its grandeur, its power to all,

had molded him, creating the foundation for the great man he was destined to become.

We shape our buildings, he said, and then our buildings shape us. Blenheim served as a painful

reminder of his inability thus far to live up to it. And so at this point, the palace is like

this entire dedication to somebody who had lived 200 years before, which is John Churchill, who was

believed to be one of the greatest generals in history. And in fact, Winston later on writes a

biography of John Churchill. And he said that he had one skill that made him indispensable. He never

lost on the battlefield. And it was because of all the wars that he had won that he actually gets

this palace. It was given to him. And so it says nearly 200 years later, the weight of John Churchill's

legacy followed his ambitious young descendant wherever he went. It's fascinating. So it's

interesting about what's taking place on these few pages, what's going on in the mind of Winston

Churchill at this point in his life. And essentially, like he's being stretched to what is possible,

right? And I think I don't have a family palace, you probably don't have a family palace either.

But I think biographies of people who achieve great things actually stretch what you think is

possible. And if you think about it, it's kind of this weird closed loop, because people that

live lives so remarkable that somebody wrote a book about them, wrote a biography about them.

In their biographies, you realize that they're reading biographies too. And so it just goes on

and on and on. And so as prone to happen at this point in history, there's another war that the

British are fighting. And so Churchill had already written like two or three books at this point,

mostly about his time at war. And so he winds up becoming the best paid war correspondent in England.

And so he's going to go to South Africa for the Boer War. And his approach is remarkably consistent.

So it says when it came to taking advice, Churchill was his mother's son. He was defiantly

determined to decide for himself where he would go and what he would do. And so he starts writing

about this. The reason he wants to do this is one, he's looking for glory to parlay back into

political power, right? But he also thinks that he's a gifted writer. He says he had long had faith,

quote, in my pen, the success of his books had only strengthened his already substantial confidence.

Churchill was no hack and he knew it. My literary talents do not exist in my imagination alone.

And so he has to go on this two week trip on a boat to get from England to South Africa.

And he's struck by the arrogance and overconfidence of the British military officers that are on

the boat with him. This is again, there's a lot of similarities between what's taking place in

1899 and 1900 in South Africa coming from the British as we covered last week, 40 years after

this, the British attitude and I guess opinion towards the Japanese that took place in the late

1930s, early 1940s. It's essentially the same thing. It says some of our best officers were on board,

Churchill wrote, and they simply could not conceive how, quote, irregular amateur forces like the

Boers could make any impression against disciplined professional soldiers. And so right away,

immediately, in fact, before Churchill's boat even gets there, the Boers, I would describe them as

this, they're perpetually prepared. The British, here's the problem, the British are utterly predictable.

The Boers know the terrain, their knowledge of the game is going to give them an edge. They're

going to wind up killing one of the most famous British generals and just rolling over him even

before Churchill gets there. And so after I read through this section, I was making my notes, I just

wrote to myself, I don't ever want anyone to be able to guess my next move. And it's eventually,

this turns around, you know, about a year from now, but not after the loss of a ton of British

supplies, soldiers, generals, they just, the Boers just kick their ass. Whatever waves of panic the

British army might have imagined, the reality was starkly different. The Boers were not frantically

preparing for war. They weren't rushing together maps and men's supplies and ammunition. They

didn't have to. There had never been a time either in their own lives or in those of their forebears

where they had not been ready to fight. Every Boer man and boy between the ages of 16 and 60,

and many much older and younger than that set out for war. There was no need to enlist in the army

because there was no standing army. And there was no need to find a uniform because there was no

uniforms, uniforms. This is the Boer perspective. Okay. Uniforms are something soldiers wore and

Boers were fiercely adamant that they were not soldiers. A term they found deeply offensive.

They referred to themselves only as citizens. This is an example of how they were perpetually

prepared. The average Boer man was accustomed to living off of just a handful of staples, coffee,

brown bread, and dried meat. They had been stockpiling weapons. When it came to marshmanship,

it was impossible to compete with the Boers. They were used to hunting lions. Their lives

depended every day on the speed and accuracy of their shooting. They were the finest mass of

rifle armed horsemen ever seen Churchill wrote and the most capable mounted warriors since the

Mongols. They were also determined to win. They felt that they had no other choice. They believed

that this land was their birthright and a gift from God. So a boy growing up in their culture

learned how to shoot a rifle as soon as he was strong enough to hold one. Everybody in their

culture had spent the great majority of their lives at war in one form or another. And so it

wasn't just the British generals that were on the boat with Churchill that thought like these guys,

these are like little farmers, we're the greatest empire, we're going to roll right through them.

In fact, this is the death of this guy named Penn Simmons. So Penn Simmons is a famous general.

When Churchill is getting close to South Africa, another boat pulls up and writes out like a big

sign telling them that Penn Simmons was killed. And the people that were on the boat with Churchill,

the arrogant generals and people in the military couldn't believe it. And he was killed because

of British overconfidence. That's what gets them killed. This is just like their attitude 40 years

later against the Japanese episode 318. If you haven't listened to last week's episode,

Penn Simmons continued to insist that there was no cause for concern. He scoffed that no

boar commando would dare attack a British brigade. I feel perfectly safe, he said. And so the next

day at five in the morning, they get attacked. And his arrogance is not just in words, it's in

actions as well. So they're getting attacked. They don't know the terrain. They don't know how

many people it's draining to. They didn't know how many people are attacking them. They were

completely unprepared. And he does some weird things where he decides he refuses to make

himself blend in. In fact, he goes out of his way to make sure that the enemy knows who he is.

He insists that his aid to camp ride by his side holding a dashing scarlet pennant. And so if you

are the army fighting this guy and you have their leader saying he's waving like a giant red flag,

here I am. What do you think is going to happen to him? He winds up getting into a fight. He says

he had been shot in the stomach and he said, I am severely mortally wounded. The general on the

other side and they wouldn't even call him a general. This guy named Batha. Sending somebody

like Penn Simmons in pursuit of somebody like Batha in this land and terrain is like sending

a cow in pursuit of a rabbit. Batha knew the region well. He had been born nearby and had

grown up herding cattle over hundreds of miles of its scrubby grassland. The British on the other

hand knew almost nothing about this place or its surroundings and had no idea what tactical

opportunities or dangers it held. So not only are the British utterly predictable and not only

do they not know the terrain, but they're also excessively slow. This reminds me of something

that I learned from reading about Ernest Shackleton. I'll get to in a minute. In comparison to the

astonishingly mobile boars who were able to wage war with little more than men, horses, and guns

and to move from battlefield to battlefield at a moment's notice, the British army moved at a

glacial pace weighed down by the sheer number of its possessions. And it goes into detail of all the

weird things, kind of like creature comforts that they carry into battle into war. It's just very

bizarre behavior. And if you've ever read the famous book Endurance, which is the story of

Ernest Shackleton, there's a line in there that's one of my favorite ideas that I've ever come across

in any book that I've read. And it says, from studying the outcomes of past expeditions,

he believed that those who burdened themselves with equipment to meet every contingency

had fared much worse than those that had sacrificed total preparedness for speed.

That's a description of the boars. They had sacrificed total preparedness for speed.

And we see another bizarre choice. This is, again, just like the British in Singapore,

where they'd make, they're in the tropics. It's 100 degrees, it's humid, it's disgusting out,

and they're making them wear these wool caps and these costumes, high-climbing costumes,

these uniforms that are made for much colder climates. They refuse to adapt

to the actual environment that they're operating in. So it says to the boars,

however, even the khaki uniform seemed elaborate, if not ridiculous. British officers wore high,

peaked pitch helmets that shaded their eyes from the sun, but were hot and uncomfortable

and made easy targets for boar sharpshooters. It's remarkable how so much of human nature

repeats. And you just see this over and over again. So now we get to the point where I mentioned

earlier that Churchill didn't act British, that he was, he acted Rooseveltian. So there's a bunch

of other war correspondents that are going to be stationed in and around Churchill. And one of these

guys had spending a lot of time with Churchill, and he was like, man, this is, this is another

Teddy Roosevelt. Atkins had been with Teddy Roosevelt in Cuba. So it says, Atkins found

Churchill not just amusing, but fascinating. He had seen his like only once before in Cuba

during the Spanish-American War. Atkins, who was used to the almost extreme discretion and

modesty of British military men, was startled by Roosevelt's blatant self-promotion. But he

didn't hold it against him. In fact, he found it honestly refreshing. Nor did Atkins believe that

Churchill was simply boasting when he reeled off his accomplishments and outlined his audacious plans.

He thought that Churchill, like Roosevelt, was probably just telling the truth. And Churchill,

like Roosevelt, was willing to put himself in harm's way to take a risk to get what he wanted.

So he's talking about, he's like, I got to get to the front. You can't be a war correspondent,

and he says he's a war correspondent, but he's armed. He's going to wind up playing a decisive

role in the battle and trying to like save a bunch of people. It's just like this quasi, like,

almost like a soldier slash reporter. But what he realizes is like, the rest of these war

correspondents are not the rest of them, but some of them are scared. They don't want to get to the

front. And so he feels taking this risk gets him ahead of the vast majority of people that refuse

to do so. This is a quote from Churchill, a man should get to the front at all costs for every

50 men who will express a desire to go on service. There's only about one who really means business,

and he will take the trouble and run the risk of going to the front. So there's a bunch of examples

of the difference in the way the British approach war and the way that the boars approach it. So

the British war was like this grand adventure. And you can kind of see it with some of the

weird decisions they make on the battlefield. To the boars, it was a trade. And so it says,

for the boars, war was not an exciting adventure, but the cold, cruel, inescapable business of life.

The bore went out in a business like way to kill men, as he would to kill dangerous wild beasts.

And he saw no more glory in dying at an enemy's hand than in being eaten by a lion. And so the

boars do everything possible to try to win. So if you're having a shootout with somebody,

you're going to take cover behind rocks or whatever you can, right? The British wouldn't

at the very beginning. Eventually, they're like, oh, they're, first of all, the boars can, they're

way more accurate. So they can, you know, they hunt lions, they're used to hitting targets from

far distances. And so they wound up killing a bunch of British soldiers. And this is the British

response. They were beginning to see the advantages of blending into their surroundings, being quiet,

quick, and even ducking. We are learning lessons every day from the bore. We are getting to know

his game and learning to play it ourselves. Nothing but being shot at will ever teach men

the art of using cover. Now that statement, the art of using cover. So the way Churchill is going

to get caught, they are using the British are moving the railways to move supplies and troops

and everything else, right? They have these things called the British armored train. It is the most

misnamed thing I've ever heard in my life. So picture a shipping container with the top cutoff.

And so because the British are so predictable, the boar set a trap, they knew exactly what they'll

do. So they cause this train that Churchill's on to retreat, they had put a bunch of rocks around

this corner. So they knew once the train hits it, the train's going to derail. All of these British

soldiers are going to tumble out of this ridiculous non armored armored train, and they can just pick

them off as they please. And so that's exactly what happens. Churchill's actually incredibly brave.

There's all these eyewitnesses about what he did. He's going to wind up surviving. He winds up

helping other people survive too. And this is where he gets captured. But this is actually,

this is what was said about Churchill. It says Winston is like a strong wire that stretched,

always springs back. He prospers under attack and disparagement. He lives on excitement. The more

he has to fight for the greater the obstacle, the greater the triumph. And so he's taken prisoner,

they're forced to march to where they're going to hold all the prisoners in this like makeshift

prison. What was interesting though, is one, he flips out immediately because he just can't

accept the fact that he's forced to submit to obey and to adore to another person, right?

But he's also shocked at the civility. It says he was struck by the civility of the men, meaning

the people that were had taken him captive, the Boers. If you listened to last week,

essentially Churchill is in the exact opposite environment that the forgotten Highlanders,

that the Gordon Highlanders were in. And so even on this march, they were being civil to him. They

said, you need not walk fast. One of them said in perfect English, take your time. When Churchill

lost his hat, another Boer had tossed him his own. And this level of compassion came straight from

the top of the person running the Boer army at the time. When they kill Penn Simmons, what I

mentioned earlier, the leader of the Boer army, this guy named Joe Burr, had actually sent Penn

Simmons widow a letter of sympathy. Then he demands that the Boers treat wounded British as

they would treat their own men. And in many cases, they were even more compassionate to the British

than they were to their own men. They gave the wounded the blankets off their own saddles and

slept themselves on the naked Velt. So the word Velt is actually used over and over again. I had

to look it up. It's actually an uncultivated country or grassland in Southern Africa. But I

could not fathom the treatment of these British POWs after what we went through last week. Listen

to this. The Boers allowed their prisoners almost unheard of latitude. They were permitted to receive

visitors to buy newspapers and to be waited on by their soldier servants. So some people like

Churchill, they actually went to war with like a man servant. The prisoners could buy almost

anything they could afford from cigarettes to bottled beer to even clothing, bedding, towels,

and even a new suit. And yet is through this imprisonment, right? Churchill's personality

is revealed to us through this imprisonment. This is like the four seasons compared to the

stuff that was going on with Alistair Urquhart in Singapore and Japan last week. Although Churchill

acknowledged that he was the least unfortunate kind of prisoner to be, he had hated his captivity

with an intensity that surprised even him. He could not bear the thought of being in another man's

control. And so immediately he goes, starts going crazy. He can't focus. He's miserable. Churchill

would allow nothing to distract him from his one overriding, all consuming goal escape. And so he

starts hatching all these different plans. And then, especially at this age, he may have been this

whole life, but he has a giant mouth. He just can't shut up. And so he tells people what he's

going to do that he's still around other military officers that outrank him so they can tell him,

Hey, you can't do this. When some of the senior officers found out about his wildly ambitious

plan, they quickly put an end to it all. Churchill was disappointed, but as ever unrepentant, who

shall say what is possible or impossible in these spheres of action, one cannot tell without a trial

was his response. And so eventually he is going to hatch a plan with two other people. In fact,

actually, these two other people come up with the plan and then Churchill goes off on his own. He's

actually the only one out of the three that is able to escape at this point, which is why the

book said at the beginning wasn't planning to be alone without food, without a compass, without a

plan. But that's just how it happened. But this is wild. This is what he does. Like, I, I don't

know the word for this. I keep using the word megalomaniacal. I don't even know what it is. But

what this guy does is he's going to escape before he escapes. He writes a letter to the secretary

of state for war of his enemy. And he leaves it on his bed. So it is found and discovered after

he escapes unable to leave without having the last word regarding his imprisonment. Churchill

had written a letter to the secretary of state for war and left it where it could not be missed.

It was an imprudent not to mention dangerous thing to do. Keep in mind, he is hundreds of miles away

from even neutral territory. And he's deliberately poking the bear kind of like, look what I did,

I escaped. And this causes the entire like nation to be mobilized. And they send out like thousands

of pictures of him looking for him. They even put out a poster saying you can capture him dead

or alive. This was not a smart thing to do. And so the way he escapes is rather basic. He just

waits for the guards to move. And then he goes to an area of the fence that's not guarded. It's

nighttime. And then he just jumps over it. But what he did after that, that was fascinating,

where he goes out and like the, the prison is right in this town. And he just decides, he's

like, okay, what am I going to do? Do I try to sneak out? And he's like, no, I'm just going to act

as if I belong here. And so he said, he made no attempt to hide or even keep in the shadows.

I said to myself, always more audacity, this is one of my favorite, might be my favorite idea in

the book, because at every turn that is, that is Churchill's guiding maxim, always more audacity.

So he knows he has to get to Portuguese East Africa. What he doesn't know is how he's going to get

there with no food, no weapon, no compass. So it's like, well, how do I even know if I'm going in

the right direction? And so he's, he realizes, hey, I'm just going to follow the train tracks.

Now he's outside of town, he found the train tracks, he's sitting like hiding in a bush,

and he asked himself, he's like, well, what train should I take? And then he instantly

answered the first one, of course. But what he realizes without any supplies, he only has a few

days to figure this out. And nearly everywhere he turns, he risks getting captured or potentially

killed. And so the first night that he's free, he knows he has to try to make cover the most

distance as possible, because in the morning, they're going to discover the fact that he wasn't

there. And the fun, it's kind of a rather humorous way that they discover that Churchill had escaped.

This also speaks to the fact that this really wasn't like prison like conditions.

Guards would bring you coffee in the morning, you actually could get regular haircuts and

shaves. So the way he's discovered is because he had forgotten that he had made an appointment for

a shave. And the barber was going around, couldn't find him anywhere. And so he's going around asking

everybody's like, where the hell's Churchill? Where's Churchill? The people that were inside

the camp that knew he escaped were trying to talk him out. It was like, oh, he's sick or he's in

the bathroom. Eventually the barber creates such a stink and refuses to leave. That is how the guards

realized that Churchill had escaped. And so it was during this uncertain period of him trying to

figure out how the hell do I get to Portuguese East Africa? He's alone at night. And what's

fascinating is you ever hear this term that there's no atheists in a foxhole? Well, Churchill's

doc, like he wrote a lot about it. He was not a religious man. And yet at maybe the deepest

darkest point of his life, he finds himself in hiding. And he spends the night praying. And he

said he prayed long and earnestly. And a day or two later, he gets the biggest break of his life.

He is running low on food. He is not he has no shelter. He's all alone. He has no idea what

the right move to make is. And he's only 25 years old at this time. And so he desperately needs a

break more than any time in his life ever up until this point. And so it says throughout his adult

life, which had largely been made up of a series of wars, each one following hard on the heels of

the last Churchill had had moments of worry, fear and even despair. But never before had he

been tentative this time, because I think he understands like this is life or death, right?

This time for perhaps the first time in his life, he was paralyzed with indecision. And so as he had

been following the train tracks, he jumped onto some trains and then jumped off. He kept seeing

these like little collections of civilization. And he saw one that even in the middle of the

night was lit up. And so he walks towards it. It is three in the morning, he walks up to and he

realizes it's a coal mine. There's a bunch of small houses on the actual property of the coal

mine, right? He has to take a risk. And so he's describing how he felt at this point. Remember

three in the morning, he'd been on the run for multiple days, very little water, almost no food,

no weapon, no compass, no shelter, nothing, right? No knowledge that he's even on the right path.

Instead of says his strength was slipping. The prospect of further futile wanderings

terminated by hunger, fever, discovery or surrender. What other choice did he have?

He advanced towards the house and knocked upon the door. And what happens next is unbelievable.

By an incredible stroke of luck, Churchill knocked on the door of John Howard, the mines

manager and one of the few Englishmen who had been allowed to remain in the area during the war.

When Howard agreed to help Churchill, Churchill said he felt like a drowning man pulled out of

water. Saying that's incredible luck, I don't even think is is good enough description, right?

In this area, this part of the world that he's in, there's 110,000 square miles around him.

And somehow Churchill had stumbled upon one of the few places in 110,000 square miles,

where it was still possible to find an Englishman. There had been a proclamation by the Bohr

government ordering British subjects to leave the country two months earlier. This guy was allowed

to stay because a German owned the mine and said that his presence, this Englishman's presence

was integral for the successful continued operation of the mine. And even more remarkable,

earlier that day, the government had been out to the mine looking, they're searching house to house

to house, every single spot looking for Churchill. This is where the part of the book where they

said they had printed out over 3,000 pictures of Churchill's face, largely spawned on from the

fact that he decided to write that stupid letter to the Secretary of State of War. And so John Howard

may be running the mine, but it's also, there's a pun of Dutch people there, there's Bohr people

there. He's like, listen, I'm going to help you. I'm committed to help you get out of the country,

right? I'm going to help you escape. He's going to give Churchill unbelievable amount of resources.

But until I come up with a plan, there's only one place I can put you. And he puts him deep down in

the mine in like a stall for a pony. There's absolutely no lights down there. It's pitch dark,

and it's covered in rats. And so John and a small group of other Englishmen and people that want

to help Churchill wind up taking him down there, then Churchill sees him walk out and he has this

realization, right? Because like you see the lantern, the light slowly disappear into the distance.

And it says his fate now resting in the hands of men he did not know, but would have to trust.

And so after several days of planning and trying to figure out a way to get Churchill out,

they realized like they can't just leave him down there. It's completely dark. It's rather inhumane.

There's like this secret hiding space in his office. Churchill still can't go anywhere,

and he's got to be sneaked food, but he's leases inside. And during that, like it's actually light

and he has access to books. So that's another thing like fundamental understanding of Churchill.

He was a terrible student, but an incredible reader. For most of his life, Churchill had taken

refuge in books. He had never liked school, finding it a grim, joyless struggle, and himself more often

than not at the bottom of his class. He wasn't well liked by the other boys, and his parents had

all but abandoned him. So I haven't even touched upon his relationship with his mom or his father

who's passed away at this point in the story. When I read that other book called The Young Titan,

I'm sure I'll go into more detail about that. This is just about this incredible escape

that takes place in Africa, with this idea where I'm pretty sure his dad thought he was dumb.

Obviously not dumb. So it says he wasn't well liked by the other boys, and his parents

had all but abandoned him. So he was left with few places to turn for solace and friendship.

The greatest pleasure I had in those days was reading Churchill said. He would read books on

history, philosophy, economics, and evolution. He read for four or five hours every day.

I remember reading biographies of Aristotle and Nasses. So later on in his life, towards the end

of his life, Churchill's the most famous person in the world. And he's actually on, he spends a lot

of time aboard Aristotle and Nasses' yacht. And what he does is he has that same schedule where

he'd wake up, wouldn't leave bed, and he would just read and read and read for hours and hours in bed

when I'm getting out like noon or something like that. So that habit of just reading for

hours and hours and hours every day when he had essentially like a kid he kept for most of his

life. This is a really important point you need to make. As much as he's a formidable individual,

he has unbelievable levels of self belief, he's obviously willing to take great risks and to try

to like go after what he wants in life. Churchill could not have done this alone. Other people had,

they had to go to great lengths to help him escape or he would have never happened. And they're doing

so if they get caught under the penalty of death. So they come up with this idea. There's a guy that

works at the mine that also has a side business where he buys wool from the Germans and then he

ships it to the coast. And that's exactly to the port where Churchill will have to go. This is the

first like neutral territory, which is Portuguese East Africa. Okay, so they have this idea. Well,

we have these giant bales of wool that we're shipping by train enough to fill seven box cars.

I think we can hide you inside one of these. And this is what I mean that he has to put his fate

completely in the hands of other people. They do this. And so it says as soon as he burrowed into

one of the wool bales, he would be obliged to rely on chance or worse to Churchill's perspective,

someone else's intelligence and cunning. This state of affairs was far less appealing to him

than the dangers he would face if he were once again on his own. And so he gets in there and look

at all the things they have from they gave him a gun, they gave him enough food to sustain him

for a journey that was twice as long. So you can watch chickens to eat loaf of bread, some fruit,

that kind of stuff. They gave him three bottles of tea and a bottle of whiskey. And this is not a

big area. The area that they set up for him is just tall enough so you can sit up so you can't

stand and then just long enough to lie down. Now here is the crazy thing. Charles Burnham,

right, which is the guy that owns this wool business. He's just a shopkeeper. And he decides

it's now his obligation to go with Churchill to make sure he gets there to do safe because he's

got a bribe that the whole, this entire book is just a series of bribes. And so he decides not

only would he turn a blind eye, Churchill crawled into one of his boxcars, but he would ride with

him to make sure that he actually made it. So he's obviously not in the wool barrels. He's in

a compartment on the train. And so it says the train would have to stop at several stations

along the way and Burnham knew that it would be inspected by armed guards. Someone would have to

intervene. And so unexpectedly, the bribes start really early. Burnham had expected to bribe a few

men before he and Churchill reached their final destination, but he now realized that he would

have to open his wallet before they even left. And so sometimes they want money at other stops on

like the different train stations. They actually want like bottles of whiskey. And so at every stop

along the way, you have Burnham. So this is what I mean about like, he's running interference for

Churchill. All Churchill can do is either sit up or lay down. He cannot make a sound. He can't do

anything. His life is completely in Burnham's hands. And there's all these guards everywhere.

And so they get close. And like, sometimes he also is like, Hey, you want some coffee? He'll

like distract the guards. Let's go walk and get coffee. He'll do whatever he can to keep them away

from Churchill's hiding spot. And so this lasts for three days, three days where he's stuck inside

this compartment, right? Then once they cross the border, this is what I mean about his maximum is

always more audacity, right? As soon as he was certain that no one could see or hear him, he

forced his head out and felt the wind rushing through his hair. He lifted his revolver and shot

it again and again and again. This is just like, so I mean about the like, Churchill's little nuts.

He's going to write a letter before he escapes to the Secretary of State of War. And he just crosses

over the border. That doesn't mean he's safe yet. And he just decides, Hey, I'm so I have to celebrate.

He's not free. He's still stuck in the train when he's doing this.

Lewis's little revolver shoots it again and again and again, and literally screaming for joy. And

he said, I sang and I shouted and crowed at the top of my voice. I was carried away by

thankfulness and delight. The problem is he was not yet out of the enemy's grass until he steps

inside the doors of a British consulate. He could still be recaptured. So eventually they

stop at the final destination, right? Burnham is still with them. Burnham sneaked across the

border as well. He gets Churchill out of there says Churchill leaped from the train and it was

covered in cold dust, looking black as a sweep. So like the people that cleaned chimney sweepers.

So now there's another dangerous part of the trip because now they have to get from the train

station to the British consulate. Burnham has to Burnham knows area. He has to lead him through

this. He actually gets seen transporting a stranger to the British consulate later on. He

actually gets questioned. And they threatened to kill him, but they could never prove that it was

Churchill. And again, his life, his very life is in Burnham's hands. As Churchill followed Burnham

through the turning chaos, the two men did not exchange a single word or even acknowledge each

other's existence. With no idea where he was, Churchill turned tight corners, passed small

houses, crossed street after street until suddenly Burnham stopped, standing in silence, the older

man gazed across the street, his eyes on the roof of a large building. Churchill suddenly realized

with a catch in his throat, flying from his roof where the bright red and blue colors of the Union

Jack. And we see through his actions that even after this ordeal, his personality remains the same.

Crossing the street, Churchill passed through the gates across the garden up to the front door,

thin, exhausted, covered in suit from head to toe with a grazed gleam of triumph in his eyes.

He demanded to see the council general, the council secretary who had no idea who this filthy

madman was, attempted to turn away. Be off, he said. The council cannot see you today.

Instantly filled with outrage and fury, Churchill did not even acknowledge the fact that the

secretary had spoken. Shouting at the top of his lungs, he simply repeated his demand,

insisting that he see the council personally at once. So great was his indignation and so loud

his voice that it carried up to an open window. Wondering who could possibly be making such a

racket, the council general himself put his head out the window. A moment later, the council

stepped up to the young man standing at his door and asked his name. It was one of the last times

in a long life that anyone would ever again need to ask Winston Churchill that question.

What an ending. For the full story, I highly recommend buying the book. If you buy the book

using the link that's in the show notes in your podcast player, you'll be supporting the podcast

at the same time. That is 319 books down 1000 ago, and I'll talk to you again soon.

Machine-generated transcript that may contain inaccuracies.