Founders - #319 The Making of Winston Churchill Part 1

Starting point is 00:00:00 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 hacked 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

Starting point is 00:00:45 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 vaguest 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.

Starting point is 00:01:29 It's written by Paul Johnson. It's only like 170 or 180 pages long, and I thought it was excellent. It's episode 225 if you haven't listened to it. But what was 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

Starting point is 00:02:02 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, 20, 30, maybe 40 years of somebody's life. And so I ordered two books that I could find on young 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 author of that book as well. So if I'm reading to understand

Starting point is 00:02:44 what Winston Churchill was like, I might as well start with the author that 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's 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 was 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

Starting point is 00:03:27 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 becoming 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

Starting point is 00:04:05 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 in 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

Starting point is 00:04:45 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 and to 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 just like, I don't even know how to describe it, like unbelievable, relentless self-belief, almost like this God complex. And usually with that,

Starting point is 00:05:24 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, than 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, like, you're not being Victorian, you're not acting like you're an aristocrat. What are you doing?

Starting point is 00:05:54 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, that's 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 and 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 was his destiny. For that, he was willing to risk anything, even his life.

Starting point is 00:06:26 And that's the important thing. He was willing to risk his life on things that he believed in. You know, they said 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,

Starting point is 00:06:53 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 Pashtuns. 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

Starting point is 00:07:36 describe it. Megalomania might be the way you describe it. You'll see what I'm talking about in a minute. In his actions, it just shows 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. It's incredible the way this guy thought about himself.

Starting point is 00:08:11 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 Churchill, you could his behavior. You could 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

Starting point is 00:08:41 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'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 in the knowledge that he would be impossible to miss. I rode on my gray pony all along the front of the line of the skirmish line where everyone else was lying down in cover.

Starting point is 00:09:28 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,

Starting point is 00:09:54 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 an 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

Starting point is 00:10:38 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 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 an 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,

Starting point is 00:11:19 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 had witnessed, His faith in himself and 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

Starting point is 00:11:59 without any disturbance of body or mind. But just because he has this level of self-belief doesn't mean he's always right. He thought he could leave the army, right? He's like, okay, I think I've done enough. I'm going, I want to run. His whole goal is like get glory in war and then parlay that into public office, right? Then get elected to like a, you know, basic level and 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 tow rope, he said, and commit myself unaided

Starting point is 00:12:39 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

Starting point is 00:13:17 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 got himself on the ticket, whether he was ready or not. In his own mind, of course, he was more than ready.

Starting point is 00:13:43 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 this election because this entire book is about his time in the Boer War and specifically the fact that he becomes 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 at a young age, though, is just how much he would practice. He has this relentless combination of practice and self-confidence.

Starting point is 00:14:18 Obviously, the public praises people for what they practice in private. Churchill's known to 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,

Starting point is 00:14:53 and would do so throughout his life. A friend would later joke that Winston has 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

Starting point is 00:15:23 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 is 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,

Starting point is 00:16:11 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

Starting point is 00:16:51 believed to be one of the greatest generals in history. And in fact, Winston 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 I was sitting here thinking 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 life 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

Starting point is 00:17:55 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.

Starting point is 00:18:32 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

Starting point is 00:19:06 this, the British attitude and, I guess, opinion towards the Japanese that took place, you know, 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. Here's the problem. The British are utterly predictable.

Starting point is 00:19:42 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, supplies and ammunition. They didn't

Starting point is 00:20:25 have to. There had never been a time, either in their own lives or in those of their forebearers, 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 man was accustomed to living off of just a handful of staples, coffee, brown bread,

Starting point is 00:21:11 and dried meat. They had been stockpiling weapons. When it came to marksmanship, it was impossible to compete with the boars. 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

Starting point is 00:21:51 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.

Starting point is 00:22:27 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 Boer 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 raining to. They didn't know how many people are attacking them. They were completely unprepared.

Starting point is 00:22:59 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 aide to camp ride by his side, holding a dashing scarlet pennant. And so if you're the army fighting this guy and you have their leader saying, 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, is this guy named Botha. Sending somebody like Penn Simmons in pursuit of somebody like Botha in this land and terrain is like sending a cow in pursuit of a rabbit. Botha knew the region well. He had been born nearby

Starting point is 00:23:43 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,

Starting point is 00:24:15 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,

Starting point is 00:24:46 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 Boers. 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-content costumes, and 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 Boers, however, even the khaki uniform seemed elaborate, if not ridiculous.

Starting point is 00:25:27 British officers wore high peaked pitch helmets that shaded their eyes from the sun, but were hot and uncomfortable and made easy targets for Boer 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,

Starting point is 00:25:46 that 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, spending a lot of time with Churchill, he's like, man, this is another Teddy Roosevelt. Atkins had been with Teddy Roosevelt in Cuba. So it says, Atkins found Churchill

Starting point is 00:26:03 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.

Starting point is 00:26:44 He says he's a war correspondent, but he's talking about, he's like, I got to get to the front. You can't be a war correspondent. He says he's a war correspondent, but he's armed. He's going to wind up playing a decisive role in a battle and trying to save a bunch of people. So he's like this quasi, almost like a soldier slash reporter. But what he realizes is the rest of these war correspondents, or 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

Starting point is 00:27:26 and the way that the Boers 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 Boers, it was a trade. And so it says, for the Boers, war was not an exciting adventure, but the cold, cruel, inescapable business of life. The boar went out in a businesslike 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.

Starting point is 00:27:59 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 wind 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.

Starting point is 00:28:25 We are learning lessons every day from the boar. 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 cut off.

Starting point is 00:28:54 And so because the British are so predictable, the Boers 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.

Starting point is 00:29:25 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.

Starting point is 00:29:39 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

Starting point is 00:30:05 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.

Starting point is 00:30:41 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 veldt. So the word veldt 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,

Starting point is 00:31:15 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 manservant. 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

Starting point is 00:31:46 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 his 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.

Starting point is 00:32:18 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's 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,

Starting point is 00:32:52 which is why the book said at the beginning he 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. I don't know the word for this. I keep using the word megalomaniacal. I don't even 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

Starting point is 00:33:11 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,

Starting point is 00:33:44 look what I did, I escaped. And this causes the entire 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.

Starting point is 00:34:11 But what he did after that, I thought was fascinating, where he goes out and 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? 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 Churchill's guiding maxim, always more audacity.

Starting point is 00:34:41 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 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'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 and potentially killed and so the first night that he's free he knows he has to try to make cover

Starting point is 00:35:19 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 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, 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.

Starting point is 00:35:56 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 was 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.

Starting point is 00:36:31 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

Starting point is 00:36:55 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 he walks towards it. It is 3 in the morning. He walks up to it, and he realizes it's a coal mine. There's a bunch of small houses on the actual property of the coal mine, right?

Starting point is 00:37:33 He has to take a risk, and so he's describing how he felt at this point. Remember, 3 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, it weapon, no compass, no shelter, nothing, right? No knowledge that he's even on the right path. Instead, it 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 mine's manager, And what happens next is unbelievable. man pulled out of water. Saying that's incredible luck, I don't even think is a good enough

Starting point is 00:38:25 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 Boer 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.

Starting point is 00:39:09 This is where the part of the book where they said they had printed out over 3000 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 ton of Dutch people there. There's Boer 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 them 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 were willing to help Churchill wind up taking him down there. Then Churchill sees him walk out and he has this

Starting point is 00:39:53 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 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

Starting point is 00:40:30 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. 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.

Starting point is 00:41:14 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 Nassus. 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 Onassis' 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. He wound up 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

Starting point is 00:41:49 most of his life. This is a really important point I 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 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

Starting point is 00:42:25 Churchill will have to go. This is the first neutral territory, which is Portuguese East Africa. So they have this idea, well, we have these giant bales of wool that we're shipping by train, enough to fill seven boxcars. I think we can hide you inside one of these. And this is what I mean. 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 for him. They gave him a gun. They gave him enough food to sustain him

Starting point is 00:43:09 for a journey that was twice as long. So he got a bunch of 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. The whole, this entire book is just a series of bribes. And so he decides, not only would he turn a blind eye as Churchill crawled into one of his boxcars, but he would ride with him to make sure that he actually made it.

Starting point is 00:43:50 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,

Starting point is 00:44:08 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, 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.

Starting point is 00:44:24 All Churchill can do is either sit up or lay lay down he cannot make a sound he can't do anything he's his life is completely in Burnham's hands and there's there's all these guards everywhere and so they get close and like sometimes he uh 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

Starting point is 00:44:59 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 a 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. Lifts his 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 grasp. Until he steps inside the

Starting point is 00:45:41 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. It says Churchill leaped from the train and it was covered in coal 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 knows the area. He has to lead him through this. He actually gets seen transporting a stranger to the British consulate.

Starting point is 00:46:12 Later on, he actually gets questioned and they threaten 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 churning 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, were 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

Starting point is 00:46:56 the gates, across the garden, up to the front door. Thin, exhausted, covered in suit from head to toe, with a grayish 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.

Starting point is 00:47:41 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 on your podcast player, you'll be supporting the podcast at the same time. That is 319 books down, 1,000 to go, and I'll talk to you again soon.

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Founders - #319 The Making of Winston Churchill Part 1

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