Winston Churchill. We all remember his steady hand guiding Britain through the darkest days of World War Two. But that legendary leadership wasn’t just a gift; it was earned, forged in a lifetime of breathtaking action and direct confrontation with war. On Our American Stories, we’re diving into the untold tales of Churchill’s early years, exploring the harrowing battlefields and daring adventures that prepared him for his greatest challenges.
From facing down enemy fire in Afghanistan to daring escapes during the Boer War, Churchill didn’t just witness history – he made it, often with bullets flying. Though he famously disliked war, he possessed a remarkable knack for it, a complex spirit that rose to every challenge. Join us now as Dr. Larry P. Arnn shares how these extraordinary, character-building experiences shaped Winston Churchill, revealing the grit, resilience, and unique perspective of a man who would one day stand firm for freedom.
📖 Read the Episode Transcript
He didn’t like war. He was really good at it. You know, he fought. First time he fought was in Afghanistan. He walks up and down, upright, behind the rocks. It’s fought up in the rocks by the hills. And so he’d walk up and down so they could shoot at him. So they would write about him, writing back the reports and the dispenses, they call it, about the, and so they got used to that, so they didn’t mention his name anymore. So he bought a horse and rode that up and down. And then the next place he fights is in the Sedan, and he’s in a cavalry charge, last big one, and people talk about him about what he was like on a battlefield. Then the biggest thing, the best thing, was he went to South Africa, and they’d made a rule that you couldn’t write articles for the press if you were a serving officer. And they made that rule for him because he was the most famous commentator on all of the wars he was in and became a public figure, including talking bad about the generals. And he was a second lieutenant, and so what he would do then is he would resign his commission and serve and write articles for a while, and then he’d joined back up and served some more. And at the moment he gets on this armored train, and he knows it’s a bad idea. He’d been on the dang thing before. Think about it for a minute. An armored train is a stupid idea because they’re very heavily armored and stuff, but you know exactly where they’re going, and they got to have the tracks. And so he said, “Well, I don’t know,” and this guy Haldane says, “Please come with me. I want you to come.” So he gets on the dang train, and it’s attacked, and it’s derailed, and he’s a journalist, right, and they’re all cowering, and there’s hills on both sides, and rocks and people behind it, and there’s small arms fire and artillery fire. They were thirteen killed, and everybody’s in a panic. And so he gets out, and he walks the circle out in the open around the locomotive, you know, and investigated bullets coming down, you know, and he doesn’t notice them. “God did not make such a force as I merely to stop a bullet.” Churchill was confident, and so he comes and opens the door and he says, “Wait, we can get this thing going.” They work for an hour. He’s the one that works out in the open, and they get the train going, right? And then, you know what he says when it’s over? He says to Haldane, “He’s eventually captured, by the way. He could have got away, but he didn’t want to leave the other guys behind. And of course he escapes, by the way, and becomes a national hero and gets elected to Parliament.” But on the scene he says to Captain Haldane, “Thank you for letting me do that. Isn’t that weird?” He said, “The whole Derbyshire Light Infantry has seen that, and now I’m going to be elected to Parliament.” He was a fighter; his spirit rose in the face of war, but he hated it too. Then he’s a politician, and then a big war comes, the First World War, and you know, people mistrusted Winston Churchill, and one of the reasons is they trusted him to tell the truth. And he was very ambitious and very quick, and that meant that they were always afraid that no matter what he got his mits on, he was going to take it over. And that’s because he did. He just couldn’t be stopped. But at the beginning of both World Wars, one of them, Herbert Asquith, is the Prime Minister, and the other, Neville Chamberlain, is the Prime Minister. Within three months of the war broken out, they made him the chairman of the Committee to coordinate the whole war, because he had energy and he knew what to do. John Colville, one of the best witnesses for Churchill, was a Chamberlain guy in the Prime Minister’s office. When Churchill took Chamberlain’s place in May of nineteen forty, up to diary, it was illegal. This is a violation of the Official Secrets Act. But he kept keeping his diary. And it’s good that he did, because here’s what he thought. “They’re Chamberlain people. He’s steady. Churchill’s a wild man. This is going to be terrible,” and then two weeks later he’s writing, “Oh, this is how you fight a war.” Churchill was good at it. He loved it, and he hated it. When the wars broke out, he, every time a big one broke out, he had foreseen it, and he’d spent at least a decade trying to stop it and failed. Where did that come from? In eighteen ninety-eight, Churchill is on a battlefield in the Sudan, and he sees a charge. And I think this is the earliest instance I can see of it, underman’s down on them, and really the first, one of the first, for sure. Islamic republics had taken the city of Khartoum, which is a thousand miles down the Nile from Alexandria, where the mouth is up in the Mediterranean. And this Mahdi of Allah was his title. He took the city and he publicly beheaded a man named General Gordon, a figure of the Empire and a heroic man. And they sent evidence of it to London, and they said, “We got to go get them.” They couldn’t go by boat. The Nile is impassable for much of its length, so they sent a camel corps, and it got chopped to pieces. And so then they employed an engineering kind of general named Kitchener, with whom Churchill had many dealings, much of them unhappy. And Kitchener figured out how to do it. They put a whole bunch of stuff on boats, and they floated them down to the place where the Nile was impassable, and then they took the stuff off. And what it was was a railway, and they built a railway. Then they put all the boats and all the troops and all the equipment on the locomotives, on the trains, and they took them down to the place. Then they put it all back on the boats. And now they’ve got a major army with gunboats outside Khartoum, and thirty-five thousand dervishes charge. The one that got the farthest got within one hundred yards, one hundred and fifty yards, a football field and a half. They could hardly see the British lines. And the British didn’t lose thirty people, and they killed twenty percent of the dervishes. He says, “The white flags, that’s the front line.” Troops carrying big white flags of the dervishes come over the hill. They have no sense of the impending tragedy. They were most inferior in artillery, and so they opened with that. He describes the bullet shearing through muscle and bone, and the sand and the sweat and the blood and the screaming. The infantry back at the British lines fired steadily and stolidly. Although they were interested in the work, it became tedious after each looked down the sights. There were fewer targets than the one before. Then they say that soon the barrels began to melt, and they had to bring water jackets and keep changing them, and they had to bring more. There’s a factory for killing. And he never calls the British brave. He calls the dervishes. And you know, Churchill didn’t like these dervishes, but at the time of the battle, only they are brave. And then he reflects to himself. He says, “Used to be bravery was the chief asset in war. Is it machinery? Now that’s a heck of a reflection for somebody twenty-six years old.”
The heck of a reflection. Indeed, those lines by Dr. Arnn. “Churchill was a fighter. His spirit rose in the face of war, but he hated it too.” And this is the essence of Churchill rising at the time when England needed him to rise. When we come back, more of Churchill in battle, Churchill in conflict, and I mean real life war in battle. Here on Our American Stories. And we returned to Our American Stories and our story.
On Winston Churchill and war.
When we last left off, Dr. Larry P. Arnn, president of Hillsdale College, was telling us that although Winston Churchill hated war, he was very good at it and had a profound understanding of it even as a young man. Was also a great writer. Here’s Dr. Arnn on one of the observations Churchill made about war. Let’s return to the story.
What he wrote was, “If you’re forever at war, then that disturbs the liberal society. The liberal society is where we get to be important, just ordinary people. But if everything is conscripted, as it must be,” he says, “the way war is going, then there will be no room for any of us to be free. And that means that’s got to be stopped. You got to find a way to win, and win fast, and not fight if you can help it.” He was always, you know, in nineteen fifty-four, Winston Churchill refused Dwight Eisenhower to go to Vietnam with him. So what I’m describing here is an entire life of a man who’s a fighter and is good at it and loves it, and tries to stop it on the argument that we must spare ourselves so we can live like free people. And when you see Hitler coming, do you see why he understood him? He urgently sets about the job getting the country to rearm because we’re in a position to stop him without a fight, and we’ve got to do that. And remember this, we can only see Churchill after he became the greatest man in the world and did the greatest things he did. But of course, most of his life is not like that. Most of his life is him being the most reluctant guy to call on his people to sacrifice their way of life. But then nineteen forty comes, and in some kind of poetic and ironic cosmic justice, he’s the one picked to fight the war. But now the Germans have beaten the French, and the Germans are in alliance with the Russians, and we are distant. And so then, of course, as the France is collapsing, and he’s flying back and forth begging the France to stay in the war. And you know, he’s picked Prime Minister because that’s a piece of hard medicine, and at last they’re ready to take it. And so he goes over there, and he begs them, and they quit anyway, having a treaty not to do it. And so he destroys their fleet in the port of Oran in North Africa, and he won’t send them any more airplanes. And then France falls anyway. And so then Edward Halifax, Edward Wood Lord Halifax, is the Foreign Minister, and he’s the chief of the appeasers, along with Chamberlain. And he brings a proposal conveyed through Mussolini, Hitler’s henchman, not yet in the war, and says, “We want to talk peace. We’ll be really generous.” And I want you to see, this is a dramatic demonstration of what life demands of us. And we’ll never know until Heaven whether we were right or not. I’ll explain why, because this guy, who’s the one who’s trying to stop this war from happening, he’s the only one who doesn’t want to open a peace conference. And the reason is, it’ll be in the papers, and then the whole war effort, a Britain, pitiful thing that it is, will collapse. And he’s the Prime Minister. But they don’t vote in the cabinet. They have a discussion, and the Prime Minister has the authority to summarize what they’ve decided, and if you don’t like it, you quit. And so if he says we’re going to fight on, and Halifax says “I quit,” the government falls. He doesn’t have the power, and so he had to do something more questionable than vote. He had to talk them into it. It’s amazing that he did. He talks for an hour. He didn’t have time to write the speech out, which is very uncommon. Two people took notes, and we have the notes. He described the war situation in blank terms. “We’re going to be up against overwhelming odds. There’s going to be a naval battle,” remember we still have a navy, “but that will go the way of an air battle. And they have more airplanes, but they have to fight over here on our side. We don’t know how that’s going to go, but there’s good hope. And then, you know, if they land, the towns they’re going to take first have names like names in New England, and the Americans will come and help us. That’s the hope. Remember, we’re the hope.” At this point, he’s familiar with the workings of the Great World War like no one else. He’s as familiar with that as I am familiar with the operations of this college. That’s infinitely larger. Right? But he can just think about it and see it, and he can see, “gonna need us. I’m gonna have to talk them into coming.” But meanwhile, “I got a hold on,” right? And he closes the speech with this, and I’m asking you to remember the last person to say this. He says, “I’ve been thinking in these last few days whether it is part of my duty to open negotiations with that man. And I believe that if I were for a moment to consider parley or surrender, every one of you would rise up and tear me down from my place. If this Island story is to end, at last, let it end when each of us was choking in his own blood.” He talked them into that. They leaped up and patted him on the back, and for the rest of his life, friend and enemy still had the same friends and enemies. They treated him like the greatest man in the world. And my point is, you can’t be sure that was the right thing, because you know what Britain lost? That’s what costs Britain its greatness. That’s a factual point. And Churchill himself had made the case a million times, “We can’t do that.” And it’s not like he just said, “I’m the Prime Minister, you got to do it.” He had to summon from himself a speech that there’s no living person he’s responsible for that. And then, of course, he watched it collapse and become a little country. They were having to borrow money from us to get food after the Second World War, the greatest nation on Earth for two hundred years. He hated that. But you know what the choice was, because when it gets to the end, and you can only make decisions like this when there’s no alternative. This is what Churchill teaches us about war. There are two final points. The first one is, if you get to the place where you’re going to surrender your power to resist to the worst man in history, better to die. There are Frenchmen who have ancestors who signed orders to round up Jews because otherwise their families would be shot. Better to die. That’s the first lesson. You don’t make extreme judgments except extreme circumstances, and then pray for the strength to make them. But the second was, do you know what this proved to Churchill? It’s the greatest thing of all. It’s what he lived his life to prove. His whole life he conceived it. He thought, “These things are getting so big, war and production and nations and science, that people don’t matter anymore.” And sure enough, the doctrine of Hitler and the doctrine of Stalin is precisely that people don’t matter anymore. “Throw up your hands. You have to be on the side of history or else everything is vain.” But he’s talking about choice. What do chance and choice have to do with each other? Are they opposites? Are they the same? He says, “You know your own life is dominated by accidents. Means you see that the stuff we do is significant.” And he says, “Along these pathways, that’s where you can see,” quote, “the profound significance of human choice and the sublime responsibility of men.” And Churchill was searching for that all his life. And that means on the twenty-eighth of May, when he walked in that room, he was the only one who could have done that. He thought God put him there.
And you’ve been listening to Dr. Larry Arnn, president of Hillsdale College, tell one heck of a story about perhaps the most important man of the twentieth century. “If you’re forever at war, there was no room for anyone to be free.” And it took a warrior to understand the consequences of war. And as Dr. Arnn said, “the sublime responsibility of choosing.” And by the way, Dr. Arnn may be the only one who could have done what he just did. Sir Martin Gilbert has passed. The story behind the story of Churchill the Warrior, here on Our American Stories.
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