in: Character, Knowledge of Men, Podcast

• Last updated: September 30, 2021

Podcast #544: The Audacious Life of Winston Churchill

When we seek an example of great leadership, one man who often comes to mind is Winston Churchill — the iconic, visionary prime minister, who guided his country through war and stood firmly for his beliefs and impervious to his critics. But how did Winston become the legendary British Bulldog?

My guest today seeks to answer that question in his biography, Churchill: Walking with Destiny. His name is Andrew Roberts, he’s a journalist and historian, and we begin our conversation discussing why he thought another Churchill biography was needed. We then shift to the life of Churchill, beginning with a childhood in which young Winston often felt neglected. Andrew then discusses Churchill’s military career, why Winston was so eager to see action on the frontlines, and how he parlayed those experiences into becoming the world’s highest paid journalist by his mid-twenties. Andrew then explains how Churchill also became one of the 20th century’s great historians and how his appreciation of history and sentimental outlook colored his worldview and shaped his leadership. We also discuss why Churchill was one of the few leaders to foresee the threat that Hitler posed. We end our conversation discussing whether some of the current criticisms of Churchill, such as the allegation that he masterminded genocide in India, really hold weight.

Show Highlights

  • Why write yet another bio of Winston Churchill?
  • What was Churchill’s childhood like? How did it influence his later leadership?
  • Why did Churchill feel he was destined for greatness?
  • Winston’s military career, and his desire to see action
  • His early success as a journalist and his career as a writer
  • Churchill’s love of history and how it led to his success as a leader
  • His unconventional “religious” views 
  • His blunders while in charge of the Royal Navy 
  • Churchill’s wilderness years 
  • How was Churchill so stoic in the midst of criticism?
  • Churchill’s relationship with his wife Clementine 
  • Winston as a father 
  • What happened with Churchill met Theodore Roosevelt?
  • Churchill’s emotions, sentimentalism, and Romanticism
  • Roberts’ take on the modern criticisms of Winston Churchill 
  • Was Churchill born a great leader? Or did he fashion himself as one?
  • What are the leadership lessons we can take from Churchill?

Resources/People/Articles Mentioned in Podcast

Churchill walking with destiny book cover by Andrew Roberts.

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Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. When we seek an example of great leadership, one man who often comes to mind is Winston Churchill, the iconic visionary prime minister who guided his country through war and stood firmly for his beliefs and impervious to his critics. But how did Winston become the legendary British bulldog?

My guest today seeks to answer that question in his biography, Churchill: Walking with Destiny. His name is Andrew Roberts. He’s a journalist and historian, and we begin our conversation discussing why he thought another Churchill biography was needed. We then shift to the life of Churchill, beginning with a childhood in which young Winston often felt neglected. Andrew then discusses Churchill’s military career, why Winston was so eager to see action on the front lines, and how he parlayed those experiences into becoming the world’s highest paid journalist by his mid-20s.

Andrew then explains how Churchill also became one of the 20th century’s great historians and how his appreciation for history and sentimental outlook colored his worldview and shaped his leadership. We also discuss why Churchill was one of the few leaders to foresee the threat that Hitler posed, and we end our conversation discussing whether some of the current criticisms of Churchill, such as the allegation that he masterminded genocide in India, really hold weight. After the show’s over, check out our show notes at Robert joins me now by phone.

Okay. Andrew Roberts, welcome to the show.

Andrew Roberts: Thank you very much indeed.

Brett McKay: So you have a new biography out about Winston Churchill, Churchill: Walking with Destiny. Now Churchill is probably one of the most written about individuals of the 20th century. Why did you think the time was right for a new biography about him?

Andrew Roberts: You’re right. There are no fewer than 1,009 biographies of Winston Churchill, so it’s perfectly reasonable to ask why on earth the public needs a new one. The answer is that in the last decade, there have been an avalanche of new sources on Winston Churchill that have become available. I was the first Churchill biographer ever to be allowed to see the Queen’s father’s diaries. King George VI met Churchill every week of the war on a Tuesday at lunchtime and wrote down everything that the prime minister told him.

Also, there have been 41 sets of papers from different people that have been deposited at the Churchill archives in Cambridge over the last 10 years, and there have also been various very important diaries, for example, Ivan Maisky, the Russian ambassador, that’s been published, and other things like that, verbatim accounts of the war cabinet.

So all in all actually, there is easily enough to write a book like this one does. It has something on every page that has appeared in no Churchill biography before.

Brett McKay: So new information, new insights, gives greater context.

Andrew Roberts: That’s right.

Brett McKay: Let’s start with Churchill, because I think most of us know him as the scowling bald guy during World War II, but his whole entire life was incredible. Let’s start with his childhood. What was that like, and how did that influence the leader that he would become during World War II?

Andrew Roberts: Well, he had a pretty unhappy childhood, really. His father and mother were very busy people and his father was Chancellor of the Exchequer in the British government and his mother was a hugely popular high society socialite. Although they were successful in their own fields, they had no time really for their son Winston, or Winston’s younger brother Jack, who as a result, were very badly neglected. You can see in their letters the desire for love and attention that really didn’t get given to either of them.

In Winston’s case, where his father was actually unpleasant to him, actively disdainful and aloof and unpleasant, his response was actually the counterintuitive one, which was to adore his father, worship him, especially after his death in 1895, when Churchill was 20 years old, and he sought to emulate his father. It was the major reason for him to go into politics.

Brett McKay: Yeah. The letters were heartbreaking that he would write when he was at boarding school. I think there was one letter, his father was just two miles away and Winston was like, “Please come visit me. I want to see you,” and his dad didn’t even respond to him.

Andrew Roberts: I know. Again and again, and worse than that, they actually complained that Churchill was being needy and not writing, when in fact, it was them who didn’t write and Churchill who wrote letter after letter begging them to show him some interest and visit him.

Brett McKay: What’s also interesting, even as a young man, as a teenager, Churchill felt he was destined … the book’s called Walking with Destiny. He felt he was destined for greatness. Why did he think he was destined for greatness?

Andrew Roberts: Yes. I think in what would be almost a psychological disorder in other people, it was certainly a very powerful influence on him, this idea that he would, as he told a 16-year-old … When he was a 16-year-old schoolboy, he told another 16-year-old schoolboy, his friend at Harrow, Merlon Devins, said to him, “There will be a great upheaval and a terrible struggle in my life and I will be called upon to save London and save Britain,” and of course, that’s an extraordinary thing to say at age 16, but half a century later, precisely that happened.

Brett McKay: So he went to boarding schools as a young man or as a boy. After that, he went to military school and he had a military career. What was his military career like as a young man?

Andrew Roberts: Well as you say, he went to the Royal Military Academy at Sandhurst, so that was his university, really. Then he went off to fight on the northwest frontier of India against the various tribes that attacked the British Empire up in the north there, attempting to attack the Punjab, and he went off to Cuba to watch the Spanish attempt to put down the uprising of the Cuban rebels. In 1895, he went to South Africa and to the Sudan, and in fact, he fought in five campaigns on four continents before he entered politics.

Brett McKay: One thing about him is not only did he go to these places, but he wanted to see action. He wanted to be where the danger was at. Why was he so eager for that?

Andrew Roberts: I think not so much that he wanted to be where the danger was, but where whatever it was that was important was happening. He wanted to see for himself whatever was going on, and that of course, in the military career, did mean where the danger was, but also in his political career, he tended to want to be wherever it was that the most important thing was happening. So it wasn’t that he was, as some people have charged, a sort of danger junkie who got excitement from bullets flying. He just wanted to make sure that he was actually on the spot of whatever was most important that was going on, which eventually made him, actually, the world’s best-paid war correspondent.

Brett McKay: Yeah. As a 20-year-old, he went to South Africa for the Boer Wars, not to fight, but to report on it.

Andrew Roberts: That’s right. Yes. It’s extraordinary really, the way in which he was able to do both, in a sense. He was a officer in the British army. There was no doubt which side he was on. When his train was ambushed by commandos, he of course took the command of the men there on the ambushed train and managed to get part of it back through enemy lines. There was no doubt that he was first and foremost a soldier, but one who would then write about everything that was going on. It was an interesting thing that was even then fairly unusual, and today, totally unknown.

Brett McKay: But when he also wrote about war. He often tended … some people would say he romanticized it, and that he was kind of a war monger. Do you think that claim or that criticism holds true or has any water?

Andrew Roberts: I don’t think it does at all. He actually did come to the sharp end of war. He saw men just like at the end of the Battle of Omdurman, where he took part in the last great cavalry charge of the British empire, with the dead and wounded strewn over, thousands upon thousands of them strewn over the battlefields. So he knew the horrors of war, and knew them up close. But there’s no denying that he found it much more exciting than peacetime. It wasn’t, as I said earlier about about his general attitude, that he was a sort of attention-seeking junkie. He was somebody who really appreciated that in war, if you’re going to write about it, you need to be up close and personal.

Brett McKay: So yeah, by the time he was 25, he had fought in various campaigns around the world, became one of the highest paid war correspondents in the world, all before 25. That can make you feel really bad about yourself, because I think when I was 25, I think I was in law school, and that was it.

Andrew Roberts: It’s worse for me. I was working in the city. I was a merchant banker, an investment banker, and yeah, absolutely. I mean this guy, the things that he had achieved already by the time he was 25, and he said that in his wonderful autobiography, My Early Life. He said, “20 to 25, those are the years, those are the years that you can really get down to taking risks and no one will blame you for mistakes,” and it’s a wonderful series of phrases that he comes out with in his book.

Brett McKay: Another thing people don’t know about Churchill, besides his political career, is that he was actually one of the most notable historians of the 20th century. He was a prolific writer. Where did he learn his craft? Was he formally educated in history?

Andrew Roberts: No, he wasn’t actually. He was in that he went to Harrows School, which was good, and there were good history teachers there, but he didn’t take that beyond school age and yet, he wrote 37 books, many of which were history books and biographies. It was his passion. After making his living by his pen as a war correspondent as we mentioned earlier, because his father didn’t leave him very much money and he had to take care of his brother and his mother, he wrote, and one of the things that he was always interested in and driving emotional force in his life was his sense of history. So he wrote history books, and he won the Nobel Prize for Literature for them.

Brett McKay: How do you think his appreciation for history shaped his outlook on his life? Did it make him like this sort of staunch reactionary traditionalist? Or was it something else that happened?

Andrew Roberts: Well, no, he … First of all, he wasn’t a staunch reactionary traditionalist until later on in his career. He crossed the floor of the House of Commons in 1904, became a liberal and was one of the founders of the British welfare state with David Lloyd George. But what it did do was to allow him to see various threats to Britain in their overall historical context, and so that was why … one of the reasons why he was one of the only people, certainly the first person in British politics, to warn against the threat posed by Hitler and the Nazis, because he saw the attempt at Germanization of Europe as something that was in the long continuum of British history, going back to the Spanish Armada and Louis XIV and Napoleon, and so on. So this was an essential prerequisite, really, for his being able to place the Nazi threat in the correct historical context

Brett McKay: And it also seemed like, the way you described it throughout the book, is that his love of history and the past allowed him to be very forward-thinking at the same time.

Andrew Roberts: That’s right. Yes, he was. Another example will come of course after the Second World War, when he was the first person in the West of any note to warn against the Soviet threat, the danger posed by Stalinism to Eastern Europe and to the whole of Europe. That speech that he made in Fulton, Missouri, in March 1946 was deeply unpopular and he was accused of being a warmonger and denounced in the press and in both Congress and Parliament and so on, but actually showed tremendous foresight.

Brett McKay: Another thing, his appreciation for history and his knowledge, his thorough knowledge of British history, that came to be very helpful during World War II, because it seemed like he’d fall back on that as he was trying to mobilize and keep the British people together during all the bombings and the threat of Nazism coming to them.

Andrew Roberts: Yes, very true. He certainly did. He would talk about the Spanish Armada and about Drake and about Admiral Nelson and the dangers to Britain back in the Napoleonic Wars, and he would therefore use history as a way of basically telling the British people, “Look, you’ve been here before, there’ve been threats of invasion in the past. This is how we dealt with it, this is what we do, and we came through and we will win.” So he used history very powerfully as a way of bolstering morale and fighting demoralization.

Brett McKay: Was Churchill a religious man? Did he have that as sort of a bedrock for … because he seemed so steadfast. Was religion that sort of bedrock for him? Was it something else?

Andrew Roberts: He … It wasn’t really religion, no. He believed in an almighty, but when you look theologically at it, the sole duty of the almighty seems to have been to look after Winston Churchill. Churchill had many, many brushes with death in his life, had many accidents where he nearly died, and he believed in what he called invisible wings that were beating over him and protecting him. But he was not a conventionally religious man in any way. In fact, he describes his relationship to the Church of England as being like that of the flying buttress, in that he supported the church, but from the outside.

Brett McKay: Some have described Churchill as sort of spiritual but not religious, in the sense that as you said he didn’t go to church, but he still had a real capacity for wonder and a sense of the transcendent and he believed in absolute good and evil and the heroic clash between those forces. He had a firm moral code, a bedrock of principles like honor, loyalty, and courage, and he would take time to contemplate. He would sit by his fireplace at Chartwell reflecting. He also seemed to have a different kind of faith, as well, a sort of faith in the British empire.

Andrew Roberts: Yes, he had a secular faith in the British empire, in a sense of also the sort Whiggish progression of history, he believed that people were moving forward. I’m not sure he felt that way after Auschwitz and the death camps were revealed, I’m not sure that he had this sense that mankind was getting better very much after that. But nonetheless, for most of his life, he tended to believe in a general sense of human progress.

Brett McKay: Churchill after the Boer War, he got elected to Parliament and had a political career and then he was put in place as the First Lord of the Admiralty. But he made some blunders there. Can you talk about what those blunders were and how it affected his political career?

Andrew Roberts: Yes. Well, as First Lord of the Admiralty, he was in charge of the Royal Navy and he came up with this idea, in many ways a genius concept, which was to get the Royal Navy through the Dardanelles Strait between Europe and Asia, and moor it off Constantinople, modern-day Istanbul, and basically knock Turkey, knock the Ottoman Empire out of the central powers, which would’ve been a brilliant scheme if it had come off, one of the great coups of World War I.

But unfortunately, as a result of some mine laying the night before the the attack, we lost six ships, the Allies lost six ships on the day of the 18th of March, 1915, and it was catastrophic. Instead of calling the whole thing off, Churchill insisted on a land offense on the European side, on the Gallipoli peninsula, which ultimately led to the killing or wounding of no fewer than 147,000 Allied troops.

Brett McKay: What happened to his career after that, after that happened?

Andrew Roberts: Well, he was forced to resign was the first thing that happened, in November 1915. But thereafter, even when he was brought back into the government again later in the First World War, every time he gave a speech at public meetings, someone would shout out, “What about the Dardanelles?” And this would carry on for another 15 … longer, years of his career.

Brett McKay: Was this the time that was known as Churchill’s wilderness years?

Andrew Roberts: The wilderness years actually starts in 1930, when he resigned from the Shadow Cabinet, from the conservative Shadow Cabinet, and then spent 10 years warning against Hitler and the Nazis. But prior to that, he had a long period in government when he was Chancellor of the Exchequer and Minister of the Colonies and various other important posts like that, up to the Conservative defeat in the 1929 general election.

Brett McKay: Well, how did those mistakes he made that happened in World War One, the Dardanelles, how did that set him up for success during World War II? Did he learn from that experience?

Andrew Roberts: He did learn, yes. No, exactly. He made terrible mistakes in his life. I don’t want for a moment anybody to think that Churchill was not a deeply flawed individual. He certainly was, and he made a series of mistakes. He made a mistake as Chancellor of the Exchequer in going onto the gold standard at the wrong time, at the wrong price in 1925. He got women’s suffrage wrong. He got the abdication wrong. He got the Dardanelles, as I mentioned earlier, very badly wrong. This is not a man who got everything right in his career by any means.

However, he was a politician who learned from his mistakes, and to pick up the one that you mentioned, the Dardanelles, he never once overruled the British chiefs of staff during the Second World War. So even though constitutionally he could, as Minister of Defense, he actually never once did that, and that was the great message that he took, the great lesson that he learned from that catastrophe.

Brett McKay: So we mentioned that Churchill was one of the few people who saw the dangers of Nazism when it started coming to rise and his appreciation for history, his knowledge of history allowed him to do that. But did he have any personal experience that gave him an almost unshakable belief that Hitler had ambitions to conquer Europe?

Andrew Roberts: Yes. Churchill, as well as being historian and seeing Nazism as an historical threat in terms of the past, Churchill also was a philosemite. He liked Jews. He got on with Jews personally, he’d grown up with them, his father had liked Jews, he represented Jewish constituency. He was a Zionist, a supporter of the Balfour Declaration. And so of course, he had an early warning system for the evils of the Nazis and Adolf Hitler far earlier on than a lot of the other people sitting on the benches with him of his age and class and background in Britain at that time, many of whom were antisemitic. So that was another of the ways that his sort of personal beliefs and background allowed him to be the first major British politician to warn against what was happening.

Brett McKay: He was also one of the few leaders who actually read Hitler’s Mein Kampf and he tried to tell people, “Okay look, he says right here in the book what he plans on doing.” I think another thing you mentioned, too, was when he was working in India, he saw jihadis. He saw jihadist extremists.

Andrew Roberts: Yes, yes. Well, not just India, also of course the Sudanese campaign where he was fighting against the forces of the Khalifa. All of the drive, really, of the Khalifa’s army came down to Islamic fundamentalist fanaticism. So you had the sense that he, both in India and Africa, came up very close and personal to the fanaticism, in this case, religious fanaticism, of course, but a fanaticism that he was to spot again 30 years later in Hitler and the Nazis.

Brett McKay: One thing that happened throughout Churchill’s life is that he always got pushback. He was always getting criticized. He was described as a pusher, something you didn’t do. Right? You weren’t supposed to be publicly ambitious. Right?

Andrew Roberts: Yeah.

Brett McKay: And then but also, he got criticized for all the things he did, but it didn’t seem to faze him all that much. What was it about Churchill’s character or past experience in life that allowed him just to be so stoic in the face of so much criticism thrown at him?

Andrew Roberts: Well, I’ve got a rather politically incorrect response to that, really, which is that I know it’s tremendously bad to have a sense of entitlement in public life today, but he was tremendously entitled. He was the son … well, the grandson of a duke, he’d been born in a palace at the very apex of Victorian society, which he considered to be the greatest society up until that point in the history of the world.

So he really didn’t care very much what other people thought of him, which of course is not always very good in democratic politics. But boy, did he need that in the decade of the wilderness years in the 1930s, when he was shouted down in the House of Commons, decried, he nearly had his seat taken away from him by the Conservatives, he was attacked in the press constantly. He had a thick skin, partly down to his extremely sort of grand background, that allowed him not to care what other people thought of him.

Brett McKay: Yeah. There’s a picture in the book of him when he was seven and he looks like an aristocrat, even at seven years old.

Andrew Roberts: I know that way that he’s got his hand on his hip and, and his-

Brett McKay: His nose pointed up.

Andrew Roberts: Yes, exactly, and he’s seven years old and he might as well be a duke himself.

Brett McKay: So yeah, you didn’t have that middle class status anxiety. He wasn’t worried about his place. He knew what his place was and he just kept on buggering on.

Andrew Roberts: Precisely that. Yes, there wasn’t a middle class bone in his body, and he knew it.

Brett McKay: But here’s the interesting thing. He was an aristocrat, but he wasn’t a snob.

Andrew Roberts: No, no. He didn’t have any snobbishness that I was able to spot in four years of reading his papers and his letters and all that, and actually, when you look at his friends, although two of them admittedly were dukes, the next sort of seven or eight of his closest friends were lower middle class, came from very humble backgrounds some of them, and he treated them absolutely precisely the same as people who were born to the purple.

Brett McKay: So an important person in Churchill’s life was his wife, Clementine. What role did his wife play in his career throughout his life?

Andrew Roberts: She was very important, actually. He didn’t take political advice very well from most people, but he would take it from Clementine. He had this sense that she was only interested in his best interests, unlike some other politicians and other advisors, and so that gave her a special imprimatur and her advice was usually very good, in fact.

He somebody who loved his wife very dearly and was faithful to her and they had a very happy marriage, but he also respected her political opinions, although we did not ask her about grand strategy or take her advice on, or even ask for her advice and she certainly never gave her advice on sort of military matters or anything like that.

Brett McKay: Well, speaking of Churchill’s family life, he did have four children. What was his relationship like with them? Did he replicate what happened with him and his father? Or did he try to do something different?

Andrew Roberts: Sadly, he did, to an extent, replicate what happened with his father. He had a terrible relationship with his son, Randolph, who he nonetheless called after his father, who was a heavy drinker and had none of the charm of his father; some of the brilliant intellect of his father, but they had endless rows. He loved him, but very soon after they got together on every occasion pretty much, there would be a bad-tempered spat. So it wasn’t very happy.

One of his daughters died very young, and that was a tragedy for the both of the parents. Then there were two other daughters who … sorry, three other daughters, two of whom died early, one as a result of suicide and the other as a result of drinking. So it was not uniformly happy. The other daughter, Mary Soames, lived to a lovely, happy old age and was personally completely delightful. But no, overall, it’s very difficult to be the son or daughter of a great man, and although he himself pulled it off, his children didn’t.

Brett McKay: Yeah, I’ve seen that in the lives of other great men like Theodore Roosevelt, who is very much like Winston Churchill as I was reading this, had very similar lives, but his family life, his kids had a lot of problems, as well.

Andrew Roberts: That’s right. It’s not easy, is it? You see it again and again in history, that so much is expected and if the child can’t live up to that, then it’s often in some form of self-destruction that the whole sort of process pans out.

Brett McKay: Yeah. Speaking of Theodore Roosevelt, I’m a big fan of him and as I was reading this, I was like, their lives were very similar. Both were sort of … Churchill was obviously an aristocrat, Roosevelt was sort of a scion of New York, but they both had that same temperament of seeing the action, wanting to be where everything’s at. Both literary men, as well. Both became great leaders of their country. Do these two ever cross paths when-

Andrew Roberts: Yes, they met once and they didn’t get on, and when Theodore Roosevelt’s daughter, Alice, was asked why, she said, “Oh, they’re far too alike,” and I think there’s something in that. I think that might well have been the reason. I think they spotted that they were very alike and as a result, that they clashed rather than became firm friends.

Brett McKay: So the popular image of Churchill is a sort of scowling, no-nonsense man wearing a bowler, chomping on a cigar. But the Churchill that emerges in your book is very emotional. He’s funny and he’s full of life. He’s also imaginative, sometimes had premonitions about things, and allowed intuition to guide his decisions. So he seemed to really feel things deeply. How do you think Churchill’s sentimentalism and romantic outlook helped him as a leader?

Andrew Roberts: Well, he was … Precisely, you’re right. He was driven by his passions to an extraordinary degree. He burst into tears 50 times during the Second World War, for example, which must have been quite off-putting to see the prime minister in the House of Commons starting to cry. But nonetheless, people recognized that he wasn’t the buttoned-up Victorian aristocrat. He was actually a sort of throwback from to an earlier era, the romantic, Regency figure, where people did wear their hearts on their sleeves. They didn’t mind sharing their emotions in public.

Brett McKay: In recent years, there’s been a lot of criticisms lobbed at Churchill, like he was a racist, that he tried to commit genocide in India during World War II, that he was the mastermind behind the Dresden bombings. Based on this new information you’ve gotten, is there much validity to these criticisms?

Andrew Roberts: I don’t think there is, really. No, not when it’s seen in its proper historical context. Churchill was at school while Charles Darwin was still alive, and people did believe that there were hierarchies of races in those days. However absurd and, indeed, obscene we might think that today, at the time, it was considered an actual scientific fact.

What he took from that was actually the exact opposite of what Hitler and the Nazis took from it, which was that he believed that the British had a profound responsibility and duty to the native peoples of the empire, and that’s what he dedicated his life to. So I see this criticism of him in some way encouraging genocide at the time of the Bengal famine as being absolutely … Well, as well as factually incorrect, also completely the opposite of what Winston Churchill was trying to do.

In fact, when you look at his letters to President Roosevelt asking for for wheat and grain to be sent to India, not just Roosevelt; as well, the prime ministers of Australia and Canada as well, he wouldn’t be doing that if he was a genocidal maniac. He did everything that was possible at the time to save the starving Bengalis, but of course with the normal places that one buys grain in these circumstances, such as Burma and Thailand and Malaya under Japanese occupation, it was next to impossible to get grain in overseas. These are perfectly reasonable responses, I think, to a totally unreasonable, a-historical series of attacks on him.

With regard to the bombing of Dresden, which I go into in some detail in my book, the fact is that the railway nodal points from east to west went through Dresden and the Russians begged us to destroy these, and we did the best we possibly could on the night of the 13th of February, 1945. The reason that so many people died in Dresden, and by the way, it was about 20,000, not the 120 that the Nazis claimed, which unfortunately some ex-historians like David Irving also propound … The reason, nevertheless, that 20,000 people died was that the local Gauleiter of Dresden didn’t provide proper air raid precautions in the city, not thinking that it was ever going to be hit. But it was hit, and it was a perfectly reasonable military target.

Brett McKay: Churchill became a great leader during World War II. Do you think he was born a great leader? Or did he fashion himself into one?

Andrew Roberts: He very much fashioned himself into one. He went out very deliberately as a young man to become a great man, and you see this again and again in the early chapters, I think, of my book. He felt that he was walking with destiny, but it was very much a destiny that he was going to fashion himself.

Brett McKay: What do you think are the leadership lessons people could take today from the life of Churchill?

Andrew Roberts: Oh, there are so many. There are some on pretty much every page. His foresight, which we’ve gone into; his personal courage, both physical and moral; his ability to learn from lessons; his sheer resilience coming back from disaster after disaster, really.

Brett McKay: Well, Andrew, this has been a great conversation. Where can people go to learn more about the book?

Andrew Roberts: Well, the first place I’d like them to go to obviously is their local independent bookshop or Amazon. But the reviews are on my website, But really, the best thing if you want to know more about Winston Churchill is to get the book.

Brett McKay: Well Andrew Roberts, thank you so much for your time. It’s been a pleasure.

Andrew Roberts: It’s been a delight. Thank you very much indeed.

Brett McKay: My guest today was Andrew Roberts. He’s the author of the book, Churchill: Walking with Destiny. It’s available on and bookstores everywhere. You can find out more information about his work at his website, or check out our show notes at, where you can find links to resources where you can delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Check out our website at, where you can find our podcast archives as well as thousands of articles we’ve written over the years, including an in-depth series about life lessons from Winston Churchill., and if you’d like to enjoy ad-free episodes of The Art of Manliness podcast, you can do so with Stitcher Premium. Go over to, use code Manliness, you can sign up for a month free trial. Download the Stitcher app on Android or iOS and start enjoying ad-free episodes of the Art of Manliness podcast.

And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on iTunes or Stitcher. It helps out a lot. And if you’d done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always, thank you for the continued support. Until next time, this is Brett McKay reminding you not only to listen to the AOM podcast, but put what you’ve heard into action.

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