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The Strategists: Churchill, Stalin, Roosevelt, Mussolini and Hitler – How War Made Them, And How They Made War
Churchill. Hitler. Stalin. Mussolini. Roosevelt. Five of the most impactful leaders of WW2, each with their own individualistic and idiosyncratic approach to warfare. But if we want to understand their military strategy, we must first understand the strategist.In The Strategists, Professor Phillips Payson O'Brien shows how the views these five leaders forged in WW1 are crucial to understanding how they fought WW2. For example, Churchill's experiences of facing the German Army in France in 1916 made him unwilling to send masses of British soldiers back there in the 1940s, while Hitler's mistakes on the Eastern Front were influenced by his reluctance to accept that conditions had changed since his own time fighting. The implications of the power of leaders remain with us to this to truly understand what is happening in Ukraine, for example, requires us to know what has influenced the leaders involved.
This is a history in which leaders – and their choices – matter. For better or worse.
This is a history in which leaders – and their choices – matter. For better or worse.
400 pages, Hardcover
Published August 15, 2024
214 people are currently reading
5270 people want to read
About the author
Phillips Payson O'Brien
11 books86 followersPhillips Payson O’Brien is a Professor of Strategic Studies at the University of St. Andrews in Fife, Scotland, where he has taught since 2016. A graduate of Trinity College in Hartford, Connecticut, O'Brien earned a PhD in British and American politics and naval policy before being selected as Cambridge University’s Mellon Research Fellow in American History, and a Drapers Research Fellow at Pembroke College.
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Displaying 1 - 30 of 44 reviews
October 8, 2024
An interesting character study of the five leaders, but lacking depth and context. Certainly Hitler and Mussolini were flawed leaders – megalomaniacal, egotistical, and motivated by lifelong animosities and prejudices, and aspirational visions of personal grandeur. This did not make them strategists. As was Churchill, they were micro-managers taking control of every aspect of their war efforts. Churchill, however, was persuadable – if his chiefs of staff were against something, he acceded to them. He recognized their expertise, their responsibilities and their opinions. Hitler and Mussolini did not. Churchill, as with FDR, was the duly elected leader of a nation at war and thus accountable to the electorate, and to the institutional prerogatives of the government – parliament, Congress, constituents. O’Brien basically shrugs off these considerations and inherent limitations. Thus the serious flaws and short-comings of the dictators resulted in catastrophe – the institutional and doctrinal limitations and duties of the democratically elected leaders guided and sharped their decisions and leadership – to the ultimate overwhelming victory of the Allied effort.
FDR was an exceptional war leader – but a terrible domestic leader. His domestic policies and initiatives extended the Depression for years beyond that point at which the rest of the world had recovered. O’Brien ignores that dichotomy. FDR was secretive to the point of compulsion; deceptive, misleading – he left everyone with whom he interacted with the strong impression that he agreed with them... and yet almost never did. He made decisions on impulse as much as on reflection. His trust and interaction with his military staff was excellent, and his decisions were as much logistically based as they were “end game” based. Certainly his single most decisive influences were political ones... FDR was the quintessential political animal, to his core. O’Brien faults him rightly for ignoring Truman, but then blames Truman for deteriorating relations with Stalin and the USSR ... ignoring FDR’s equally dismissive treatment of his prior VP.
Stalin is depicted as a paranoid killer, until Germany invaded and then his “practical side” took over and he became an effective war leader, deferring to military advice and expertise. And that is true, to a point – but O’Brien ignores the ideological components of Stalin’s leadership, and his dominance, personal and ideological, over his government and the military. Stalin did not change – but he did adopt a different persona for the purpose of winning the war and for the ruthless purpose of establishing himself as the savior of mother Russia. The wonder is that General Zhukov survived the post-war period. Stalin did not evolve as a strategist, he responded true to his personality and character – as did Hitler and Mussolini – without ameliorating limitations or controls. None of them had a parliament, Congress or electorate to which they were responsible. None of them had any personal or institutional restraints or boundaries... and the results were theirs.
O’Brien seems to think that the Cold War that followed WWII was a mistake, that Churchill instigated it, and Truman was at fault for stumbling into it because FDR never took him into his confidence. That’s frankly ridiculous. Stalin was never going to be a friend. FDR’s conceit was that he could charm Stalin and win him over to the freedom based principles of democracy and national independence. The truth is that Stalin used FDR’s hubris and vanity to get his (Stalin’s) way throughout the war, and never made any concessions to the Allied efforts, needs or policies. O’Brien ignores Stalin’s conquest of eastern Europe in concert with Hitler’s German, his destruction of Poland, the deliberate pause in operations allowing the Germans to destroy Polish resistance in Warsaw, the subjugation of eastern Europe. Stalin had a vision, and cooperation with the West was not part of it – not during the war, and certainly not after it. Confronting the reality of Stalin by Churchill and Truman post-war was necessary, and only possible because FDR was dead – and the Cold War was unavoidable.
So the book is limited. The character studies of the five leaders, from their early formative years forward, is interesting, revealing – but O’Brien’s insistence upon describing it all as an evolution of them as strategists is awkward – too simplistic and more a device to make his thesis different or significative. It just doesn’t work for me... there is too much he ignores that had equal or more substantive effect on the course of events.
FDR was an exceptional war leader – but a terrible domestic leader. His domestic policies and initiatives extended the Depression for years beyond that point at which the rest of the world had recovered. O’Brien ignores that dichotomy. FDR was secretive to the point of compulsion; deceptive, misleading – he left everyone with whom he interacted with the strong impression that he agreed with them... and yet almost never did. He made decisions on impulse as much as on reflection. His trust and interaction with his military staff was excellent, and his decisions were as much logistically based as they were “end game” based. Certainly his single most decisive influences were political ones... FDR was the quintessential political animal, to his core. O’Brien faults him rightly for ignoring Truman, but then blames Truman for deteriorating relations with Stalin and the USSR ... ignoring FDR’s equally dismissive treatment of his prior VP.
Stalin is depicted as a paranoid killer, until Germany invaded and then his “practical side” took over and he became an effective war leader, deferring to military advice and expertise. And that is true, to a point – but O’Brien ignores the ideological components of Stalin’s leadership, and his dominance, personal and ideological, over his government and the military. Stalin did not change – but he did adopt a different persona for the purpose of winning the war and for the ruthless purpose of establishing himself as the savior of mother Russia. The wonder is that General Zhukov survived the post-war period. Stalin did not evolve as a strategist, he responded true to his personality and character – as did Hitler and Mussolini – without ameliorating limitations or controls. None of them had a parliament, Congress or electorate to which they were responsible. None of them had any personal or institutional restraints or boundaries... and the results were theirs.
O’Brien seems to think that the Cold War that followed WWII was a mistake, that Churchill instigated it, and Truman was at fault for stumbling into it because FDR never took him into his confidence. That’s frankly ridiculous. Stalin was never going to be a friend. FDR’s conceit was that he could charm Stalin and win him over to the freedom based principles of democracy and national independence. The truth is that Stalin used FDR’s hubris and vanity to get his (Stalin’s) way throughout the war, and never made any concessions to the Allied efforts, needs or policies. O’Brien ignores Stalin’s conquest of eastern Europe in concert with Hitler’s German, his destruction of Poland, the deliberate pause in operations allowing the Germans to destroy Polish resistance in Warsaw, the subjugation of eastern Europe. Stalin had a vision, and cooperation with the West was not part of it – not during the war, and certainly not after it. Confronting the reality of Stalin by Churchill and Truman post-war was necessary, and only possible because FDR was dead – and the Cold War was unavoidable.
So the book is limited. The character studies of the five leaders, from their early formative years forward, is interesting, revealing – but O’Brien’s insistence upon describing it all as an evolution of them as strategists is awkward – too simplistic and more a device to make his thesis different or significative. It just doesn’t work for me... there is too much he ignores that had equal or more substantive effect on the course of events.
November 22, 2024
Disappointing book, but some redeeming factors.
Part of this may have been my expectations, but I expected a more rigorous analysis of the strategy/grand strategy given the title. What is given, for the first half of the book, are mini-biographies of the Five. On top of that, there is a lot of psychoanalysis during the first half of the book too, which I don't care for, especially in a book about great power politics and grand strategy.
The second half does delve into the strategies, though I found it to be lacking in really insightful analysis. I've read much of this in other books. And even in the second half, there's a lot of psychoanalysis that is out of place. But here are the pros.
Pros:
-The book is very readable. O'Brien writes well. Some history books can be laborious reads (or listens even) if the author isn't able to keep things interesting (sometimes a history book has to be "boring" but with this topic, it didn't have to be, and O'Brien delivered on this count.
-There is good analysis of Roosevelt's strategy in particular. There are some good anecdotes throughout on all Five at points, but I think O'Brien has some blind spots that could have made the analysis much better. Because the topic of this book is a good one. It's an interesting study which I would like analyzed. If O'Brien or someone ever perhaps wrote an extended version of this book/topic, maybe with some other historians' opinions, this could be a fantastic, insightful book.
Cons:
-Analysis of Churchill, Hitler, and Stalin. I don't like how these guys were covered in this. I feel it misses the mark. A lot of the analysis seemed outdated or narrow. For example, O'Brien diagnoses Stalin as the Worst-Best-Worst strategist. By this he means that Stalin's early grand strategy (and battlefield strategy was the worst of the five, arguably with Mussolini). Then Stalin became the best from 1941 onwards, then BECAME the worst again because he chose to launch a Cold War he couldn't win.
I know it's very easy to judge things in hindsight, but in a book like this I think you HAVE to try to view things from the leaders' perspective. Just because 1989 happened doesn't mean the strategy was poor. Especially since Stalin died in 1953. I think Stalin was probably the best strategist from 1943 to 1945. This is fair. However, I would have liked some real analysis of why Stalin's strategy prior to 1941 was terrible. Yes, I know that Barbarossa happened, but why did it happen? Why did the Germans advance so far? Was this because of bad strategy on Stalin's part, or did he come close to a masterstroke and Hitler just beat him to the punch?
O'Brien says Stalin gave Hitler the means to assault his Soviet Union by signing the Pact with him. But why did Stalin do that? Example: no military analysts of the time thought that France would fall in six weeks. No one. France falling so quickly did not factor into Stalin's calculus and had France held out longer, bled the Germans more, or straight up stopped them like in WWI, Stalin would have been able to attack Germany whenever it liked while the German forces were divided. So I don't think Stalin was a bad grand strategist because he calculated France would put up a stiffer fight than she did. It could have easily been a masterstroke. And I know that it doesn't really matter what could have been, it matters what it is, but given that literally no one thought France would collapse in six weeks, I think one has to at least understand WHY Stalin signed that pact.
I also think the conclusion that the Soviet Union could not have won the Cold War that Stalin launched (I'll agree he launched it, but he had reasons) a very loaded claim. Why? Why couldn't the USSR win the Cold War? What if the Sino-Soviet Split didn't happen? What if the USSR and China were able to cooperate? Maybe we end up in a world where the USA is a garrison state surrounded by a Red World. I think that's a grandiose claim to make, and in addition, it doesn't account for the fact that Stalin was a committed Marxist. He wasn't going to sit back and be content with being Roosevelt/USA's junior partner if he could help it. A world revolution was waiting.
When it comes to Hitler, the analysis is really uninspired. It's a lot of psychoanalysis which I again don't care for, particularly in a military study (if I want psychoanalysis of Hitler I can read Ian Kershaw or Robert G.L. Waite). I really don't understand why historians want to paint Hitler as an incompetent, egotistical buffoon. Okay, let's say that's all true. How on earth did it take the three world superpowers so long to beat this guy? They can't have been so brilliant in that case. Anyway, all of the brilliant maneuvers and victories Germany had in WWII are never attributed to Hitler by O'Brien, but all the defeats are chalked up to him and there's no explanation for this.
Why? Hitler certainly made several strategic mistakes but O'Brien paints him as totally incompetent. Obviously he wasn't. You don't take out France in six weeks (despite being outnumbered) and reach the Gates of Moscow by being lucky (it's like saying Napoleon was a bad strategist because he eventually lost) (Note: Napoleon was obviously a better strategist than Hitler, just making a point). And a lot of decisions that seem poor in hindsight or aren't properly analyzed crop up in this book. For example, O'Brien just casually throws out that Hitler's decision to split his forces to take the Ukraine during Barbarossa rather than drive on Moscow with his full force was incredibly stupid and a result of Hitler's bad preconceptions of war and his ideology. Okay, what happens if the Soviets outflank you from the Ukraine since you haven't mopped them up down there and you have this huge salient going toward Moscow? I would have liked further analysis as to WHY this was a bad decision rather than just saying "this was a bad decision" because I'm not sure it was.
A large part of the reason the war did go on so long that the Allies were the ones repeatedly underestimating Hitler rather than the other way around. It's said that the Germans horribly underestimated the Soviets. Okay, sure, but you don't get 20 miles from the Kremlin by "underestimating" your enemy. Obviously, thorough enough preparations were made to get them there and had the weather been fifteen degrees warmer, who knows what would have happened?
With Churchill, I would just like some analysis as to why Churchill continued a war (O'Brien says Churchill's goal was to maintain the British Empire) that was certain to doom the Empire? Why was Churchill in an alliance with the two most anti-imperial countries on earth at the time (the USA and USSR).
-In general there's a lot of Monday Quarterbacking in this book, which is not what you want to see. There were some obviously bad decisions made in WWII, some of which O'Brien identifies. Mussolini invading Greece stands out as one that was poorly conceived and poorly executed. But a lot of decisions that Stalin, Hitler, and Churchill made should have had deeper analysis, rather than just dismissing some of their decisions or in some cases just accepting some of their decisions.
Readable enough book, not particularly insightful analysis, leaves the reader wanting.
Part of this may have been my expectations, but I expected a more rigorous analysis of the strategy/grand strategy given the title. What is given, for the first half of the book, are mini-biographies of the Five. On top of that, there is a lot of psychoanalysis during the first half of the book too, which I don't care for, especially in a book about great power politics and grand strategy.
The second half does delve into the strategies, though I found it to be lacking in really insightful analysis. I've read much of this in other books. And even in the second half, there's a lot of psychoanalysis that is out of place. But here are the pros.
Pros:
-The book is very readable. O'Brien writes well. Some history books can be laborious reads (or listens even) if the author isn't able to keep things interesting (sometimes a history book has to be "boring" but with this topic, it didn't have to be, and O'Brien delivered on this count.
-There is good analysis of Roosevelt's strategy in particular. There are some good anecdotes throughout on all Five at points, but I think O'Brien has some blind spots that could have made the analysis much better. Because the topic of this book is a good one. It's an interesting study which I would like analyzed. If O'Brien or someone ever perhaps wrote an extended version of this book/topic, maybe with some other historians' opinions, this could be a fantastic, insightful book.
Cons:
-Analysis of Churchill, Hitler, and Stalin. I don't like how these guys were covered in this. I feel it misses the mark. A lot of the analysis seemed outdated or narrow. For example, O'Brien diagnoses Stalin as the Worst-Best-Worst strategist. By this he means that Stalin's early grand strategy (and battlefield strategy was the worst of the five, arguably with Mussolini). Then Stalin became the best from 1941 onwards, then BECAME the worst again because he chose to launch a Cold War he couldn't win.
I know it's very easy to judge things in hindsight, but in a book like this I think you HAVE to try to view things from the leaders' perspective. Just because 1989 happened doesn't mean the strategy was poor. Especially since Stalin died in 1953. I think Stalin was probably the best strategist from 1943 to 1945. This is fair. However, I would have liked some real analysis of why Stalin's strategy prior to 1941 was terrible. Yes, I know that Barbarossa happened, but why did it happen? Why did the Germans advance so far? Was this because of bad strategy on Stalin's part, or did he come close to a masterstroke and Hitler just beat him to the punch?
O'Brien says Stalin gave Hitler the means to assault his Soviet Union by signing the Pact with him. But why did Stalin do that? Example: no military analysts of the time thought that France would fall in six weeks. No one. France falling so quickly did not factor into Stalin's calculus and had France held out longer, bled the Germans more, or straight up stopped them like in WWI, Stalin would have been able to attack Germany whenever it liked while the German forces were divided. So I don't think Stalin was a bad grand strategist because he calculated France would put up a stiffer fight than she did. It could have easily been a masterstroke. And I know that it doesn't really matter what could have been, it matters what it is, but given that literally no one thought France would collapse in six weeks, I think one has to at least understand WHY Stalin signed that pact.
I also think the conclusion that the Soviet Union could not have won the Cold War that Stalin launched (I'll agree he launched it, but he had reasons) a very loaded claim. Why? Why couldn't the USSR win the Cold War? What if the Sino-Soviet Split didn't happen? What if the USSR and China were able to cooperate? Maybe we end up in a world where the USA is a garrison state surrounded by a Red World. I think that's a grandiose claim to make, and in addition, it doesn't account for the fact that Stalin was a committed Marxist. He wasn't going to sit back and be content with being Roosevelt/USA's junior partner if he could help it. A world revolution was waiting.
When it comes to Hitler, the analysis is really uninspired. It's a lot of psychoanalysis which I again don't care for, particularly in a military study (if I want psychoanalysis of Hitler I can read Ian Kershaw or Robert G.L. Waite). I really don't understand why historians want to paint Hitler as an incompetent, egotistical buffoon. Okay, let's say that's all true. How on earth did it take the three world superpowers so long to beat this guy? They can't have been so brilliant in that case. Anyway, all of the brilliant maneuvers and victories Germany had in WWII are never attributed to Hitler by O'Brien, but all the defeats are chalked up to him and there's no explanation for this.
Why? Hitler certainly made several strategic mistakes but O'Brien paints him as totally incompetent. Obviously he wasn't. You don't take out France in six weeks (despite being outnumbered) and reach the Gates of Moscow by being lucky (it's like saying Napoleon was a bad strategist because he eventually lost) (Note: Napoleon was obviously a better strategist than Hitler, just making a point). And a lot of decisions that seem poor in hindsight or aren't properly analyzed crop up in this book. For example, O'Brien just casually throws out that Hitler's decision to split his forces to take the Ukraine during Barbarossa rather than drive on Moscow with his full force was incredibly stupid and a result of Hitler's bad preconceptions of war and his ideology. Okay, what happens if the Soviets outflank you from the Ukraine since you haven't mopped them up down there and you have this huge salient going toward Moscow? I would have liked further analysis as to WHY this was a bad decision rather than just saying "this was a bad decision" because I'm not sure it was.
A large part of the reason the war did go on so long that the Allies were the ones repeatedly underestimating Hitler rather than the other way around. It's said that the Germans horribly underestimated the Soviets. Okay, sure, but you don't get 20 miles from the Kremlin by "underestimating" your enemy. Obviously, thorough enough preparations were made to get them there and had the weather been fifteen degrees warmer, who knows what would have happened?
With Churchill, I would just like some analysis as to why Churchill continued a war (O'Brien says Churchill's goal was to maintain the British Empire) that was certain to doom the Empire? Why was Churchill in an alliance with the two most anti-imperial countries on earth at the time (the USA and USSR).
-In general there's a lot of Monday Quarterbacking in this book, which is not what you want to see. There were some obviously bad decisions made in WWII, some of which O'Brien identifies. Mussolini invading Greece stands out as one that was poorly conceived and poorly executed. But a lot of decisions that Stalin, Hitler, and Churchill made should have had deeper analysis, rather than just dismissing some of their decisions or in some cases just accepting some of their decisions.
Readable enough book, not particularly insightful analysis, leaves the reader wanting.
October 15, 2024
Phillips O’Brien’s “The Strategists: Churchill, Stalin, Roosevelt, Mussolini, and Hitler--How War Made Them and How They Made War” is a compelling exploration of the complex interplay between war and leadership. This book provides an in-depth analysis of how five of the most influential figures of the 20th century navigated the tumultuous landscape of World War II, shaping not only the conflict itself but also their own legacies. O’Brien adopts a unique approach by examining these leaders not only as historical figures but as strategists who were deeply influenced by the war. The narrative is well-researched and offers a fresh perspective on how Churchill, Stalin, Roosevelt, Mussolini, and Hitler each approached the war differently. O’Brien dives into their personalities, decision-making processes, and the political and military contexts that influenced their strategies.
One of the book's strengths is its ability to balance detailed historical analysis with engaging storytelling. O’Brien provides fascinating insights into how these leaders’ personal experiences and beliefs shaped their wartime strategies. For instance, Churchill’s indomitable spirit and eloquence are contrasted with Stalin’s ruthless pragmatism, while Roosevelt’s diplomatic skills are explored alongside Mussolini's faltering leadership and Hitler’s destructive ideology.
The book doesn’t shy away from critiquing these leaders, offering a nuanced view that acknowledges both their strengths and their flaws. O’Brien’s analysis of Hitler is particularly insightful, illustrating how his strategic blunders and ideological obsessions ultimately led to his downfall. While the book is rich in detail, some readers might find the sheer volume of information overwhelming. However, for history enthusiasts and those interested in leadership studies, this depth provides a rewarding experience. O’Brien’s ability to weave together political, military, and personal threads creates a vivid tapestry of World War II leadership. In “The Strategists,” O’Brien successfully blends academic rigor with an accessible narrative, making it a valuable read for anyone interested in understanding how these iconic figures were both shaped by and shapers of war. It’s a thought-provoking examination of leadership under the most extreme circumstances, offering lessons that resonate even today.
One of the book's strengths is its ability to balance detailed historical analysis with engaging storytelling. O’Brien provides fascinating insights into how these leaders’ personal experiences and beliefs shaped their wartime strategies. For instance, Churchill’s indomitable spirit and eloquence are contrasted with Stalin’s ruthless pragmatism, while Roosevelt’s diplomatic skills are explored alongside Mussolini's faltering leadership and Hitler’s destructive ideology.
The book doesn’t shy away from critiquing these leaders, offering a nuanced view that acknowledges both their strengths and their flaws. O’Brien’s analysis of Hitler is particularly insightful, illustrating how his strategic blunders and ideological obsessions ultimately led to his downfall. While the book is rich in detail, some readers might find the sheer volume of information overwhelming. However, for history enthusiasts and those interested in leadership studies, this depth provides a rewarding experience. O’Brien’s ability to weave together political, military, and personal threads creates a vivid tapestry of World War II leadership. In “The Strategists,” O’Brien successfully blends academic rigor with an accessible narrative, making it a valuable read for anyone interested in understanding how these iconic figures were both shaped by and shapers of war. It’s a thought-provoking examination of leadership under the most extreme circumstances, offering lessons that resonate even today.
July 20, 2025
Coming into the book, I was somewhat put off by the thesis of the book (that these 5 WW2 leaders were driven by specific, idiosyncratic strategy that they developed in the lead-up to WW2 earlier in their lives, especially WW2) but by the end, I was somewhat bought in, more than I expected to be. The narrative history of the book was consistently engaging, and a fun read. You can tell that O’Brien is deeply intrigued by the Air-Sea element of WW2, and those parts of the book were the best, and O’Brien’s writing on Churchill and Roosevelt’s strategy the most interesting.
This book makes it incredibly clear that any chances of a German victory of any kind were utterly shattered by late-41, and a total victory impossible as early as mid-40. Also learnt a fair bit about WW1 naval strategy. Definitely interesting stuff.
This book makes it incredibly clear that any chances of a German victory of any kind were utterly shattered by late-41, and a total victory impossible as early as mid-40. Also learnt a fair bit about WW1 naval strategy. Definitely interesting stuff.
October 16, 2025
In winsome prose O'Brien traces the biographies of the 5 great strategists of World War II and shows how their World War I experiences deeply shaped their personalities and choices made in WWII. O'Brien makes a compelling case for the air-sea super battlefield and how Roosevelt's choices ultimately turned the course of the war.
January 16, 2025
This book highlights the big 5 leaders of world war 2 and how their previous service developed their leadership styles .
October 10, 2025
Anekdotisch geschreven en overstijgt het oppervlakkige niet.
July 8, 2025
This book has one major and weird geographic error that I am apparently the first reviewer to catch, along with several errors of interpretation and / or framing, a couple of those also shading into errors of fact.
For this and more, it deserves and earns a good, crushing, one-star review.
I expected to grok-slam this book, while doing so with a critical eye, given what I had thought of O’Brien’s bio of Admiral Leahy, reviewed here.
I spotted an error of the WTF type early on, which I’ll note in a minute.
I only saw that because I hit on the top of the first Mussolini chapter. Having read one or more bios of each of the other four, I skipped most the pre-World War II stuff. (That said, some low-star reviewers call out things like O'Brien's psychologizing, and it should be remembered he stated up front that his Leahy bio would be an opinionated one.)
I've never heard of the "Dalmatian Mountains." Wiki has no such listing. It DOES say the Isonzo River begins in the Julian Alps. There ARE mountains in Dalmatia, but none by that name and Dalmatia is part of Croatia and not either Slovenia or Italy. So, WTF?
As far as grok-slamming in general?
More than half this book, up to page 234, is about WWI years. Add in a brief interlude and we get to page 250 out of less than 450 body copy pages cover World War II. O’Brien tries to posit that each of the five was strongly influenced by their service in World War I, or the Russian Civil War, with Stalin. Doesn’t fly.
FDR surrendered the idea of a battleship Navy after Pearl forced his hand. While mobility in a general way was part of the Russian Civil War, Stalin had no special concepts for tanks and couldn’t have achieved non-tanker mobility without Lend-Lease. Churchill had World War II manpower reasons, not just the lessons of WWI, for keeping casualties restricted. Hitler may have been more locked in by his WWI experiences, I’ll admit. Mussolini was simply an idiot.
So, much of the first 55-60 percent of the book is semi-wasted, at minimum.
There's other problems, two biggies in the conception of the book.
First? After Munich, and his failure to play successful negotiator between Hitler on one side, and Chamberlain and Daladier on the other, Mussolini had less and less of his own grand strategy, to pick up on my “idiot” comment above. (O'Brien essentially admits this.)
That was even more true after he decided to attack France in June 1940 rather than being left in the dust, even though Hitler didn't want this. (It's a nice bit of counterfactual history to ponder Italy staying neutral.)
Second? No, no one person led Japan's military dictatorship throughout the war, but, other than battles between army and navy at times, it DID have a grand strategy that it kept largely in its own control throughout the war. One example? Hitler declaring war on the US Dec. 11, 1941 but Japan never declaring war on the USSR.
So why aren’t they here?
I think, based on his Leahy book, it’s because O’Brien is an ardent subscriber to the Great Man theory of history. Not a “ding” for that, but yes, something of note. Actually, it IS a bit of a ding, because he’s trying to force a Great Man square peg into a hole that, if not round, is at best pentagonal.
Also, omitting them apparently omits discussion of the Pacific War, and thus, of how Churchill’s and Roosevelt’s grand strategeries (sic) balanced the theaters.
As for Stalin being worst-best-worst on grand strategy? One two-starrer is right. On the first worst, Stalin had no idea France would collapse that quickly in 1940; the Molotov-Ribbentrop pact wasn’t stupid. On the second worst? Yea, if there's no split with China or something, the Cold War maybe turns out differently.
Could Stalin have made a deal with neither side, as far as 1939? Yes, but Hitler might have invaded Poland anyway, and given Franco-British reluctance to cede the Baltics, they still wouldn't have made a deal to ally with Stalin to fight Hitler. They didn't in reality. Stalin not making the deal means the German frontier for Barbarossa is almost 200 miles further east. Would Stalin have attacked without coordination with the West? Probably not. And, had France and Britain done the same Sitzkrieg as in reality? Hitler might have started bullying Stalin.
Halifax vs Churchill to succeed Chamberlain is far more complicated than presented, and O'Brien being at a British university should know better. A prime minister sitting in the Lords was one issue; another was that Halifax was too tainted with Chamberlain.
He is right about Hitler's various stupidities on air war, one of the few unambiguously correct things in this book.
While noting Britain made as many fighters in the second half of 1940 as Germany overall, and Hitler's hope for more quick victories, the idea of "total war" — or refusal of it by Hitler — isn't explicitly discussed by O’Brien. In discussing the run-up to Barbarossa on the Soviet side, O’Brien again hints at Germany’s lack of total war preparation, but doesn’t discuss in detail.
It gets worse.
Starting on 317, he discusses Roosevelt’s war preparation. Leahy is of course interjected here, complete with claim Roosevelt had been priming him to be chief of staff for years. By title, yes, Leahy WAS chief of staff: “Chief of staff to the Commander in Chief,” ie, a military chief of staff ONLY.
Page 333 and following? This “air-sea super-battlefield” sounds nice but is kind of tosh and tommyrot and is topped by another phrase, that I'll drop right here: “Boots on the ground.” (This was the thesis of his first book, which I will certainly not read.)
Given the failure to quickly get usable cross-Channel ports better than the Normandy ones, no, Anvil was not relatively unimportant. Strange for the air-sea power guy to say that.
The idea that, at Yalta, we had no desire for Stalin to enter the Pacific War? High-grade bullshit. First, not only did we not have any idea if a plutonium gadget would work, we also did not know when we could get enough highly enriched U-235 for a gun bomb if we couldn’t make a plutonium gadget. As for “conventional” war, the idea that a blockade alone would work was a bullshit pipe dream of Navy guys like Leahy and Ernie King. O’Brien simply can’t be taken seriously here, needs to read the book "Downfall," and "Unconditional" while I'm at it, to learn the facts of the matter, and with that, I think we’re in 1-star territory.
That’s especially if you add in his superficial analysis of FDR’s 1944 Veep pick — and superficial it is. No, FDR didn’t dislike Truman. In reality, they weren’t close enough personally for like or dislike. FDR himself knew the score on the party and Wallace, too. And, the cheap psychologizing? Yes, some small part of Roosevelt may have thought he could live out the fourth term, or that it would make him presidentially immortal, but he let the mask slip more than once in 1944.
For this and more, it deserves and earns a good, crushing, one-star review.
I expected to grok-slam this book, while doing so with a critical eye, given what I had thought of O’Brien’s bio of Admiral Leahy, reviewed here.
I spotted an error of the WTF type early on, which I’ll note in a minute.
I only saw that because I hit on the top of the first Mussolini chapter. Having read one or more bios of each of the other four, I skipped most the pre-World War II stuff. (That said, some low-star reviewers call out things like O'Brien's psychologizing, and it should be remembered he stated up front that his Leahy bio would be an opinionated one.)
I've never heard of the "Dalmatian Mountains." Wiki has no such listing. It DOES say the Isonzo River begins in the Julian Alps. There ARE mountains in Dalmatia, but none by that name and Dalmatia is part of Croatia and not either Slovenia or Italy. So, WTF?
As far as grok-slamming in general?
More than half this book, up to page 234, is about WWI years. Add in a brief interlude and we get to page 250 out of less than 450 body copy pages cover World War II. O’Brien tries to posit that each of the five was strongly influenced by their service in World War I, or the Russian Civil War, with Stalin. Doesn’t fly.
FDR surrendered the idea of a battleship Navy after Pearl forced his hand. While mobility in a general way was part of the Russian Civil War, Stalin had no special concepts for tanks and couldn’t have achieved non-tanker mobility without Lend-Lease. Churchill had World War II manpower reasons, not just the lessons of WWI, for keeping casualties restricted. Hitler may have been more locked in by his WWI experiences, I’ll admit. Mussolini was simply an idiot.
So, much of the first 55-60 percent of the book is semi-wasted, at minimum.
There's other problems, two biggies in the conception of the book.
First? After Munich, and his failure to play successful negotiator between Hitler on one side, and Chamberlain and Daladier on the other, Mussolini had less and less of his own grand strategy, to pick up on my “idiot” comment above. (O'Brien essentially admits this.)
That was even more true after he decided to attack France in June 1940 rather than being left in the dust, even though Hitler didn't want this. (It's a nice bit of counterfactual history to ponder Italy staying neutral.)
Second? No, no one person led Japan's military dictatorship throughout the war, but, other than battles between army and navy at times, it DID have a grand strategy that it kept largely in its own control throughout the war. One example? Hitler declaring war on the US Dec. 11, 1941 but Japan never declaring war on the USSR.
So why aren’t they here?
I think, based on his Leahy book, it’s because O’Brien is an ardent subscriber to the Great Man theory of history. Not a “ding” for that, but yes, something of note. Actually, it IS a bit of a ding, because he’s trying to force a Great Man square peg into a hole that, if not round, is at best pentagonal.
Also, omitting them apparently omits discussion of the Pacific War, and thus, of how Churchill’s and Roosevelt’s grand strategeries (sic) balanced the theaters.
As for Stalin being worst-best-worst on grand strategy? One two-starrer is right. On the first worst, Stalin had no idea France would collapse that quickly in 1940; the Molotov-Ribbentrop pact wasn’t stupid. On the second worst? Yea, if there's no split with China or something, the Cold War maybe turns out differently.
Could Stalin have made a deal with neither side, as far as 1939? Yes, but Hitler might have invaded Poland anyway, and given Franco-British reluctance to cede the Baltics, they still wouldn't have made a deal to ally with Stalin to fight Hitler. They didn't in reality. Stalin not making the deal means the German frontier for Barbarossa is almost 200 miles further east. Would Stalin have attacked without coordination with the West? Probably not. And, had France and Britain done the same Sitzkrieg as in reality? Hitler might have started bullying Stalin.
Halifax vs Churchill to succeed Chamberlain is far more complicated than presented, and O'Brien being at a British university should know better. A prime minister sitting in the Lords was one issue; another was that Halifax was too tainted with Chamberlain.
He is right about Hitler's various stupidities on air war, one of the few unambiguously correct things in this book.
While noting Britain made as many fighters in the second half of 1940 as Germany overall, and Hitler's hope for more quick victories, the idea of "total war" — or refusal of it by Hitler — isn't explicitly discussed by O’Brien. In discussing the run-up to Barbarossa on the Soviet side, O’Brien again hints at Germany’s lack of total war preparation, but doesn’t discuss in detail.
It gets worse.
Starting on 317, he discusses Roosevelt’s war preparation. Leahy is of course interjected here, complete with claim Roosevelt had been priming him to be chief of staff for years. By title, yes, Leahy WAS chief of staff: “Chief of staff to the Commander in Chief,” ie, a military chief of staff ONLY.
Page 333 and following? This “air-sea super-battlefield” sounds nice but is kind of tosh and tommyrot and is topped by another phrase, that I'll drop right here: “Boots on the ground.” (This was the thesis of his first book, which I will certainly not read.)
Given the failure to quickly get usable cross-Channel ports better than the Normandy ones, no, Anvil was not relatively unimportant. Strange for the air-sea power guy to say that.
The idea that, at Yalta, we had no desire for Stalin to enter the Pacific War? High-grade bullshit. First, not only did we not have any idea if a plutonium gadget would work, we also did not know when we could get enough highly enriched U-235 for a gun bomb if we couldn’t make a plutonium gadget. As for “conventional” war, the idea that a blockade alone would work was a bullshit pipe dream of Navy guys like Leahy and Ernie King. O’Brien simply can’t be taken seriously here, needs to read the book "Downfall," and "Unconditional" while I'm at it, to learn the facts of the matter, and with that, I think we’re in 1-star territory.
That’s especially if you add in his superficial analysis of FDR’s 1944 Veep pick — and superficial it is. No, FDR didn’t dislike Truman. In reality, they weren’t close enough personally for like or dislike. FDR himself knew the score on the party and Wallace, too. And, the cheap psychologizing? Yes, some small part of Roosevelt may have thought he could live out the fourth term, or that it would make him presidentially immortal, but he let the mask slip more than once in 1944.
October 6, 2024
While well researched and an excellent format for telling the story of the most famous leaders of World War II, the book fails to find a voice of its own beyond the most assured and common facts. The author is continually putting very hard-lined assumptions and emotional states of leaders in black and white terms that lean to the side of made up in the most egregious parts. This is the most googling I have done reading a non-fiction book and that is not a good thing given this is one of the most studied and published upon parts of our human history.
I would generally avoid this book, if the author had stuck to the facts and setup the book with better context and the nations under the leaders at large there would have been more consistency here. It too often fails to meet a consistent standard of historical writing and there are many books on these leaders that do a much better job.
I would generally avoid this book, if the author had stuck to the facts and setup the book with better context and the nations under the leaders at large there would have been more consistency here. It too often fails to meet a consistent standard of historical writing and there are many books on these leaders that do a much better job.
September 11, 2024
This book has useful information, it is well written and its fundamental hypothesis has some merits if we accept that individuals’ acts and decisions influence historical events to a limited scale. The impact of an individual on the course of historical events is considerable if it is studied within its limited scale; however, social, economical trends influence the history on much larger scale.
One sentence at the end of the book, which states that national interests of a country is a vague term, is very important and true. But rather than individuals shaping countries policies, vested interest groups representative of different echelons of society do it.
One sentence at the end of the book, which states that national interests of a country is a vague term, is very important and true. But rather than individuals shaping countries policies, vested interest groups representative of different echelons of society do it.
July 6, 2025
Although Phillips O’Brien has recently become well-known for his insightful analyses of the Russian invasion of Ukraine (covering both the incompetence of the Russian strategy, the weakness of the Biden and European response, and the desire of Trump to play Mussolini to Putin as dictator), his main area of academic expertise lies in the strategy of the Second World War. Having previously controversially argued that the air-sea strategy employed by the Western Allies was far more important than the huge land battles of the Eastern Front in defeating Nazi Germany, he here turns to the impact of personality in strategy. Exploring the development and application of the thinking of the five key strategists of the war (Hitler, Stalin, Churchill, Mussolini, and Roosevelt), O’Brien powerfully demonstrates that their personalities and approaches were central to the direction taken by their countries during the war, overriding their advisers and the governmental institutions around them. This was sometimes for good, often for ill. In so doing, O’Brien helpfully shows how the Clausewitzian ideal of a rational assessment of ends, ways and means is so rarely seen in the reality of national strategy. We delude ourselves even by searching for it.
It should be noted here that it appears many reades have misunderstood tghe purpose of O'Brien's book. This is not a set of parallel biographies, or a history of the Second World War from the perspective of the five leaders. It is very specifically an exploration of the factors that formed their approach to strategy, and then the consequences of those different approaches to the strategic decisions made during the Second World War. The very fact that so many reviewers seem unable to grasp this may itself underline how weak the concept of strategy is in our current culture, and hence how important this book.
As O’Brien shows, all five of the strategists of the Second World War were shaped by their experiences in the First World War. Hitler, as a junior infantry corporal, saw the power of heavy weapons based on superior German technology, and the power of the ‘will’ to resist defeat. Stalin achieved success through a radical paranoia, yet observed the need for effective logistics. Mussolini saw how pretending to be powerful could achieve results. Churchill retained his boyish obsession with the British Empire, but shifted from his earlier rashness to a greater caution. Roosevelt was a convert to a Mahanian focus on control of the routes of trade, and the ability to charm his way to power.
None of the five come out well from O’Brien’s analyses. All but Roosevelt emerge as narcissistic and convinced that only they could save their countries. But Stalin learned to listen to his expert advisers, and Churchill became less rash. Overall, Roosevelt emerges in the most positive manner, except that he threw away the victory achieved in 1945 by giving no hint of his postwar vision to his successor, Truman. In some ways, Roosevelt's greatest weakness as a strategist was his narrow focus on winning the war, rather than having a clear sense of what he was winning it for. That is perhaps an abiding weakness of American power over the past century and more - the ability to apply overwhelming military force to defeat the opposing forces on the battlefield, but little idea of how to use that to achieve the political ends that must always lie behind undertaking warfare.
Perhaps the most interesting part of the book is where O’Brien explores key points of the Second World War, comparing and contrasting the different strategic approaches of the five strategists. Here, through demonstrating how the approach of one of the leaders brought misunderstanding and disaster, whereas the approach of another allowed a deeper recognition of the situation and an effective response, he gives tools that permit us to understand the strategic development of situations in our own times. As such, this is a book not just for historians but also for those seeking to direct the challenges and conflicts that we face today. Highly recommended.
It should be noted here that it appears many reades have misunderstood tghe purpose of O'Brien's book. This is not a set of parallel biographies, or a history of the Second World War from the perspective of the five leaders. It is very specifically an exploration of the factors that formed their approach to strategy, and then the consequences of those different approaches to the strategic decisions made during the Second World War. The very fact that so many reviewers seem unable to grasp this may itself underline how weak the concept of strategy is in our current culture, and hence how important this book.
As O’Brien shows, all five of the strategists of the Second World War were shaped by their experiences in the First World War. Hitler, as a junior infantry corporal, saw the power of heavy weapons based on superior German technology, and the power of the ‘will’ to resist defeat. Stalin achieved success through a radical paranoia, yet observed the need for effective logistics. Mussolini saw how pretending to be powerful could achieve results. Churchill retained his boyish obsession with the British Empire, but shifted from his earlier rashness to a greater caution. Roosevelt was a convert to a Mahanian focus on control of the routes of trade, and the ability to charm his way to power.
None of the five come out well from O’Brien’s analyses. All but Roosevelt emerge as narcissistic and convinced that only they could save their countries. But Stalin learned to listen to his expert advisers, and Churchill became less rash. Overall, Roosevelt emerges in the most positive manner, except that he threw away the victory achieved in 1945 by giving no hint of his postwar vision to his successor, Truman. In some ways, Roosevelt's greatest weakness as a strategist was his narrow focus on winning the war, rather than having a clear sense of what he was winning it for. That is perhaps an abiding weakness of American power over the past century and more - the ability to apply overwhelming military force to defeat the opposing forces on the battlefield, but little idea of how to use that to achieve the political ends that must always lie behind undertaking warfare.
Perhaps the most interesting part of the book is where O’Brien explores key points of the Second World War, comparing and contrasting the different strategic approaches of the five strategists. Here, through demonstrating how the approach of one of the leaders brought misunderstanding and disaster, whereas the approach of another allowed a deeper recognition of the situation and an effective response, he gives tools that permit us to understand the strategic development of situations in our own times. As such, this is a book not just for historians but also for those seeking to direct the challenges and conflicts that we face today. Highly recommended.
November 14, 2025
Roosevelt: read that Mahanian history of naval warfare and internalized the importance of controlling the lines of communication across the sea. Extended that insight to the air-sea super battlefield. underSecretary of the Navy but had an actual interest and willingness to learn and tour the relevant sites and ships. Wanted America to have the strongest Navy but was sensitive to Americans' lack of appetite for war or high military spending. Mama's boy. Protective of American manpower, prioritized machines and aid for the allies. Biggest mistake was not properly preparing his successor (Truman) for leadership. Fell into the fallacy of "only I can do this" even as his body was failing.
Stalin: paranoid but pragmatic. Made big mistakes like trusting Hitler but was able to adapt and do what was necessary to survive. Shaped by his experience as a rising star in the communist party. Found a patron in Lenin, consolidated power, hid mistakes, manipulated the truth, purged anyone he distrusted even at the expense of military expertise. By the end of Stalingrad he had internalized concepts like deep battle and allowed his commanders greater autonomy to make tactical decisions. Perhaps the best at manipulating the other grand strategists, he solicited and received materiel support from the U.S. despite the earlier alliance with Hitler. He liked Roosevelt better than Churchill, Boar vs Captain kgb nicknames. Very persuasive with Roosevelt's emissaries. Greatly expanded the Soviet Union during the war and as part of the peace.
Churchill: defend the empire at all costs. Even if the homeland falls, the empire will fight on. Prioritized keeping lines of communication open with the colonies, especially India. Wanted to focus on the Mediterranean as an extension of imperial policy. Protective of British manpower, also prioritized machines and technology. Was eventually outmaneuvered and overruled by his fellow grand strategists. Forced into the d-day landing, forced to give up empire after the war, lost the election almost immediately after the war ended. Politically ambitious from the very beginning. Sought out military postings that allowed him to see the world, the colonies, modern warfare, the importance and fragility of the British empire. Prone to impulsive displays of bravado like cavalry charges and Gallipoli.
Mussolini: somewhere between a propagandist and a soldier. Always managed to avoid intense combat, spent most of the war away from the front in the mountains or on leave. Fell for his own machismo and willpower delusions. Did not prepare Italian military for war. Had imperial aspirations in Africa and tried to ride Hitler's coattails into territorial expansion. Pretended to be a great power without doing any of the work to actually accumulate power.
Hitler: stuck in a ww1 infantry mindset. The absolute supremacy of artillery, biggest guns win wars, airplanes mostly as tactical support for the infantry. Failed to prepare for war with britain, not enough planes or ships. No strategic bombing capabilities. Invaded Russia because he couldn't conquer britain. Initiated a two front war he could have and should have avoided. Suffered from early successes that caused him to take on greater and more direct control of military operations. Prioritized ruinously expensive projects that were not in line with the military's needs. Insisted on dive bomber capabilities for first jet fighter. Insisted on ever larger, heavier, more expensive tanks which could only be produced in small numbers. Delusional
Stalin: paranoid but pragmatic. Made big mistakes like trusting Hitler but was able to adapt and do what was necessary to survive. Shaped by his experience as a rising star in the communist party. Found a patron in Lenin, consolidated power, hid mistakes, manipulated the truth, purged anyone he distrusted even at the expense of military expertise. By the end of Stalingrad he had internalized concepts like deep battle and allowed his commanders greater autonomy to make tactical decisions. Perhaps the best at manipulating the other grand strategists, he solicited and received materiel support from the U.S. despite the earlier alliance with Hitler. He liked Roosevelt better than Churchill, Boar vs Captain kgb nicknames. Very persuasive with Roosevelt's emissaries. Greatly expanded the Soviet Union during the war and as part of the peace.
Churchill: defend the empire at all costs. Even if the homeland falls, the empire will fight on. Prioritized keeping lines of communication open with the colonies, especially India. Wanted to focus on the Mediterranean as an extension of imperial policy. Protective of British manpower, also prioritized machines and technology. Was eventually outmaneuvered and overruled by his fellow grand strategists. Forced into the d-day landing, forced to give up empire after the war, lost the election almost immediately after the war ended. Politically ambitious from the very beginning. Sought out military postings that allowed him to see the world, the colonies, modern warfare, the importance and fragility of the British empire. Prone to impulsive displays of bravado like cavalry charges and Gallipoli.
Mussolini: somewhere between a propagandist and a soldier. Always managed to avoid intense combat, spent most of the war away from the front in the mountains or on leave. Fell for his own machismo and willpower delusions. Did not prepare Italian military for war. Had imperial aspirations in Africa and tried to ride Hitler's coattails into territorial expansion. Pretended to be a great power without doing any of the work to actually accumulate power.
Hitler: stuck in a ww1 infantry mindset. The absolute supremacy of artillery, biggest guns win wars, airplanes mostly as tactical support for the infantry. Failed to prepare for war with britain, not enough planes or ships. No strategic bombing capabilities. Invaded Russia because he couldn't conquer britain. Initiated a two front war he could have and should have avoided. Suffered from early successes that caused him to take on greater and more direct control of military operations. Prioritized ruinously expensive projects that were not in line with the military's needs. Insisted on dive bomber capabilities for first jet fighter. Insisted on ever larger, heavier, more expensive tanks which could only be produced in small numbers. Delusional
This entire review has been hidden because of spoilers.
May 28, 2025
When starting this book, I realized that there was a good chance that I'd find it too basic for my purposes. However, having enjoyed O'Brien's biography of Admiral William Leahy, and his defense of the Anglo-American war-making system that prioritized sea and air power, I figured that it was worth a shot.
As it turns out, my more negative suspicions were accurate. Where this book is at its best is in the capsule portraits O'Brien provides of his strategists as young men, and the experiences that baked in their strategy preferences.
The problem is that this takes up 40% of the page count of the actual narrative, leaving the reader a mad gallop over the course of WWII from the perspective of what O'Brien calls "The Five." I think that this is far from the worst synopsis of the war that could be written, but it does start looking like a fool's errand after a bit. If you don't care too much about the biographical background, you might be better off reading O'Brien's earlier books, even if all you know about the high-level direction of WWII are the names of these men. For me, the big killer of this book is the notion that you can write about grand strategy in WWII without dealing with the motivations of the men who led the Japanese Empire.
My final thought is that O'Brien can be very polemical in terms of writing about these long-dead men, as it's not news that while men make history, they seldom make it as they would like. Perhaps the real point is that this might be a poison-pen letter to the electorates in those societies that still have a viable electoral process as to how they need to make better choices. O'Brien was very bitter over the election of Trump, with his well-known tendencies to seek agreement with Moscow at Kyiv's expense; likely to gain an ally against Beijing.
As it turns out, my more negative suspicions were accurate. Where this book is at its best is in the capsule portraits O'Brien provides of his strategists as young men, and the experiences that baked in their strategy preferences.
The problem is that this takes up 40% of the page count of the actual narrative, leaving the reader a mad gallop over the course of WWII from the perspective of what O'Brien calls "The Five." I think that this is far from the worst synopsis of the war that could be written, but it does start looking like a fool's errand after a bit. If you don't care too much about the biographical background, you might be better off reading O'Brien's earlier books, even if all you know about the high-level direction of WWII are the names of these men. For me, the big killer of this book is the notion that you can write about grand strategy in WWII without dealing with the motivations of the men who led the Japanese Empire.
My final thought is that O'Brien can be very polemical in terms of writing about these long-dead men, as it's not news that while men make history, they seldom make it as they would like. Perhaps the real point is that this might be a poison-pen letter to the electorates in those societies that still have a viable electoral process as to how they need to make better choices. O'Brien was very bitter over the election of Trump, with his well-known tendencies to seek agreement with Moscow at Kyiv's expense; likely to gain an ally against Beijing.
August 30, 2025
You thought that everything that could be written about the Second World War had been written? Think again.
O'Brien brilliantly illustrates how you can bring truckloads of new insights in a book that is accessible and extremely enjoyable to read.
The originality of the book lies in the emphasis on the protagonists' formative experiences in colonial wars (in the case of Churchill, at least) and in the First World War, and how this affected their strategic thinking in the Second World War. O'Brien has chosen not to go into too much detail on the development of the Second World War itself , and therefore this book will mainly benefit readers who are already familiar with the major developments on the battlefield. (if you are interested in the details of the development of the Western Allies' grand strategy during the Second World War, the book to read is the incomparable "Masters and commanders" by Andrew Roberts)
There is just one point where I disagree with O'Brien, and that is on Churchill's decision to send ground troops to Greece after Mussolini's disastrous invasion. O'Brien is right to commend Churchill for evacuating the Commonwealth troops as soon as the Germans joined the Italians in the campaign, but this overlooks the point that the decision to send boots on the ground was a major mistake in the first place (maybe the only major mistake Churchill made during the war): even the Greeks thought it would make little difference, whether or not the Germans would invade, but those troops were sorely needed in Libya to finish off the Italians before the Afrika Korps was ready to launch a major counterattack. One can only start to imagine how the Malaya and Singapore campaign would have developed if the Axis had been kicked out of Africa in 1941, and all those troops would have been available in the Far East.
O'Brien brilliantly illustrates how you can bring truckloads of new insights in a book that is accessible and extremely enjoyable to read.
The originality of the book lies in the emphasis on the protagonists' formative experiences in colonial wars (in the case of Churchill, at least) and in the First World War, and how this affected their strategic thinking in the Second World War. O'Brien has chosen not to go into too much detail on the development of the Second World War itself , and therefore this book will mainly benefit readers who are already familiar with the major developments on the battlefield. (if you are interested in the details of the development of the Western Allies' grand strategy during the Second World War, the book to read is the incomparable "Masters and commanders" by Andrew Roberts)
There is just one point where I disagree with O'Brien, and that is on Churchill's decision to send ground troops to Greece after Mussolini's disastrous invasion. O'Brien is right to commend Churchill for evacuating the Commonwealth troops as soon as the Germans joined the Italians in the campaign, but this overlooks the point that the decision to send boots on the ground was a major mistake in the first place (maybe the only major mistake Churchill made during the war): even the Greeks thought it would make little difference, whether or not the Germans would invade, but those troops were sorely needed in Libya to finish off the Italians before the Afrika Korps was ready to launch a major counterattack. One can only start to imagine how the Malaya and Singapore campaign would have developed if the Axis had been kicked out of Africa in 1941, and all those troops would have been available in the Far East.
September 16, 2025
Interesting book with the premise that experiences in WW I were the foundation for the various strategies used by Roosevelt, Churchill, Stalin, Hitler, and Mussolini in WW II. As in his previous book "How the War was Won", O’Brien claims Air and Sea power won the war and that the Allies won because Roosevelt and Churchill prioritized both, to the detriment of the U.S. and British armies. Conversely, Hitler lost the war because he put all Germany’s resources into developing powerful artillery and heavily armored tanks to the detriment of the Navy and Luftwaffe.
Mussolini is portrayed as a functional, deluded, imbecile and Stalin comes across as closer to Churchill than Hitler and who was willing to suspend his distrust and ideological differences with the Western Allies in order to beat Germany. Said suspension of differences lasted only until Stalingrad was secured, after which it was game-on for post-war supremacy in Eastern Europe as Churchill surmised but couldn’t convince Roosevelt. Hence Yalta, the Iron Curtain, and the Cold War.
O’Brien is certain he is right about cause and effect regarding how the war was won. Therefore, his tone in this book is akin to a self-fore-filling prophecy. That aside, the biographical sketches of the five leaders are extremely interesting and do provide an excellent analysis of their individual priorities and decision-making processes. As a stand alone work on leadership in WW II, much too laser focused on specific aspects of the individuals in question, in addition to virtually ignoring the War in the Pacific, to be a primary source. As an adjunct to more well rounded individual biographies it becomes an interesting addition to the WW II canon of literature.
Mussolini is portrayed as a functional, deluded, imbecile and Stalin comes across as closer to Churchill than Hitler and who was willing to suspend his distrust and ideological differences with the Western Allies in order to beat Germany. Said suspension of differences lasted only until Stalingrad was secured, after which it was game-on for post-war supremacy in Eastern Europe as Churchill surmised but couldn’t convince Roosevelt. Hence Yalta, the Iron Curtain, and the Cold War.
O’Brien is certain he is right about cause and effect regarding how the war was won. Therefore, his tone in this book is akin to a self-fore-filling prophecy. That aside, the biographical sketches of the five leaders are extremely interesting and do provide an excellent analysis of their individual priorities and decision-making processes. As a stand alone work on leadership in WW II, much too laser focused on specific aspects of the individuals in question, in addition to virtually ignoring the War in the Pacific, to be a primary source. As an adjunct to more well rounded individual biographies it becomes an interesting addition to the WW II canon of literature.
June 13, 2025
Dalam konteks sejarah perang, para pemikir strategis memainkan peran yang sangat penting dalam membentuk jalannya pertempuran dan bahkan menentukan hasil dari konflik besar. Buku ini mengungkapkan bagaimana para pemimpin militer yang legendaris, mulai dari jenderal kuno hingga tokoh modern, mengembangkan dan menerapkan teori-teori perang mereka, serta bagaimana teori-teori tersebut telah membentuk dunia seperti yang kita kenal saat ini. Menggali lebih dalam ke dalam pikiran-pikiran yang telah merumuskan taktik, strategi, dan filosofi perang, pembaca akan diajak untuk memahami seluk-beluk cara mereka merancang kemenangan melalui medan pertempuran dan diplomasi.
Buku ini juga menyoroti hubungan antara teori dan praktik, serta dampak dari keputusan-keputusan tersebut pada jalannya sejarah global. Para penggemar sejarah, mahasiswa yang tertarik dengan teori perang, serta para profesional militer atau individu yang tertarik dengan cara berpikir strategis dalam konteks lebih luas, akan menemukan banyak hal berharga di dalamnya. Dengan narasi yang mendalam dan analisis yang tajam, buku ini sangat cocok bagi mereka yang ingin memahami peran besar para strategis dalam membentuk peristiwa-peristiwa penting sepanjang sejarah perang. Para pembaca yang tertarik pada teori strategi militer, studi sejarah, atau analisis politik juga akan menemukan wawasan yang berharga. https://blog.periplus.com/2025/05/26/...
Buku ini juga menyoroti hubungan antara teori dan praktik, serta dampak dari keputusan-keputusan tersebut pada jalannya sejarah global. Para penggemar sejarah, mahasiswa yang tertarik dengan teori perang, serta para profesional militer atau individu yang tertarik dengan cara berpikir strategis dalam konteks lebih luas, akan menemukan banyak hal berharga di dalamnya. Dengan narasi yang mendalam dan analisis yang tajam, buku ini sangat cocok bagi mereka yang ingin memahami peran besar para strategis dalam membentuk peristiwa-peristiwa penting sepanjang sejarah perang. Para pembaca yang tertarik pada teori strategi militer, studi sejarah, atau analisis politik juga akan menemukan wawasan yang berharga. https://blog.periplus.com/2025/05/26/...
September 30, 2024
The way wars are fought, and even their outcomes, may come down to the personal quirks of a handful of people. That’s the thesis of this fascinating book, and the author makes a compelling case. Perhaps the Second World War was not typical in the way the leaders of the main European combatants were each able to dictate their nation’s actions. But in that war, at least, it arguably was crucial that, for example, Roosevelt was fascinated by navies since his childhood and Hitler experienced the First World War in the trenches. Whether or not you are persuaded by the argument, the book is worth reading just for its descriptions, rich in details and insights, of the protagonists’ careers. One main point worth pondering in view of the current Ukraine war is the overriding importance of decisions on what kind sof weapons to build (reflecting the author’s inportant 2015 work on air-sea power in the Second World War, “How the War Was Won” — another great read).
February 17, 2025
This is a very long book that will give you a deep dive into the upbringing and history of these five WW2 strategists. I've read dozens and dozens of books on WW2 and this one offers a different view. Most of the leaders were plain stupid, made mistakes due to narcissistic personalities, particularly Hitler and Mussolini. The devil incarnate. Even Churchill and FDR had faults and made stupid decisions regarding the war. Stalin killed so many people-that was his way and everything that came out of his mouth was a lie. Mussolini was a serial rapist and a brutal evil abusive man. There's nothing to like about these dictators.
FDR didn't really like Churchill in the beginning and there was an undercurrent of anti-imperialism from FDRs viewpoint. He was so ill at the end, he should have been removed, but this seems to be normal for politicians. Some things never change-human nature. Enjoy!
FDR didn't really like Churchill in the beginning and there was an undercurrent of anti-imperialism from FDRs viewpoint. He was so ill at the end, he should have been removed, but this seems to be normal for politicians. Some things never change-human nature. Enjoy!
March 10, 2025
This is an amazing book that examines (almost) the entire lives of the five key strategists. It examines the development of their strategic thinking and their ability to adapt or not adapt to the various challenges before and during WW2.
The two leaders who served as infantry in WW1 were amazingly lucky never being in the center of the "meat grinder" battles. They left WW1 with an infantrymans POV on what weapons and strategies are important to win.
Roosevelt and Churchill were not natural allies but they shared such a strong bond on air and naval strategy that they worked so well together. This book goes a lot into Churchill's behaviour and especially Roosevelts both as he developed his military strategy and as his body was failing him at the end of the war.
Stalin is kind of the misfit who has the limitations of the first two but manages to overcome some of his limitations. The destructive effect of the war on all five is discussed in the last chapter.
The two leaders who served as infantry in WW1 were amazingly lucky never being in the center of the "meat grinder" battles. They left WW1 with an infantrymans POV on what weapons and strategies are important to win.
Roosevelt and Churchill were not natural allies but they shared such a strong bond on air and naval strategy that they worked so well together. This book goes a lot into Churchill's behaviour and especially Roosevelts both as he developed his military strategy and as his body was failing him at the end of the war.
Stalin is kind of the misfit who has the limitations of the first two but manages to overcome some of his limitations. The destructive effect of the war on all five is discussed in the last chapter.
November 22, 2025
Look at the 5 "War Lords" of the War in Europe: Stalin, Mussolini, Hitler, and Churchill. Pretty standard stuff. The look at Stalin and Mussolini's military attributes before WW 2 was the most interesting.
Like most current day authors, O'Brien has to pretend FDR was some sort of military mastermind, when in fact, he was driven almost entirely by his political beliefs and his advisors. FDR's only real strategy was to pursue "Germany first" and keep Stalin happy so'd he keep killing Germans. Oh, and in 1942, GI's had to be fighting the German army -somewhere.
And while FDR meddled in naval matters, but was perfectly happy to let Stimson, Patterson, Arnold and Marshall run the ground/air war. As Alanbrooke once complained "Marshall doesn't see FDR for weeks, while I have to deal with Winston every day".
Like most current day authors, O'Brien has to pretend FDR was some sort of military mastermind, when in fact, he was driven almost entirely by his political beliefs and his advisors. FDR's only real strategy was to pursue "Germany first" and keep Stalin happy so'd he keep killing Germans. Oh, and in 1942, GI's had to be fighting the German army -somewhere.
And while FDR meddled in naval matters, but was perfectly happy to let Stimson, Patterson, Arnold and Marshall run the ground/air war. As Alanbrooke once complained "Marshall doesn't see FDR for weeks, while I have to deal with Winston every day".
November 29, 2025
I really enjoyed this book. It’s very readable. I’ve read maybe 10–20 books on the Second World War at this point, and this one gave me a fresh perspective. Focusing on the leaders and the choices they made worked well for me. I liked seeing what shaped those choices, and how their earlier lives fed into their thinking later.
The sections on their backgrounds are short but interesting. I knew almost nothing about Roosevelt’s early life, so that part stood out. Seeing how those experiences formed his ideas helped make sense of his approach during the war.
The writing is smooth. Compared to people like Antony Beevor or James Holland, this one is much easier to get through. Phillips O’Brien writes in a clear way that keeps you moving.
If you read a lot about this period and want something that looks at the big decisions through the people making them, this is a good one.
The sections on their backgrounds are short but interesting. I knew almost nothing about Roosevelt’s early life, so that part stood out. Seeing how those experiences formed his ideas helped make sense of his approach during the war.
The writing is smooth. Compared to people like Antony Beevor or James Holland, this one is much easier to get through. Phillips O’Brien writes in a clear way that keeps you moving.
If you read a lot about this period and want something that looks at the big decisions through the people making them, this is a good one.
December 30, 2024
Those familiar with WWII and the five main European leaders won't find many new facts in this book, but it is an interesting study of those men and how their WWI experience influenced their decision-making in the Second World War. It's not super in-depth, and I think the author makes a reach in claiming that the First World War was always front of mind with these guys, but as the evidence shows it was definitely a factor. More than anything I think this book is a study less on strategy and more on leadership style.
February 26, 2025
this is a history of the Second World War, but it begins in the late 19th century covering the early ages of, and the events influencing, Churchill, Roosevelt, Stalin, Hitler, and Mussolini. These early-life events are skillfully tied to the strategies adopted by these people as war leaders. Enjoyed this a lot, although the last chapters are generally a simple retelling of well-known history.
FYI, the actual text is not nearly as long as it initially appears to be due to extensive photos, notes, and bibliography all appended to the end.
FYI, the actual text is not nearly as long as it initially appears to be due to extensive photos, notes, and bibliography all appended to the end.
November 24, 2024
Great insights and an enjoyable read
I received a free copy of this book. I enjoyed this take on the important WWII world leaders. I learned aspects of these leaders that I didn’t know from Stalin’s military follies in WWI to Hitler’s strategic blunders in WWII that cost him the war. I’m very much of the camp that your past experiences impact your future and O’Brien portrayed this with the characters he focused on.
As a student of history, I highly recommend this book
I received a free copy of this book. I enjoyed this take on the important WWII world leaders. I learned aspects of these leaders that I didn’t know from Stalin’s military follies in WWI to Hitler’s strategic blunders in WWII that cost him the war. I’m very much of the camp that your past experiences impact your future and O’Brien portrayed this with the characters he focused on.
As a student of history, I highly recommend this book
February 9, 2025
Excellent book on overall grand strategy in WWII, and how it was influenced by the WWI experiences of each of the five national leaders (Churchill, Roosevelt, Stalin, Hitler and Mussolini). A very engaging book (hard put down once I started it!) that links each leader's WWI experience to specific decisions or approaches they took to influence their nation's WWII strategy.
September 14, 2024
Disappointing
Very easy read, and created an excellent story. But overall, lightweight. Use of language at times quite judgmental, and without real substance.
The book ended with a very poor and rushed conclusion.
Very easy read, and created an excellent story. But overall, lightweight. Use of language at times quite judgmental, and without real substance.
The book ended with a very poor and rushed conclusion.
September 26, 2024
A fresh insight
A very different way of looking at the war with some really important takes. Seemed to finish early is the only problem, kinda expected a bit more analysis though equally that meant that the key points are clear.
A very different way of looking at the war with some really important takes. Seemed to finish early is the only problem, kinda expected a bit more analysis though equally that meant that the key points are clear.
January 1, 2025
A good look into how the personal experiences of WWI shaped the grand strategy of the five leaders of WWII. I was particularly interested in the different approaches Churchill and Roosevelt took towards the war.
September 5, 2024
Very disappointing; Author clearly has an agenda within this book’s premise. Didn’t bother to finish, as facts were slanted . Too bad; was looking forward to reading it.
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