The Five: Q&A with Phillips O’Brien

How the contrasting personalities and backgrounds of a quintet of national leaders shaped WWII strategy

Featured image by Universal History Archive/Universal Images Group via Getty Images.

A black-and-white image of Phillips O'Brien wearing a shirt.
Historian and author Phillips O’Brien.
(Photo: John Hendry)

The Second World War saw grand military strategy play out on the largest ever scale, stretching across most of the Earth. Looking down at this complex strategic situation were what Phillips O’Brien calls “The Five”: Winston Churchill, Adolf Hitler, Joseph Stalin, Benito Mussolini and Franklin D Roosevelt. He tells their story in his latest book: The Strategists: Churchill, Stalin, Roosevelt, Mussolini and Hitler – How War Made Them, And How They Made War.

O’Brien spoke with History of War to discuss each of “The Five’s” background and character, and how that translated into the way that they led their nation’s grand strategy. He then considers how the Allied ‘Big Three’ (Roosevelt, Churchill and Stalin) began to butt heads as the war came to an end and the post-war world was formed. Finally, O’Brien shares his thoughts on how the Russo-Ukraine War shows how flawed individuals can still hijack grand strategy.


How did the dictators’ (Stalin, Mussolini and Hitler) character and grand strategy differ from the democrats’ (Churchill and Roosevelt)?

To begin with, Roosevelt and Churchill were not the ones driving policy and Churchill was only brought into the cabinet after Hitler went to war and invaded Poland. The dictators were the active ones, deciding how and when the war would break out. The one difference was that Mussolini lost his nerve in the summer of 1939.

Winston Churchill wearing a hat and overcoat and carry a cane next to soldiers operating a large cannon.
Churchill observes British soldiers operating a static 3.7in (94 mm) anti-aircraft gun during the Blitz.
(Photo: Hulton Archive/Getty Images)

Mussolini was not ready for this war and nervous about it breaking out. When Hitler came to him and said he was about to attack Poland, Mussolini wriggled out of his commitments. Hitler didn’t necessarily think he would be starting the Second World War and thought he could take steps to prevent the British and the French from intervening. But Hitler certainly was willing to risk the Second World War. What he needed to do was to get Stalin on board and he did that as Stalin was keen for a deal.

How did the dictators differ in their approaches to public opinion?

Hitler was the most concerned [of the dictators] about public opinion. He wasn’t worried about an election but about whether the German people would see the war through, and that goes back to his First World War experiences. Hitler had a love-hate relationship with the German people. He thought Germans were tremendous and sophisticated and should rule Europe. On the other hand, Hitler also believed they lost their nerve at the end of the First World War and that they had betrayed the army. 

A black and white photograph shows Hitler looking out over a large crowd
Hitler addresses soldiers at a Nazi rally in Dortmund, Germany.
(Photo: Hulton Archive/Getty Images)

He explained that it was the Jews that undermined German morale and weakened Germany, but to what degree he could fully trust the German people was always in the back of his mind. During the war, Hitler provided the Germans with a relatively high standard of living. He ensured they had much more food than other people in Europe and a relatively high level of consumer goods. Women also weren’t forced into the workforce early in the war. Hitler was sensitive to public opinion, and he wanted to keep the German people from suffering deprivations in the war. It’s why he lost his mind about Allied bombing.

“Hitler was sensitive to public opinion, and he wanted to keep the German people from suffering deprivations in the war. It’s why he lost his mind about Allied bombing.”

Stalin didn’t care much about public opinion, although in 1941, when the German invasion happened, he reached out to Old Russia and the Orthodox church and tried to dial back on hardline Bolshevik policies. Stalin did what he thought would win the war and was willing to have the Soviet people suffer, though he did keep his industrial workforce well-fed. Meanwhile, Mussolini became disillusioned with the Italian people because he believed they were not as tough as he would have liked them to be. I think that was a sign that the Italians had a lot of good sense.

How did Stalin’s growth as a strategist during the Second World War compare to Mussolini and Hitler relative decline?

Stalin was fascinating in that way. I call him the worst and best grand strategist. In many ways, he was disastrous from 1939 to 1941, empowering Hitler with the Nazi-Soviet pact and allowing massive German expansion. Stalin enabled Germany to get strong and provided them with a massive amount of resources. When reports came to them that Hitler was about to attack, he poo-pooed them. It’s hard to think of a more disastrous series of grand strategic errors than Stalin made.

However [eventually] Stalin began making much better choices… When things got really bad in 1941, he was not overthrown. If Stalin were a lower-level Bolshevik, he would use the opportunity to overthrow the leader. But, he had so cowed the Soviet Union’s leadership that they couldn’t function without him. That gave him confidence that he would see the war out and wouldn’t have to worry about a coup or anyone trying to kill him. After time, that seems to have freed Stalin up to realise what he should and shouldn’t do. 

To begin with, Stalin interfered with a lot of lower-level military decisions and that’s when things went wrong, resulting in Soviet defeats and high losses. By the end of 1942, he stepped back and understood that his forte was high politics and grand strategy. He had a Red Army that was becoming good at what it was doing and he would let certain trusted officers run the campaigns.

Strategically, who do you think was the strongest and weakest of ‘The Five’? 

I think Hitler and Mussolini, [were the weakest] but not because they lost. Mussolini was a disaster because he grossly overestimated Italian capacity. He didn’t have to join the war if you compare him to Franco. Mussolini made the right choice in the summer of 1939, but he couldn’t stay away. He went into the war because he wanted to take parts of France. Mussolini was foolish in many ways and didn’t understand the long-term course of the war. He thought Germany was going to win, and therefore, he needed to join it.

Related: Mussolini’s World War 2: Inside the Nazi puppet-state

Hitler stands next to Mussolini, both in military uniform. Mussolini is performing a Fascist salute
Mussolini and Hitler watch a Nazi parade staged for the Italian dictators’s visit to Germany.
(Photo: Bettman)

Hitler was actively the worst leader. As the war went on, he started to meddle more in things completely outside his knowledge. Hitler trusted fewer people and became more self-obsessed, believing he was the only person who knew how Germany could win. He made a series of decisions and interferences in the war that actively sped up the defeat.

Related: 3 bad decisions that cost Hitler World War 2

Of course, the Allies would probably win, particularly once the US was in, because they were much more powerful. There was a different kind of dynamic among the leaders [once they knew] they would be on the winning side. As Churchill said, the day after Pearl Harbor was his best sleep. 

Churchill was, in many ways and oddly, the most tragic, because he had a way he wanted to fight the war [but had to go against it]. It was not a bad strategy and Churchill had a significant understanding of Britain’s strengths and weaknesses. Until early 1943, he was successful. From the second half of 1943 onwards, Roosevelt and Stalin steamrolled him. That wasn’t Churchill’s fault. He fought very hard to get what he wanted. Churchill just couldn’t stand up to the combined pressure of the US and USSR. 

Roosevelt was very successful in his general overview and understanding of industrial warfare. Certainly, people who lived in America liked Roosevelt because he didn’t want many Americans to die. As a domestic politician, he was sensitive to casualties. Roosevelt also had a great weakness from 1944, which was his hubris. Roosevelt believed he was invaluable to the war effort even though he was dying. He should not have run for reelection in 1944. That was an irresponsible decision. 

Stalin started off very poorly from 1939 to 1941 but then started stepping back and knowing his strengths and weaknesses. That was why he ended up with a small resource base. The Soviet Union was not as economically powerful as the US, but it gained a lot in Eastern Europe. Stalin almost threw that away after overplaying his hand in 1945 and triggering the Cold War. 

Overall, the Allied leaders had strengths and weaknesses but didn’t sabotage their war efforts. I think that is the difference, as Hitler and Mussolini actively sabotaged [their nations’ interests].

Related: How the war in Europe was won


To read our full interview with Phillips O’Brien, including his thoughts on the lessons from The Strategists that still apply, pick up issue 137 of History of War