“Who was the best strategist, Hitler, Churchill, or Stalin?”

Peter Lewerin
7 min readJul 10, 2021

This is one of the more common questions asked about WWII by laymen. It does seem like a straightforward question. But, to begin with, are we talking about one of the domains of strategy, like military strategy, or in strategic ability in general?

Hitler

Hitler undoubtedly made some major mistakes in general strategy by pursuing some goals despite not having the resources to achieve them, such as starting WWII in the first place and staying on his target to invade USSR without making peace with Britain. When he declared war on USA it was already clear that USA would be coming for him, so this wasn’t as much of a strategic mistake as a political decision to steal USA’s thunder.

At the end of the 1930s, Hitler was greedy, impatient, and anxious. He knew that his dream of recovering the borders of the final days of the Second Reich was almost within reach, but his army still needed to grow and improve its materiel, especially in terms of transport and armoured vehicles. On the other hand, for every month he waited, USSR would grow stronger.

Nazi Germany was corrupt and inefficient, and Hitler’s closest associates in the party were by disposition murderers and thieves, just waiting to become that in fact. He could not depend on them. If the German military were to sober up from their own dreams of greatness, they might topple him and restore either the Monarchy or the Republic.

So, the strategically unsound choice Hitler made was to go forward now, to keep everyone busy, and hope for the best. He guessed that the military would be reluctant to go against him during a war, and that any domestic opposition could be dealt with once the military kept still. For him personally, it was the best choice, because there was a possibility of winning. Not starting a war could only bring missed opportunities and political defeat in the end. The idea of Germany recovering much of its former glory even if he himself was deposed didn’t sound good to him.

In military strategy, Hitler has had a very bad reputation since the early Cold War, for several reasons. NATO did not want USSR to be able to credibly paint them as a continuation of the German aggression against USSR, so it was important to distance themselves from Hitler and the Nazis even if several of the latter were employed in various capacities. Also, surviving German generals wrote memoirs of the war where they took credit for good decisions (even if Hitler played a part in them) and blamed Hitler for any mistakes they made.

Hitler wasn’t a terrible military strategist, but he was self-taught and modern-minded while the officers around him on most command levels were proud of their traditions and education, and also fairly conservative. If Hitler sometimes would micromanage, issue categorical orders, and set the important command structure aside, it had a lot to do with the fact that his orders could be distorted or ignored at some point in the chain of command. He was definitely too much of a gambler to be a really successful war leader, though.

Hitler also failed in the operational area, between strategy and tactics. For instance, he never learned to quantify and reckon with quantities like attrition or tactical edge. There, on the other hand, for several years he had help from the German military whose skills in leadership and improvisation made his plans work even when not quite realistic.

Churchill

Somewhat like Hitler, Churchill was ruthless, a gambler, a bit of a modernist in the military domain while conservative in others, and determined to uphold the Empire. The British High Command were often able to curb his ruthlessness (such as when he called for poison gas to be used), but they couldn’t always stop him from gambling (such as when he threw away the likely victory in Libya to bolster the hopeless defence of Greece). Until the victory at El Alamein and the Americans landing in north-west Africa there wasn’t much very much to be done in the realm of strategy except build bridges to USSR and USA and keep the whole military apparatus (reasonably) supplied and willing to fight, “Keep Buggering On”. Once the Germans were on the retreat and strategy could be made, Churchill found that his was only one of several voices, and that his voice counted for less for every year.

Stalin

The NKVD technicians worked hard to obtain a confession from the prisoner who had been Konstantin Rokossovsky, formerly a RKKA senior officer and Civil War veteran who had been denounced as a spy in 1937 by a colleague named Adolph Yushkevich.

In NKVD prison, his torturers would try to soften him up to make him more open to signing a confession and then pipelining him to a trial and to execution or prison camp. They were experts, employing many different techniques from simple beatings to the more delicate such as using pliers on his fingernails. Twice he found himself in front of an execution squad, only to be sent back to his cell. Still, he never confessed, and despite being provoked by false prisoners he never blamed Stalin either.

The NKVD had to send him to trial without a confession. When he was told the name of his denouncer he told the court that he would sign a confession if he was allowed to confront Yushkevich. The court allowed it, and sent for the man. This turned out to be problematic, though, because Yushkevich had died in 1920, which Rokossovsky of course knew.

On 22 March 1941 the prisoner was taken out of his cell by a couple of NKVD officers. He knew better than to ask, or ask about his wife and daughter. Anything could follow. But the NKVD men took him to a dentist, who measured him for stainless steel dentures to replace the front teeth he had lost in the interrogation chambers. He was taken to a tailor to get a new senior rank uniform. A doctor examined his many injuries. Alone in a hotel room that night, he read his new orders that made him a komkor (Corps Commander, the Red Army hadn’t brought back traditional ranks yet).

That summer, the Germans invaded, and a terrible time followed when Stalin and the Stavka would prefer brute-force tactics with unorganised formations against the most sophisticated army in the world. Rokossovsky did his best with the resources he had and went on to become one of the most resolute and strategically skilled generals in the Red Army, rising in the ranks and in commands.

On 22 June 1944 the greatest artillery barrage in the history of warfare broke loose over the German Army Group Centre. Four Soviet fronts (a formation between an army group and an army in size) were ordered to pin down the defending German armies, take the fortified towns that had been set up to offset the German inferiority in numbers and resources, and break through the German front to take control over the complete operational depth of the army group. The total victory of the Soviet arms over the Germans meant that the Germans had to call in formations from other theatres and reduce the eastern front to basically a screening force without any ability to resist strong Soviet assaults.

Rokossovsky’s 1st Belorussian Front was one of the formations that were to carry out the first phase this massive operation, with the specific goals of taking the fortified town of Bobruisk, disabling the elite German 9.Armee, and opening the way for exploitation forces to advance on Minsk.

Rokossovsky had been summoned to Stalin to plan the strategy of his front. Such meetings could go various ways: Stalin might actually want to hear the general’s ideas, he might let the general make a case for his ideas, or he might tell the general “this is what you are supposed to do”. Full stop. When Rokossovsky entered the conference room Stalin waved him up to the map table and pointed at Bobruisk, telling him “Your front will make a concentrated assault towards the city to achieve maximum force.” Stalin was still fond of the head-on mass assaults that had cost so much Soviet blood earlier in the war. Rokossovsky said “No, comrade. We will make a two pronged approach to break through here, and here.”

“Go and think it over” Stalin said without losing his composure, indicating the window wall. A little while later, Stalin called him up again and repeated his order. “two break-throughs, comrade Stalin, two break-throughs”, Rokossovsky insisted. This was repeated twice more, but the third time Stalin put his hand on Rokossovsky’s shoulder and said “Your confidence speaks for your sound judgement”.

The fighting at Bobruisk was extremely hard with heavy initial losses, but when the 9.Armee finally broke Rokossovsky’s front swept clean. A small remainder of the German force broke out and escaped, but most of the Germans had surrendered or been killed. The glorious 9.Armee was no more.

From then on, Stalin stopped talking about “General Rokossovsky” and instead called him “Konstantin Konstantinovich” like a trusted and liked workmate.

In early 1945, three marshals of the Soviet Union were approaching Berlin with their fronts: Rokossovsky with the 2nd Belorussian Front, Zhukov with the 1st Belorussian, and Konev with the 1st Ukrainian. All of them of course wanted the glory of capturing Hitler’s city and ending the war. The question was what orders Stalin would give. Would they make a concerted attack, essentially competing for the Reichstag building, or would one front lead and the others take the flanks? Stalin’s orders arrived: Zhukov would take the city, assisted by Konev while preparing for a south-west push to meet up with the Americans. Rokossovsky was to double back and mop up East Prussia and the Baltic coast westwards: essentially, he was told to leave by the back door.

Stalin was a cipher. Churchill had said about Russia “It is a riddle, wrapped in a mystery, inside an enigma; but perhaps there is a key.” Stalin was a cipher wrapped in an image of a wise avuncular man waving from the tribune, covered by the official documentation of destalinization. The key was thrown away long ago. Every man and woman in the Red Army ought to have had chills along their back every time Stalin set a military order on paper. But he ultimately won against some very strong strategists, if only because it could happen that a man who had gone from being a walking dead man in political prison could appear before him in a general’s uniform and be allowed to defy him.

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Peter Lewerin

Algorithmician, history buff, non-practicing hedonist. Whovian, ghiblist: let there be wonder. Argumentative, punster, has delusions of eloquence.