Churchill had his faults, but he was a far better strategist than his generals were

Churchill had his faults, but he was a far better strategist than his generals were


Tom note: This is an excerpt from my new book, Churchill and Orwell: The Fight for Freedom. This section discusses the problems Winston Churchill’s military subordinates had with him, and evaluates whether they were correct in dismissing him as a strategic amateur.

In June 1944, after the D-Day landings in Normandy, his top military advisor, General Alan Brooke, wrote in his diary that, “We had a long and painful evening of it listening to Winston’s strategic ravings.” He denounced Churchill in his diary as “a complete amateur of strategy [who] . . . swamps himself in details he should never look at and as a result fails ever to see a strategic problem in its true perspective.” His bottom line on Churchill was, “Never have I admired and despised a man simultaneously to the same extent.”

Much of what Brooke wrote in his diary during the war, and what others would charge after it — often in response to Churchill’s self-centered World War II memoirs — was accurate. Churchill displayed many faults as a war leader. He neglected logistics. He failed to appreciate the role of naval aviation and several other major aspects of the war. Like many in Britain, he continued to see aircraft carriers as the eyes of the fleet, outliers to help direct cruisers and battleships, rather than as the new striking arm of the fleet, replacing battleships. He underestimated the impact that German submarines would play in the war. Like his generals, he underrated the military power of Japan while overvaluing the staying power of the British military in Asia, especially at the stronghold in Singapore. Generally, wrote one of his researchers, “it is not unfair to say that Churchill suffered from a number of misconceptions, if not delusions, about the Far East which affected his decisions as a statesman and his writing as a historian.”

Early in the war, Churchill had persisted in believing that victory might be achieved mainly by bombing Germany, rather than by invading it, probably because he could offer no other plausible theory of how Britain, before the American entry, might prevail. “When I look around to see how we can win the war I see that there is only one sure path,” he wrote in July 1940, “. . . and that is an absolutely devastating, exterminating attack by very heavy bombers from this country upon the Nazi homeland. We must be able to overwhelm them by this means without which I do not see a way through.”

He frequently was diverted by military raids and indirect attacks, often to the detriment of the main goal. “Winston adored funny operations,” commented his intelligence advisor, Sir Desmond Morton. He overestimated the gains to be had by invading Italy. He was the major driver behind the landing at Anzio, southwest of Rome, which became one of the worst quagmires of the war for the Allies. Relying too much on his experience of World War I, he failed to appreciate how much the mechanization of military power during World War II devalued the role of foot soldiers and elevated the importance of artillery and tanks. That blind spot probably also led him to underestimate how militarily effective the Americans would be in 1944 – 1945. This likely caused him to drag his feet on landing in France while pushing for more attacks on the periphery of the Axis.

Yet, for all that, on the big things, Churchill was more often right than wrong. He certainly was more right than most of his subordinates, which is why there was such value in his continual questioning of them. Looking back on the war’s strategic quandaries, Churchill mused, “It is always right to probe.” He was correct, profoundly so. His persistent interrogation of subordinates amounted to “a continuous audit of the military’s judgment,” wrote Eliot Cohen, the American strategist and historian.

Other wartime leaders would do well to imitate his inquisitive approach. They should not look for consensus, and instead should examine differences between advisors, asking them for the reasons for their different views. This is a way of discovering the assumptions that subordinates may have made without realizing it. If meetings are not contentious, they probably are not productive — especially planning sessions. This is often unpleasant, especially for the advisors, but it is the best way to develop strategy and to uncover one’s weaknesses before the enemy does. The essence of strategy is making hard choices, deciding between what Dwight Eisenhower once called the essential versus the important. Churchill excelled at that task.

Summarizing Churchill’s strategic thinking, Cohen concluded, “He saw war policy in terms of large building blocks which together created a structure of victory. Very few people can or do think in this fashion.” Most striking, Cohen added, was Churchill’s sense of strategic timing — first buying time to build up the British military and await the American entrance into the war, then agreeing to invade Europe in 1944.

Also to Churchill’s credit, he understood that he needed someone like General Brooke to argue with him. It was, after all, Churchill who first noticed Brooke, promoted him to lead the British military, and kept him there for years. 

Excerpted from Churchill and Orwell: The Fight for Freedom (Penguin Press, 2017), by permission of me.

Photo credit: Wikimedia Commons