Churchill as a Red Teamer

I am updating and re-posting some articles I wrote and never published from over the years. I’m going to be posting some war fiction as well that didn’t make the cut in some contests.

Many histories agree that Winston Churchill’s early life prepared him for his unique role as an Allied commander during WWII and legendary statesman. Similar in some regards to a previous historical Red Teamer that I discussed in 2013, President U.S Grant.

They shared early focuses on technology for battlefield mobility and overcame significant career setbacks for national victories. Churchill unlike many politicians fought on the front lines in small wars (India, Africa) and on the Western Front as a battalion commander. His dubious rise to fame was as a correspondent in the Boer Wars. These experiences gave him a unique advantage as a war time Prime Minister. Churchill though a great politician, orator, and leader was like many red teamers a rebel, cynic, and a flexible mind. Red Teamers internalize their experiences and resources available to objectively meet mission demands, while continuously identifying and defeating road blocks in organizational thought and process. Churchill best exemplifies the example of the Lion from RTJ law # 35, and in his early career is where he developed the characteristics to become the type of leader that British Red Teamers would need in WWII.

Churchill certainly benefited from being born as a son of Lord Randolph the Duke of Marlborough, but like Grant, Winston was not a talented student. Surprisingly, he examined into the Cavalry branch for it required lower academic standards than the Infantry Branch at Sandhurst. (The Opposite Situation for Grant who accessed into Infantry for those reasons). Early on in life, it was clear that Churchill had great aspirations and used his position in the Army as a means to create a cult of personality. Unlike Grant, whose fame and popularity leading to his Presidency was an effect of his position as the Union military leader, Churchill volunteered for increasingly dangerous operations as a means to create fame which would ultimately leverage his political aims. As an early adventure-journalist and Army officer, Churchill quickly rose to fame with his dispatches from campaigns in India and Africa. As a civilian embedded journalist, he pulled off a journalistic caper of legend with the Great Train Raid and escape during the Boer War. His service in the Army and his self-service as a writer and journalist allowed him to spring-board his political career starting as a member of parliament. Churchill in many ways hacked the British empirical career progression, by leveraging the popularity of the masses with his journalistic appeals promoting himself into more senior positions significantly faster than his peers.

As with many of our historical red teamers, Churchill suffered a debilitating failure when serving as Lord of the Admiralty during the Gallipoli campaign of 1915–1916. The operation at Gallipoli was a daring amphibious campaign to unlock the stalemate of the Western Front and reopen the Dardanelles straits to aid Russian Allies with ports on the Black Sea. The operation was ultimately doomed for many reasons, timing, lack of amphibious technology, and the omni-present actions of enemy forces. In the wake of this failure, Winston Churchill resigned his post and found himself in an unimaginable position for a modern day politician as a battlefield battalion commander on the western front. As a Battalion Commander in France, Churchill faced his own mortality and led men in the difficult trials of combat. He witnessed the effects of the stalemate of trench warfare, and had keen appreciation for the capacity of enemy forces which would lead to his later obsessions with military technology.

Why does this change of events matter? A leader of red teams who uniquely understands the constraints of his subordinates is more open to alternative courses of action, particularly if it saves lives or completes the mission. Churchill is more intimately familiar with the strains of combat by the time he was at the national command level in WWII than any other national level leader during the conflict. The failure of Gallipoli and later in 1939 the disaster at Dunkirk uniquely shaped British amphibious operations throughout the remainder of the war. Churchill because of his experiences on the Western Front as a combat leader and the disaster in the Dardanelles contributed to his championing technology programs such as tanks, aircraft, and amphibious support vessels when traditional leaders retreated from battlefield lessons learned. Furthermore, failure can teach a leader humility and perspective. As seen with US Grant and with Churchill, professional failures and the lessons learned during the ensuing recovery ends up defining their leadership methods. This dogged determination in the face of opposition and criticism is the hallmark of a red team leader. On the lead up to WWII, Churchill voiced a growing concern with the spread of Nazism and Hitler’s expansionist aims in Europe was faced with significant opposition from the Chamberlain government. This voice of dissent grew into the clear voice of leadership for the British nation in the dark days ahead leading to a productive relationship with one of history’s favorite Red Team individuals R.V. Jones.

Mike Denny is an Army National Guard aviation officer and company commander. Formerly, he served as a Field Artillery officer while on active duty. As a civilian, he is an executive management professional and occasional contributor to Task and Purpose, The Bridge, and Red Team Journal. The views expressed in this article do not reflect the official policy or position of the U.S. Army, the Department of Defense, or the U.S. Government.