Six Things You Didn’t Know About Winston Churchill: Leadership Lessons

He was one of those Renaissance men, in spite of his flaws

5 min readJun 12, 2021


Photo by Kristina G. on Unsplash

Remarkable humans almost always have serious flaws, and Winston Churchill was a truly remarkable person with a remarkable life. Despite the stories of anti-semitism and his love of colonialism, both normal among the British aristocracy at the time, he had many positive accomplishments beyond saving Britain from the Nazis.

Born the number two son (his older brother got the dukedom and the enormous palace), he had to constantly strive to be admired by his distant parents. Chubby, unhealthy, prone to drink, and often broke, he nevertheless had a life that if you read it in a novel it would seem unreal.

He was captured as a young cavalryman and escaped through enemy lines after saving a train full of soldiers

Churchill was a fearless soldier though not very disciplined and extremely opportunistic. He was a talented polo player and worked as a journalist while still in the cavalry, a conflict of interest. During the Boer war between South Afrikkaners and the British, he found himself on a full troop train and sensed an ambush, based on his childhood obsession with battle strategy.

He managed to help avoid the ambush, saving hundreds of soldiers from capture but was captured himself. He escaped and made his way through 300 miles of hostile territory and he was lauded as a great hero when he emerged in friendly territory. He was in his early twenties.

He commanded a battalion in WWI after getting kicked out of the government

Churchill served in the highest offices of the British government, including Prime Minister and Cabinet level roles. But in between he often hit bottom popularity-wise as he fell out of favor or screwed something up. In WWI it was the battle of the Dardennes Straits where the navy took a terrible beating by the Turkish while trying a landing.

Though Churchill was blamed at the time, history has shown that it was very conservative admirals with little actual battle experience whose reluctance to commit…




Mastodon:, Writer, nine non-fiction books, two novels, Buddhist, train lover. Amateur cook, lover of life most of the time!