Autumn 1895 (Age 21)

Cuban Escapades

Later in life Churchill reflected on his years in the 4th Hussars. He recalled that the young officers envied the decorations and experiences of their senior colleagues and wondered whether their own chance to win glory would ever come.

The ever pro-active young Winston created his own opportunities by procuring permission to go to Cuba during his five months’ leave from the army. He also contracted I with the Daily Graphic for occasional reports.

He travelled to Cuba via New York. Although his mother warned he would find that city boring, his experience was quite the opposite. In America he first encountered a paper dollar, which he called “the most disreputable coin the world has ever seen.” Nor was he impressed by American newspapers:

(“… the essence of American journalism is vulgarity divested of truth”) but he found “that vulgarity is a sign of strength. A great, crude, strong, young people are the Americans—like a boisterous healthy boy among enervated but well-bred ladies and gentleman.”

When he finally saw Cuba he felt as if he had “sailed with Long John Silver and first gazed on Treasure Island.” On his twenty-first birthday he “…heard shots fired in anger, and heard bullets strike flesh or whistle through the air.” Later he was in more immediate personal danger with bullets passing within a foot of his head.

From Cuba Churchill planned to bring back a quantity of Havana cigars to lay down in the cellar of his mother’s house. In Cuba he also learned the merits of a midday siesta, concluding that “the rest and spell of sleep in the middle of the day refresh the human frame far more than a long night. We were not made by nature to work, or even to play, from eight o’clock in the morning till midnight.”

Back home there was some criticism of Churchill’s escapades. One newspaper suggested that “…sensible people will wonder what motive could possibly impel a British officer to mix himself up in a dispute with the merits of which he had absolutely nothing to do. Mr Churchill was supposed to have gone to the West Indies for a holiday, having obtained leave of absence from his regimental duties at the beginning of October for that purpose. Spending a holiday in fighting other peoples’ battles is rather an extraordinary proceeding even for a Churchill.”

Related Story

Join Now

Join NowPlease join with us to help preserve the memory of Winston Churchill and continue to explore how his life, experiences and leadership are ever-more relevant in today’s chaotic world. BENEFITS >BECOME A MEMBER >

WinstonChurchill.org

The International Churchill Society (ICS), founded in 1968 shortly after Churchill's death, is the world’s preeminent member organisation dedicated to preserving the historic legacy of Sir Winston Churchill.

At a time when leadership is challenged at every turn, that legacy looms larger and remains more relevant than ever.