The Rise of Jennie Churchill’s son, Winston: A Future Prime Minister Running Headlong into Adventure

It sounded like a mother indulging a small child:

“I understand all right–& of course darling it is natural that you shd want to travel & I won’t throw cold water on yr little plans,” wrote Jennie Churchill to her son.*  

Twenty-year-old Winston was bored and—with ten weeks before reporting to duty in India with the Fourth Hussars—concocted a “little plan” with his friend Reginald Barnes: they would sail to Havana and observe the bloody civil war there.  His deeply romantic view of battle drew him to Cuba like steel to a magnet.

Jennie pulled the necessary strings with her various lovers, and Winston soon blissfully found himself under fire:  ‘There is nothing more exhilarating than to be shot at without result,’” he wrote. Flying bullets are “‘a sound in the air sometimes like a sigh, sometimes like a whistle, and at others like the buzz of an offended hornet.’”*

Winston and Reginald made it safely through their three-week stay with three significant results for Churchill.  First, his boyhood interest in war and strategies found adult expression. Second, his five lively reports for The Daily Graphic were well received and encouraged him to begin a career of writing that would span over five decades.  Third, in he acquired a habit that became his trademark:  he loved smoking Cuban cigars.

One battle wasn’t enough to satisfy, though.  Two years later in 1897 while Churchill was back in England enjoying The Season, an uprising broke out near the Malakand Pass in northwest India. He dropped all plans, made the 2,000 mile trip back to India in five days, and got leave from his regiment so he could again come under hot fire, again as a correspondent.*  His reports described the tension of being stalked by native fighters, the torture endured if captured, the skill of the British military.  Afterwards, Jennie used her influence to get his war dispatches published as The Story of the Malakand Field Force, a book so popular that even the Prince of Wales complimented him on it.

 The next year Winston had had it with mere reporting: he wanted to be officially in the fighting.  Sir Herbert Kitchener was leading troops to avenge the butchering of General Charles Gordon and his men at the town of Khartoum in the Sudan.  This conflict was irresistible to Churchill, so he requested to be assigned to Kitchener’s force. Kitchener refused. Undeterred, Churchill asked the Prince of Wales–and even the Prime Minister who finally agreed to help a young man who was only a lieutenant. He later wrote gripping descriptions of the arid desert wastelands, the sinister dervishes who opposed them, and cavalry charges where the enemy would wait patiently on the sand “to hamstring the horses with their knives.”** 

Churchill thought it all “’magnificent’” and praised the “persevering British people who, often affronted, usually get their own way in the end’”–as he himself did.*

He could scarcely believe his good luck when another large conflict came.  This war would make him a rock star of the British Empire.

Next Time: Winston Churchill, Rock Star

Blog Note:  One last adventure of the youthful Winston Churchill will be described in the next blog and then we will let him alone for a while.  We are following all aspects of England here, not just the military and political.

Manchester, William.  The Last Lion:  Winston Spencer Churchill, Visions of Glory, 

1874-1932.  New York:  Little, Brown and Company, 1983; pp. 223, 228, 251, 280.

**Wright, William.  Omdurman 1898:  Battle Story. Gloucestershire:  The History Press, 2012; p. 108.

2 thoughts on “The Rise of Jennie Churchill’s son, Winston: A Future Prime Minister Running Headlong into Adventure”

    1. Trisha, I want to highlight information that will surprise, interest, and inform–and I want to keep a mix of travel, landscapes, history, and culture. So there’s plenty to explore. ‘Glad it’s working for you so far!


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