The German Wehrmacht and Adolf Hitler’s panzer corps devastated the British military through France and Belgium. Hitler twice stopped his forces from delivering the kill shot on British troops at the French port known as Dunkirk — the location of one of the largest naval evacuations in history. Historians predict that Hitler’s decision to halt his army for three days in May 1940 was to give Winston Churchill, Britain’s new prime minister at the time, “a sporting chance” — despite having them completely surrounded.
While Hitler and Churchill were making strategic moves far and away from front-line combat on the battlefield, another Churchill was gaining near-mythical status for his otherworldly tactics, brazen leadership, and his mystifying ability to confuse the enemy and inspire his peers. On May 27, 1940, Lt. Col. John Malcolm Thorpe Fleming Churchill stood at the base of a tower and watched a German patrol approach a hill overlooking the French village of L’Epinette.
The first Nazi officer who appeared in sight was hit center mass from 30 yards — sparking the signal for the ambush. The German’s deadly wound was not from a gunshot but from an arrow fired from a longbow. Alongside two infantrymen from the Manchester Regiment, Churchill unsheathed his basket-hilted claymore medieval sword and commanded orders to maneuvering elements to take out the remaining German patrol. The British officer’s legend leading men in combat armed with a bow and arrow was born, and throughout World War II he repeatedly proved the worth of his nicknames — “Mad Jack” and “Fighting Jack.”
But who exactly was “Mad Jack” Churchill, and what emboldened him to carry medieval weapons into modern combat?
Churchill was born in British-controlled Hong Kong and raised among Anglo-Scottish parents in England alongside his two brothers, Thomas and Robert (both would also have stellar World War II exploits). He received his education at a private institution called King William’s College on the Isle of Man and Royal Military College in Sandhurst, England. Here he fostered a passion for history and poetry and had a romanticism toward adventure that birthed a broader fascination for castles, plants, animals, and insects.
He was commissioned into the 2nd Battalion of the Manchester Regiment in 1926 and arrived in Rangoon, Burma, to receive further training. He rode a Zenith motorcycle 1,500 miles from his signals course in Poona, India, mistakenly crashing into a water buffalo along the way. In Burma, he balanced his motorcycle on railroad ties as he listened for any signs of oncoming trains. While on duty he participated in flag marches traveling down the Irrawaddy River, Burma’s largest and most frequented commercial highway, to visit villages to collect intelligence on suspected bandits.
Before he left Burma and later the Army with a decade of service in 1936, he learned to play the bagpipes in Maymyo — now known as Pyin Oo Lwin — Mayanmar, an interest piqued by his Scottish heritage. He worked as a newspaper editor in Nairobi, Kenya, and his chiseled jawline led to gigs in male modeling. The adventurer gained attention in England as an entertainer, took a small role in the 1924 film The Thief of Baghdad to advise on archery techniques, and even showcased those skills from 200 yards at the World Archery Championships held in Oslo, Norway, in 1939.
After earning the statistic for the last bow and arrow kill by a British officer in combat, Churchill volunteered for No. 2 Commando, a special operations unit that gained notorious status for daring coastal raids. Dressed in a kilt and holding a set of bagpipes, Churchill played an impressive rendition of the tune March of the Cameron Men before the commandos took part in the ironically named Operation Archery (sometimes called the Måløy Raid), against German positions on the island of Vågsøy, Norway.
During the Italian amphibious landings in Sicily and Salerno he personally captured 42 German soldiers and an 81mm mortar team armed with only his sword. “In my opinion, any officer who goes into action without his sword is improperly dressed,” Churchill later reasoned. During a nighttime commando raid in Yugoslavia on the island of Brac, Churchill was wounded, captured, and imprisoned in the Sachsenhausen concentration camp near Berlin. He tunneled a route out of the prison camp with another Royal Air Force prisoner but was captured and transferred to a more secure location in Austria, where he successfully escaped once more.
He was found by an American reconnaissance unit eight days later walking on a busted ankle after train hopping 150 miles across the Swiss Alps near Brenner pass. Following the war and into his 40s, he rescued an estimated 500 Jewish doctors and patients held hostage at a hospital in Jerusalem after the Hadassah Convoy Massacre in 1948.
“People are less likely to shoot at you if you are smiling at them,” he quipped while holding his blackthorn cane. In the 1950s, “Mad Jack” retired from military service with two Distinguished Service Order awards and found a passion for refurbished steamboats along the Thames. He also participated in motorcycle speed trials to quench his thirst for excitement.
“He didn’t brag about these things at all, but he would be happy to talk to anyone who asked, particularly if it was over a couple of nice glasses of wine in the evening,” his son Malcolm later said. Churchill was a humble warrior beyond what history proclaimed. He died in 1996 at age 89.
Matt Fratus is a history staff writer for Coffee or Die. He prides himself on uncovering the most fascinating tales of history by sharing them through any means of engaging storytelling. He writes for his micro-blog @LateNightHistory on Instagram, where he shares the story behind the image. He is also the host of the Late Night History podcast. When not writing about history, Matt enjoys volunteering for One More Wave and rooting for Boston sports teams.
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