The Legend of ‘Mad Jack’ Churchill: The Soldier Who Fought WWII with a Bow, Sword, and Bagpipes
- Sep 3, 2024
- 7 min read
Updated: Jul 28
"Any officer who goes into action without his sword is improperly dressed." That was John Malcolm Thorpe Fleming Churchill's actual justification for carrying a basket-hilted Scottish broadsword into battle against the German army in 1940, and he wasn't joking. He also carried a longbow and a full set of bagpipes, and used all three in combat, at a point in history when most soldiers were relying on rifles and artillery. He was known as Mad Jack, and unlike most nicknames earned in wartime, his hasn't been exaggerated much at all.
Not Actually Related to That Churchill
Jack Churchill was born on 16 September 1906 in Ceylon, now Sri Lanka, no relation to the wartime Prime Minister who shared his surname. His family moved to Hong Kong and then back to England, where he attended King William's College on the Isle of Man before graduating from the Royal Military College at Sandhurst in 1926. He wasn't the only remarkable Churchill brother in that war. Thomas, one of his two younger brothers, also became a commando commander and led the 2nd Special Service Brigade at the Battle of Monte Cassino. Their youngest brother, Robert, served as a lieutenant in the Royal Navy and was killed in action in 1942, a loss that sits quietly behind Jack's own legend and rarely makes it into the retelling.
His first posting was to the Manchester Regiment in Burma, where he developed two habits that would define the rest of his life: playing the bagpipes and covering absurd distances by motorcycle. In 1930 he rode more than 1,500 miles from Rangoon to Poona in India to attend a signals course, on roads that in many stretches didn't exist yet. He also reportedly lost a fight with a water buffalo along the way, though he made it back in time for the Burma Rebellion regardless.
He left the army in 1936 and spent a few years figuring out what a man like him does in peacetime. He worked as a newspaper editor in Nairobi, took on some modelling work, and got seriously into archery, good enough that he worked as an archery double in the 1940 film The Thief of Bagdad and represented Great Britain at the 1939 World Archery Championships in Oslo. He also nearly won a bagpipe competition, placing second in the officers' class at the Aldershot piping championships in 1938, notable partly because he was the only Englishman competing against around seventy Scottish pipers.
Back in His Red Coat
When Germany invaded Poland in 1939, Churchill rejoined the Manchester Regiment and shipped out to France. "I was back in my red coat," he said afterward, "the country having got into a jam in my absence." During the retreat toward Dunkirk in May 1940, near the village of L'Epinette, Churchill and two other soldiers spotted a group of approaching German troops. Churchill drew his longbow and shot one of them before the rest of his men opened fire with conventional weapons. It's usually cited as the last confirmed kill by bow and arrow in the history of the British Army, though it's worth being honest that Churchill himself almost never talked about his own exploits, and the handful of secondhand accounts that exist don't even agree on where the arrow struck. Whatever actually happened in that field, the story stuck, and separately, Churchill's actions helping salvage a tank under fire during the Dunkirk operation earned him his first Military Cross.
A Sword at Vaagso, and 42 Prisoners in Sicily
Churchill volunteered for the newly formed Commandos and by December 1941 was second-in-command of No. 3 Commando during Operation Archery, a raid on the German garrison at Vaagso, Norway. As the landing craft ramps dropped, he strode ashore playing March of the Cameron Men on his bagpipes before switching to grenade and sword as the fighting started. The raid succeeded in under ten minutes, and it earned him a bar to his Military Cross.
By July 1943 Churchill commanded No. 2 Commando during the Allied invasion of Sicily. Near the town of Piegoletti, he and a corporal identified as Ruffell crept alone into a German position at night, using the glow of enemy cigarettes to locate sentries in the dark. Churchill took one guard at swordpoint, used him as cover to move between the remaining posts, and talked the entire garrison into surrendering. He and Ruffell walked out with 42 German prisoners captured using nothing but a sword and nerve, a scene that wouldn't be out of place next to Corporal Wojtek, the Polish Army's beer-drinking, ammunition-carrying bear, on the very short list of things about the Second World War that sound more like myth than history.
Captured, and Not Interested in Staying That Way
Churchill's luck ran out in 1944 on the Dalmatian island of Brac, off the coast of Yugoslavia, when his unit was hit by mortar fire and effectively wiped out. Churchill himself survived only because he'd stepped away from the group to play his bagpipes. He was knocked unconscious by a grenade blast and captured, eventually ending up at Sachsenhausen concentration camp.
He didn't stay long. Along with another officer, he crawled out through an abandoned drain under the perimeter wire and made it roughly a hundred miles on foot toward the Baltic coast before being recaptured near Rostock. He was released not long after, when a sympathetic army unit intervened on his behalf. Transferred to a prisoner of war camp in the Austrian Tyrol, he escaped again during a blackout, this time trekking well over a hundred miles across the Alps until he ran into American troops near Verona, Italy, where he reportedly greeted them by asking for a cigarette.
The war in Europe ended before he could get back into it, and by his own account he wasn't thrilled about the timing. "If it hadn't been for those damned Yanks," he's quoted as saying, "we could have kept the war going for another ten years." He made it as far as India hoping to join the fight against Japan before that war ended too.
One Last Fight, in Jerusalem
Churchill's career didn't end with the war. He transferred to the Seaforth Highlanders and then the Highland Light Infantry and was posted to Mandatory Palestine, where in 1948 a Jewish medical convoy heading to Hadassah Hospital on Mount Scopus was ambushed by Arab fighters in Jerusalem. British forces had been ordered to stay out of the fighting, but Churchill tried to intervene anyway, reportedly walking toward the ambush alone and unarmed except for a blackthorn stick, on the theory that, as he put it, people are less likely to shoot you if you smile at them. One of his soldiers was killed in the exchange and his offer of help was turned down, so he pulled his men back. Days later, though, he successfully coordinated the evacuation of around 700 doctors, students and patients trapped at the besieged hospital. A road on Mount Scopus is named Churchill Boulevard in his honour to this day.
Surfing Into Retirement
Somewhere in the middle of all this, Churchill found time for a family. In March 1941, between the fall of France and his Commando raids, he married Rosamund Margaret Denny, granddaughter of the Scottish shipbuilding magnate Sir Archibald Denny. They had two sons, Malcolm in 1942 and Rodney in 1947, and by every account Churchill was a genuinely gentle, unassuming presence at home, a sharp contrast to the man leading sword charges overseas.
Churchill retired from active combat duty in the late 1940s but stayed in uniform for another decade, qualifying as a parachutist and working as a land-air warfare instructor in Australia, where he took up surfing. He built his own board and, in 1955, became the first person recorded riding a tidal bore wave, the standing wave that travels up certain rivers against the current, for more than a mile, on the Severn Bore in England. That stunt is now credited with helping start the sport of tidal bore surfing, which people still practice on rivers around the world. He picked up one more film credit too, playing an archer on the walls of Warwick Castle in the 1952 film Ivanhoe.
He formally retired from the army in 1959 at 53, and settled into a version of civilian life that was still, by any normal standard, a little unhinged. He refurbished old steamboats, built radio-controlled model warships with his wife Rosamund, and made a habit of startling fellow commuters on his train home from London by calmly opening a window and hurling his briefcase out of it, timed precisely so it landed in his own back garden and saved him the trouble of carrying it the rest of the way.
Jack Churchill died at home in Surrey on 8 March 1996, aged 89. A newspaper obituary at the time put it about as well as anyone has: had Churchill not existed, it would have been impossible to invent him, since no fictional hero with his story would seem credible.
