Mad Jack Churchill: The Sword-Wielding War Hero

The Officer Who Thought Modern War Needed a Broadsword

By 1940, warfare had guns, tanks and bombers. John Malcolm Thorpe Fleming Churchill went into it anyway with a Scottish broadsword on his belt, a longbow and arrows around his neck, and a set of bagpipes under his arm. His men called him "Fighting Jack." History remembers him as Mad Jack — and he is, without much competition, the most gloriously eccentric hero Britain produced in the Second World War.

He wasn't related to the Prime Minister, though the Germans would later assume otherwise, with consequences of their own.

An Unlikely Start

John Malcolm Thorpe Fleming Churchill was born in 1906 into a family already well accustomed to distant postings — his father served as an engineer with the Ceylon Civil Service before being appointed Director of Public Works in Hong Kong, where the family later lived. Young Jack was educated at King William's College on the Isle of Man before passing through the Royal Military College, Sandhurst, and being commissioned into the Manchester Regiment in 1926.

His first posting took him to Rangoon, Burma, where peacetime soldiering did little to dampen his appetite for adventure. Sent to Poona for a signals course, he made the 1,500-mile return journey by motorcycle along roads that frequently weren't roads at all — at one point riding along railway sleepers to cross a bridge, and at another point losing a straight fight with a hostile water buffalo. It was also in Burma that he first took up the bagpipes in earnest, tutored by the Pipe Major of the Cameron Highlanders, and by his own account he never fully put them down again.

By 1936, garrison life had lost whatever charm it once held. Churchill resigned his commission and moved to Nairobi, working as a newspaper editor and — improbably — a male model, before his archery and bagpipe skills won him work as a film extra. He appeared in The Thief of Bagdad and A Yank at Oxford, took second place in the military piping competition at the Aldershot Tattoo — reportedly to the mild irritation of the Scottish competitors he beat — and in 1939 represented Great Britain at the World Archery Championships in Oslo, where he was said to be capable of placing an arrow accurately at 200 yards.

Then Germany invaded Poland, and Churchill went straight back to the colours.

"Any Officer Who Goes Into Action Without His Sword Is Improperly Dressed"

That line was Churchill's own, and he meant every word of it. He carried the sword everywhere, despite it being distinctly against regulations for a modern infantry officer, and he never once left it behind.

The most famous test of his eccentricity came during the retreat to Dunkirk. In May 1940, his unit ambushed a German patrol near the French village of L'Épinette. As the story is told — and it's one repeated in most accounts of his life, though Churchill himself later suggested his bows had been damaged earlier in the campaign, so the detail carries a note of legend alongside the record — he brought down the lead German soldier with a longbow shot from around thirty yards, in what's often cited as the last recorded longbow kill in warfare. His unit then held off the rest of the patrol with machine-gun fire until their ammunition ran out, before Churchill led the survivors back through enemy lines under cover of darkness, having taken a bullet to the shoulder in the process.

Whatever the precise truth of that single moment, what isn't in dispute is what came next: a commando career built almost entirely on nerve, and a growing reputation that even his own high command struggled to categorise.

Bagpipes Into Battle

Churchill volunteered for the newly formed Commandos and made his pipes as much a part of his kit as his rifle. At Operation Archery — the raid on the German garrison at Vågsøy, Norway, in December 1941 — he stood at the front of the landing craft as it approached the shore, playing "March of the Cameron Men" while bullets began to fly. As the ramp went down, he threw a grenade, drew his sword, and ran into the fight. The raid destroyed German fish-oil factories and stores worth thousands of tons to the German war effort, and Churchill was awarded the Military Cross for his part in it.

By the summer of 1943, now commanding No. 2 Commando during the Allied invasions of Sicily and Salerno, he pulled off his single most audacious feat. Sneaking into the German-held town of Molina at night with only a corporal for company, he identified the enemy sentries by the glow of their cigarettes, took one at swordpoint, and used the threat of his weapon to persuade the rest of the garrison to surrender. By morning he had captured an observation post, a mortar squad, and 42 prisoners — using nothing but his sword. Ever practical, he had the prisoners carry their own mortar and ammunition back down the pass, along with the wounded on a cart, remarking afterwards that it looked like "an image from the Napoleonic Wars." He then walked back into the town alone to retrieve the blade itself, which he'd lost in the scuffle. For the action he was recommended for the Victoria Cross and awarded the Distinguished Service Order — the first of two he would earn during the war.

Capture, Sachsenhausen, and a Bagpipe Encore

In May 1944, leading a mixed force of commandos and Yugoslav Partisans in support of Tito's resistance movement, Churchill was ordered to raid the German-held island of Brač. The landing went wrong; the Partisans he was leading held back, and Churchill and his small party of commandos found themselves cut off, surrounded and, one by one, killed or wounded around him. Churchill himself was the last man still fighting — and, true to form, he was doing it with his bagpipes rather than a weapon, playing "Will Ye No Come Back Again" in what he later admitted was a fairly hopeless attempt to signal for help, when a grenade explosion knocked him unconscious.

His captors, convinced they'd caught a relative of the Prime Minister, sent him to the section of Sachsenhausen concentration camp reserved for prominent prisoners. It didn't hold him for long. Churchill escaped through a drainage tunnel with a group of fellow officers, was recaptured shortly afterwards, and was eventually transferred south as Allied forces closed in. In the final chaos of the war's last weeks he slipped away from his guards for good and walked roughly 150 miles across the Alps on a broken ankle before being picked up by an American reconnaissance unit — bringing an already improbable war to an entirely fitting close.

After the War

Peace didn't suit him any better than it had the first time. Restless, he even qualified as a British Army parachutist after the war, reportedly to become one of the oldest men to do so at the time — keen, as ever, not to miss out on anything. In 1948, while serving in Palestine, Churchill is credited with helping rescue around 500 people trapped during the Hadassah Convoy Massacre near Jerusalem, walking calmly towards armed attackers and reasoning simply that "people are less likely to shoot at you if you are smiling at them." He later took up motorcycle speed trials and restoring steamboats on the Thames, surfing the Severn Bore for good measure, and lived until 1996, dying at the age of 89.

The Legend and the Man

Historians have occasionally questioned how much of the Mad Jack story is embellishment and how much is documented fact, and it's a fair question to ask of any legend this colourful. But the paper trail — Military Crosses, a Distinguished Service Order awarded twice, a recommendation for the Victoria Cross, and a war diary held at the National Archives — leaves little doubt that the substance behind the myth was real. His two brothers, Thomas and Robert, both distinguished themselves in the war in their own right, Thomas rising to Major-General and Robert losing his life in the Fleet Air Arm in 1942, suggesting a family disposition towards courage that Jack simply expressed more theatrically than most.

Churchill never sought to explain himself, and perhaps that was the point. As one British newspaper put it in his obituary: had Churchill not existed, he would have been impossible to invent.