The Story of Mad Jack Churchill

The Second World War was one of the most brutal conflicts of modern times, largely due to the huge technological developments. Yet while his comrades were busy driving tanks, firing machine guns and throwing grenades, Jack Churchill chose to go into battle with a longbow, a Scottish broadsword and a set of bag pipes like some sort time travelling Scottish knight.

Jack Churchill, no relation to British Prime Minister Winston Churchill, was born in 1906 in Colombo, British Ceylon (present day Sri Lanka). The family would later relocate to British ruled Hong Kong in 1910 where Jack’s father, Alec Churchill served as Director of Public Works on the Executive Council. 7 years later the family would return to England with Jack graduating from the Royal Military College, Sandhurst in 1926. He would go onto to serve in Burma with the Manchester Regiment until 1936 when he left to work as a newspaper editor in Kenya while also occasionally doing a bit of male modelling on the side. Not one to just sit around, Jack also stared in several films including ‘The Thief of Bagdad’ and ‘A Yank at Oxford’.

The Thief of Bagdad poster

Yet only 3 years after leaving the army, Jack joined up once again to fight in the Second World War. He was sent to France as part of the British Expeditionary Force (BEF), where he became famous for wielding a sword. One of the most common myths surrounding Jack is that he was the last person to kill an enemy soldier with a long bow, but Jack himself confessed that he never actually got the chance to use his bows, with a lorry crushing the weapons earlier in the campaign. It was his use of sword and bow that earned him the nicknames ‘Mad Jack‘ and ‘Fighting Jack Churchill

A basket handled broadsword, the type of sword Jack carried into battle

Norway was Jack’s next destination, where he was second in command of No.3 Commando in Operation Archery, a raid on a German garrison. Jack led the charge from the landing craft, playing “March of the Cameron Men” on his bagpipes, following up by lobbing several grenades before charging forward. As a reward for his heroic, if not odd actions, Jack was awarded the Military Cross.

Jack would go onto fight in Italy in 1943, and later in Yugoslavia in 1944. It was in Yugoslavia where Jack led a failed attack on the German held island of Vis. Only Churchill and six men reached their objective before being met with mortar fire. This killed everyone but Churchill who played “Will Ye No Come Back Again?” on his bagpipes as the Germans approached. He was eventually knocked unconscious by a grenade and captured, before being transferred to Sachsenhausen concentration camp.

The gates of Sachsenhausen concentration Camp

But Jack wasn’t your average Prisoner of War. In September of 1944, only a few months after his capture, Jack and fellow Prisoner RAF officer Bertram James staged an escape through an abandoned drain. The pair’s aim was to make it to the Baltic coast but they were unfortunately captured only a few miles from their goal. In the last few weeks of the war, Churchill was transferred to Tyrol, a VIP concentration camp in Italy staffed by SS and the Death Head Unit, one of the most brutal units in the German Paramilitary. Tyrol served as the location of the most important prisoners the Nazi’s had with prisoners being transferred from all over Nazi territory, something done on the direct orders of Adolf Hitler himself. This was done in an attempt to hold the prisoners hostage, in the hopes of securing immunity for high ranking Nazi’s. The prisoners eventually became suspicious that they would soon be executed and aired these concerns to high ranking German Army staff. The German army moved in and freed the prisoners. Churchill walked 93 miles to Verona where he met with an American Armoured Unit.

The idyllic landscape of Tyrol

Now most people would decide to retire at this point, returning home to the sunny(ish) shores of England. Not Jack though who sought out more conflict, and had himself sent to Burma where the Pacific War still raged on. Yet by the time Jack reached India, the U.S had dropped two Atom bombs on the towns of Hiroshima and Nagasaki, ending the conflict. I know what you’re thinking, ‘I bet Jack was relived’. Nope, Jack was not impressed stating “If it wasn’t for those damn Yanks, we could have kept the war going for another 10 years!”.  Hmm, that’s certainly one way to look at it Jack!

After the Second World War, Jack was redeployed to British Palestine in 1948. After attempting to assist a Hadassah medical convoy that found itself under attack by Arab forces, Jack found himself in a dire situation. He offered to evacuate members of the convoy in his armoured vehicle, going against military orders to keep out of the fight. Before they could evacuate, however two of the convoy trucks caught fire, tragically killing 77 of the 79 people inside. After the massacre, Jack coordinated the evacuation of 700 Jewish doctors, students and patients from the Hadassah Hospital on the Hebrew University campus on Mount Scopus in Jerusalem where the convoy was headed. In recognition of his brave actions the street leading to the hospital was renamed Churchill Boulevard.

Hadassah Hospital

It seems this was enough for Jack, who retired from active service and took an army desk job. Not that he slowed down at all, taking up surfboarding, parachuting, more acting, more archery and being a good old fashioned eccentric. Jack became well known for his eccentric ways, often scaring passengers and rail staff by throwing his briefcase out of the train window on his ride home. His explanation for his odd actions were that he didn’t want to carry his briefcase home so he would throw it into his own back garden as the train passed.

Jack would live to the ripe age of 89, dying in the March of 1996 in Surrey. From his broad sword wielding days of World War Two to evacuating medical staff in Jerusalem, it’s clear that Jack Churchill was a true hero, even if he was a bit of an odd one.


Maj.-Gen. Thomas B. L. Churchill, C.B., C.B.E., M.C, The Churchill Chronicles, , 1986

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