When Jack Churchill died in 1996, one British newspaper said in its obituary that it would have been impossible to invent him because a fictional character with his story would not have been credible.

But why is that? What exactly is so unbelievable about a man who charged into battle in World War II wielding a broadsword and who shot at Nazis with a longbow? A man who played the bagpipes while his unit was making a landing into enemy territory? A man who, time and time again, narrowly escaped death because fortune truly favors the bold? A man who, when he finally had it with the military life, went on to become a surfer?

Truly, there is nothing weird about that, at least not to “Mad Jack” Churchill – a man proclaimed by the Royal Explorers Club as one of the greatest adventurers to have ever lived.  

Early Years

“Mad Jack” was born John Malcolm Thorpe Fleming Churchill on September 16, 1906, in Surrey, England. His father, Alec Fleming Churchill, worked as an engineer and, later, Director of Public Works, which meant that he moved the family around a lot for his job. Churchill first grew up in the former British colony of Ceylon, now Sri Lanka, and then Hong Kong before relocating again to England. Jack had two younger brothers who would also go on to have distinguished careers in the military, although not nearly as colorful.

Churchill received his education at the Dragon School in Oxford and King William’s College on the Isle of Man before enrolling in the Royal Military College at Sandhurst. He finished military school in 1926 and joined the 2nd Battalion of the Manchester Regiment on deployment to Burma, now Myanmar.

Over there, Churchill didn’t see a lot of action, mostly patrolling the Irrawaddy River by boat to check up on villages along the way. He found various hobbies to pass the time. This is where he first started playing the bagpipes, tutored by the Pipe Major of the Queen’s Own Cameron Highlanders, a regiment first raised back in 1793. He also bought a Zenith motorcycle and took it for road trips through Southeast Asia. He had a memorable, but dangerous encounter while riding across India when he ran into a water buffalo.

For a while, it seemed like Churchill’s military career would be a short and unmemorable one. After getting bored with military life, he retired from the Army in 1936. He went on a grand tour of Europe, accompanied by another former member of the Manchester Regiment who became a prominent soldier in his own right by the name of Rex King-Clark.

Churchill took advantage of these free years by putting one of his greatest skills to good use – archery. He took part in competitions, even representing Great Britain at the 1939 World Archery Championships in Oslo, Norway. His proficiency even earned Jack a few small movie roles where he portrayed archers in films such as The Thief of Baghdad and A Yank at Oxford.

The War Begins

Churchill enjoyed his time away from the military, but, as soon as World War II started, he joined up with the Manchester Regiment again and was deployed to France as part of the British Expeditionary Force (BEF).

This is where Churchill established his “colorful” persona and became known as “Mad Jack” or “Fighting Jack Churchill”, as he was also sometimes called. The extent of his “peculiarities”, shall we say, is still a matter of debate. Churchill himself was never one to tout his own accomplishments so most stories come from secondary sources. When you are dealing with a grand persona like that of “Mad Jack”, it is pretty easy to mix up myth with truth.

First off, there was the sword. Churchill, indeed, carried one with him because, in his own words, “any officer who goes into action without his sword is improperly dressed”. It is often said that Churchill favored the Scottish claymore. That is not strictly correct, as we are not talking about the famous, large, two-handed great sword. Instead, he wielded a smaller, one-handed version also called a claybeg to avoid confusion. The main differences between the two, apart from the size, were that the claybeg had a basket hilt instead of a cross hilt and was single-edged, unlike its larger counterpart. Churchill probably chose this weapon because it had been used for hundreds of years as the full-dress sword for officers of the Highland regiments.

 

“Mad Jack” did not get to use his sword in combat too often. Instead, he relied on it to signal and inspire the men, as can be evidenced by a photograph of a charge exercise in Inveraray.

Then there was the bow & arrows. Churchill certainly had the skill to use them effectively and often took them on patrols as they were a silent weapon. He is credited with making the last recorded kill with a bow & arrow in World War II when he took down a German soldier in 1940.

Finally, to complete the look, “Mad Jack” Churchill also carried a set of bagpipes. He would often play a few rousing renditions before battle to boost the men’s morale. The “March of the Cameron Men” was an old favorite.

Archery Practice at L’Epinette

Of course, all of Churchill’s eccentricities would not have been looked upon so fondly by his men if he wasn’t also a capable leader. When he joined the BEF, he was made second-in-command of the 4th Infantry Brigade with the 2nd Battalion. His unit was part of the Dyle Plan or Plan D, an effort by the French army and its allies to stop the German invasion through Belgium.

This did not turn out so well. The Allies kept losing battle after battle and had to retreat while German troops kept advancing westward. Eventually, this culminated in the Battle of Dunkirk but, before that, Churchill and his men had their own little moment of glory in the tiny French village of L’Epinette near Richebourg.

By this point, Churchill was in command of the unit because the original commander had been injured in battle. Their goal was to patrol the Maginot Line and secure the Allied retreat. On May 27, 1940, “Mad Jack” and two infantrymen were covering the rest of his unit when they saw a small group of five German soldiers approaching.

This was the infamous moment when Churchill took out his longbow and shot one of the enemies before his squadmates opened fire with the more traditional machine guns. The reason this is infamous, apart from the obvious, is because different sources give differing accounts. Some say the target was an officer, others that he was a soldier. Some say that Churchill hit him square in the heart while others claim the arrow went in the neck or the stomach.

Some sources even assert that the illustrious moment never happened at all and that “Mad Jack” himself later confessed that he had lost his bow earlier in the campaign.

Indeed, if it did happen, then hitting the German sergeant in the heart would make the most sense. Churchill was an elite-level archer. He would have the skill and forethought to go for the lethal shot on the most valuable target.

During the fight, Jack took a bullet in the shoulder, but was also rewarded with the military cross for his bravery. He then fought at Dunkirk where he sustained another minor injury.

Commandos at Vågsøy

Following the evacuation at Dunkirk, Churchill returned to England, but was already eager to get back to the fighting. In 1941, he joined the British Commandos and took part in Operation Archery, also known as the Måløy Raid. This was a British effort to launch a raid on German forces occupying the Norwegian island of Vågsøy. Churchill was dispatched with the No. 3 Commando battalion where he, once again, served as second-in-command.

The raid started in the early hours of December 27. Unbeknownst to the Allies, the German side also had an additional unit of light infantry mountain troops called Gebirgsjäger which was there on leave. This prolonged the battle and increased the number of casualties, but the British were still successful. They took about 100 prisoners, freed around 70 Norwegian resistance fighters, sunk 15,000 tons of shipping and obliterated strategically-significant docks, warehouses, and fish-oil plants. Moreover, if the Nazis wanted to maintain control of the area, they would have to redirect troops which could have been used elsewhere.

Churchill was in charge of one of the five parties that the Commandos were divided in. He led his men into action with another stirring rendition of “March of the Cameron Men”. Afterwards, he threw a grenade, took out his sword and charged into battle.

“Mad Jack” sustained an injury during this fight for which he received another military cross. The exact nature of the injury, however, remains something of a mystery. It is possible that Churchill was hurt by a British demolitions charge which detonated too close to him. In another version, the explosion caused the wall that Churchill was leaning against to crumble and fall on top of him.

In, perhaps, the most fitting story, during the British retreat, Jack “liberated” a bottle of wine to celebrate their success. Again, a charge went off in close proximity and smashed the bottle, sending a sharp shard of glass flying towards Churchill.

Jack returned to England triumphantly to recuperate, but he would soon experience tragedy. Six months later, his younger brother Robert who was a lieutenant with the Royal Navy was killed in action off the coast of Malta.

Strange Strategy in Salerno

The newly-promoted Lieutenant-Colonel Churchill was now in charge of the No. 2 Commando battalion which was assigned, in 1943, to take part in the Allied invasion of Italy.

The unit first landed in Sicily and then in Salerno. Both times, “Mad Jack” had his trademark sword on his waist, bow & arrows strapped around his chest and bagpipes under arm. It was an unusual sight but, then again, so were Churchill’s tactics which, nevertheless, proved effective.

Although Italy withdrew from the war, the Germans still had troops in the Bay of Salerno. The Allies initiated “Operation Avalanche” with the goal of eliminating the Nazi presence. Churchill’s commandos had the task of disabling the artillery fire on the western half of the bay.

During the final counterattack, “Mad Jack” came up with a counterintuitive strategy. He knew that the location made a surprise attack impossible. Instead, he went for the complete opposite. He organized his men in six parallel columns. They attacked in the middle of the night, repeatedly shouting “Commando” to avoid friendly fire. The battalion won the fight, completed its objectives and took 136 prisoners but, somehow, Churchill’s crowning moment came afterwards.

Precious Prize in Pigoletti

Jack excelled as a commando. He liked to carry out stealthy raids and counterattacks, leading small teams of hand-picked soldiers. One night in Italy, he went out accompanied by just a corporal, hoping they might run into a German or two.

They did. They spotted two figures smoking cigarettes in the darkness. They were Nazi soldiers, part of a group digging trenches in the nearby village of Pigoletti. Churchill and his corporal snuck up and subdued them, taking one each. “Mad Jack” then used his soldier as a human shield and entered the village with his sword drawn. He went from one small digging team to another, taking them by surprise and forcing them to surrender. In the end, he took 42 prisoners and made them march back to his camp. He had them carry their own mortars, bombs, and wounded to slow them down. Churchill even allowed the soldiers to keep their weapons, but he did make sure to remove all the rifle bolts. He was further rewarded with the Distinguished Service Order.

Disaster at Brač

Next up for Churchill was to take part in the Maclean Mission in 1944 in Yugoslavia. The country had quite an adept resistance force known as the Partisans which was led by Josip Broz Tito and was causing plenty of headaches for the Nazi war machine. The main purpose of the mission was to establish contact with the Partisans, find out all there was to know about them and help them fight the Germans however possible.

Image suggestion: Yugoslav Partisans

“Fighting Jack” and his commandos were tasked with conducting a raid on the island of Brač. Specifically, they wanted control of Vidova gora which, at 2,560 ft, is the highest peak not only on Brač, but the entire Adriatic Islands.

This mission did not turn out so well for Churchill. Once again, he led the charge by playing the bagpipes as his men ran into battle. However, the position was heavily fortified, including mines and artillery. Only a few men, Churchill included, managed to reach the objective and they were also incapacitated by shrapnel from mortar fire. The remaining survivors were taken prisoner.

Prisoner of War

What happened next was a nice moment of serendipity or karma, depending on what you believe. The man in charge of the POW camp was one Captain Hans Thornerr. He treated his prisoners well. As a show of gratitude, Churchill wrote him a “thank you” letter and even invited him to England, after the war, to have dinner with him and the wife. Thornerr kept the lette

r and it saved his life later when he was captured by Yugoslav forces and tried as a war criminal.

During his time as a prisoner, “Mad Jack” was moved around a lot and this was mostly because the Germans incorrectly thought he might be related to Winston Churchill. First, he was taken to Berlin for interrogation and, afterwards, was sent to the Sachsenhausen concentration camp in Oranienburg. He was held in Special Camp A which, as its name would imply, was reserved for prominent prisoners of war.

 

Churchill was not there for long because he started working on an escape plan almost as soon as he arrived. In September 1944, he and a small group of British officers dug a secret tunnel and made their way out. Among his co-escapees was Royal Air Force officer Bertram James. He took part in no less than 13 breakouts from Nazi POW camps during World War II. Just a few months prior to this, he was among the men who escaped from Stalag Luft III in the event immortalized in books and cinema as “The Great Escape”.

Back to Churchill, he sprained his ankle during the breakout at Sachsenhausen and, while he never complained about it, it did slow him down. He was recaptured near the town of Güstrow and, this time, was sent to another prisoner camp in Tyrol in Austria. Of course, Jack managed to escape again one night when the floodlights were not working. He made his way through the Alps into Italy where he was found and rescued by an American recon unit.

On the Way to Burma

His time spent as a prisoner did nothing to dull Churchill’s appetite for action. The Germans might have surrendered, but the Japanese were still waging war in the Pacific theater. He went off to fight them in Burma, but by the time he had reached India, the Americans dropped the atomic bombs on Hiroshima and Nagasaki and the Japanese forces had capitulated. Half-jokingly, “Mad Jack” said to one of his friends that “if it hadn’t been for those damned Yanks we could have kept the war going for another ten years”.

After the War

The Second World War might have ended, but there were plenty of other conflicts for a man like Jack Churchill. He took advantage of the more relaxed atmosphere to fulfill some of his less-important military goals. He took parachuting courses and joined the 5th Parachute Battalion, successfully executing his first jump on his 40th birthday. He also entertained his love of everything Scottish by transferring to the Seaforth Highlanders and becoming commander of a Scottish regiment.

The Hadassah Medical Convoy Massacre

Churchill’s last bloody moment in battle occurred in 1948, during the final months of the British Mandate of Palestine. He was deployed as an officer with the Highland Light Infantry, 1st Battalion, at a time when conflicts between Jewish and Arab forces were common in the region. 

On April 13, a convoy of medical staff and supplies escorted by members of the Jewish paramilitary organization Haganah was on its way to Hadassah Hospital on Mount Scopus in Jerusalem when it was ambushed by Arab fighters.

Churchill and his men were in the area and, although British orders were to stay out of the fight, he tried to evacuate members of the convoy in an APC. Possibly apocryphal, but the story goes that “Mad Jack” walked alone towards the ambush, smiling and carrying a blackthorn stick. His reasoning was that “people are less likely to shoot you if you smile at them”.

Meanwhile, his Highland Light Infantry provided cover fire, but one of the British soldiers was killed in the shootout. Churchill’s offer of help was turned down out of belief that Haganah forces will come to the rescue with a better coordinated effort. With one of his soldiers down and his assistance refused, Jack withdrew his men. Haganah forces did not arrive in time and two of the convoy trucks caught fire, killing 77 of the 79 people aboard.

Later on, Churchill assisted with the evacuation of Hadassah Hospital, bringing around 500 medical staff and patients to safety.

Life Out of the Spotlight

Churchill’s military career lasted until his retirement in 1959, but the last decade or so was significantly less exciting than the escapades that preceded it. He spent this time mostly as an instructor at various training facilities such as the Army Apprentices School in Chepstow and the Land/Air Warfare School in Queensland, Australia.

Churchill’s private life was in stark contrast to his military service as it was quiet and unassuming. In 1941, he married Rosamund Margaret Denny, granddaughter of Sir Archibald Denny, a famed naval architect. Together, they had two sons named Malcolm John Leslie Churchill and Rodney Alistair Gladstone Churchill.

During his years down under, Jack became a fan of surfing and continued his hobby when he returned to England. He had his final brush with fame in 1955 when he became the first person to ride the wave of the River Severn. Afterwards, he kept out of the limelight until he died in 1996 in Surrey, aged 89.

Churchill avoided the headlines for the last decades of his life, but he still retained traces of the rambunctious young man who treated the Second World War as one giant, thrilling adventure. He kept busy by refurbishing steamboats, making radio-controlled model ships and taking part in motorcycle speed trials.

When he worked in London, Churchill enjoyed freaking out fellow train passengers on his commute back home by calmly getting up, opening a window and throwing his briefcase outside. But there was always method to Jack’s madness. What the other riders did not know was that he was actually hurling the briefcase in his own back garden so he would not have to carry it from the train station.