Mad Jack – A Real WW2 Mad Man

Here's the amazing story of 'Mad Jack Churchill', the man who fought with a bow and sword in WWII.

March 6, 2023・

19 min read

World War 2 was the most destructive conflict our world has ever seen; a brutal, global war fought with tanks, warplanes, machine guns and even bows and arrows! Jack Churchill was a British Army Officer who battled the German army in a totally unique way, charging through Europe with a bow and arrow, a sword and a set of bagpipes.

Of all the heroes that fought in World War 2, few were as weird or wonderful as Jack. So, let's put on our helmets, load up our rifles, and charge forth, into a tale of male-modeling, sword-fighting, perilous escapes and surfboarding, running through the legendary life of Mad Jack Churchill.

Early Days

Believe it or not, Mad Jack wasn’t born in a cloud of hellfire and air-raid sirens. He was born in 1906, growing up in a sleepy village called Dormansland in the English county of Surrey; a place that’s better known for country walks than warfare.

Despite this, Jack always wanted to be a soldier. After studying at King William’s College on the Isle of Man, a teenage Jack Churchill, no relation to Winston Churchill, was accepted into the prestigious Sandhurst Military Academy, allowing the wannabe war-hero to finally train to become an Officer.

Jack was a brilliant trainee, and despite having a few run ins with his superiors for being rebellious, Jack graduated from Sandhurst in 1926. He was soon assigned to the second battalion of the Manchester Regiment, the young Officer grabbing his bow, fastening his scabbard and shipping out to join his squad in the British Colony of Burma.

Jack’s unique weapon choice immediately started to turn heads, and when asked about his use of a sword, Churchill simply replied, ‘any man who goes into battle without his sword is not properly dressed.’

Likewise, he also knew how effective, silent, and accurate a bow could be in the right hands, leading him to favor it despite the availability of firearms. In Burma, Jack was itching to use his weapons, but unfortunately, there wasn’t much actual conflict to be found, and most of his duties involved further training.

Bored with the monotony of peacetime, Jack spent most of his service picking up new hobbies. He paid homage to his Scottish ancestors by learning the bagpipes from a Scottish soldier, and he also traveled across Asia on a motorbike.

Most road trips usually involve fast-food dinners and games of ‘I spy,’ but Jack’s were a bit more adventurous. The soldier biked over 1,500 miles from Rangoon to Poona in India, reportedly crashing into a water buffalo en-route.

Luckily, Jack’s bike wasn’t damaged, and he was able to continue his journey. During his travels, he had to repeatedly push his bike across tall, treacherous railway bridges, balancing his bike on the rails as he walked across the sleepers.

After 10 years of service, despite his exciting adventures in his off-time, Jack grew bored of military life, retiring from the army in 1936 to pursue, well, to put it modestly, some other interests. As you might’ve come to expect by now, these were far from standard fare.

Over the next few years, Jack acted in an American movie called ‘A Yank at Oxford,’ worked as a male model in Kenya, competed in a military bagpiping competition and represented Great Britain at the world archery championships in 1939. Talk about a Jack of all trades.

At this point, Jack’s résumé was pretty impressive, but all the posing, piping and arrow firing didn’t satisfy him, and the soldier longed to launch into battle and fight for his country. Of course, much to the horror of most of the world, Jack’s wish would very soon come true, leading to some of the most truly astounding events in Jack’s life. And things got really crazy!

World War 2 Hero

On the 1st of September 1939, the German army invaded Poland, an action that started the most destructive war in human history, World War 2. Both Britain and France were allied with Poland, and just two days later, they declared war on Germany.

As the British army started to move into Europe, a 33-year-old Jack jumped at the chance to rejoin the army, blowing the dust off his sword and shipping out to France with the British Expeditionary Force.

This time, Jack was jumping straight into the action. Assigned to the Manchester Regiment once again, Jack was stationed on the French-Belgian border in St Amand, and not long after he arrived in Europe, the German army initiated their Blitzkrieg to invade France.

The Blitzkrieg was a surprise attack tactic that used tanks, air support and a huge number of foot soldiers, charging through France from multiple angles to break through the allied line of defense and take the country in one swift motion.

As the blitzkrieg advanced, Jack and his regiment met the invaders with force, conducting fierce ambushes and raids on the advancing troops, attempting to slow down the attack. They say that you should never bring a knife to a gunfight, so Jack brought a sword instead, reportedly leading these attacks by raising his sword to the sky and charging into battle.

He also spent time riding his motorbike through the battlefield, reportedly often being seen biking around the war-torn French countryside with his bow strapped to his back.

As you can imagine, stories soon started to circulate about the sword-wielding, bagpipe playing soldier who was terrorizing German forces. The most famous of these stories comes from May 1940, after Jack and his men were forced to retreat from the incoming Blitzkrieg, falling back to the French village of l’Epinette.

On the 27th of May, the advancing Germans reached the village, and Jack and his men were forced to make a final stand. Shot and surrounded, an injured Jack reportedly battled against the Germans with two duel-wielded submachine guns. As if he wasn’t already badass enough.

He then climbed a tower, switched to his bow and shot a high-ranking German officer on the ground, the shot becoming the last recorded case in history of a British soldier killing an enemy with a bow and arrow.

Unfortunately, though, some legends are just legends, and Mad Jack later said that he didn’t even have his bow at L’Epinette, losing it earlier on in the war. That being said, given that Jack is reported to have successfully defeated enemies elsewhere during the war using his bow, he still holds the title, even if the exact scenario is often misremembered.

Regardless, Jack’s real actions at L’Epinette were still heroic, and were pretty close to the rapidly-spreading tales of his actions, save for the bow, of course. The L’Epinette skirmish still left Jack bruised, bloody, and shot, with a bullet embedded in his shoulder.

And however much of the stories that were spreading across Europe about Jack were true, the German army are thought to have caught wind of them, Jack’s name striking fear into the hearts of the Ally's enemies.

Despite their best efforts, Jack’s squad wasn’t able to slow down the Blitzkrieg. The German Army eventually advanced past them, cutting them off from their allies and placing them in enemy territory, in German-controlled Northern France.

Despite being trapped behind enemy lines and surrounded by the might of the German army, Jack refused to surrender. He waited until the dead of night before sneaking his entire company through the German lines, leading his regiment out of hostile territory before heading through Estaires, and up to Poperinge, Belgium.

At this point, the Blitzkrieg had totally overwhelmed France, and Germany was on the brink of fully seizing control of Belgium too. The British army had hastily fallen back, leaving Jack and the rest of the British Expeditionary Force, or BEF, with no choice but to make their way to the beaches of Dunkirk.

They’d been ordered to retreat there for escape across the channel to Britain, but once they made it to Dunkirk, it was clear it wouldn’t be plain sailing. Jack, and around 350,000 other British soldiers were effectively stranded on the beach until the 30th of May.

Finally, Jack’s Manchester Regiment was rescued by a patchwork fleet of civilian lifeboats, yachts, and fishing vessels. Many of these boats were sailed by brave civilians, thousands of ordinary people sailing across the English Channel to save their soldiers from the clutches of the advancing German army.

Once the BEF were safely rescued and sailed back home, both the British public and government believed that a German invasion of Britain was imminent. However, this attack never came, the Germans opting not to invade Britain due to the strength of the British Royal Navy and their failure to defeat the British Royal Air Force and achieve air superiority.

Instead, Germany turned its focus eastward, to eastern Europe and ultimately Russia, meaning the war was far from over, but what of our boy Mad Jack Churchill?

Well, the British Expeditionary Force were safe and sound back in Britain, and most of the soldiers were happy to be back home. However, all the tea and crumpets in England couldn’t cheer up Mad Jack. He hated the fact that the BEF had been forced to retreat, and the officer couldn’t wait to get back into Europe and rejoin the fight.

Commandos Operations

While in England, he caught wind of a new volunteer unit called the Commandos, a special forces unit so fearsome and well-trained that they later inspired the creation of the British SAS, and the French Naval Commandos and the United States 1sr Ranger Battalion.

It was the perfect place for a soldier like Jack, and after a grueling period of special forces training, he was ready to return to battle, joining the Number 3 Commandos as the second in command. For his first mission, Mad Jack was heading up North, taking part in an amphibious assault on a German base in Vågsøy, Norway.

The mission, ironically, was called Operation Archery, and our favorite archer was on the very first landing craft, playing a roaring rendition of the traditional Scottish song, ‘March of the Cameron Men’ on the bagpipes as the Commandos charged towards the beach.

When the landing craft hit the sand, Churchill jumped forward with his bagpipes, before throwing a grenade and charging into battle with his sword held high.

The men followed Churchill’s charge, and after an intense fight, they took Vågsøy, destroying ammunition stores, and capturing several German troops. Pleased with the victory, Jack decided to celebrate by blaring the bagpipes once again, his men dancing along to the music, and filming Jack on a very early form of handheld video camera.

Jack was later awarded the Military Cross and Bar for his fierce charge in Vågsøy and previous actions in France. The war hero finally had a taste of victory, and he soon came back for more, returning to Europe in 1943, this time as the leader of the Number 2 Commandos. Jack and his squad took part in the British invasion of Italy, tasked with overpowering and destroying a German artillery gun in a small town called Piegolelle.

The 11 Commandos approached the town at night, and it soon became clear that they were greatly outnumbered, the village being heavily defended by German troops. Usually, an outnumbered Commando unit would attempt a stealth attack, but Piegolelle was also surrounded by thick undergrowth and grape vines, the difficult traversal and rustling of the plants ruling out any chance of a silent approach.

Thankfully, Jack was never a big fan of stealth, and the Commando came up with a different plan, deciding to attack the village as suddenly and as loudly as possible. You might say it was a small-scale Blitzkrieg of their own!

Jack organized his troops into six parallel columns surrounding the village, telling them to yell ‘COMMANDO’ at the top of their lungs before charging, screaming at the enemy as they attacked.

The yelling minimized the risk of the Commandos accidentally shooting each other in the dark undergrowth, as they knew where their squad mates were at all times. It also confused the Germans, the Commandos yells reportedly making them believe that they were being attacked by a giant army.

As the screams and gunfire fell on the Germans from all sides, they didn’t know which way to turn, allowing the Commandos to enter the village and start to overpower the German defenses.

On usual raids, all this screaming would’ve included a backing track of Jack’s bagpipes, however, as the Number 2 Commandos fought against the defending Germans, Jack took a step back from the action, grabbing one of his corporals and setting off into the night, attempting to sneak behind the German line of defense amid all the chaos.

As they flanked Piegolelle, Jack and the corporal soon found a patrolling guard. The pair waited before bursting out of the shadows, holding the guard at sword-point and taking him prisoner. They then took the captured guard to the next sentry post, ordering him to call out to his fellow German soldiers.

As the soldiers came to greet their friend, Jack and the Corporal held them up at sword-point, taking them prisoner too. They repeated this process at every sentry post, and by the end of the assault, the duo had taken 42 prisoners and an entire mortar crew, all with Jack’s sword, the Corporal’s revolver, and the impressive power of catching your enemy off-guard.

Happy with their haul, Jack and the corporal returned to the other Commandos, discovering that they’d successfully overpowered the Germans, taking 136 prisoners, and destroying the threatening artillery gun.

Once again, Jack’s heroism had resulted in victory, and the soldier received the Distinguished Service Order for his bravery at Piegolelle, one of the highest military decorations a British soldier can receive.

Jack and the Number 2 Commandos had helped the allies to take the toe of Italy, but they weren’t done yet, and their next mission would prove the most shocking of all. Churchill led his squad up through Europe and into Yugoslavia. Here, the Commandos were tasked with raiding the Yugoslavian Island of Brač, helping an army of resistance fighters overthrow the occupying Germans.

In May 1944, Jack and two Commando units landed at Brač, attempting to gain access to some German gun emplacements. As the Allies battled their way through the island, only 6 of the Commandos actually made it to their objective.

Once in the vicinity, the surviving commandos were hit by a mortar strike, the explosion killing and wounding the entire team, apart from Churchill. The indestructible Jack was left relatively unharmed, but he knew that he was outnumbered, and without his men to fight alongside him, he stood no chance of defeating the advancing troops.

Instead, Jack pulled out his bagpipes and played a sorrowful rendition of Scottish folk song ‘Will Ye No Come Back Again,’ mourning his fallen men. The German army clearly weren’t a fan of bagpipes, because an enemy soldier soon threw a grenade at Jack, the explosion knocking him out cold. That’s right, even a grenade couldn’t kill Jack, it just made him real sleepy.

Prisoner Of War

When Jack woke up, he was a prisoner of war, captured by the Germans and taken behind enemy lines. At the time, Germany had implemented the ‘Commando Order,’ stating that all captured Commandos should be killed immediately, without trial. This could’ve been the end for old Jack if it wasn’t for his surname.

It turned out, the Germans mistakenly believed that Jack was a relative of Winston Churchill, Britain’s prime minister. Jack was escorted to Berlin for interrogation, and in an unexpected twist, due to his wrongly assumed high political status, was treated extremely well.

The German army treated him so well, in fact, that Jack famously wrote the German Garrison leader a note, inviting him to a family dinner if he ever found himself in Britain after the war. After being interrogated, Jack was transferred to a special VIP section of Sachsenhausen concentration camp in Oranienburg.

Jack’s wrongly assumed famous family meant that he survived the camp, but don’t be mistaken, his pleasant treatment was well and truly over. Jack was starved and beaten at Sachsenhausen, the guards subjecting the POW’s to inhumane conditions.

At Sachsenhausen, any day could be your last, so Jack started planning his escape right away, teaming up with three Royal Air Force officers to dig a tunnel out of the camp. After months of digging, the tunnel was complete, and Churchill and the RAF officers crawled their way to freedom before attempting to walk 110 miles to the Baltic coast.

The soldiers almost made it, but just before they saw the sea, they were picked up by the Germans, taken back to Sachsenhausen before being transferred to another concentration camp in Niederdorf, Austria.

Once again, Jack was starved and beaten at the camp, but the guards never broke Jack’s spirit, and it wasn’t long before Churchill attempted to escape again. On a night in April 1945, the camp’s lighting system failed, plunging the area into total darkness. Jack quickly sprang into action, disappearing into the shadows, climbing through the fence and escaping the camp.

Jack decided to travel on foot, intending to walk 150 miles to Verona, foraging for vegetables as he traveled south. After eight days of walking, an injured and weary Churchill stumbled onto a country road, walking straight into the path of a column of Armored vehicles.

Jack feared the worst and prepared for capture before realizing that all of the vehicles proudly displayed the white star of the United States Army! Jack quickly hobbled over to the Americans and flagged them down, excitedly explaining that he was a British officer, and that he wanted to join them in battle.

The G.I’s however, just frowned, explaining that the Germans had already surrendered, and the war in Europe was over. Instead of being happy at an allied victory, Jack was incredibly disappointed, saddened that he’d missed a year of the war as a POW.

Hungry For Conflict

The Americans explained that there was more conflict to be found in the East against the Japanese Axis forces. So, as soon as Jack had recovered from his time in the camp, he hopped on a plane and traveled to Burma, excited by the prospect of fighting out in the Pacific.

However, as Jack flew across the world, an American plane started a journey of its own. This plane was to prove hugely significant, because it was heading straight for Hiroshima. By the time Jack arrived at his destination, the USA had dropped 2 Nuclear Bombs on Japan, the weapons of mass destruction decimating Hiroshima and Nagasaki, ending the second world war for good.

Japan had surrendered, and the surviving troops of World War 2 realized that they could finally go home, hurriedly traveling back across Asia and Europe to be reunited with their families. Jack was less excited, quoted saying ‘if it wasn’t for those damn Yanks, we could have kept the war going for another 10 years!’

As amusing as that comment is, it does raise a point about Jack that’s a little hard to ignore. At a certain point, bravery borders on insanity. And it soon became apparent that Jack’s childhood ambition of becoming a soldier, had been overshadowed by his wish to die as one, with Churchill’s family later explaining that he’d fully intended to die in battle and be buried in the Union Jack.

This became even more clear when Jack decided to stay in the Army after World War 2. He qualified as a parachutist at 40 years old, hoping to fight, and potentially die, in another battle.

Jack briefly fought in British-occupied Palestine, taking part in the conflict that resulted in the establishing of Israel. Here he famously evacuated over 700 doctors, students and patients from the Hadassah hospital, after an ambush by forces from the Arab Higher Committee.

After all this conflict, Jack was stationed in Australia, serving as an instructor at the land-air warfare school. While down-under, Churchill added another activity to his growing list of hobbies: surfing.

The soldier became a passionate surfer, and when he returned to England he spread his love of shredding, catching waves on a surfboard that he designed himself. If only he’d had the surfboard while storming the beaches of France in WW2! That would’ve been insanely cool.

Either way, the soldier had traded war for waves, and after working at an army desk job for a few years, he clearly gave up on his dream of dying in battle, deciding to retire from the army in 1959.

Retirement and Legacy

Now, when most people retire, they move to Florida and get a membership at the local golf course. But this is Mad Jack Churchill we’re talking about, and the veteran’s eccentricity continued well after leaving the army.

The story goes, that every time Jack would take the train, he’d startle the train guards and passengers by opening the train’s window, and launching his briefcase outside as they approached his station.

People started to think that the famous ‘Mad’ Jack Churchill had actually lost his mind during the war. However, Jack later explained that he lived by the train tracks, and he was throwing the case directly into his own back garden, saving him from carrying it home from the station.

Even in retirement, Jack’s weird and wonderful life continued to entertain those around him, and the officer’s antics have made him a legend. Figurines and comics have been made in the officer’s honor, and Jack was named one of the finest explorers and adventurers of all time in a 2014 book written by the Royal Norwegian Explorers Club.

Although Mad Jack never got the chance to die in battle, he lived out the rest of his life in Surrey, living to the ripe old age of 89, before passing away peacefully at home in 1996. The soldier may have died, but his legacy lives on.

Jack’s story teaches us that, whether you’re rushing into battle with a sword, building your own surfboard, or throwing your suitcase out of your train’s window, life’s more interesting when you’re a little bit mad.

If you were amazed at Jack Churchill's story, you might want to read about the greatest warriors of all time and this article about the worst roles you could be assigned in WW2! Thanks for reading!