Millions fought in WWII, but there was only one Jack Churchill. What did he do? What didn’t he do?
1. He Was A Mad Lad
Old black-and-white photos fail to capture how colorful Jack Churchill was. He was the legendary British officer who defeated armed enemies with a bow, sword, and bagpipes. He chased any kind of danger and adventure—and the only thing he refused to do was die. He earned his nickname “Mad Jack” ten times over…and then some.
2. He Was Born To Serve
Churchill was born in British Ceylon (now Sri Lanka) in 1906. He came from a family of civil servants. His father’s work for the British Empire took the family all over the world. It was a no-brainer for Churchill and his two younger brothers to join the family tradition. However, following in these footsteps would eventually lead to tragedy for some members of the Churchill family.
Unknown Author, Wikimedia Commons
3. He Craved Action
Churchill loved adventure, but it didn’t always love him back. The 20-year-old joined the army after graduating from a military academy. He found himself in Burma (now Myanmar). But he also found there wasn’t much to do. Therefore, he became interested in riding motorcycles and playing the bagpipes.
Since he wasn’t getting his adrenaline fix at work, Churchill found it elsewhere.
Cassowary Colorizations, Flickr
4. He Was Always An Adrenaline Junkie
Jack Churchill didn’t just attract danger, he chased it. When they needed him to travel from Myanmar to India for a class, most people took a ship. But that was too boring and safe for him. He decided to ride his motorcycle for the entire journey—all 1,500 miles of it. He learned the hard way that everyone else took the ship for good reason.
5. He Loved Taking Risks
There’s running into danger, and then there’s creating it—but unusual perils and obstacles never phased Jack. This included coming face to face with a massive and aggressive water buffalo. He even made it back in time to fight in a rebellion. Churchill didn’t just serve his country, he had fun doing it.
But even these adventures couldn’t keep this free spirit in the army forever.
Steve Garvie, CC BY-SA 2.0, Wikimedia Commons
6. He Broke The Rules
Churchill always managed to get into the wrong kind of trouble. One remarkable example was when he used an umbrella during a parade, which was a major no-no in the army. When one of his superiors demanded to know why he had committed this sin, he had the most cheeky response: “because it’s raining, sir”.
Other things like studying for the wrong promotion exam didn’t help. Churchill knew he could kiss any promotion goodbye. However, in the end, he had other plans for his future.
E. Chomette, and J. Pickaert, Wikimedia Commons
7. He Called It Quits
After a decade of service, Churchill resigned from the army. He didn’t give an explanation, but there were plenty of potential reasons. These ranged from a lack of promotions to simple boredom. But as WWII brewed in the background, it was only a matter of time before his country would need him again. For now, 30-year-old Churchill had to buckle down and figure his life out.
Hans Sönnke, Wikimedia Commons
8. He Experimented
Though Churchill only spent three years out of the army, he lived 300 lives. Throughout his lifetime, his occupations included: newspaper editor, model, entertainer, actor, professional archer, and competitive bagpipe player. Even wilder? This wasn’t even a case of jack of all trades, master of none.
9. He Had Scandalous Talents
Bagpipes: What began as a hobby turned into a full-blown obsession. Churchill, wanting to put his skills to the ultimate test, entered a competition. Churchill found himself in a sea of Scotsmen. His second-place finish caused a scandal. An Englishman playing the bagpipes better than so many Scotsmen? Unheard of. But this wasn't all.
10. He Was A World Class Athlete
Next, Churchill wanted to put his archery skills to the test. A year later, he represented Britain at the World Archery Championship. He placed 26th out of 37 men. Just a few months later, Germany invaded Poland. Playtime was over. Now Churchill had to represent his country in a bigger and deadlier competition. The prize was survival.
Missouri History Museum, Picryl
11. He Entered WWII
Churchill rejoined the Manchester Regiment and was ready to go. He quipped, “I was back in my red coat; the country having got into a jam in my absence”. But his first gig, between late 1939 to early 1940, was a let-down. Patrolling a quiet part of France wasn’t what he had in mind. He hunted down opportunities so that he could be at the center of the action.
12. He Loved Fighting
The more the conflict spread, the more Churchill was in his element. By the Battle of France, he was in the regiment's second battalion, and climbing the ranks. Churchill came alive during raids and counterattacks. However, he wasn’t satisfied with being any old leader. He wanted to be in the thick of it.
Churchill stood out not only for what he did on the battlefield, but what he did it with.
13. He Used Unusual Weapons
WWII was a modern conflict with shiny new technology, but Churchill might’ve missed the memo. Instead, he opted for a sword, a longbow, and bagpipes. When asked about it, Churchill reportedly said, “In my opinion, sir, any officer who goes into action without his sword is improperly dressed”.
He soon proved that these decisions weren't only for the sake of appearances—and made history books.
14. He Was Reassuring
Churchill was as controversial as he was courageous. But he had plenty of supporters. One wrote, “One of the most reassuring sights of the embarkation [from Dunkirk] was the sight of Captain Churchill passing down the beach with his bows and arrows. His high example and his great work … were a great help to the 4th Infantry Brigade”.
Unknown author, Wikimedia Commons
15. He Has An Unbreakable Record
Records are meant to be broken—but this one may never be. In 1940, as the Germans approached, Churchill declared, “I will shoot that first German with an arrow”. He honored his word. Almost a century later, Churchill still holds the record for the last longbow kill in battle. But Churchill’s attitude towards his heroics was shocking.
16. He Was Nonchalant
Churchill didn’t show off even though he had good reason to. An old friend recalled running into him after a battle. Churchill couldn’t have looked cooler with his motorcycle, longbow, and a hat he’d taken from a slain enemy. Yet, he only asked this friend for a strong drink. When asked about the blood on his ear, Churchill simply replied, “German machine gun”.
The Foley Suite, Mad Jack Pilot Episode
17. He Made An Entrance
Many sounds are normal during WWII battles: shots going off, screaming, and explosions. Bagpipes weren’t supposed to be one of them. But if you were with Churchill, you added this instrument to your list. Churchill played bagpipes for many reasons. These included hyping his men up before battle, as well as communication during battles. It also included lowering the morale of enemies.
Everything about Churchill made him famous.
The Foley Suite, Mad Jack Pilot Episode
18. He Had A Big Reputation
Churchill’s reputation soon preceded him. He was nicknamed “Mad Jack” and “Fighting Jack”. The longer WWII lasted, the more Churchill earned these titles even more. But for some people, “Mad Jack” wasn’t just a fun and quirky nickname. It was truly how they perceived Churchill. This could’ve been one of the secrets behind his survival against all the odds.
19. He Weirded People Out
Churchill’s survival might not only be down to bravery and skill. The other side’s stories of Mad Jack show that it was more complicated than that. Germans who had witnessed his fighting made startling confessions. The Germans admitted they didn’t always fire at Churchill because they thought he was insane.
“Mad Jack” turned out to be as divisive as WWII itself.
20. He Was Stranded
There’s only so much one man with a sword, a bow, and bagpipes can do. After the Battle of France, Allied forces found themselves surrounded and cut off. Hundreds of thousands were rescued during the Dunkirk evacuation. Churchill was among them. Rumor has it he arrived at the beaches by bicycle. On the way home, Churchill received some life-changing news.
H. D. Girdwood, Wikimedia Commons
21. He Had A New Goal
Churchill learned that a new organization, the Commandos, was being forced. The idea was so new that there was little known about it. But Churchill was an easy and simple man. The promise of action and adventure was good enough for him. He was all in. He could figure out the details later.
The Foley Suite, Mad Jack Pilot Episode
22. He Was In His Element
Turns out, the details were even better. The Commandos were special forces that focused on raids against German-occupied Europe. High risk, high reward. It was a match made in heaven. Churchill rushed off to train in Scotland. There, he took to the Commando way like a duck to water. He lived and breathed it. Then Scotland threw a curveball at him.
Beadell, S J (Lt), Wikimedia Commons
23. He Met The One
Churchill was only looking to become a Commando—he wasn’t looking for romance. But it found him anyway. Churchill didn’t just fall in love with being a Commando, he fell in love with a woman. Enter: Rosamund Denny. She was a nurse at a nearby hospital. She also happened to be the daughter of a Scottish shipbuilding baronet.
24. He Married
Churchill left Scotland as a Commando and a husband. He and Denny married in the spring of 1941. But they never got to fully enjoy their newlywed bliss: Jack was still training and WWII loomed over them. Churchill’s risk-taking might’ve sunk other marriages faster than a German submarine—but the Churchills remained happy and in love... even when the Commandos faced the terrifying unknown.
Evans, J L (Capt), Wikimedia Commons
25. He Was Tested
On December 27, 1941, Churchill and the Commandos embarked on their first mission. Operation Archery was a raid on German holdings on a Norwegian island. Up until now, they had been stuck in training. This was the first real test of the Commandos and Churchill’s leadership. The mission was pass or fail—but in the end, they passed with flying colors.
No. 114 Squadron RAF, Wikimedia Commons
26. He Pulled It Off
The Commandos did more than fight and win a battle: They seized 15,000 tonnes of supplies. This included things required to make explosives. They obliterated warehouses and docks. Operation Archery even tricked Germany into diverting 30,000 forces to Norway, instead of where it was actually needed. But right before Churchill left victorious, disaster struck.
Malindine E G (Lt), Wikimedia Commons
27. He Had A Freak Accident
Life comes at you fast. One second, Churchill was enjoying victory and a bottle. In the blink of an eye, a random explosion smashed the glass and sent shards into his face. Worst of all, the Germans weren’t even responsible. According to one version of the story, the culprit was one of Churchill’s men—and a demolition specialist at that. Oops. Churchill’s reaction was shocking.
The Foley Suite, Mad Jack Pilot Episode
28. He Laughed It Off
Most people would react with fury. But as we’ve established, Churchill wasn’t like most people. Instead, he found humor in the mishap. He even joked about the scar. Churchill later told people, “I had to touch it up from time to time with Rosamund’s lipstick to keep the wounded hero story going”. But not all Churchill men were so lucky.
The Foley Suite, Mad Jack Pilot Episode
29. He Experienced Tragedy
Service ran in the Churchill family, but endless luck did not. Jack Churchill left his brothers, Tom and Buster, with big shoes to fill.
Tom was in the Manchester Regiment with Churchill. He didn’t just make it out, he ascended to Major General. But tragically, Buster, who served in the Royal Navy’s Fleet Air Arm, wasn’t as fortunate. He met his tragic end during Operation Pedestal in Malta.
Cook H E (Lt), Wikimedia Commons
30. He Amazed People
Churchill had countless accomplishments, but this may be his greatest. In 1943, Churchill and his Commandos took part in the landings at Salerno. They had to capture a crucial German holding in what could be their toughest mission so far. The Commandos didn't have the odds in their favor. But what they did have was Churchill's interesting tactics—and they made all the difference.
31. He Was Strategic
There was a method to Churchill’s madness—and his most impressive move yet occurred during the invasion of Piegoletti. Since the underbrush made a silent attack impossible, even at night, he went in big and loud. Churchill instructed his men to run into town screaming “commando”.
Since it was pitch black, this made sure the Commandos didn’t accidentally shoot each other. It also disoriented the Germans, who were surrounded by darkness and screeching. But Churchill wasn’t with them.
32. He Was Fearless
Turns out, Churchill charged in first with his old-fashioned tools and a corporal. The Commandos didn’t just complete their mission—they did extra credit and captured 136 prisoners. Churchill was responsible for 42 of these captures. He followed this up with more successful missions, but his end loomed near. A disaster headed his way.
Lockeyear W T (Lt), Wikimedia Commons
33. He Ran Out Of Luck
Nothing lasts forever, including Churchill’s luck. In May 1944, the Commandos received a mission to capture Brač. It was an island in Yugoslavia (now Croatia). This was going to be an uphill battle. Literally. Their target was actually on a hill. The raid was never going to be easy, but it was a disaster even by those standards.
Unknown author, Wikimedia Commons
34. He Was The Last Man Standing
Churchill made a horrific discovery when he stepped foot onto the hill. Barely five Commandos made it up, and most were already wounded. In no time, he was the last man standing. Churchill confessed, “I was distressed”. He was outnumbered and outgunned. He knew it was over. But Churchill couldn’t resist doing something ridiculous.
Imperial War Museums, GetArchive
35. He Was Defiant
Expect the unexpected from Churchill. He played “Will ye no come back again” on his bagpipes until a grenade knocked him out. Churchill woke up to Germans poking and prodding him. They were checking if he was still alive. But the Germans had orders to execute commandos. No matter what. This looked like the end of Jack Churchill.
The Foley Suite, Mad Jack Pilot Episode
36. He Was Saved
In the nick of time, Churchill’s luck returned to him. A German captain took pity on him and spared his life. Instead, Churchill was taken as a prisoner. Based on his last name, the Germans thought he was related to Winston Churchill. They were disappointed to learn the two men weren’t even distant cousins. They were also disappointed to learn their new prisoner was a handful.
Unknown author, Wikimedia Commons
37. He Was A Rebel
Chaos ensued when a random fire broke out on a plane—a German aircraft that happened to transport Churchill. This was no coincidence. When Churchill left the plane, he left a departing gift of a match on a pile of papers. He played innocent with his furious captors. Churchill promised he was just smoking and reading the paper. But in all honestly, he was just getting started.
38. He Was Imprisoned
“Fighting Jack's" fighting spirit was alive and well. Even after the Germans shuttled him around Sarajevo, Berlin, and solitary confinement. Even after they decided on a final destination. Even if that was Sachsenhausen, a notorious concentration camp.
Through all this, Churchill didn’t lose hope. In September 1944, he and fellow British officer Bertram Arthur James figured it out.
MandyM, CC BY-SA 3.0 , Wikimedia Commons
39. He Escaped
After crawling beneath wire and into the unused drain, they ran for their lives. Their plan was to walk 125 miles to the Baltic Sea. For days, the Brits walked through woods, pilfered vegetables, and hitched train rides. The pair faced the elements and the massive search party hunting them down. They were so close. But the Germans caught them only a few miles from salvation.
40. He Was Imprisoned Again
Different camp, same man. The Germans could change his camp, but they couldn’t change Churchill. In Austria, the prisoner remained determined and fearless. He hoarded a rusty can, onions, and patience. All he needed was one chance. In 1945, the camp went through a blackout. Jackpot. Churchill disappeared into the darkness.
U.S. National Archives and Records Administration, Picryl
41. He Escaped Again
Second time’s the charm? This time, Churchill soloed the 150-mile trek. He found sustenance by collecting vegetables from local gardens, and would prepare his meals in his tin can. He kept going even after spraining his ankle. One day, he spotted American armored vehicles and flagged them down.
These Americans looked at the shabby man who could barely walk or talk. He claimed to be a British colonel. They believed him.
U.S. National Archives and Records Administration, Picryl
42. He Had To Fight
Churchill may have survived the impossible, but he definitely didn't feel satisfied. WWII in Europe was almost over. Churchill had missed out on the action, the opportunities, and the promotions. The battles still raged in Asia, so he rushed to Burma for a last hurrah. But it ended before he even arrived. The horrific destruction of Hiroshima and Nagasaki had already come to pass.
He lamented, "If it wasn't for those darn Yanks, we could have kept the war going another 10 years!"
43. He Was Too Risky
To make matters worse, Churchill missing the action was probably preventable. His son Malcolm admitted, “He shouldn't have been captured as much as he was a colonel and shouldn't have been in the front lines. However he was a fighting soldier and he didn't care much for being at the back filling out paperwork”.
Some people aren’t built for peace, and Churchill was one of them.
44. He Was Nonstop
Once again, Churchill had to figure out his life outside the army. This time, he was 39 years old, a husband, a father of two, and a decorated veteran. But his wild adventures included: paratrooper, actor, army instructor, surfer, army administrator, motorcyclist, and steamboat refurbisher. He even managed to be the hero one last time.
45. He Saved More Lives
WWII may have come to an end, but Churchill wasn't finished yet. He transferred to the Seaforth Highlanders and ended up in the Middle East. Plenty of conflict, danger, and blood awaited him there. Churchill even evacuated 700 people from Jerusalem. Turns out, he managed to get his last hurrah. But even Churchill’s fire could only burn for so long.
46. He Calmed Down
Churchill and retirement seemed like a match made in misery. But he never stopped surprising people. By 53, he mellowed out enough to enjoy a slower life. He spent time with Rosamund, raised his family, sailed ships, and played with remote control boats. However, Churchill still couldn’t resist a little mischief in his middle age.
Naval History and Heritage Command, Picryl
47. He Pranked People
Even in his regular life, Churchill knew how to pull off an amusing stunt. For instance, passengers on one train startled when he flung his briefcase out the window. He did it out of the blue like a lunatic. But once again, there was a method to Churchill’s madness.
He wasn’t throwing his bag out into the unknown. Turns out, Churchill aimed and threw the bag as the train passed his garden. Churchill didn’t have to carry his briefcase home and he got to mess with people.
48. He Had A Surprising End
Churchill going out too soon in a blaze of glory wouldn’t have been surprising. But he loved life, and it loved him back. He passed at 89 years old, well past the life expectancy at the time. He lived one heck of a life. One obituary claimed it was impossible to write a fictional character like Jack Churchill because it was too unbelievable. They were right.
49. He’s One of the Greats
The Royal Explorers Club ranked Churchill as one of the greatest adventurers and explorers of all time. He’s in good company with greats like Charles Darwin. Espen Lazarus, the club’s co-founder declared, “I would rate Jack Churchill as one of, if not the most, inspirational and impressive people we have researched in relation to the book”. But not everyone agrees.
Rakesh.infosys, CC BY-SA 4.0, Wikimedia Commons
50. He Has Skeptics
Historian Mike Loades confesses he isn’t “entirely sure this is the clear-cut, honorable boy's adventure story it first appears to be”. He doubts Churchill’s sword and bow were better than conventional tools. Loades sees them as liabilities in many situations. He can't help but feel that Churchill was showboating more than anything else.
Other accuse Churchill of being a bad and dangerous leader. Jack Churchill was a great man, but for some, the jury is still out on whether he was a good man.
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