Legendary Facts About “Mad” Jack Churchill, The Master Of Survival

September 16, 2024 | Alicia B.

Legendary Facts About “Mad” Jack Churchill, The Master Of Survival


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.

Jack Churchill in suitMirrorpix, Getty Images

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.

Colonial era mansionUnknown 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.

А soldier Jack Churchill in uniformCassowary 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. 

A soldier on motorbikeRijksmuseum, Picryl

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.

Bull Water BuffaloSteve 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.

Man with umbrellaE. 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.

Start of WW2Hans 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.

Lieutenant Colonel John Malcolm Thorpe Fleming Churchill in suitMirrorpix, Getty Images

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.

People playing bagpipesMarc Roberts, Flickr

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. 

Team at Archery ContestMissouri 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. 

The British ArmyImperial War Museums, Picryl

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.

The-British-Army in WW2Imperial War Museum, Picryl

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.

A soldier Jack Churchill in the waterWar Office, Wikimedia Commons

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”.

British troops line up on the beachUnknown 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.

Major Jack Churchill in uniformWar Office, Wikimedia Commons

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”.

Actor playing Jack ChurchillThe 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.

Bagpipe and  helmetThe 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.

The British Army in ItalyImperial War Museum, Picryl

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.

British soldiers from WW2 in London inspecting peopleKessell, Wikimedia Commons

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.

British soldiers on bicycles and cartsH. 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.

Actor playing Jack ChurchillThe 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.

British Commandos practicing assault tacticsBeadell, 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.

Gold wedding ringspixabay.com, Picryl 

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.

British CommandosEvans, 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.

Operation Archery in  NorwayNo. 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.

British Infantry in shipsMalindine 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.

Actor playing Jack ChurchillThe 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.

Actor playing Jack ChurchillThe 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.

Operation Pedestal in MaltaCook 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.

Planes after landingImperial War Museums, Picryl

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.

British army in uniformImperial War Museum, Picryl

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.

British Commandos waring uniformsLockeyear 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.

British soldiers in uniformUnknown 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.

British solders in uniformImperial 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.

Actor playing Jack ChurchillThe 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.

Winston Churchill in a black suitUnknown 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. 

Lieutenant Colonel John Malcolm Thorpe Fleming Churchill in suitMirrorpix, Getty Images

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.

Sachsenhausen concentration campMandyM, 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.

British prisoners of warImperial War Museums, Picryl

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.

Liberated prisoners in AustriaU.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. 

Two exhausted menU.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!"

Destructed Hiroshima and NagasakiFelton Davis, Flickr

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.

British soldier in uniformImperial War Museums, Picryl

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.

British solider on motorcycleImperial War Museums, Picryl

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. 

Seaforth Highlanders in uniformImperial War Museums, Picryl

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. 

Ship in the oceanNaval 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.

Train in the stationMarty Bernard, Flickr

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.

Flowers for funeralDigital museum, Picryl

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. 

Charles Darwin in black suitRakesh.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.

Actor playing Jack ChurchillThe Foley Suite, Mad Jack Pilot Episode


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