10 Of The Strangest Moments In The History Of War

War is supposed to be grim, calculated, and terrifying. Yet if you spend enough time digging through military history, you start tripping over stories that sound less like a war diary and more like outtakes from a dark comedy.
Cavalry charging a frozen navy, admirals turning battleships into bumper cars, and commanders fighting for days against… a rock under the ocean.

This roundup of ten of the strangest moments in the history of war pulls together verified (or at least widely reported) incidents from different eras. Some are well documented, others are debated by historians, but all of them show how absurd things can get once humans mix guns, ego, and chaos.

Why Strange War Stories Matter

It’s easy to think of war only in terms of strategy and heroism: decisive battles, brilliant generals, and tragic losses. But the weird episodes – the blunders, flukes, and freak coincidences – remind us that war is also a very human mess.
Miscommunication, superstition, weather, individual stupidity, and sheer luck can shape history just as much as carefully drawn battle plans.

These strange moments don’t make war any less deadly, but they do peel back the myth of perfect control. They show us generals who miscalculate, soldiers who improvise, and ordinary people caught up in events that make absolutely no sense when you describe them over dinner.

10 Of The Strangest Moments In The History Of War

10. When French Cavalry Captured a Frozen Dutch Fleet

Naval battles are usually a matter of ships, cannons, and maybe the odd boarding action. They are almost never won by horses. Almost.

In January 1795, during the French Revolutionary Wars, a Dutch fleet became trapped in ice near Den Helder in the Netherlands. A brutal winter froze the water solid enough that a French hussar regiment and supporting infantry were able to ride and march out across the ice toward the immobilized ships. The Dutch warships, unable to maneuver or bring their full firepower to bear, were essentially sitting ducks locked into a giant frozen parking lot.

The French commander negotiated the surrender of the entire fleet, reportedly without a single casualty. Cavalry had effectively “captured” a navy – something so rare that military historians still point to it as one of the most unique feats in naval history.

It’s a great reminder that in war, climate can be as decisive as any admiral. The Dutch lost a fleet not because of poor seamanship, but because the weather turned their proud ships into very expensive ice sculptures.

9. L. Ron Hubbard’s 68-Hour Battle With an Imaginary Submarine

Before he founded Scientology, L. Ron Hubbard was a U.S. Navy officer in World War II, commanding the submarine chaser USS PC-815 off the Pacific coast. In May 1943, Hubbard became convinced his ship had picked up a Japanese submarine on sonar off Oregon. He launched into a full anti-submarine operation, dropping depth charges, maneuvering aggressively, and calling in reinforcements.

For roughly 68 hours, PC-815 and several other U.S. vessels hunted this “enemy.” They dropped dozens of depth charges, deployed blimps and patrol craft, and burned a serious amount of fuel – all while never seeing a periscope, oil slick, or debris.

When naval authorities reviewed the action, they concluded there was no submarine at all. The sonar readings likely came from a known magnetic anomaly on the sea floor and misinterpreted noises. In other words, Hubbard had waged a two-and-a-half-day naval battle against geology.

It’s funny in hindsight, but it also highlights a serious problem in modern warfare: technology is only as good as the people interpreting it. A blip on a screen can mean enemy contact – or just a grumpy rock minding its own business.

8. Two Drunk Soldiers Turn a Siege Into a Full Battle

Ancient warfare had its own brand of ridiculousness. During Alexander the Great’s campaign against the Persian Empire, he laid siege to the fortified city of Halicarnassus (in modern-day Türkiye). It was a long, frustrating operation. Troops were exhausted, tempers were short, and, as often happens with bored soldiers, alcohol entered the chat.

According to ancient sources, two Macedonian hoplites in Alexander’s army got drunk and started arguing about who was braver. Being soldiers, they decided that the best way to settle the dispute was not with, say, arm wrestling, but by charging the city walls by themselves.

The garrison inside the city saw two lone attackers and sallied out to swat them. The noise and movement attracted more soldiers from both sides, and before long, a serious engagement was underway – all sparked by a drunk macho contest. The attackers nearly seized parts of the defenses in the chaos.

In a different world, historians might be writing about the decisive “Heroic Assault of Two Hoplites” that won Halicarnassus. Instead, it survives as a cautionary tale about alcohol, boredom, and sharp weapons.

7. The British Try to Get the Ottomans High

Fast-forward to World War I in the Middle East. British intelligence officer Richard Meinertzhagen operated in the Sinai–Palestine theater and became famous for imaginative (and controversial) tricks against Ottoman forces.

One story, often repeated in popular accounts, claims that during operations near Sheria in 1917, British aircraft dropped not only propaganda leaflets but also free cigarettes to entice exhausted Ottoman soldiers. According to the tale, some of these cigarettes were laced with opium, turning the defenders into a dazed, barely functional force just in time for a ground attack.

Historians debate how much of this episode actually happened as advertised. Meinertzhagen’s own diaries are known to mix fact, exaggeration, and outright invention, and some scholars suspect he embellished his role and the drug angle. What is clear is that tobacco shortages were real, cigarette drops were used as psychological warfare, and British intelligence very much leaned into creative mind games.

Whether or not the opium detail is fully accurate, the idea of softening up enemy defenses with free “happy cigarettes” remains one of the strangest claimed tactics in modern war.

6. A Meteor Crashes Between Two Armies and Ends the Battle

Sometimes, the universe itself seems to step in and say, “You know what? Everybody go home.”

During the Third Mithridatic War in the 1st century BCE, Roman forces under Lucullus faced troops loyal to King Mithridates VI of Pontus in Asia Minor. Ancient accounts describe a bizarre incident near Otryae: just as the two sides were lining up for battle, a flaming object streaked across the sky and slammed into the ground between them.

The object was described as a molten, glowing mass – consistent with what we’d now call a meteorite. Both armies, steeped in religious belief and always on the lookout for omens, took one look at this cosmic “absolutely not” and decided that maybe today was not a good day to die. The confrontation broke off, and the battle never properly happened.

Was it a literal meteor, an embellished story, or a symbolic tale that grew over time? Scholars still argue about the details, but the episode reflects something very real about ancient warfare: morale and superstition could be as decisive as swords and spears.

5. A Missing Soldier’s Bathroom Break Helps Spark a War

On the night of July 7, 1937, near the Marco Polo Bridge outside Beijing, Japanese troops were conducting training exercises close to Chinese positions. Tensions between Imperial Japan and China were already high. Shots were fired in the dark – no one is entirely sure who started it – and confusion spread.

During the incident, a Japanese soldier, Private Shimura Kikujiro, failed to return from the exercise. His unit assumed he had been killed or captured by the Chinese. Japanese commanders demanded the right to enter the nearby Chinese-held town of Wanping to search for him. Chinese officers refused, fearing this “search” would turn into an occupation.

In reality, the missing private reportedly got lost – and, depending on the source, may simply have wandered off to relieve himself or visit a brothel before finding his way back. By the time he reappeared, both sides had mobilized reinforcements. The incident spiraled into the full-scale Second Sino–Japanese War, which ultimately blended into the broader conflict of World War II in Asia.

It’s an extreme example of escalation: a single missing soldier, a confused night fight, and clashing demands turned a local crisis into a catastrophic multi-year war.

4. The Tootsie Roll “Ammo” Drop at the Chosin Reservoir

The winter of 1950 at the Chosin Reservoir in Korea was brutally cold – we’re talking temperatures that could freeze weapons, vehicles, and skin in minutes. Surrounded by Chinese forces, U.N. troops, especially U.S. Marines, were short on everything: food, ammunition, and energy.

A later legend claims that when Marines radioed in for more 60mm mortar rounds, using their code word “Tootsie Rolls,” someone in the supply chain didn’t have the code sheet. Taking the term literally, they loaded aircraft with crates of actual Tootsie Roll candies and dropped them to the freezing troops instead of explosives.

The story goes that while this was a disaster in terms of firepower, it turned into an accidental blessing: the candy helped keep men alive in the cold and was soft enough to be used to plug bullet holes in fuel lines when warmed in soldiers’ mouths. It’s an irresistible tale of mix-ups and improvisation.

Modern historians have pointed out that the story is probably more myth than strict fact, built up later from veterans’ memories and simplified retellings. Still, it captures something true about Chosin: survival often depended on makeshift solutions, strange supplies, and a dark sense of humor.

3. A Blind King Rides Into Battle Anyway

At the Battle of Crécy in 1346, during the Hundred Years’ War, French forces clashed with a smaller but better-positioned English army. Among the French allies was John of Bohemia, a respected king and seasoned knight – who had been completely blind for about a decade.

When the battle turned against the French, John was urged to withdraw. Instead, he reportedly answered with something along the lines of, “Far be it from the King of Bohemia to flee.” He had his knights tie their horses’ reins to his so they could guide him into the fray.

The blind king charged straight toward the English lines, swinging his sword at enemies he couldn’t see. After the battle, his body was found surrounded by those of his faithful knights.

Medieval chroniclers turned this into a legendary scene of chivalric bravery – and also, depending on your perspective, of impressive stubbornness. It shows how medieval honor culture could push leaders to make decisions that made emotional sense but zero tactical sense.

2. The Man Who (Maybe) Fought for Three Different Armies

One of the most talked-about “strangest war stories” of the 20th century involves a Korean man named Yang Kyoungjong. According to popular accounts, Yang was conscripted into the Japanese army in the late 1930s, captured by the Soviets and forced into the Red Army, then captured again by the Germans and pushed into Wehrmacht service – before finally being captured a third time by U.S. troops in Normandy in 1944.

If true, that would make Yang a veteran of three different armies on two continents, fighting under three flags he had no real say in choosing. A famous photograph of an Asian-looking prisoner in German uniform taken in Normandy is often said to show him.

There’s just one problem: historians have struggled to prove Yang actually existed as described. Some military historians and popular writers have treated the story as fact, but detailed archival evidence is thin, and a major Korean documentary investigation concluded that there’s no firm proof tying the photo or the legend to a single identifiable person.

Still, the story has stuck because it reflects a brutal reality: millions of conscripted soldiers, especially from colonized or occupied regions, were dragged from one army to another with almost no control over their fate. Whether Yang was a real individual or a composite legend, his story captures the dizzying, dehumanizing chaos of World War II.

1. The British Sink Their Own Flagship in a Botched Turn

On June 22, 1893, the Royal Navy’s Mediterranean Fleet conducted maneuvers off the coast of what is now Lebanon. At the head of one column sailed HMS Victoria, the fleet flagship. Leading the other column was HMS Camperdown. Vice-Admiral Sir George Tryon decided he wanted to show off with an impressively tight formation turn.

He ordered the two parallel columns of battleships to turn inward toward each other, 180 degrees, and then continue on. The problem? The distance between the columns was less than the turning radius of the massive ships. Subordinates reportedly questioned the order, but Tryon insisted.

Physics did what physics always does. Camperdown rammed Victoria, tearing open a fatal gash in her hull. Victoria listed sharply and sank within minutes, taking over 350 sailors and the admiral himself to the bottom. There was no enemy in sight – just a catastrophic math error and a refusal to back down.

It remains one of the most infamous peacetime naval disasters in British history and a textbook example of how rank and ego can override basic common sense, even in elite military organizations.

War Is Strange, Not Just Horrible

These ten episodes aren’t isolated oddities. They live on the same shelf as other bizarre moments: Australia’s “Emu War,” where soldiers with machine guns failed to beat flightless birds; the 1969 “Football War” between Honduras and El Salvador, inflamed by World Cup qualifiers; or the “Battle of Los Angeles” in 1942, when panicked anti-aircraft gunners fired at what was probably weather balloons and nerves.

Taken together, they show that the history of war isn’t just grim statistics and tidy arrows on maps. It’s also full of accidents, overreactions, misread blips, and cosmic coincidences. Sometimes the most revealing stories aren’t the “great battles” but the times when everything went sideways for reasons no one could have predicted.

Experiences and Perspectives on War’s Weirdest Moments

So what does all of this mean for how we think about war today? Beyond the shock value and “you won’t believe this” factor, these episodes speak to the actual lived experience of people in uniform – and the people caught in the middle.

First, they show how small decisions and tiny misunderstandings can explode into massive consequences. The Marco Polo Bridge incident is the clearest example: a missing soldier, bad assumptions, and hard-line political postures helped light the fuse for a war that killed millions. It’s tempting, in hindsight, to assume that such a conflict was inevitable, but the details show how fragile the line is between “tense peace” and “full-scale disaster.”

Second, these stories highlight how war feels from ground level. For a staff officer, a battle might be a line in a report: “enemy contact, 0700 hours.” For the sailor on Hubbard’s PC-815, it was two and a half days of sleepless tension, listening for phantom propellers and waiting for the next depth charge. For the Marines at Chosin, it was trying to stay alive in lethal cold, using whatever they had – candy, duct tape, stubbornness – to keep moving.

Third, they show how culture shapes behavior on the battlefield. The blind King of Bohemia charging into Crécy isn’t just a quirky anecdote; it’s a window into medieval ideas of honor and duty. Walking away from a losing fight would have been the sensible choice, but for a knight-king steeped in chivalric values, it was unthinkable. In the same way, the French cavalry riding across a frozen harbor reflects an era in which daring improvisation was celebrated – and also an era in which no one in the Dutch command structure had seriously planned for “what if the sea becomes a road?”

There’s also a more uncomfortable angle: many of the “funny” or absurd stories sit on top of real suffering. The Emu War sounds like a comedy sketch, but it came out of economic desperation among struggling farmers. The Football War had a catchy nickname, but behind it were deep social tensions and very real casualties. Even the supposed opium-laced cigarettes and propaganda drops in Palestine were part of a brutal campaign that transformed the region for generations.

For people studying or writing about war, these strange moments can be useful tools. They grab attention – “Wait, cavalry captured a navy?” – and then open the door to deeper questions about logistics, ideology, leadership, and human nature. They’re hooks that pull readers into topics they might otherwise ignore. But they also carry a responsibility: not to let the absurdity completely overshadow the cost.

If you visit battlefields or war museums today, you’ll often see traces of this weirdness in veterans’ stories: a ridiculous misunderstanding that saved a platoon, a piece of equipment used in a totally unintended way, a surreal calm in the middle of chaos. People who’ve been to war frequently reach for humor and odd anecdotes because those are easier to share than the worst memories – and because sometimes, the only way to process something that makes no sense is to laugh at it.

Ultimately, the strangest moments in the history of war remind us that conflict is never as neat as it looks in strategy books. For every decisive charge or perfectly timed maneuver, there’s a meteor that shows up uninvited, a code word that someone misunderstands, or an admiral who refuses to listen to the laws of geometry. History isn’t just shaped by great plans – it’s also shaped by all the weird, flawed, confused humans trying to carry them out.

Conclusion

From frozen fleets and imaginary submarines to candy drops and blind kings, the strangest moments in the history of war are more than just trivia. They’re snapshots of how unpredictable conflict really is – and how often ego, error, fear, and luck stand right alongside courage and strategy.

The next time you see a clean, labeled battle map in a history book, remember that somewhere behind those arrows there was probably a private who got lost on a bathroom break, a commander who misread a signal, and at least one person wondering, “Is this really happening?”