Led By Donkeys is a podcast where military history meets the kind of dark humor that can only come from veterans who’ve seen enough PowerPoint presentations to make them question humanity’s ability to organize literally anything.
But with hundreds of episodes chronicling humanity’s most spectacular military failures, where do you even begin? Whether you’re here for the tales of armies getting defeated by their own shoelaces, generals whose strategic genius peaked at “charge directly into the machine guns,” or just want to hear two former service members slowly lose their minds while explaining how Italy managed to lose a war to literally everyone, I’ve put together the absolute best episodes that showcase military incompetence at its finest.
Episode 113 – The 47 Ronin
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Snatch up your trusty spoons and brace yourself for the greatest story of vengeance ever told.
Episode 286 – The Death of Captain James Cook
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Captain Cook arrives in the Hawaiian Islands and manages to irritate the entire population, resulting in the most hilariously unexpected outcome.
Episode 147 – The Terrible History of the Nauvoo Legion
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Joe is joined by the team from the “Brigham Young Money Podcast” as they share the fascinating tale of militant Mormonism with him.
Episode 102 – The Crippled Eagles of Rhodesia
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The Crippled Eagles were a group of American Neo-Nazis, white supremacists, and fascist supporters who flocked to the colony of Rhodesia in an attempt to uphold white nationalism. Their efforts ended in spectacular failure, marked by both absurdity and tragedy. This is the account of their downfall and demise.
Episode 296 – The Battle Of The Three Kings
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Once upon a time, the King of Portugal decided to start a war so disastrous that it didn’t just ruin his dynasty—it took out three kings in one fell swoop. It was like a royal buy-one-get-two-free sale, except instead of discounts, they got chaos, collapse, and a one-way ticket to history’s blooper reel.
Episode 126 – The Horrible Death of President James Garfield
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It’s really hard to overstate how bad this President’s death went. Think sepsis, infection, doctors digging around in his body trying to find the bullet. Yeah, it wasn’t great.
Episode 124 – Life on a U-Boat was Terrible
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Life on a WWII U-boat was about as pleasant as a root canal in a submarine-sized sardine can—and honestly, the only silver lining was that it wasn’t a long-term gig, thanks to all the, uh, *unexpected retirement plans* courtesy of explosions and drowning.
Episode 204 – The Potsdam Giants
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Joe, Francis, and Shocks dive into the story of the most bizarre military unit to ever exist.
Episode 119 – Russo-Japanese War Part 1: Willy, Nicky, and Racism
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Imperialism and racism teamed up to steer Imperial Russia into one of the most epic facepalms in military history—like a self-inflicted cannonball to the foot, but with way worse consequences.
The Death of Mussolini
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A bonus episode, but well worth a listen for the absolutely insane but true story of Benito Mussolini’s death in a suburban square alongside his mistress.
Episode 141 – The Last Stand of the Danzig Mailmen
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When the Nazis barged into Poland at the start of World War II, they didn’t kick things off with epic battles or dramatic trench warfare. Nope, their grand opening act was storming the Danzig Post Office—because nothing screams “world domination” like a postal takeover. Stamp collectors everywhere must have been *shook*.
Episode 159 – The First Chechen War Part 1: Train Robbing Rebellion
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Part 1 of the riveting four-part series on the First Chechen War: another chapter in Russia’s centuries-long tradition of enthusiastically trying to subjugate Chechnya—because apparently, nothing says “lasting peace” like repeatedly poking the same geopolitical hornet’s nest. Generations of war? What a *shocking* twist!
Episode 152 – Conrad Von Hotzendorf Part 1: Load Bearing Franz
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Ladies and gentlemen, step right up! We have a fresh contender for the title of “Worst Commander in History” entering the ring—because apparently, leading armies into disaster is now an Olympic sport, and this guy’s going for the gold medal in incompetence.
Episode 285 – The American Invasion of Quebec
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Before Benedict Arnold earned his reputation as history’s most infamous turncoat, he decided to take a crack at invading Canada—and, surprise, it went about as smoothly as a snowball fight in a sauna.
Episode 12 – General Butt Naked and the Liberian Civil War
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In what might be the most soul-crushing episode, Joe and Nick dive into the Liberian Civil War and introduce us to General Butt Naked—a warlord so wild he makes other warlords look like accountants. This guy charged into battle completely naked (yes, *completely*), leading an army of men rocking sundresses, clown wigs, and a side hustle in cannibalism. Because apparently, when you’re already drinking blood and eating hearts, pants are just too mainstream.
Episode 220 – The Battle of Lake Tanganyika Part 1: The Worst Officer in the British Navy
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During WWI, the British navy came up with a battle plan so utterly pointless it could’ve been mistaken for a prank. Naturally, their next move was to find someone just as useless to lead it—because if you’re going to waste time and resources, might as well do it with style (and maximum incompetence).
Episode 23 – Iran-Iraq War Part 1: Revolution!
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A grand story that runs six parts and starts right here.
Episode 289 – Eugene Bullard. The Coolest Man to Ever Live
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Eugene Bullard was a man who couldn’t be contained by just one title—he was a circus performer, a boxing champ, the first African American combat pilot, a club owner, a jazz legend, and even a spy. Basically, he was so cool that history still hasn’t figured out how to keep up with him.
Episode 132 – Luigi Cadorna: Redux
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Back in the day, the very first episode of this podcast was about Luigi Cadorna—because apparently, starting off with one of history’s most questionable military leaders is a “great” idea. While reliving the glory of Cadorna’s “achievements,” the host somehow managed to raise over $5,000 for displaced and needy victims of the recent war in Armenia. Take that, bad decisions—turns out even Cadorna-level chaos can lead to something good!
Episode 279 – The Battle of Stalingrad: Part 1
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The tale of one of the most gut-wrenchingly awful battles ever fought in human history. A five-parter of war mayhem.
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