5 Slapstick Failures by Modern Military Commanders

More often than you'd think, circumstances conspire to put the fate of the world into the hands of people you wouldn't trust with a Risk board.
5 Slapstick Failures by Modern Military Commanders

There are certain jobs in the world where you just assume that the people doing them are competent: It's hard to imagine a drunken, pantsless brain surgeon or astronaut. Considering that it takes longer to become a military general than either of those things, you could be forgiven for believing that only the cream would rise to the top. But more often than you'd think, circumstances conspire to put the fate of the world into the hands of people you wouldn't trust with a Risk board.

James Wilkinson Lost 1,000 of His Men to Desertion and Disease (During Peacetime)

5 Slapstick Failures by Modern Military Commanders
J. L. Bouqueto de Woiseri

Colonel James Wilkinson's resume should have served as a preview of his clusterfuck career as a general. Wilkinson first made a name for himself during the American Revolution in his report of the Battle of Saratoga, although not quite in the way you'd expect: He made up a bunch of cool stuff in his report to make himself sound like a badass. We should also mention that the report was super late because Wilkinson "stopped along the way to visit his girlfriend for a few days." Somehow this combination of dishonesty and tardiness got him promoted to brigadier general -- an auspicious position he cleverly exploited to new standards of American military suckitude.

5 Slapstick Failures by Modern Military Commanders
Charles Willson Peale

His honest, punctual rivals had all gotten themselves killed.

In 1809, while the U.S. was enjoying one of its few war-free years, Wilkinson decided to set up his camp near New Orleans so he could more easily indulge in the local culture by getting hammered and banging hookers. What he didn't realize (or, more realistically, didn't care about) was that New Orleans is mostly swamp, which meant that his soldiers had to spend their days knee-deep in mud at a time when both penicillin and athlete's-foot cream were but a distant gleam in some chemist's father's eye.

As a result, a thousand of his men -- roughly half his fighting force -- were lost, both to traditional diseases and to severe cases of fuck-this-I'm-leaving-itis. That's the largest peacetime military disaster from that period of American history, meaning that Wilkinson was such a bad general that he lost battles that weren't even being fought.

John Wesley Jarvis

He lost his camp's gold reserves to an army of hookers at the battle of "Fuck you, pay me."

But everyone has their calling, and Wilkinson eventually found out that his was being a traitor. Throughout his career, Wilkinson worked as a spy for the Spanish, sending them messages in a code that was never broken and remaining unexposed until well into the 20th century. So what we're trying to say is that the real bad guy here was the U.S. Army's screening process.

General Henri Navarre Used Himself as Bait in a Trap He Forgot to Set

5 Slapstick Failures by Modern Military Commanders
Warner Pathe News

In 1953, France was learning a lesson that America would also learn just a decade or two later: Vietnam is not an ideal place to fight a war. Desperate to turn the tide, General Henri Navarre came up with a cunning plan: He'd put his men in such an intensely vulnerable position that the Viet Minh wouldn't be able to stop themselves from attacking them. What could possibly go wrong?

5 Slapstick Failures by Modern Military Commanders
via University of Houston

"C'est magnifique! They won't be able to kill any of us once we're all dead!"

In Navarre's defense, that's actually not quite as insane as it sounds: French military technology was several decades ahead of the opposition, so a straight-up fight actually favored them pretty soundly. The problem is that Navarre approached his plan with the kind of overconfidence you can't normally achieve without an eye patch, a big leather chair, and a fluffy, white, heavily sedated cat.

Navarre's first step was to plop his army in the middle of a large valley while leaving the surrounding mountains completely unoccupied -- something everyone from a seasoned general to anyone who's seen Revenge of the Sith knows is a bad idea. On top of the immediate geographical issues, this particular valley was on the very fringe of where Navarre could expect air support, meaning that reinforcement and resupply would be unreliable in the best of times and damn near impossible during the rainy season. Anyone parachuting in would be completely blind, and all of Navarre's fancy equipment would rust or get stuck in the mud. So to recap, the enemy would absolutely come to believe that Navarre's army was helpless, because it in fact was.

5 Slapstick Failures by Modern Military Commanders
Warner Pathe News

Plan B ("Earn Vietnamese Pity") ended poorly.

As you probably noticed, this plan had one fatal flaw, and that fatal flaw was the entire plan. The Viet Minh commander, Vo Nguyen Giap, simply dragged in artillery from wherever he could find it while patiently waiting for the rainy season to hit. Once Navarre was exposed, cut off from his support, and helpless, Giap bombarded the ever-loving shit out of him from the high ground. Navarre was beaten so badly that the battle is now considered responsible for France losing the war, and it may have directly led to the South/North Vietnam split.

Luckily, nothing ever came of that.

Gideon Pillow Doesn't Get How Forts Work

5 Slapstick Failures by Modern Military Commanders
Hal Jespersen

Brigadier General Gideon Pillow achieved his military status not through training or amazing achievement, but by being an attorney and buddies with President James Polk when the Mexican War broke out. In what is probably the least surprising turn of events in the entire history of rotating occurrences, the lawyer who sleazed his way into an authority position through sheer nepotism turned out to be kind of an asshat.

5 Slapstick Failures by Modern Military Commanders
Library of Congress

But at least humorists got to mock his stupid name.

The first signs that Pillow was an idiot showed up during the battle of Camargo, when he ordered his men to pile the dirt from the trenches on the wrong side, which is kind of like using a condom to prevent pregnancy by swallowing it. When his soldiers pointed out that he couldn't sabotage their defenses any more without somehow infecting everyone with dysentery, Pillow took a look around, swallowed his pride, and totally ignored them.

After a few more years of being laughably terrible at his job, he decided it was time to get serious and turn his career around. So, Pillow wrote a letter to a newspaper in which he claimed to be responsible for a bunch of military victories he hadn't even been present for. That went as well as could be expected: Pillow was court martialed for sharing military secrets but managed to slime his way out of it by rolling a natural 20 on his "Are you friends with the president?" check.

5 Slapstick Failures by Modern Military Commanders
Matthew Brady

Yet again, our most evil and corrupt president turns out to be James K. Polk.

Once the Civil War rolled around, Pillow joined the Confederacy (we told you the "brilliant generals" thing was a myth) and quickly gained a reputation for losing battles despite outnumbering the enemy 4-1 and spending most of his time in combat hiding behind trees. His biggest fuck-up came in 1862, when he was appointed to Tennessee's crucial Fort Donelson -- right in the path of then-unknown Union commander Ulysses S. Grant. Grant had nowhere near enough troops to take the fort but decided to attack anyway, since he already knew Pillow and described him to an aide as "so incompetent that I could run straight up to his tent and wave my balls in his face, just full-on balls, and not even sweat it" (we might be paraphrasing a bit). After Grant laid the exact smackdown you'd expect, Pillow launched a convoluted scheme to distract the enemy by surrendering his 12,000 men while he and another officer escaped.

Oddly enough, the man Pillow left in charge was an old friend of Grant's, and they openly mocked the guy while the terms of surrender were sorted out, with Grant saying that even if he had caught Pillow, he would've let him go, since his work for the Confederacy was turning out to be one of the best assets the Union had.

5 Slapstick Failures by Modern Military Commanders

Ubaldo Soddu Wasn't Really "About" His Day Job

5 Slapstick Failures by Modern Military Commanders
Greece Army

One lesson you can learn from the previous example is that if your country is not at war, there are all sorts of ways to rise through the ranks of the military without being good at war stuff at all. You could probably have a long career and retire with honors as long as, you know, fighting never breaks out.

That brings us to Italian General Ubaldo Soddu.

Valdis Kursietis/Generals.dk

Who failed to live up to the promise of his first name.

Saying that Soddu was a terrible general might not be fair, since by all accounts he was fantastic at every part that didn't involve commanding troops in battle. As a charming party dude, he spent the 1930s convincing both the Nazis and the British that he was on their side, while developing very refined tastes in music and pasta. In fact, he was so good at schmoozing that he gained a reputation as a "first-class commander" despite the fact that his description of his own military philosophy was "When you have a fine plate of pasta guaranteed for life and a little music, you don't need anything more." That reads like a particularly sloppy attempt to dodge a question, since music and pasta have nothing to do with the military or, strictly speaking, philosophy -- but weirdly enough, due largely to Italy's somewhat lackluster warrior culture, his military career was actually really promising.

Right up until a war broke out.

After Mussolini's secret invasion of Greece ended up being as effective as throwing pasta at the wall, Soddu was the guy he sent to clean everything up. Most people would take a position as a commanding military officer during World War II pretty seriously, but Soddu really wasn't into the whole "fighting" thing. So, he approached the most terrifying warpocalypse the world had ever seen the way most of us approach a part-time job at Denny's: He'd start off by half-assing his way through a shift, then duck out early to go back to his tent and write music. His thing was composing soundtracks to movies, which actually doesn't sound like something that takes a lot of practice based on the pornos we've seen.

w IA
Anton Vaver/iStock/Getty Images

His work on Double D-Day left a lot to be desired.

Soddu's disastrous career on the battlefield ended after just four weeks, when his superiors realized he had no idea what the fuck he was doing (even if he did probably hear a rousing score in his head during every retreat). After his late-night groove sessions cemented his army's defeat, Mussolini ended up having to call on Hitler for support, which delayed the German invasion of Russia until winter, which ended up crippling the Nazi war machine and all but guaranteeing a victory for the Allies. See, kids, this is why you need to pay attention at your day job.

Russian Generals Had Trouble Getting With the Times

Alexander Kiyan

We don't doubt that there are some jobs where being old-fashioned is an advantage. Military general is not one of those jobs -- in real life, the Ewoks will immediately get mowed down by the Stormtroopers. Unfortunately for anyone fighting on behalf of Russia during World War II, Joseph Stalin had a nasty habit of putting grumpy old men in charge of military technology -- men who looked at innovations like rockets and tanks the same way your cranky old uncle looks at that damn smartphone you keep tweeting on at every family get-together.

via Battlefield.ru

"Those things'll give you polio, that's a fact."

For example, we have General Semyon Budyonny, who made a name for himself as an excellent soldier during the Communist Revolution of 1917, was made a cavalry leader by Joseph Stalin, and eventually had a hat named after him. This apparently went to his head, because he promptly decided that the horse was the pinnacle of human technology and would never be surpassed. While the Germans, Italians, and British were revolutionizing their armies with tanks and aircraft, Budyonny believed so strongly in the military might of horses that he briefly convinced Stalin to abolish the entire tank corps. But when Budyonny finally got a chance to face down the gigantic metal armored death guns he so arrogantly dismissed, they quickly surrounded and captured or killed all of his 665,000 men, giving Hitler his greatest military victory ever.

But Budyonny was hardly the only high-ranking Russian commander who took his equestrianism way too seriously: His colleague General Grigory Kulik was constantly claiming that anything he didn't understand (which included most things) was sabotage and decided that the best way to prepare for engaging Hitler's forces during Operation Barbarossa was to halt the production of tanks and anti-tank rockets (which he hated because they didn't sound cool when he fired them) so he could engage the state-of-the-art German war machine with World War I-era horse-drawn artillery.

5 Slapstick Failures by Modern Military Commanders
via Ukraine SSR

Anyone with this mustache was probably the wrong choice to oppose Hitler.

That would've been bad enough even if Kulik hadn't been a drunken lunatic known for screaming "prison or medal" at his subordinates (those being the two possible rewards for their efforts to obey him). Ultimately, Kulik's strategy of waving his cane and demanding that the tanks get off his lawn failed to pay off: His ineptitude allowed Leningrad to be surrounded, kicking off one of the bloodiest sieges in history. All because -- if we're being totally honest -- the guy was probably fucking his horse.

With those kinds of leaders calling the shot, it's arguably even more incredible that Russian soldiers basically won the war for everyone else.

For more military brilliance, please pre-order Jacopo's upcoming book THE GREAT ABRAHAM LINCOLN POCKET WATCH CONSPIRACY!

Always on the go but can't get enough of Cracked? We have an Android app and iOS reader for you to pick from so you never miss another article.

Related Reading: Insects could out-general all of these guys. And in fact, bees can carry out more complex sieges than most human armies. Sometimes uniform designers fail even harder than these generals, check out the Italian Carabinieri. Not had enough armed incompetence? Read about these disastrous military computer glitches.

Scroll down for the next article
Forgot Password?