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.
#5. James Wilkinson Lost 1,000 of His Men to Desertion and Disease (During Peacetime)
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.
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.
#4. General Henri Navarre Used Himself as Bait in a Trap He Forgot to Set
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?
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.
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.
#3. Gideon Pillow Doesn't Get How Forts Work
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.
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.
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.