#2. The Coup That Got in the Wrong Line
"Mad" Mike Hoare was an Irish mercenary who spent his career doing mercenary-type things in Africa. It takes a certain kind of man to pursue that sort of career, as you can imagine. He was hired to stage a coup against the tiny island country of Seychelles, which was strategically important due to its proximity to a U.S. military base. Hoare put together his mercenary army and named them "Ye Ancient Order of Froth-Blowers." (Why? Because he was crazy.)
And he really loved him some cappuccino.
They hid assault rifles in the bottom of their luggage and filled the rest up with toys, coming up with an elaborate back story that he and his men were a rugby team who were going to Seychelles to distribute the toys to poor children.
Needless to say, that back story is the highlight of what ends up being a Shakespearean farce of a revolution. The trouble started when the "rugby team" hilariously showed up at the airport of the country they were trying to take over. One of the men accidentally got into the "Something to Declare" line at customs, meaning his bag full of guns was going to get searched. And that's when this particular mercenary decided that the airport was as good a place as any to start a revolution.
"We start by liberating that gift shop. Then on to the Sbarro, and glorious victory."
Wrong-Way Froth-Blower assembled his gun and shot the customs guy before he could get away, and the other mercenaries joined the gunfight as well. Then, Mad Mike did what any other insane person in his situation would do -- he hijacked a plane to go home. Once in the air, Hoare tried to make the pilot open the doors so they could dump their guns into the ocean, but the pilot pointed out that this would make the plane depressurize and they would all die. You'd think a colonel would know that, but nope.
Once the plane landed, the conspirators were arrested, obviously. But don't feel bad for Mad Mike. He's gone on to write books, recruit honorary members to his mercenary club and rock a beret harder than any man has a right to.
"I'm going for sort of an A-Team, with just a hint of The Three Stooges."
#1. A Night in the Museum (For Hugo Chavez)
Before Hugo Chavez became the cancer-riddled despot we know today, he was just an angry upstart with a dream of couping the shit out of Venezuelan president Carlos Andres Perez. So, like every other rebel on this list, he put together a terrible plan. Despite knowing that he only had the support of 10 percent of the military of Venezuela and a team of backstabbing cutthroats, Chavez decided there was no better time for a rebellion than February 4, 1992. With five whole army units under his command, Chavez rolled into Caracas with four goals: capture the president, capture senior generals, broadcast their goals from the Historical Museum and wait for the angry masses to join their cause. What could go wrong?
"Sir, permission to shit myself?"
They were greeted with machine gun fire.
By the time Chavez and his team of misfits got to Caracas, someone had already spilled the rebel beans. Chavez convinced the guards at the museum that he and his men were only there to reinforce the troops for the other side, if they could just let them in, please. Wouldn't you know it? The idiots fell for it! Success!
Except the communication equipment that was supposed to broadcast the rebellion never got there. Phones? Also not there. So on the night of February 4, Hugo Chavez found himself locked in a museum with no way of communicating with the outside world. We can only hope the exhibits came to life and terrorized them while they were there, but the historical record is strangely silent about that part.
"This kind of stuff never happens to Castroooo!"
The crazy thing is that the rebels running the show in other cities across Venezuela had totally taken their cities. But Chavez didn't know that -- he didn't have a phone. He was forced to just sit in the museum like a dumbass all night. It wasn't until the next morning when the president used Good Morning, Venezuela to announce that there had been a failed uprising the night before that Chavez even realized he had lost.
Chavez surrendered, but asked to broadcast his surrender on television as well -- just so his fellow conspirators would surrender peacefully. Here's where you have to remember that Chavez did eventually achieve his goal; up until this point, no one had ever heard of Hugo Chavez, the idiot who trapped himself in a museum during his own coup. Within six years he would be the "popularly" elected president of the country.
"So then I flung open the doors like this, and I was all like, 'When I become president, you're so fired!'"
See? Sometimes the crazy shit pays off.
For more insanity out of history, check out The 6 Most Insane Underdog Stories in the History of Battle and The 5 Most Epic Battles of Will That Would Not End.