Che Guevara

Guevara didn't fuck around.  Outnumbered almost ten to one and operating out of a base deep in the Cuban mountains, El Che's mobile bands of guerilla troops wreaked havoc across the countryside, and Guevara repeatedly led his troops to victory in battle - serving up piping-hot Molotov cocktails to anything even remotely flammable, winning over the hearts of the populace, harassing the nationalist army every time they stopped to take a leak, and smashing the morale of anyone who tried to stand against his crazy rampaging throng of pissed-off peasants.  He moked out the well-trained Cuban army like it weren't no thang, and his innovations and tactics in the fields of guerilla warfare were so balls-out and effective that they are still studied in military academies across the globe as an example of what it means to be the fucking shit.  Today, he is believed by many to be the 20th century's foremost theoretician and tactician in guerilla warfare, which is kind of impressive, considering that he never received any formal military training.

In addition to dropping his enemies nuts-first onto an automatic fruit-juicing machine, Che was also respected and feared as a ruthless executioner who didn't hesitate to pull out his nine and gun down deserters, quitters, cowards, IT guys, donkeys, trombonists, and anybody else who didn't support him or like him or appreciate the fact that Karl Marx was totally sweet to the max.  In the Cuban Revolution, Che was the guy who personally made sure that the badass old Joseph Stalin axiom rang true:  "In the Red Army, it takes more courage to retreat than advance."

Batista's army eventually decided they couldn't fight Che in the mountains or the countryside without getting their teeth punched out through the backs of their faces, so they retreated to the cities.  So of course Guevara just went in, surrounded the cities, perpetually attacked the demoralized military, and started taking the urban centers one-by-one, capturing many of them without a shot.  He just showed up at the gates, whipped out his huge nutsack, and the terrified defenders raised the white flag immediately.

After years of campaigning, in December 1958 Che's revolutionary forces assaulted Santa Clara – the final stronghold of the Cuban Nationalist army.  This heavily-fortified military instillation was garrisoned by 6,000 soldiers, a dozen tanks, an airfield full of bombers, an armored train, a lance of Assault-Class BattleMechs, and countless other assorted heavy weapons, but Che was apparently all out of give-a-fuck.  He led just a few hundred men into the city, captured the train, surrounded the key military and government installations, and drove off or killed the defenders.  Batista, knowing his number was about to be up, shit himself and fled the country immediately after hearing about the fall of Santa Clara.  Castro and Che entered Havana in 1959, and the first successful Socialist revolution in the Western Hemisphere was over.

As an interesting side note, the borderline-insane and crazy-awesome Nintendo game Guerilla War, strongly believed by all people named Amazing Ben to be one of the top-five greatest and most ridiculous top-down shooters ever created, was based off of Che and Fidel's balls-out two-man invasion of Cuba (in Japan, the game is called Guevara, but they couldn't really get away with releasing it under that name here in the States).  If the game is any indication of historical fact (which it isn't), these men actually achieved the task of Communist overthrow of the Cuban Dictatorship by running around all over the place like madmen, shooting fully-automatic missile launchers at armored bulldozers, lassoing people from the back of a speeding mine cart, and crushing hordes of soldiers under the treads of a tank that has a flamethrower attached to its turret.  Here's a copy of the ROM file, if you're interested.

Now, you can say what you want about Che Guevara's radical, extremist Pinko Commie political beliefs, but you have to admit that it's pretty fucking sweet that he and Fidel almost single-handedly overthrew a third-world country despite having virtually no prior military experience or training.  Seriously, that's the kind of shit that almost every high school-age guy wishes he could do – get some of his buddies together, invade an island, and install himself as supreme dictator over his own country.  Che Guevara just fucking went out and did it, which kind of rocks.

After the revolution, Che was appointed the chief of La Cabana prison, where he tried and summarily executed a couple hundred government and military employees who were pissing him off.  In case you were wondering, this mostly-arbitrary, Judge Dredd-style system of justice is why pretty much every Cuban exile completely fucking hates this guy's guts with an uncontrollable shaking hate-rage.  To them, he's known as the "Butcher of La Cabana", which quite honestly sounds like the title of a bad sci-fi horror movie about a guy who kills bikini-clad spring break co-eds by prowling the swimming pools at some posh five-star party resort.  Still, any time you have someone with a nickname that features the word "Butcher" in it, it's a pretty good indication that this person really isn't to be fucked around with.

After La Cabana, Che served as the President of the National Bank, the Cuban Minister of Finance, and a bunch of other crazy shit.  He went on diplomatic missions throughout the world, yelled at the United Nations a bunch of times, fought off the Bay of Pigs invasion, and tried to get the Soviet Union to ship him a few hundred intermediate-ranged nuclear warheads (this last part didn’t really work out so well).  When a Communist revolution broke out in the Congo in 1964, he headed out there to see what was shaking.  He arrived in Africa with 120 Cuban advisors, linked up with the rebel army, and helped them fight against hardcore CIA-trained mercenaries deep in the jungles of one of the world's most formidable jungles.  The revolution failed, but hey, you can't win 'em all.

In 1966 Guevara swam to Bolivia with sixteen other guerilla warfare experts, and together they tried to incite a revolution that would instigate another Vietnam-type response from the United States.  He thought his actions (and the eventual American intervention) would inspire the entire Bolivian populace to revolt, but it didn't really work out so well for him.  Instead of sending the entire military, the US sent a detachment of CIA operatives and badass Army Rangers to hunt him down and take him out.  Che was wounded twice in an intense gunfight in October 1967, and was summarily executed by Bolivian soldiers outside the town of La Higuera.  When his would-be executioner hesitated to pull the trigger and end the life of this hardcore revolutionary, Che defiantly shouted his badass final words:

"Shoot, coward!  You are only killing a man!"

Sources:

Anderson, John Lee.  Che Guevara.  Grove, 1997.

Dorfman, Ariel.  "Che Guevara".  Time. June 14, 1999.

Guevara, Che.  Guerilla Warfare.  Rowman & Littlefield, 1997.

Van Dijk, Rudd.  Encyclopedia of the Cold War.  Taylor & Francis, 2008.