Osceola
"I will make the white man red with blood, blacken him in the sun and rain, and the buzzards will feast upon his flesh."
If there's one thing that Colonial America was awesome at, it was fucking over the Indians. Using everything from broken treaties and shady business deals to crazy obscure airborne diseases and ball-shooting machine guns, we did everything we possibly could to exploit, subjugate, and/or completely relocate the native peoples of North America. While for the most part this was a pretty successful (if unsavory) operation - tomahawks and spears generally aren't much of a match for artillery batteries and portable nuclear missile launchers - some Native American tribes seriously didn't feel like putting up with our stupid bullshit. They took up arms, fought like a divorced couple on the Jerry Springer Show, and did whatever they could in defense of their homelands and their lifestyles. Of all the native tribes that started shit with the U.S. Army, none put up a more lengthy or ferocious resistance than the Seminole Tribe of Florida, particularly while under the guidance of a badass war chief known as Osceola.
Osceola was born in 1804 in the small village of Tallassee, Alabama. When he was still a young man his tribe migrated to a reservation in central Florida, mostly to avoid conflict with the Europeans, Americans, and rival Creek Indian tribes, all of whom were continually fucking with them for no reason at all. Osceola and his peeps chilled out in area code 407 for a while, peacefully living off the land, rocking the black drink and wrestling giant man-eating alligators just to prove how big their balls were, but unfortunately back in these days it was pretty much impossible for American Indians to avoid having white people try and fuck with them. Seriously, white people were like the paparazzi of the 19th Century - no matter where you went you couldn't fucking escape them. Not long after Osceola arrived at the reservation, a bunch dumbass white people started building homes on the outskirts of Indian Territory, and for some reason they got all pissed off that there were Indians near their homes. You'd think that it's common sense that if you don't like Indians, you shouldn't move next door to them, but whatever. Anyways, the colonists ended up getting cheesed off because their black slaves kept escaping the plantations and running over to the reservation, and the Seminoles (who were pretty chill with everyone) weren't really interested in sending a bunch of innocent men and women back to a life of brutal servitude. The Seminoles would allow the runaways to join their tribe, any slave catchers sent into Indian Territory found themselves being used as live-fire target practice for badass Seminole bow-hunting snipers. There were also reports that some of the more daring Indian braves kept sneaking into Disney after dark and stealing free rides on Space Mountain, but this was never confirmed.
Unfortunately for the 'Noles, President/Indian Hater Andrew Jackson had the colonists' back. As part of the bullshit Indian Removal Act, he put together the Treaty of Payne's Landing in 1832 - a document that basically told all the Seminoles living in central Florida that they needed to sign over their land, pack up their shit and move out to Oklahoma, a desolate place where, as I understand it, the wind comes sweeping down the plains like all the fucking time. Nobody wants to live in Oklahoma, and the Seminoles certainly weren't down with this bullshit attempt by the government to usurp their ancestral lands. When the U.S. Director of Indian Affairs brought this crap to the chief of Osceola's tribe, Osceola thought it was such a horseshit treaty that he whipped out his knife on the spot and jammed it right through the paper, lodging it firmly into the table below. Then he probably pimp-slapped the G-Man so hard that his moustache fell off and said something hilarious like, "Cut that jibba jabba, fool!"
Once it became obvious that any attempt to relocate the Seminoles would be met with firm backhands to the face, swift kicks to the ballsack and bad references to 1980s sitcoms, the U.S. Army began preparing to get what they wanted by using the time-tested method of declaring full-on war. They brought in three full assloads of soldiers and weapons, and before long a number of increasingly bloody skirmishes were breaking out between the white settlers and the Seminoles. Osceola quickly realized what was going down, and knew he needed to get his warriors ready to chuck some fucking tomahawks into some stupid-looking American faces. Though he wasn't a tribal chief, he was charismatic as hell, and he went from tribe to tribe recruiting and organizing warriors with his natural leadership and unwavering devotion to the cause. Before long, he had organized a force of somewhere between 1,000 and 1,400 warriors ready to hack and slash their way to autonomy. Osceola was so dedicated to the cause that he didn't have time to fuck around with chumps who didn't support him, either. One time, he talked to some pussy-ass chieftain who said he was going to agree to terms with the Americans, load up the cargo van with apple pies and hamburgers and head out for the land where the wind comes right behind the rain. Osceola viewed this as the ultimate act of betrayal and cowardice, so he dueled the chief on the spot, killed him in single combat with a flying 360-degree atomic backbreaker, and recruited the tribe's warriors into his growing army.
It wasn't long before the Seminoles began fighting back like a self-reliant housewife in a bad Lifetime Original Movie. Though he had no supplies, little in the way of weapons, and no reinforcements to speak of, Osceola took his war parties against the full might of the U.S. Army like a squadron of X-Wings assaulting the Death Star in the space above Yavin IV. He launched hit-and-run attacks against technologically and numerically superior American patrols, flying in out of nowhere, ambushing the shit out of the enemy, killing anyone foolish enough to not immediately run screaming into the woods, and then looting the supply trains. Using these tactics, Osceola was able to secure a large stockpile of weapons and medical supplies, which he then used to launch raids on American villages and towns. The contant Seminole attacks had many panicked white settlers taking the first train back to Whiteyville, and the tribes bolstered their numbers by destroying a bunch of huge plantations and recruiting the freed slaves into their ranks.
OMG ZERG RUSH
One of the greatest victories of this stage of the war came on 23 December 1835, when a group of 170 Seminole warriors ambushed two companies of U.S. Army regular infantry while they were on the march through some dense woods. Osceola's men attacked seemingly out of nowhere, catching the soldiers off-guard and opening up with several volleys of arrows and musket fire, followed by intense hand-to-hand combat where the braves went to town with their tomahawks like a rampaging horde of psychotic half-blind lumberjacks. When the smoke cleared the Seminoles had suffered three casualties, and killed 106 of the 108-man American detachment. The same day, a raiding party personally led by Osceola killed the Director of Indian Affairs along with his entire personal bodyguard. A month after that, Seminoles ambushed an Army detachment as they attempted to ford a small river, taking out 75 soldiers while they were stuck in waist-deep water.
Osceola's early attacks were incredibly successful largely because the American Army was more out of its element than Sid Vicious in a Boca Raton retirement community. The swampy marshes of the Everglades were home to the Seminoles, but the terrain was not at all conducive to the U.S. strategy of engaging in large, set-piece battles. Malaria took a heavy toll on American soldiers slogging through the swamp, any attempts at large-scale military maneuvers were slowed down to a crawl, and the Seminoles could easily strike quickly and fade back into the Everglades without having to worry about any kind of U.S. pursuit. One time, a U.S. General actually attempted to send a 5,000-man regiment out to ambush a Seminole village deep in the swamp in an effort to completely crush the resistance movement. It took the Noles about two seconds to figure out what was going on, and by the time the blundering Americans stumbled their way into the village it was more deserted than a John Tesh concert.
Throughout 1836 the Seminoles pressed their attack and tried to avoid getting involved in any kind of large-scale engagment. A combination of sieges, disease, and gunshot wounds to the face took its toll on the Americans, and several critical U.S. forts were captured during this time. However, attrition was also beginning to wear on Osceola's warriors. While the Americans seemingly had an infinite amount of manpower, the Seminoles could not replace warriors that were killed or wounded in action, and before long their ranks were thinner than an Anorexic European model or Bruce Willis' hairline. Osceola was fighting a losing battle against impossible odds but he adamantly refused surrender in any form, vowing to battle the American encroachment on his territory until his last breath (and then probably even after he died - coming back and haunting the shit out of the U.S. generals from beyond the grave or something).
Unfortunately, it wasn't long before Osceola got screwed over worse than Bret Hart at Survivor Series 1997. Osceola was contacted by some total bastard named General Thomas Jessup to meet for truce negotiations one day, and when Osceola met Jessup under a white flag he was ambushed, captured, imprisoned, and thrown in a South Carolina brig. Since he was a well-respected commander with a reputation for being a tactical military genius, he was actually housed in the officer's quarters of the brig and given free reign of the facility. Even so, Osceola was not the sort of badass who could tolerate living in captivity when he could be out kicking asses. He died of Malaria on 20 January 1838, less than three months after his bullshit capture. He was buried with full military honors by the U.S. government.
Osceola valiantly defended his homeland and fiercely resisted the forced removal of his people for over three years. He never backed down, never compromised, and didn't flinch in the face of a battle he seemingly had no chance of winning. His shady, underhanded capture only served to piss the Seminoles off even more, and they would continue fighting the U.S. Army for many years after Osceola's death. Ultimately, the resistance was so hardcore and costly for the United States that the government eventually said, "fuck it", and left the Seminoles alone. To this day, the Seminole tribe of Florida remains unconquered. Not only that, but they also fucking own the Hard Rock Cafe, rule a multi-billion dollar gambling and entertainment empire, and pretty much own half of South Florida... not bad for a group that once found itself locked in a desperate life-or-death struggle for their own survival and the continuance of their way of life.
"The government is in the wrong, and this is the chief cause of the persevering opposition of the Indians, who have nobly defended their country against our attempt to enforce a fraudulent treaty. The natives used every means to avoid a war, but were forced into it by the tyranny of our government."
- Maj. Ethan Allen Hitchcock, US Army