Osceola was named Billy Powell at his birth in 1804 in the Upper Creek village of Talisi, which means "Old Town". The village site, now the city of Tallassee, Alabama, was located on the banks of the Tallapoosa River about 20 miles (32 km) upstream from Fort Toulouse where the Tallapoosa and the Coosa rivers meet to form the Alabama River. His mother was Polly Coppinger, a mixed-race Creek woman, and his father was most likely William Powell, a Scottish trader.

In 1814, after the Red Stick Muscogee Creeks were defeated by United States forces, Polly took Osceola and moved with other Muscogee refugees from Alabama to Florida, where they joined the Seminole. In adulthood, as part of the Seminole, Powell was given his name Osceola (/ˌɒsiːˈoʊlə/ or /ˌoʊseɪˈoʊlə/). This is an anglicized form of the Creek Vsse Yvholv (pronounced [asːi jahoːla]), a combination of vsse, the ceremonial black drink made from the yaupon holly, and yvholv, often translated "shouter" but referring specifically to the one who performs a special whoop at the Green Corn Ceremony or archaically to a tribal town officer responsible for offering the black drink.

In April 1818 during the First Seminole War, Osceola and his mother where living in Peter McQueen's village near the Econfina River, when it was attacked and destroyed by the Lower Creek allies of U.S. General Andrew Jackson that were led by William McIntosh. Many surviving Red Stick warriors and their families, including McQueen, retreated south into the Florida peninsula.

In 1821, the United States acquired Florida from Spain (see the Adams-Onis Treaty), and more European-American settlers started moving in, encroaching on the Seminoles' territory. After early military skirmishes and the signing of the 1823 Treaty of Moultrie Creek, by which the U.S. seized the northern Seminole lands, Osceola and his family moved with the Seminole deeper into the unpopulated wilds of central and southern Florida.

Through the 1820s and the turn of the decade, American settlers continued pressuring the US government to remove the Seminole from Florida to make way for their desired agricultural development. In 1832, a few Seminole chiefs signed the Treaty of Payne's Landing, by which they agreed to give up their Florida lands in exchange for lands west of the Mississippi River in Indian Territory. According to legend, Osceola stabbed the treaty with his knife.

Five of the most important Seminole chiefs, including Micanopy of the Alachua Seminole, did not agree to removal. In retaliation, the US Indian agent, Wiley Thompson, declared that those chiefs were deposed from their positions. As US relations with the Seminole deteriorated, Thompson forbade the sale of guns and ammunition to them. Osceola, a young warrior rising to prominence, resented this ban. He felt it equated the Seminole with slaves, who were forbidden by law to carry arms.

Thompson considered Osceola to be a friend and gave him a rifle. Osceola had a habit of barging into Thompson's office and shouting complaints at him. On one occasion Osceola quarreled with Thompson, who had the warrior locked up at Fort King for two nights until he agreed to be more respectful. In order to secure his release, Osceola agreed to sign the Treaty of Payne's Landing and to bring his followers into the fort. After his humiliating imprisonment, Osceola secretly prepared vengeance against Thompson.

On December 28, 1835, Osceola, with the same rifle Thompson gave him, killed the Indian agent. Osceola and his followers shot six others outside Fort King, while another group of Seminole ambushed and killed a column of US Army, more than 100 troops, who were marching from Fort Brooke to Fort King. Americans called this event the Dade Massacre. These nearly simultaneous attacks catalyzed the Second Seminole War with the United States.

In April 1836, Osceola led a band of warriors in an attempt to expel U.S. forces from Fort Cooper. The fortification was built on the west bank of Lake Holathikaha as an outpost for actions against the local Seminole population. Despite running low on food, the U.S. garrison had enough gunpowder and ammunition to keep the Seminoles from taking the fort before reinforcements arrived.

On October 21st, 1837, in what historian Thom Hatch called "one of the most disgraceful acts in U.S. military history", Osceola was captured after U.S. forces disingenuously agreed to meet under a white flag of truce. Osceola was arrested along with 81 of his followers. He died in prison a few months later, on January 30th, 1838.

• A Seminole Warrior Cloaked in Defiance

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