Although neither a hereditary nor an elected chief, Osceola was the defiant young leader of the Seminole in their resistance to Indian emigration. In 1835 he plunged his knife into the treaty he was asked to sign that would move his people from their swamplands in the Southeast to the unoccupied territory west of the Mississippi. This action precipitated the Second Seminole War--a seven-year game of cat-and-mouse in the Florida swamps against federal troops.

Tricked into talking peace, Osceola was captured in 1837 while carrying a white flag of truce and was imprisoned in Fort Moultrie, South Carolina. This treachery so outraged George Catlin that he went immediately to the prison. He and Osceola became friends, and Osceola willingly posed for his portrait. "This gallant fellow," wrote Catlin, "is grieving with a broken spirit, and ready to die, cursing the white man, no doubt to the end of his breath." Soon after this portrait was completed, Osceola died of malaria.

Osceola's name was derived from the Indian term "Asiyahola," the cry given by those taking the ceremonial black drink that was supposed to cleanse the body and spirit.