In 1832, a few Seminole chiefs signed the Treaty of Payne's Landing, where they agreed to give up their Florida lands in exchange for lands west of the Mississippi. Osceola and many other Seminole were outraged by this treaty; Osceola reportedly stabbed the treaty with a dagger and said, "This is the only treaty I will make with the white man!"
His band of about 4,000 men successfully held over 200,000 United States Army troops at bay for over ten years by employing hit and run guerilla warfare tactics from bases deep within the wilderness swampland that was then central and south Florida.
On the orders of General T.S. Jessup, Osceola was arrested as he arrived for truce negotiations in 1837. He was imprisoned at St. Augustine and then Fort Moultrie, South Carolina, where he died and was buried with full military honors.
Osceola County, Florida, was named after him.