Osceola (Asi-Yahola) was a Seminole leader who was very important to the Seminole War and Fort King in particular. Named Billy Powell at birth, Osceola was the most famous of the warriors during the Seminole War despite not being native to Florida or a member of the ruling clan. He was born in Alabama and, along with his mother, was driven to Florida after his peoples’ defeat in the Creek Civil War in 1814.
Osceola is often referred to as “Chief Osceola” but in fact, he was never a Chief. He was, however, a charismatic leader and remained steadfast in his refusal to leave Florida for the Indian Territory.
During the First Seminole war, it was reported that Osceola frequently barged into the Indian Removal Agent Wiley Thompson’s office, disrespecting him with complaints and shouts and using language that was less than cordial. Overall, they had an unstable relationship. After one such incident, it is said Wiley Thompson had Osceola shackled and detained for several nights at Fort King. Osceola vowed to get revenge for the indignities shown him.
When the Seminole decided to take up arms against the United States’ Indian removal policy, Osceola killed Wiley Thompson and others at Fort King – an attack that was swift and calculated and brought him to the forefront of the Seminole War.
Almost two years later, Osceola and another leader, Coacoochee – Wild Cat – along with many of their followers, were captured under orders from General Thomas Jesup at a site near Fort Peyton, where they had traveled to participate in peace talks under a false flag of truce. Their capture by deceit created a national uproar and was described as “one of the most disgraceful acts of American military history.”
Osceola was originally held at Fort Marion in Saint Augustine where he became deathly ill and was unable to escape with Coacoochee and others. He was later transferred to Fort Moultrie in South Carolina where he died on January 30, 1838 at the age of 34, and only three months after his capture.
His charisma, bravery, unwillingness to conform and cunningness in battle made him a hero among many. He was buried with military honors at Fort Moultrie.
FACT OR FICTION? According to some historians, Osceola’s hatred for the Indian Agent Wiley Thompson was much more personal than it appeared on the surface. Some accounts of Osceola tell us he visited Fort King in the company of one of his wives, Che Cho Ter or “Morning Dew” and others for the purpose of trading. Che Cho Ter’s mother was allegedly an escaped slave, and in accordance with the slave laws, any offspring would hold the same position as the mother; thus, Thompson supposed that Che Cho Ter was a slave. In this account, he seized her and returned her to slavery. Osceola became enraged and was taken into custody in irons at Fort King. Soon released, Osceola vowed to get vengeance for the indignities shown to him and his wife and this was the impetus of his attack on Wiley Thompson and others six months later.
Some say there is no proof this ever happened. However, the story does hold some plausibility, given it is consistent with slave laws at the time and given this scene played out across the Florida frontier over and over as escaped slaves were captured and returned to slavery.
It is a documented fact that Osceola visited Fort King in June 1835, and during that visit had a hostile encounter with Thompson who had him “placed in irons.” Some reports of the incident indicate that Osceola had become angry when the Indian Agent had forbidden the sale of guns and ammunition to the Seminoles. Others attribute his arrest to his wielding of a knife or arguing over liquor.
Since there is no way to definitively substantiate the stories, they remain “lore” – part of the traditions and knowledge on the subject passed on through word of mouth – and for now, we classify them as neither fact, nor fiction.