Osceola, raised in the Muscogee Creek area of Alabama, migrated with his family to Florida after the Creek War (1813–1814). Arriving as a refugee, he became an influential leader in the Seminole resistance against the US government’s “Indian Removal” policies. He served as an advisor to the Seminole chief, Micanopy, and was a key strategist in the fight against US government demands to cede territory and relocate to lands west of the Mississippi River.
On October 25, 1837, while negotiating a treaty under “white flag” protections, Osceola, along with eighty-one other members of the treaty party, were captured by the US Army. Despite this betrayal of the accepted rules of parley, which caused both national and international backlash, he was imprisoned in St. Augustine’s Castillo de San Marcos. He was soon transferred to Fort Moultrie, South Carolina, where he perished three months later.
Some in St. Augustine believe that Osceola’s ghost still haunts the city, even though he died in another state. Some even assert that he was executed in or near the city, not at Fort Moultrie at all, and that his head still “floats around” Castillo de San Marcos. Still others place the haunting at Fort Mose, north of St. Augustine.
According to literature and folklore scholar Jason Marc Harris, ghost folklore in St. Augustine, including apparitions of Osceola (or perhaps just his head), is intertwined with colonial violence and ethnic tensions. “Unresolved guilt haunts the streets, paces along the walls of the fort Castillo de San Marcos, clangs the bars of the Old Jail, and rustles the drapes of Flagler College,” he writes.
“Implicit in the ghost legend of Osceola’s decapitated head is the violation of a defender of aboriginal inhabitants of Southeastern United States,” notes Harris. Though not all area folk tales are sympathetic to indigenous peoples, ghostly experiences depicting violence by Native American people are the outliers. For example, “a woman who worked for [a] tour allegedly had a ghostly experience in the Huguenot cemetery, where French Protestant victims of the Seminoles had been buried after a stagecoach attack.” But for the most part, “[r]estless victims—not perpetrators—of violence and betrayal predominantly haunt the streets and shores.”