December Twenty-Eighth, Eighteen Thirty-Five

The day the Second Seminole War began was December twenty-eighth, eighteen thirty-five, and it was one of the deadliest in the history of American conflicts with Native peoples.

Two events happened on the same afternoon, miles apart, coordinated deliberately.

To the south, along the military road between Fort Brooke at Tampa Bay and Fort King here at Ocala, a column of about one hundred ten soldiers under Major Francis Dade was marching north. The Seminoles had shadowed them for five days through pine flatwoods and hammock. When the column crossed into high ground thick with palmettos and oaks, Chief Micanopy fired a single shot, by arrangement the signal for the attack to begin. What followed lasted for hours. When it ended, all but three of Dade's men were dead. Only two of those survivors made it back to Fort Brooke alive. The engagement became known as the Dade Massacre, and it sent shock through the American military establishment from Florida to Washington.

While that ambush played out to the south, Osceola led a smaller group to the edges of Fort King. Agent Wiley Thompson, who had jailed and humiliated him, stepped outside the fort that afternoon to take a walk after dinner. Osceola shot him. Thompson and four others were killed.

The two strikes had been planned together, a coordinated act of war on a single day. The United States had not seen it coming.

What followed was seven years of war in the Florida swamps and hammocks, a conflict the United States never clearly won. The Seminole cost the federal government an estimated forty million dollars and the lives of thousands of soldiers. The road that runs east from downtown Ocala still carries the name of the officer who died on it. You may already have driven part of it.