In 1835 Osceola was everywhere and the garrisons in northern Florida were spread thin trying to pin him down. There were other Seminole leaders, Coacoochee, Tiger Tail and John Horse but the American public and the Army brass in Washington and Florida were fixated to the point of obsession on Osceola. They dismissed two men who were more senior to Osceola at the time, Abiaka, a war leader and medicine man who was Osceola's mentor, and Micanopy, Leading Chief of the Seminoles. Both were old men and considered to be doddering old fools. They were far from. Both were crafty, smart, strategic thinkers who had the respect of their people and knew how to handle themselves on a battlefield. Osceola was Tustenegge or leading warrior, of Micanopy's band of Seminoles, meaning that Osceola took orders from Micanopy, not the other way round.
On the morning of December 28, 1835, Micanopy and his warriors were waiting for Osceola to join them before ambushing a column of men heading from Fort Brooke to Fort King, in present-day Ocala, Florida. The men were under the command of Brevet Major Dade. Dade had been born in Virginia in 1793 and joined the army in 1813, when he was 20 years old. He had no formal training in the military, but would have had some on-the-job experience during the War of 1812. In a peacetime army, opportunities for promotion were few and far between. Brevetting, or giving an officer a nominal rank instead of a full promotion kept some mobility in the ranks. Dade was brevetted major in 1828 and posted to Florida with the 4th Infantry Regiment as the Second Seminole War broke out in 1835.
As his men marched up the old Spanish King's Highway toward Fort King, Dade hadn't posted scouts. Contrary to what's usually portrayed in movies, the area isn't swampy jungle. There was space between the trees and Dade no doubt thought he could easily spot any warriors sniping through the trees. If Osceola showed up, Dade was ready. Little did Dade or Micanopy know that Osceola was away on personal business. He was lying in wait near Fort King for Indian Agent Wiley Thompson to venture out of the fort. Thompson would taken an evening walk that night and run into a bullet from his worst enemy.
Meanwhile, on the King's Highway, Micanopy's men crept ever closer to the infantry column, its heavy wagons bogged down in mud, the men beginning to straggle along the trail. The Seminole knew their home range and could crawl and creep through brush as well as anyone. They didn't need to stand to shoot. As the day dragged on and Osceola didn't show up, Micanopy gave the signal to attack. He took aim from behind a tree on Major Dade himself and dropped him with a shot in the head. His men quickly surrounded the stranded column, coming so close that one warrior later said they could hear the sergeants cussing at their men and the situation. Next to fall was Capt. George W. Gardiner, who was no doubt doing more cussing than anybody. In the end 107 soldiers were killed and 2 wounded, of which one died later on. Only two men survived. Seminole losses were 3 killed and 5 wound.
Despite this dismal failure, or because of it, Dade has several places named after him. Miami-Dade County, Florida, Dade County, Georgia, Dade County, Missouri, Dadeville, Alabama and Dade City, Florida. There was also a Fort Dade, now decommissioned. Dade and his men are buried at St. Augustine National Cemetery near Osceola's brother-in-law, Major David Moniac, killed in another battle. A monument marks the battlefield in Dade Battlefield Historic State Park, where a reenactment is held every year.
Never underestimate your enemy.
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