Billy Bowlegs and the Bananas That Launched a War

Before his name was etched into Florida’s wartime memory, Billy Bowlegs, born Holata Micco, was known across Manatee County not as a threat, but as a neighbor. A chief among the Seminoles, Bowlegs was a familiar figure in the mid-1800s, walking freely through early settlements, including the village of Manatee, where he dined with pioneer families and visited without fear.

Accounts preserved by the Manatee County Historical Society describe a man who wore brightly trimmed tunics, moccasins, and silver-dollar medallions bearing the likenesses of Presidents Van Buren and Fillmore, gifts from Washington dignitaries. Plantation owner Robert Gamble once called him “a very handsome man… strong and active, bright, cheerful and pleasing in manner”.

Bowlegs had reason to believe peace could hold. He’d never instigated violence against local settlers and often tried to maintain friendly ties. Mary Wyatt, a settler who once hosted him at dinner, reportedly asked if he’d fight them should war return. “Oh yes, kill,” he replied matter-of-factly. “But I do it kindly”.

That uneasy peace unraveled in December 1855. U.S. troops under Lt. George Hartsuff, while surveying Seminole territory, destroyed Bowlegs’ personal garden in Big Cypress Swamp. It wasn’t just any garden—it was acres of carefully cultivated banana trees and vegetables meant for gifts and sustenance. Bowlegs, enraged, went to the soldiers’ camp demanding compensation. Instead, he was mocked, shoved, and thrown into the mud.

Later that night, war paint was drawn. By Christmas morning, Bowlegs and his warriors struck Hartsuff’s camp. Several soldiers were wounded, and the Third Seminole War had begun.

Over the following months, Bowlegs led a series of retaliatory raids along the Peace and Manatee Rivers. Even Dr. Joseph Braden’s fortress-like home—now remembered as Braden Castle—was attacked while guests were inside. Though the house was defended, six enslaved people and several mules were taken by Bowlegs’ men.

The federal government responded by putting a price on Bowlegs’ head—$500 for him or any of his warriors. Settlers retreated into makeshift forts, and the U.S. Army pressed southward. But Bowlegs, like his ancestors, knew how to survive in Florida’s wild terrain. He avoided capture for years, striking where he could, until finally accepting the government’s terms in 1858.

That spring, he and more than 160 Seminoles were deported from Egmont Key. As the steamer Grey Cloud pulled away, Bowlegs—described as short, proud, and wrapped in ostrich feathers—looked back at the land he would never see again.

According to Edge of Wilderness by Garnet S. Matthews, Bowlegs’ removal marked the final chapter of open Seminole resistance in Florida and the beginning of a new era for settlers in Manatee County.

Today, his legacy lingers not just in history books, but in the very landscape of Manatee County—a reminder that long before roads and rooftops, this land was home to warriors who called it sacred.