Micanopy was nearly 40 years old when he became a chief of the Seminole people. He began to acquire large amounts of land and cattle and hired more than 100 fugitive slaves to work his estates and cattle operations. These slaves were encouraged to inter-marry with the Seminole and were considered their equals, unlike the prevailing view from the whites at the time. Slaveholders from Florida and neighboring states demanded that the Seminole capture and return slaves who had escaped to Florida.
The pressure from these slave owners and Jackson’s Indian Removal Act in 1830 led to the Treaty of Payne’s Landing which Micanopy, along other Seminole leaders, refused to sign. Micanopy joined younger chiefs and Seminole leaders such as Osceola, Alligator, and Wild Cat in opposition to the treaty and formed a resistance to their removal. Micanopy planned and led the raid on Major Francis Dade and his 110 soldiers in what has become known as the Dade Massacre. This event, along with Osceola’s raid on Fort King that same afternoon, were the start to the Second Seminole War.
In 1838, Micanopy was captured with Osceola and others by General Thomas S. Jesup’s forces while under a false flag of truce. This breach of honor by the U.S. military was considered an outrage by much of the public. Micanopy was eventually sent with 200 other Seminole to Indian Territory in Oklahoma after his imprisonment in South Carolina. Micanopy died at Fort Gibson on January 2, 1849.