As was common practice among elite Seminole, he hired more than 100 fugitive slaves[citation needed] to work his estates during the early nineteenth century.
By the Treaty of Moultrie Creek in 1823, the Americans seized 24 million acres of Seminole land in northern Florida.
American development of large cotton plantations in Florida resulted in planters enslaving more people as workers, and some continued to escape the harsh regime.
While working to negotiate a peaceful resolution between the Seminole and local authorities, Micanopy refused to sign the treaty.
In December 1838, Micanopy was captured by General Thomas S. Jesup's forces under a flag of truce when he had already agreed to sign a peace treaty.
In 1845, he was one of the signatories of a treaty with the US, which gave the Seminole of western Florida semi-independence from the Creek Nation in Indian Territory.
As the Seminole had a matrilineal kinship system, his sister's son, Jim Jumper, succeeded Micanopy as principal chief.
At that time, the United States required tribes that supported the Confederacy to make new treaties, providing for the emancipation of all enslaved people and granting those who wanted to stay with the Seminole equal rights as citizens.