In the opening years of the nineteenth century, Seminoles mounted an organized resistance to the new order spreading across the Deep South. Buoyed by the return of William Augustus Bowles at the end of 1799 and by his renewed promises of British support, they joined with the adventurer to raid Spanish settlements. For a brief period in late May and June 1800, Seminoles succeeded in taking the Spanish fort on the St. Marks River below present-day Tallahassee. Thereafter, they raided plantations, stealing slaves and destroying property, until the Spanish captured Bowles in late May 1803. Though Bowles intended to establish and profit from a regular trade between British merchants in the Bahamas and Florida Indians, Seminoles had their own reasons for participating in his plans. According to Tuskegee Tustanagee, they believed that by harassing the Spanish and dividing the Creeks, “the United States or Spain will give them presents as the British formerly did for the sake of union among the Indians and a firm peace between them and the white people.”

The political ferment in Florida might have led directly to a conflict between dissidents and supporters of the new order except that an eight-year stretch of famine and disease intervened beginning in 1804. During the hungry years, as Muskogees called this period, wealthy Creeks continued to fare well, while hunters and hoers suffered without relief.