In this chapter, Jackson Pearson offers an intriguing interpretation of filibusters and settler rebels in the Gulf South with his exploration of land speculation in the Louisiana-Texas borderlands. From 1811 to 1821, numerous filibustering expeditions, organized in American Louisiana, attempted to exploit the turmoil that spread across New Spain, including Texas, in the wake of Padre Miguel Hidalgo’s revolutionary movement. The series of filibusters and corresponding Spanish retributive campaigns created crises of loyalties and refugees in the Louisiana-Texas borderlands, particularly in the area near Nacogdoches. By 1818, Pedro Procela and José de la Bega, notable Nacogdoches landowners and notaries, conspired with U.S.-based filibusters to create an independent republic in Texas. Coined the James Long Expedition, the filibusters invaded Texas in 1819 and declared the creation of a new, independent nation, with Procela and de la Bega appointed to its governing body, the Supreme Council of the Republic of Texas. As Pearson meticulously details, Procela and de la Bega helped design a land speculation scheme to undergird the new republic—even before the attempted Spanish overthrow had taken place. By analyzing the roles of Procela, de la Bega, and others, Pearson illuminates the centrality of land in settler rebellion, as well as the gray areas that separate rebels and revolutionaries from opportunists.