In this chapter, Jane Plummer probes the motivations and strategies of Anglo-American filibusters during the West Florida Rebellion of 1810. Spanish West Florida was a somewhat chaotic environment of diverse colonists during the early 1800s, a territory that, despite its strategic value to imperial dominion over the interior of North America, failed to curry the active support of Spanish authorities. Meanwhile, the young United States had set its sights on the region for acquisition. But unwilling to wage an official war against Spain, the so-called Virginia Dynasty presidents of Thomas Jefferson, James Madison, and James Monroe turned to filibusters, including the likes of John Rhea, Fulwar Skipwith, and Philemon Thomas, to enact their expansionist agenda. According to Plummer, filibusters were ready-made rebels who were officially independent of any government yet clearly agents of the new American republic. Significantly, Plummer’s study of the West Florida Rebellion shows how filibusters and their state sponsors latched onto the rhetoric and legacies of the American Revolution.