This essay examines the legal inquest of José María Gonzales, a peninsular vassal of African descent whom in 1809 the authorities in the Captaincy General of Venezuela accused of being a fugitive from slavery and a traitor to the crown. In form, procedure, and outcome, this case is similar to others from the late Bourbon period. The context, however, was radically different. Following the Napoleonic invasion of Spain, Venezuela was governed by the Junta Suprema Central y Gubernativa de España e Indias. This legal inquest thus offers a point of entry to examine the transformations of the Spanish monarchy at this unique juncture. Using a microhistorical lens, this essay contextualizes Gonzales, the system of justice, and the intervening officials in the milieu of the War of Spanish Independence to illuminate significant changes to the notions of freedom and loyalty in Spain and Venezuela.