This dissertation explores the effectiveness of Spanish economic institutions in a borderland region. Recent studies have illuminated the diverse actions that native groups enacted in response to Spanish colonialism ranging from allying with the Spanish for military support to cleaving out a wedge in the market economy. Current work has considered issues of transculturation, indigenous agency, persistence, and autonomy; however, these examinations focus on the scale of the household or local economy, and do not situate native agents within a larger economic network, nor do they consider the agency of Spanish and other European actors in the context of a colonial economy. Colonial Pensacola, Florida provides an ideal stage to witness where monolithic trade policies meet economic reality, but this context is not unique. All over the world, past and present, individuals, groups, and institutions innovate and improvise within and against the global market and capitalistic trade policies. Understanding how this process played out in the past can lead to a better understanding of how people in local contexts navigate their daily lives within a globally connected economy.Methods include archival research, traditional artifact analysis, and chemical composition and isotopic analysis of glass beads and lead shot using Laser Ablation-Inductively Coupled Plasma-Mass Spectrometry (LA-ICP-MS) and acid dissolution to study the role that both colonial and native people played in disrupting or contributing to colonial economic institutions in eighteenth-century Pensacola, Florida. Although broadly recovered from sites, lead shot and monochrome glass beads lack diagnostic physical or stylistic characteristics that would facilitate interpretations of production, distribution, and use patterns. The chemical methods are used in conjunction with a close examination of historical documents to provide evidence of how goods moved through colonial and indigenous communities, foregrounding the importance of economic agency among settlers and natives, even when these practices challenged idealized models of mercantilism and colonial government regulations. Results from analysis of the three datasets illuminate both legal and illicit exchange among the Spanish, French, British, Apalachee, Yamasee, and Upper Creek. Historical correspondences document illicit trade, and the chemical analysis of the glass bead and lead bullets corroborates and supplements historical data.