This dissertation examines José Campeche (1751-1809), a prolific artist of African descent who was born and lived his entire life in San Juan, Puerto Rico. Campeche created hundreds of works over the course of his career, as he participated in drafting projects administered by the Spanish colonial government, designed and constructed catafalques for state funeral ceremonies, created religious paintings of saints and Marian imagery for churches and for private devotion, painted the official royal portraits for coronation ceremonies, and executed portraits for the highest-ranking members of San Juan society, including governors, their wives, military officers, bishops, and members of the criollo elite. Campeche's illustrious career coincided with an era of cultural transformation in Puerto Rico, when large-scale architectural projects commenced in San Juan to augment the city's defenses and to renovate and reorganize urban spaces in the aftermath of the Seven Years War, and the population of the island increased exponentially through the end of the eighteenth and into the nineteenth centuries. Though Campeche lived and worked during a time of great social, political, and religious change in Puerto Rico and the Spanish Empire, the impact of these transformations and Campeche's role as a social and artistic agent within them has yet to be extensively addressed in relation to his body of work. Most studies that exist on Campeche pursue questions about the artist's biography and training, and attempt to classify his works, establish dates and provenance, and investigate source material with little examination of the artist's lived condition as a colonial subject and its impact on his artistic production. This dissertation seeks to ameliorate the issues evident in the present state of the literature on Campeche and offers a different perspective on the artist's life, career, and artistic production. It endeavors to examine the intersections between the creation and use of Campeche's work, events and conditions specific to Puerto Rico during the late eighteenth and early nineteenth centuries, and the numerous changes taking place concurrently across the Spanish Empire under the Bourbon regime. This project considers Campeche as a complex historical subject of African descent embedded in a colonial system whose lived experiences and artistic production were shaped by and responded to both local and imperial forces and were further informed by the circulation of ideas, people, and things throughout the Caribbean and greater Atlantic World. As such, it argues that Campeche's work provides an important lens into the ways in which he negotiated the opportunities, social realities, and contradictions of his specific late Spanish colonial milieu and served as a simultaneous product and agent of cultural transformation in Puerto Rico.