At the end of the Thirty Years’ War (1618–48), Raimondo Montecuccoli (1609–80), an Italian military entrepreneur in Austrian Habsburg service, attempted to transition from a career on the battlefield to a career at court in Vienna. In 1653, he won a diplomatic assignment to Queen Christina of Sweden’s court, which allowed him to showcase his political skills and abilities. However, Montecuccoli’s mission changed dramatically when Christina abdicated the Swedish throne, moved to the Spanish Netherlands, and converted to Catholicism. At Christina’s request, Montecuccoli made several trips to the Spanish Netherlands and Rome from 1654 to 1656, evolving into Christina’s confidant and advisor while continuing to serve his Habsburg patrons. This study examines Montecuccoli’s journal and letters in the context of early modern entrepreneurialism, networks, and imperial ideals in order to investigate the ways a military contractor navigated politics and what sort of influence such an individual wielded beyond the battlefield.