In the post-Byzantine period, the rulers of the north-Danubian principalities of Wallachia and Moldavia, through their monetary gifts and donations, played central roles in the continuation of religious life within and beyond the borders of their domains. This essay charts the patterns of patronage of two key donors – Neagoe Basarab of Wallachia (r. 1512–1521) and Peter Rareș of Moldavia (r. 1527–1528; 1541–1546) – in order to underscore their piety and the broader implications of their activities. Through the extant textual and material evidence, this study engages with aspects of the desires, collaborations, and effects of patronage from these two important rulers within Wallachia and Moldavia, respectively, and to far-off places like Mount Athos and the monastery of Saint Catherine at Mount Sinai. This study reveals a complex web of personal, spiritual, and ideological facets of leadership and identity that shaped a culture of donations and piety rooted in Byzantine models and transformed in local contexts through the desires and ambitions of each individual ruler.