As elected leaders of monastic institutions, abbots and abbesses had to walk a fine line between a monastic lifestyle, in which spiritual devotion and retreat from the world was of paramount importance, and the obligations and priorities of a CEO, with a clear need to engage with the world of politics, finances and other concerns outside of the spiritual realm. Given these sometimes competing responsibilities, the roles played by abbots in the production of art and architecture are not always clear. We would expect that abbots, as institutional leaders, were often responsible for the organization of major architectural projects within the monastery and involved with the creation of at least the more prominent items associated with liturgical performance, but the surviving documentation of artistic and architectural works from the Middle Ages does not offer a clear or consistent picture of how such projects would have been initiated and completed. The extant documentary record raises many questions about how patronage might be used to advance the interests of the entire monastic community, certain individual members of that community, or parties external to the monastery. An investigation of the actions of abbots as patrons can flesh out our understanding of how the visual arts were valued during this period, whether or not the production of certain types of objects should be considered as representative of the culture of the monastery, and the ways in which works of art and architecture could be put to use as political tools. In the case of St Albans, the thirteenth-century writings of Matthew Paris offer important insights into the life of the abbey and patronage of the abbots in the late eleventh and early twelfth centuries. In this essay, I will explore how Matthew's Gesta abbatum monasterii Sancti Albani might enable us to gain a fuller appreciation of the roles that abbots played in constructing the material richness of a monastery. Although almost none of the works of art commissioned during the abbacies of Paul and Richard survive, Matthew's text, coupled with our knowledge of extant works of art from other locations, can be used to visualise and better understand the material contributions of these two early Anglo-Norman abbots of St Albans.