This dissertation focuses on two miya mandara depicting the sacred geography of the Kumano region of Japan (late-thirteenth/early-fourteenth centuries). It demonstrates that the paintings were produced at Onjōji, a Tendai Buddhist temple in the eastern foothills of Mount Hiei, and owned by Shōgoin, its sub-temple in Kyoto. These temples were affiliated with the Jimon branch of Tendai associated with the esoteric cleric Enchin (814-891)), and were, by the time of the production of the mandara, in heated doctrinal, institutional, and political dispute over independence from the Tendai headquarters at Enryakuji. Three primary issues related to the mandara are addressed. First is the purpose of their production. The dissertation questions earlier claims that miya mandara primarily functioned as visual tools allowing mental visits to depicted sacred sites in place of expensive and arduous pilgrimages. Rather, it argues that the Kumano mandara were part of a larger contemporaneous discourse that included other forms of written and visual materialssuch as the Ippen hijiri-e and Tengu zōshi handscrolls, Shugen shinanshō, and petitions to courtand represented an orchestrated attempt to promote the spiritual superiority and legitimate the institutional autonomy of Onjōji over Enryakuji. Viewed within this context, two atypical features of miya mandara found in the Kumano mandara can be understood: the inclusion of a portrait of Enchin and of the esoteric Diamond and Womb World mandala. Lineage and power being inseparable in the religious and political culture of medieval Japan, the dissertation argues that the purpose of their placement in the Kumano mandara was to claim that the superiority of Onjōji was rooted in both Enchins Jimon lineage and his form of esoteric Tendai centered at the temple, and that each, in turn, valorized and legitimized Onjōjis claim for superiority over all other temples, especially Enryakuji. Finally, the dissertation takes up the problem of another portrait found in the mandara, which has been identified (without substantiation) as the Shingon esoteric priest Kūkai (774-835). The dissertation contests this attribution, which is inconsistent with its other findings, and offers possible avenues of pursuit for identifying this damaged and controversial portrait.