St. Anselm of Canterbury is an important figure in the history of both theology and philosophy. However, his distinction as a writer of poetry in his era remains hitherto under-appreciated. The thesis of this work argues that we find in St. Anselm’s body of work a confluence of poetry and philosophy that models a mode of theology valuable to the contemporary context. Utilizing a new Poetic/Dialectic Analytic methodology, it researches the literature that was most influential in Anselm’s monastic culture including the trivium curriculum, Boethius, Augustine, and the Psalmic liturgical tradition. After demonstrating a Medieval confluence of poetry and philosophy, the body of Anselm’s own work is likewise investigated, followed by an in depth poetic/dialectic analysis of his greatest work, the Proslogion. Finally, a discussion of the theontic semiotics of Anselm’s Neo-platonic participatory ontology connects his understanding of God’s nature as the source of all being with a doxological account of language that both articulates and demonstrates a form of theology that is simultaneously poetry and philosophy.