There are perhaps too many articles written about Chaucer. Blasphemous, I am sure, to even suggest such a thing, but the very idea of dissecting The Canterbury Tales and attempting to discern an ultimate, single meaning from them contradicts the very thing Chaucer was getting at in their creation — namely, the absence of that metaphorical pearl. We, the inheritors of the Western canon and the analytics of narrative nuance, have become Chaucer’s pilgrims; we are an audience seeking truth in the words of Chaucer just as the pilgrims seek truth through the stories they tell and hear along the road to Canterbury. What scholars, for the most part, have failed to recognize is that Canterbury, both the physical place and the spiritual ideal, is a goal that can never be realized. While there are many that hold that, should The Canterbury Tales be a more complete and cohesive body of work, we would be able to ascribe to them a more concrete and overall moral. If Chaucer’s other works are any indication, the opposite is true — it is the absence of catharsis, the absence of an objective truth (or, at the very least, the absence of an accessible objective truth), which is reflected in the narrative structure and a thematic undergirding throughout Chaucer’s works, that signifies a larger purpose for the story that is not at all hindered by the incompleteness of it. This body of work will investigate the historical context and theological discourse of the fourteenth century which influenced Chaucer’s work and the way in which Chaucer uses the narrative structure of the Canterbury Tales to reflect the subjective approach to morality and biblical interpretation that he is advocating for. This critical analysis serves as a guide for my own creative project, which begins on page 22.