It is nearly an article of faith in literary criticism and legal scholarship that Western considerations of Eastern societies demonstrate the drive toward, as Edward Said put it in Orientalism, “dominating, restructuring, and having authority over the Orient.” This essay revisits that question of West and East in two of its most prominent guises: medieval literature and modern law. It does so be examining two narratives, the first of which is Chaucer’s “Man of Law’s Tale,” a piece of Canterbury Tales related by an English lawyer that expressly measures the stature of a governing monarch in the Muslim world against concepts of sovereignty embraced by Christianity. The second narrative is the First Circuit Court of Appeals decision in Ungar v. Palestinian Authority, a piece of judicial writing that expressly measures the stature of a governing administration in the Arab world against the concept of sovereignty embraced by an American court applying international law. It is the aspiration of this paper that by setting a 14th century story up against a 21st century judgment, significant portions of Western thought dealing with non-Western societies can be canvassed at once, and that the ‘orientalism’ thesis about the West’s perceptions of the East can be put to the test.