The purpose of this paper is to explore the ramifications of the conflict between two evolving theoretical frameworks in understanding law and community in the Roman worlds. Within the legal sphere, a new strand of research that has sought to distance itself from the earlier state-centered approach, has argued that Roman policy from the Republic to the Principate was that of legal pluralism, allowing local communities to use their own laws. In studies on Roman urbanism, new work has rejected the traditional narrative of Romanization, that the spread of a Roman model of community was the work of colonists sent out from Rome and the willing adaptation of the dominant Roman culture, seeking instead to highlight provincial agency in a globalizing environment. By using examples of the legal implications of Roman expansion, the paper seeks to highlight issues such as applying post-colonial theories to the ancient world, seeking agency from the margins and overcoming the silence of the traditional sources. In doing so, it argues for the situationalizing of narratives and discussions on how actors and groups would frequently talk past each other in what may only be described as creative misunderstanding that would have important consequences for the Roman legal world.