Among all forms of city planning, the grid plan appears, historically, to be the most measurable and recognizable system of civic geography. This paper will explore how and why different social groups have been able to define the symbolism of the grid to suit their own political purposes and how governments and patrons have utilized the grid as the spatial manifestation for their political ideologies. This paper will be based on case studies of cities operating under very dissimilar political systems, i.e., the cities of ancient China and the city of Chicago in the Unites States. I argue that the American grid plan focuses on its peripheries, and that the expansive instinct of the American grid was effective in building a coherent American nation, transcending regional and class divisions. By contrast, the Chinese grid plan emphasizes the center, and the practices of urban planning in ancient China symbolized the evaluative tactics of the elite.