This article presents both sides of the debate as to whether urban teachers need structure or freedom, and then takes a stand on urban teaching in the current high-stakes assessment climate. First, we trace the 30-year development of American educational policy in the area of structuring teaching. Then, we present research from proponents of structuring the work of teaching, who argue that education, and particularly urban education, needs to be standardized and monitored. We then share literature from teacher freedom proponents who argue that educators need to adapt their curriculum and pedagogical approaches based on students’ needs and their own professional judgment. We conclude by arguing that urban teaching needs to be structured to promote freedom, in light of recent developments in the often-ignored fields of neuroscience and neuropsychology.