This commentary explores some of the most pointed criticisms of the "No Child Left Behind" (NCLB), and of high-stakes standardized testing more generally. The author focuses specifically on the impact of NCLB on urban schools -- schools which are the constant focus of reform in a culture that presumably wishes to educate its citizens in the most democratic, equitable fashion possible. The first section of this commentary broadly considers the inherent flaws and inequalities built into the NCLB testing philosophy in urban public schools, as well as its potential impact on children as young as preschool-aged. The second section considers the content of several tests and the absurdity of many of the questions we expect students to answer -- especially students of diverse cultures, linguistic and learning backgrounds who make up the majority of urban public school populations. The third section looks at what we, as a nation, are willing to pay for in comparison to other government spending, and considers whether and to what extent NCLB combats inequality in education (it does not). This section considers more closely the financial inequities inherent in our educational system and explores why NCLB is powerless to correct them and how, as the title of this commentary suggests, this legislation may even increase them.