This thesis builds on my work as an educator in the small city of Hudson, NY. It is focused on two dominant narratives about urban development in our city: the story of revitalization, and the story of risk. I begin by unpacking the celebratory story of Hudson's revitalization, drawing on oral histories to consider all that this story forgets, and the structural factors and conditions that it obscures. I examine the consequences of equating gentrification with economic health, and instead consider how what we call "revitalization" is inextricably bound with deepening inequalities. I then look at the construction of "at risk youth" to understand how our language justifies the erasure and displacement of marginalized communities necessary to this kind of economic development. I consider how young people, and especially youth of color, are imagined as both at risk of failing school, and as risks themselves to the city's growth. I utilize the lens of risk to examine the racial imaginaries that shape how we see and understand space, and the ways that seemingly race-neutral language and landscapes serve to produce and maintain racialized inequity. After examining the context of revitalization and risk in Hudson, I make an argument for the critical role educators can play at the intersection of community organizing, youth work, and urban development. Reflecting on the work of Kite's Nest, a center for liberatory education in Hudson, I consider how we can develop teaching pedagogies that aim not only to transform the experiences of young people, but also the places we live.