Transnational migration is a controversial and much-discussed issue in both the popular media and the social sciences, but at its heart migration is about individual people making the difficult choice to leave their families and communities in hopes of achieving greater economic prosperity. Vicente Quitasaca is one of these people. In 1995 he left his home in the Ecuadorian city of Cuenca to live and work in New York City. This anthropological story of Vicente’s migration and its effects on his life and the lives of his parents and siblings adds a crucial human dimension to statistics about immigration and the macro impact of transnational migration on the global economy. Anthropologist Ann Miles has known the Quitasacas since 1989. Her long acquaintance with the family allows her to delve deeply into the factors that eventually impelled the oldest son to make the difficult and dangerous journey to the United States as an undocumented migrant. Focusing on each family member in turn, Miles explores their varying perceptions of social inequality and racism in Ecuador and their reactions to Vicente’s migration. As family members speak about Vicente’s new, hard-to-imagine life in America, they reveal how transnational migration becomes a symbol of failure, hope, resignation, and promise for poor people in struggling economies. Miles frames this fascinating family biography with an analysis of the historical and structural conditions that encourage transnational migration, so that the Quitasacas’ story becomes a vivid firsthand illustration of this growing global phenomenon.