Our objective is to provide two multidimensional models (i.e., contextual-interaction and Ethnic Educator) including sociopolitical, socioeconomic, sociocultural, and sociohistorical factors explaining underachievement in Latinos. First, we critically discuss single-factor theories (i.e., deficit, resistance, social reproduction, cultural mismatch, and macrostructural constraints) explaining underachievement in Latinos. Then we examine Chicago as a multicultural/multilingual city founded by Ellis Island immigrants for making a comparative sociohistorical analysis with contemporary Latinos. Finally, we derive recommendations for researchers to use multidimensional models to uncover new knowledge about the complexity of the sociohistorical problem of underachievement in multicultural and multilingual students, such as Latinos. (Contains 1 figure.)