This article concentrates on the educational experiences of urban and suburban Mexican American youth, from recent immigrants to those that have been in the United States for generations. The article seeks to unravel the relationship between acculturation and school success by offering a holistic and longitudinal approach of three time periods: 1974, 1988, and 2004. The dynamics of Mexican American acculturation and adaptation differ across populations (People), environmental settings (Place), and across the three time periods studied (Time). The diversity of physical space, social locations, and ethnic identities within the Mexican American population needs to be recognized within such an analysis. This article highlights policy and practice designed to impact the largest ethnic minority group in the United States, a population constantly facing changes.