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Demographic projections estimate that by 2065 nearly one third of the American population will be comprised of immigrants and their children. Assessing how these groups are assimilating into mainstream society is integral to understanding patterns of ethno-racial stratification. This study examines assimilation by focusing on the disruptive “turning point” events of arrest, incarceration, high school dropout, and adolescent pregnancy. This investigation tests assimilation theories using the National Longitudinal Survey of Youth 1997, a nationally representative panel study that follows children from adolescence through adulthood. In particular, I compare outcomes for first and second-generation Mexicans and other Hispanics to those of non-Hispanic white and black respondents whose parents were born in the United States. This study employs survival analyses and generalized linear models to capture the elements of timing and sequence in experiencing these disruptive events as well as the probability of experiencing different types of events. In addition to testing for ethno-generational differences, I control for individual and family characteristics as well as the timing of certain life course events. Results indicate that members of the first and second generation are less likely to experience arrest or incarceration than their higher-generation counterparts.