We examined the association between context of entry into the United States and symptoms of depression in an older age Mexican-origin population. We found that context of entry was associated with the number of depressive symptoms reported in this population. Specifically, immigrants who arrived to the U.S. following the Mexican Revolution (1918-1928) reported significantly fewer depressive symptoms, and those who arrived following enactment of the Immigration Reform Control Act (1965-1994) reported significantly more symptoms of depression, compared to those who arrived in the Bracero era (1942-1964). These findings suggest that sociopolitical context at the time of immigration may be associated with long-term psychological well-being. They contribute to a growing body of literature that suggests that the context of immigration may have long-term implications for the health of immigrant populations. We discuss implications of our findings for understanding relationships between immigration policies and the health of Mexican immigrant populations.