In this study, I focus on three varying perspectives to understand the assimilation process of immigrants and how it affects their academic achievement. I draw from Classical Assimilation Theory, Segmented Assimilation Theory and the Immigrant Paradox. I utilize the High School Longitudinal Study of 2009 to assess whether academic performance increases or decreases across successive immigrant generations. I also assess how factors such as bilingualism, family socioeconomic status, parental and student expectations might affect the relationship between generation status and achievement. Results from OLS regression models with a Huber White correction find support for the Immigrant Paradox, which asserts that earlier immigrant generations outperform later immigrant generations. I also found that the level of bilingualism moderates the achievement gap between immigrant and third generation students. Specifically, the immigrant advantage is especially large when students have a medium level of bilingualism. Additionally, results show that family SES moderates generation status by reducing the achievement gap between immigrant and third generation students from higher SES backgrounds. Data show that parental and student expectations are strong predictors of student achievement. When interacted with generation status, I find that the immigrant advantage is reduced for children of parents who have high educational expectations.