Across the country, budget cuts to education have resulted in decreased funds available for extracurricular activities. This trend in policy may have a significant impact on future outcomes, as reflected in student success measures. Using two datasets that were collected over the last two decades, in the present study, the researcher assessed the relationship between participation in extracurricular activities and the future socioeconomic outcomes in respondents' lives, including post-secondary education, full-time employment status, and income. Two existing large-scale longitudinal studies of the U.S. secondary students, i.e., the National Education Longitudinal Study of 1988 (NELS: 88) and the Education Longitudinal Study of 2002 (ELS: 2002), served as data sources. As these surveys were conducted about a decade apart, the information they yielded was suitable for meeting the study aims. Generalized linear models, such as multiple regression and logistic regression analyses, by applying sample weights, were performed to examine the impacts of extracurricular activity participation on the aforementioned outcome measures. The implications of the study findings, including the comparison of the results from two different datasets collected at different time points, were interpreted with respect to school budget policy. Results from the NELS: 88 and ELS: 2002 were also compared to evaluate the trends in the characteristics and performance of U.S. high school students during the 1988-2012 period.