Evidence of a strong negative correlation between adolescent academic performance and mortality points to the importance of not only cognitive, but also non-cognitive, skills in predicting survival. We integrated two bodies of research to evaluate expectations regarding the role of educational attainment and trajectories of employment and marriage experience in mediating relationships between high school class rank and longevity. In particular, we used data from the Wisconsin Longitudinal Study (n = 9,232) to fit parametric mortality models from age 55 to age 77. Multiple mediator models allowed for quantification of the degree to which the association between high school class rank and mortality is mediated by life trajectories and educational attainment. Our results show that high school class rank is a statistically significant and substantively meaningful predictor of survival beyond age 55 and that this relationship is partially, but not fully, mediated by trajectories of employment and marriage experience across the life course. Higher educational attainment also mediates a substantial part of the relationship, but to varying degrees for men and women.