Transition from professional sport to nonsport endeavors has implications for postcareer health and well-being of athletes. The purpose of the current study was to examine associations among transition-related psychosocial factors and current mental health outcomes in former National Football League (NFL) players. Participants were former NFL players (n = 1,784; mean age = 52.3 ± 16.3 years) who responded to a questionnaire assessing the nature of their discontinuation from professional football (i.e., any degree of voluntary choice vs. forced discontinuation), prediscontinuation transition planning (yes vs. no), and current symptoms of depression and anxiety. After adjusting for relevant covariates, having an involuntary discontinuation and no transition plan prior to discontinuation were associated with greater depressive and anxiety symptom severity. Autonomy in discontinuation and pretransition planning are important to former NFL football players’ mental health. Increasing autonomy in the discontinuation decision and pretransition planning represent psychoeducational intervention targets for this population.