This qualitative study examined how NFL players and their family members characterized the impact of an NFL career on the mental and emotional health of NFL players. We interviewed 25 NFL players (23 former and 2 current) and 27 family members (24 wives and 3 others) to elicit players’ experiences during and following their time in the NFL. While players experienced positive outcomes from their careers, they also described important mental health challenges including feelings of depression, loneliness, and stress. Many of their concerns during their careers were linked to anxiety about job performance and job security. Post-career concerns were linked to loss of social identity and connections. Players had difficulty finding help for their concerns. We conclude with eight recommendations, including improved resources, confidentiality, and support.