Background: The 3 WINS Fitness is a free exercise program delivered by kinesiology students to underserved communities without external funding since 2011. The program’s wins focus on reducing health inequities, increasing community health, and student professional development. The objective of this study was to conduct a qualitative evaluation of the program’s value for the participant, community, and student-instructors. Methods: We conducted 9 online focus groups (n = 51), categorized by participant role and timeline in 3 WINS: participants (4 groups), student-instructors (3 groups), and combined participants and student-instructors (2 groups). Data collection for this remote qualitative study of the 3 WINS program occurred May to June 2021. The data were analyzed to determine codes and emerging themes. Results: Three main themes are presented: asset, health, and social connection. The asset theme was subdivided into subthemes: (1) professional asset for the student-instructor, (2) program asset for the student-instructor, (3) program asset to the community, and (4) program asset for the participant. The health theme was subdivided into (1) community and (2) personal health subthemes. The social connection theme was defined in any combination, as camaraderie, friendship, connections, community, and family. Conclusion: The program improves the individual participant’s health and through role modeling for their family and friends, encourages others to follow their example thus providing a positive influence on overall community health. Concomitantly, student-instructors are developing into well-trained professionals. The 3 WINS as a student-led sustainable and replicable model can address the existing call from public health to reduce physical activity health-related diseases and inequities.