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This study examines Total Osprey, a digital badge program designed to enhance career readiness among NCAA Division I student-athletes. Grounded in Identity Theory, Social Cognitive Career Theory, and Competency-Based Education, the program supports identity transition and skill articulation through modular, verifiable micro-credentials. A mixed-methods evaluation of the pilot cohort (N=289) revealed strong engagement and promising outcomes in career development, self-efficacy, and job preparation. Results highlight digital badging as a flexible, scalable tool for addressing the unique career challenges student-athletes face. Preliminary findings demonstrate feasibility and relevance, with implications for national replication. This work contributes to the scholarship on student-athlete development and provides a practical model for integrating career preparation within collegiate athletics.