Early sport specialization has been shown to increase the risk of overuse injuries in several sports, including baseball. Overuse injury can be challenging to define; therefore, a patient-reported outcome measure may be useful in determining throwing arm health over time. Major League Baseball and USA Baseball established the Pitch Smart guidelines related to pitching volume, rest, and participation to promote safe practices in youth baseball. However, compliance with these guidelines is not required. Qualitative research methodologies may provide additional insight into athlete motivation by learning about lived experiences of playing sports during an athlete’s formative years. Therefore, the purpose of this study was to determine differences in Kerlan-Jobe Orthopedic Clinic (KJOC) Shoulder and Elbow scores in college baseball athletes based on their age of specialization, as well as whether the athlete was compliant or non-compliant with the various Pitch Smart guidelines while pitching in high school. Another purpose of this study was to learn more about athletes motivations and sports experiences using qualitatrive methodologies.