Leadership development is important for society, and participating in athletics and student organizations has provided opportunities for young adults to develop and display leadership qualities (Dobosz & Beaty, 1999; Knoppers, 2011; Todd & Kent, 2004; Williams, Roberts, & Bosselman, 2011). The empirical research examining the leadership development through athletics and student organizations involvement has, unfortunately, been limited. Thus, the purpose of this study was to identify and investigate the relationship among gender, athletic involvement, and student organization involvement in relation to transformational leadership skills. Stratified random sampling and the Salant and Dillman (1994) survey methodology procedure were adopted for data collection. Data were collected from 992 college students (493 females and 495 males) in a Mid-Atlantic university. The Transformational Leadership Scale (Hellriegel & Slocum, 2004) was used as the instrument to measure the variables. Descriptive statistics and factorial ANOVA were used for data analysis. Results showed significant differences existed among gender, athletic involvement, and student organization involvement in relation to transformational leadership skills. Females, athletes, and student officers received significantly higher scores than males, nonathletes and nonstudent officers in transformational leadership.