The use of leadership programs as interventions for at-risk youths has recently gained attention in popular media and psychology literature. This type of intervention presupposes that changes in personality style as well as developmental assets can be cultivated through leadership programming. Although current literature supports the benefits of mentoring and increased community involvement for at risk youths, there is limited research available about personality changes that may occur as a result of participation in leadership programs. The present study focuses on the C5 program, a five-year leadership program for at-risk youths from inner-city areas. A cross-sectional design sampling from participants in each of the five years of the program was used to assess potential personality changes that may occur while participating in the program. In the summer of 2008, participants from each class at the two sites (total N = 316) completed the Adolescent Personal Style Inventory (APSI) and the Developmental Assets Profile (DAP). The APSI is based on the five-factor model of personality style. The DAP questionnaire is based on a developmental assets model of protective factors for youth. It was hypothesized that increased length of participation in the program will lead to significant growth in Emotional Stability, Openness to Experience, Conscientiousness, Agreeableness, and Extraversion relative to normative data. In addition, it was also predicted that developmental assets of personal, family, social, school and community contextual domains will significantly increase proportionate to length of participation in the program. Results of the present study revealed that although the mean scores of C5 participants are significantly higher than the normative sample in nine of ten variables, there was no significant growth relative to age/gender based norms for the C5 participants in either the APSI traits or the DAP contexts. This pattern of consistently higher scores in the C5 participants suggests there may be a selection bias in the C5 population.