This study reported an Outcome Mediation Cascade evaluation of the Changing Lives Program (CLP), a positive youth intervention. This study examined the effects of participation in the CLP on positive outcomes (Personal Expressiveness and Well-Being) and negative outcomes (Internalizing and Externalizing problem behaviors) as mediated by Identity Distress. 137 females and 101 males comprised the sample of this study, which draws from archival data of adolescents in alternative high schools in Miami. Findings indicated that the hypothesized model fit the data (χ2 (11) = 14.544, p = .020; RMSEA = .04; CFI = .995; SRMR = .028). Findings also provided preliminary evidence consistent with the hypothesis that in addition to having effects on targeted positive outcomes, PYD interventions are likely to have progressive cascading effects on untargeted problem outcomes.