To identify key elements that contribute to the effectiveness of a youth development program, interviews were conducted with 35 former Chicago Youth Programs (CYP) participants who remained in the program until age 18 years and went on to attend college, and 25 participants who left the program (and are currently older than age 18). Of the college participants who remained in CYP until age 18, 97% reported that the program had helped them by providing tutoring, mentoring, and financial support. In comparison, only 56% of the CYP dropouts had completed some college, and nearly 50% reported being involved in illegal activities. Many of the CYP dropouts were drawn to illegal activities for financial reasons or because they felt there was inadequate adolescent programming. All reported benefiting from their CYP participation. Incorporating financial incentives or specific adolescent programming may lead to longer youth program participation and, perhaps, more positive outcomes.