The purpose of this study is to examine how and to what extent an afterschool program for marginalized youth assists in developing workforce readiness skills through a critical positive youth development (CPYD) framework that considers the social contexts of youth. There is little research on afterschool programs that prepare youth for the workforce, even less on such programs serving marginalized youth and the role that their social contexts play in programming. Because of this, we are limited in our understanding of whether and how these programs work to prepare this population for the workforce while also providing them with the support they need to navigate the obstacles they will face as a result of their socio-economic status. A qualitative case study design that employed CPYD, a twenty-first century skills learning framework, and performance pedagogy was used to explore the Winners Initiative of New Jersey, Young Professionals Academy (YPA), an afterschool program that serves primarily marginalized youth. The study sought to understand how this program operates from the perspective of program participants, past and present, and stakeholders via the collection of program artifacts, interviews, focus groups, and in "real-time" through observations. The sample included a total of twelve student participants and three adult staff and volunteers. The following research questions guided this study: (1) What is the pedagogy and curriculum of the program? (1a) Does the program pedagogy and curriculum promote workforce skill development in its participants? If so, how? (2) Does the program pedagogy and curriculum align with CPYD? If so, how? (2a) In what ways does this alignment with CPYD help develop students while considering their social contexts? The findings from this study suggests that (1) workforce skills were developed through the program's performance-based pedagogy and curriculum, namely, improvisation activities, (2) the core elements of the CPYD framework, such as supportive relationships and empowering roles, were intrinsic to the program's pedagogy and curriculum, and (3) the program used elements of CPYD to address issues related to segregation, resource disparities, and stereotypes. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]