This research sought to uncover challenges that arose in the implementation of the Reflective Educational Approach to Character and Health (REACH) after-school programme in a low-income public school in New York City. Additionally, we wanted to find and share some of the lessons learned, to help others avoid our pitfalls when implementing quality after-school programming. At the conclusion of the year-long REACH programme that was preceded by a year-long pilot, the lead researcher interviewed six key stakeholders: (a) the coach; (b) an academic tutor; (c) the director of REACH; (d) two after-school teachers/leaders within the school; and (e) the assistant principal of P.S. 780 (pseudonym). We employed a qualitative case study approach. Field notes from observations, researcher journals, emails, and multiple interviews were used to triangulate data. Two coders first independently coded and analyzed the data using the constant comparison method, followed by a peer reviewer to further establish credibility and trustworthiness. Three themes are presented from the data analysis: (a) bridging community dynamics and REACH; (b) needing community involvement; and (c) role modeling through cultural competence. These three themes are analyzed through a lens of culturally responsive pedagogy and a new theory of positive youth development through sport. These data present a detailed account of the implementation of a sport-based after-school programme in an urban environment. The paper presents the challenges faced in the implementation of such programmes as well as lessons learned in the process.