Effective coaching over an extended period of time is the hallmark of an expert coach and correlates with the idea that a significant part of expertise in coaching is based on past experiences and interpretations of those experiences (Bowes & Jones, 2006). The purpose of this multiple case study was, through an exploration of the sport and coaching lives of one expert collegiate wheelchair basketball coach with an acquired physical disability and one able-bodied expert collegiate standing basketball coach, to identify the meanings that expert coaches assign to their sport experiences in developing coaching expertise. A life history approach was used to examine the coaches’ reflections and most meaningful experiences regarding their sporting backgrounds and the processes by which they acquired coaching knowledge. Data were collected through interviews (semi-structured and stimulated recall), field observations, a modified Q-sort interview, and documents. Using analytic induction (Huberman & Miles, 1995), data analysis revealed three themes: (a) a quest for excellence in teaching and learning, (b) building trusting relationships, and (c) moving players to action. The findings provided a glimpse into the lives and development of expertise of two distinct basketball coaches and provides coach educators with an in-depth understanding of how coaches learn in order to develop and implement appropriate and meaningful educational opportunities for coaches of athletes with disabilities.