Olympic-medal performances represent peak accomplishments in athlete development. Seanor, Schinke, Stambulova, Ross, and Kpazai identified environmental factors in a high-performance Canadian trampoline sport environment that developed decorated Olympic medalists. The current intrinsic case study was authored to further highlight the idiosyncrasies of a high-performance trampoline environment (re)presenting stories garnered from this localized Canadian sport environment. Through guided walks, a mobile method of conversational interviews, three contextual experts who are engaged in the development of Olympic athletes provided tours of their sport environment. Each contextual expert’s guided walk played out uniquely in relation to his or her ascribed role (i.e., Olympic coach, assistant coach, and Olympic champion). Three main themes were identified through interpretive thematic analysis: creating lift (subthemes: facility design, sport-culture paragons), providing a tailwind (subthemes: establishing athlete–coach partnerships, team interactions), and soaring onto the Olympic podium (subthemes: preparing athletes to be untethered, competitive collaboration). Each theme is presented through three portrait vignettes, with discrete vantages derived from each contextual expert to illuminate the context from idiosyncratic ascribed roles within the environment. These stories create a rich (re)presentation of a high-performance sport environment through the interplay of the contextual experts’ narratives, their surrounding context, and their Olympic-podium accomplishments.