This chapter uses the sport of rugby to provide examples that demonstrate how the cultivation of creativity can be achieved within high-performance contexts, offering a critical examination of how creativity is enabled through socio-cultural, pedagogical, and environmental influences. Drawing on an ecological dynamics theoretical framework, the chapter reconceptualises creativity as an emergent property of the athlete–environment system rather than viewing creativity as a fixed personal trait. In so doing, the chapter presents a case for cultivating dynamic learning environments that encourage exploration, adaptability, and attunement to affordances. Through empirical studies involving elite-level players, the chapter uncovers the nuanced interaction between players and their environment and how this shapes creative potential. Key themes include the tension between structure and freedom, the importance of self-organisation, and the role of the coach in designing environments that invite variability and improvisation using a constraint-led approach (CLA). Ultimately, this work challenges dominant narratives within sport and offers practical and theoretical insights for coaches, educators, and researchers seeking to nurture more inventive and adaptable players. It provides a compelling call to reimagine talent development through a creativity-informed, contextually grounded lens.