My aim in this article is to contribute to the discussion about how teachers and coaches come to act in appropriate ways given the complex nature of both practices. I focus on two specific dispositions or qualities from the philosophical literature, namely the virtue of care and the Aristotelian concept of "phronesis" (or practical wisdom), which have been put forward as possible explanations. I argue that care and "phronesis" are fundamental qualities for both good teachers and coaches. Talk of care and "phronesis" in the literature is welcome, but these concepts are themselves complex. Care and "phronesis," like other virtues are context-specific, difficult to acquire (or teach) and their particular expression depends on a host of complex factors, not least one's character and personal and professional experience. I illustrate my argument with reference to a former professional football player who exhibited symptoms of personality disorder from an early age and who presented challenges to his teachers and coaches through his disruptive behaviour.