“What are you prepared to do to win?” This is a question that any serious competitor will at one time or another have to consider. The answer that one is inclined to make, I shall argue, is revealing of the deeper character of the individual participant in sport as both physical competitor and moral person. To that end, I examine one of the classic responses to the question, gamesmanship, which can be characterised as an attempt to win one game by (...) playing another. I contend that gamesmanship is a deliberate strategy of competition that has certain paradoxical outcomes; while it may produce an enhanced competitive environment that calls forth superior performances from participants, its more aggravated manifestations are in the long term athletically self-destructive for those who rely on them as a competitive device, and argue the presence of more profound underlying moral failings as well. (shrink)