The fundamental difference between the positive sciences and philosophy is that the former cannot be fully self-critical. The limits of the self-criticality of the positive sciences consist of their fundamental demand to presuppose an ontological platform from which to employ their methodology. In this way, sports science, in all of its productivity, rests on the platform, postulated by modern physics, of the “mathematicization” and “quantifiability” of the natural world. Philosophy fulfills its second order function as it critiques and clarifies these basic platforms for study. Transcendental philosophy, however, in addition to acting as the clearing house for the positive sciences, has explanatory power. This project employs transcendental philosophy, not in its critical, but in its explanatory function. Transcendental philosophy comes in various forms, however, the difference depending on the use of logic. The fundamental difference between formal and transcendental logic is that the former is deductive, and the latter is descriptive. Transcendental philosophy in the Kantian tradition examines the a priori conditions for the possibility of experience in an attempt to ground the sciences; it does so deductively making use of formal logic. Transcendental philosophy in the Husserlian tradition examines the original sense-giving sources of subjectivity that ground and accomplish all scientific knowledge (2: p. 5); it does so descriptively making use of transcendental logic. Therefore, to employ Husserlian phenomenology in an attempt to explain the phenomenon of play requires an internal, descriptive account of playing. Philosophies of play, even in the arena of sport, have been quite fruitful. In The Question of Play, Drew Hyland proposes a philosophical account of play, which is ontological, as contrasted to other ontical accounts of play via history, psychology, and sociology. Hyland’s contention is that a philosophic “stance” of play is one of “responsive openness” (5: p. 47). My project differs from his insofar as I do not want to describe the essential structures and stance of play in general, a task his account does quite well. I do not intend to add something to the concept of play. Rather, I want to describe and account for our ability to play at all. I imagine that I am not alone in marveling at the abilities of the elite athlete to hit Roger Clemens’s fastballs and return Andy Roddick’s serves, but my amazement includes even my own ability to play. Thus, whereas my description will be from the perspective of the experienced subject, it will not only apply to extraordinary phenomena, but to the experience of all athletes who truly play. This stipulation of true play allows me to define in this article what in fact constitutes true playing.