The so-called “weak thought”, theorized by the Italian postmodernist philosopher Gianni Vattimo (born in 1936), considered one of the most important Italian philosophers, has dismantled the main concepts on which Western philosophy was based (that is, the notion of Truth, God, Reason, an absolute foundation to thought, etc.). This philosophy, which is inspired by Nietzsche’s nihilism, by Heidegger, and by the philosophy of hermeneutics and deconstruction, offers a critical starting point not only to rethink, in a less rigid way, our Western culture, its philosophy, and its problems, but also the ethical principles and educational values that guide human life. Sport - as a human phenomenon and philosophical problem characterized by the presence of values, norms, behaviors, and rules that involves the action of human beings who interact and communicate “in” and “by” the game - can also be read in the light of this emerging philosophical theory. The aim of this study is to demonstrate that weak thought and its fundamental categories can be used and applied from a theoretical point of view in order to interpret and understand sport, deconstructing its meanings and its sociocultural and educational values. Using the critical contribution of weak thought, in this study we will reflect on and rethink in a new way some of the main concepts considered absolute and fundamental to sport’s logical and philosophical structure, such as “winning” and “losing”, “referee” (which embodies the principle of “authority”), “opponent”, “freedom” in the game, “rules”, and respect when one plays. The purpose of this study is to undertake a critical reflection on the limits of the concept of sport proposed by the Western tradition and to lay the foundations for a new model of ethics and education for the sports of the future.