The aim of this paper is to examinate risk as a philosophical strategy in the works of Jacques Derrida and Jean-Luc Nancy, starting from the criticism that Derrida submits to the use of Touch in Nancy's works, contained in one of Derrida's latest books, On touching, Jean-Luc Nancy (Stanford University Press, 2005). In this work Derrida deconstructs Phenomenology of touch throughout Philosophy, but at the same time highlights what possible weaknesses may bear touch as a concept and as a sense. This weakness of touch comes from it's risky chance of being reappropiated by the Metaphysical discourse that would define it on the basis of an Ontology of Presence. Derrida points that Nancy risks himself with it's confidence on Touch, the concept and the sense, and because of this it may return all the work under the claim of the Metaphysical tradition in Philosophy. But, since Derrida criticises Nancy and claims that he is a gambler, a risky gambler, we made a quick review of Derrida's previous works, to find if this risk metaphor has something to do with deconstruction. We found that even grammatology risks not being born at all, nor as a science or as a project, because of the risks involved in working with words of Metaphysics. Many appeareances of risk can be found in Derrida's works, and most, if not all of them, have some duty to do with the philosophical strategies or tactics that Deconstruction puts to work, to maintain the undecidability of aporias. This is something that Derrida claims even for the biographical relations to his own works. So, starting from this point of view, risk may not be some cheap critic to a deconstructive discourse, but mostly a different way of integrate, without synthesizing, the works of Derrida and Nancy.