Reflective judgment, since Arendt’s lectures on Kant’s aesthetics has received a wide political reading. Besides its applications, one theoretical aspect revealed by judgment consists in opening up a radically distinct perspective on the alternative between ideal and non-ideal justice. The validity of judgments, indeed, by being subtracted to the fulfillment of abstract principles can be best characterized by the non-replicable singularity of its formulated occurrences. It is precisely such non-replicability that subtracts judgment validity from a compliance to ideal conditions. Exemplarity, in fact, allows for the possibility of a case-by-case adjudication versus what would be a mechanical application of a norm. By being context-sensitive and by looking at what is the best solution within given circumstances, reflective judgment does not recur to a normatively idealized scenario in order to prove its validity (such as it is for instance the Habermasian ideal speech situation or the Rawlsian hypothetical contract/original position). On the contrary, judgments confront particular points of view without renouncing to some form of positional impartiality. The non-ideal form of justice that judgments disclose are what Wittgenstein has defined in terms of the capacity to “look through” phenomena by remaining within phenomena themselves. The implications of this change of perspective is far reaching in case of theories of justice. First, due to the intersubjective nature of judgmental activity, as well as to its contextual sensitivity, reflectivity of judgment seems strictly interconnected to discourse-practices in as far as this is interpreted differently from a paradigm of discourse theory; secondly, the narratives accompanying the formulation of a valid judgment connect the emotional and imaginative patterns of memory (re)constructions with the intellectual pretence of a subjectively universal agreement. Even though judgment validity is contingent and limited in space and time, universal communicability (Kant) is thus so regained.