Orthodoxy and heresy in psychoanalysis continuously interact with and inform each other according to a principle of mutual influence. Greenberg’s seminal contributions to psychoanalysis reflect his commitment to a ceaseless dialectical tension between orthodoxy and heresy. The analyst’s heresy/orthodoxy matrix is suggested as a way of conceptualizing this tension, one that is applicable to the personal and intellectual journey of every analyst. Resisting adjudication as well as enduring and being enriched by cacophony are among the guiding principles of Greenberg’s vision of comparative psychoanalysis and an explicit focus in his most recent work. In my reading of Greenberg, maintaining an optimal tension between orthodoxy and heresy is a core intellectual value.