The purpose of this chapter is to critically examine the “post-critical” turn in educational leadership discourse. More specifically, given the interrelation between critical theory and social justice educational leadership (SJEL), I shall explore the relation between what I have called a dilemmatic approach to SJEL and critical (educational leadership) theory. A dilemmatic approach to SJEL constitutes a particular species of critical theory and thus of SJEL, which deviates in important ways from how SJEL is typically theorized in critical leadership discourse. Rather than grounding critical theory and SJEL on the notions of “diversity,” “difference,” and “inclusion,” a dilemmatic approach centers on moderation. In this conceptual chapter, I shall begin by briefly portraying the development of critical theory in the field of educational leadership and its influence on SJEL. I shall explore the radical “post-critical” turn in educational leadership discourse, and the unfavorable ramifications of employing a radical critical perspective for applying social justice policies and actions. As a first step in connecting critical theory to moderation, I shall first discuss the meaning of moderation and its implications for the field of educational leadership. I shall then discuss the work of Robert Starratt, a prominent voice in the movement of educational leadership discourse toward ethics and critical thinking, and who at the same time, I shall argue, has set the stage for the development of a critical theory and dilemmatic approach to SJEL that is grounded on moderation. I shall conclude by a brief depiction of a dilemmatic model of SJEL, which I argue offers a more comprehensive, nuanced, and self-correcting (self-critical) form of critical leadership theory that is able to address the complexities and ethical considerations that educational leaders face in working toward social justice.