In this essay, we contend that there continues to be a lack of attentiveness in educational leadership and policy to addressing how critical educators "emotionally" navigate social and political issues generally, and racism particularly--both of which are emotional issues. As such, using brief examples of reflections from critical educators in urban educational leadership, we conduct a theoretical textual analysis of "emotions" in a time of heightened emotion, using the 2015 Baltimore Uprising as a case. In our critical-humanities-oriented essay, we focus on documenting narratives as large social concerns. Our theoretical treatment of emotion reveals the ways such treatments can be applied to school leadership for the purposes of praxis on critical practice in times of widespread conflict. These concerns include matters of emotional labor in educational sites (as microspaces permeated by racial turmoil unfolding in macrospaces). We foreground how racial (in)justice in educational leadership and policy is inherently an interplay of emotions that is sometimes dichotomous. Our observations mark a radical shift in how critical researchers and stakeholders conceptualize policy and political matters in schools.