This article interrogates the question of what it means to be a scholar-commentator in the digital age. Deploying an autoethnographic style, the essay asks about the role of power and responsibility in teaching, research, and public commentary, particularly in the context of studying and engaging in Jewish politics. The article addresses questions about the proper role of the scholar in the academy and the role of subjectivity and political commitments in structuring scholarship, pedagogy, and public engagement. It also examines how one’s view of the profession can seem to shift through the emergence of new writing outlets and new forums for public engagement. Finally, the author investigates how a scholar’s own political commitments can shift over time, how one seeks to shore up identification on social media while trying to change hearts and minds through the op-ed pages, and how community identification can serve as a buffer and motivator for particular forms of research and political action.