Four instructors reflect on teaching large scale online sport sociology courses at a major Midwestern public research university in the Trump era. We provide an autoethnographic perspective from the perspective of one faculty member, one doctoral candidate, one doctoral student, and one first year doctoral student of some happy surprises as well as major and common pitfalls in attempting to engage and teach undergraduate students in critical analysis of sport through two separate courses with enrollments of 750 each. We also reflect on the role of the institution and the role of the instructor as they complement and contradict each other. This includes our engagement in course group-discussion assignments with students who represent a range of political standpoints and our attempts to support underrepresented students in those class discussions.
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