During the months leading up to and immediately following President Donald Trump’s election, the unique intersection of classroom academic freedom and teacher and students’ first amendment rights would be duly tested, as headlines reminded citizens, parents, and pundits that the reach of raw emotions and political viewpoints did not stop at the schoolhouse door. School and classroom-based events would eventually test the norms of community, the interpretation of legal precedents, the resolve of district and school leadership, and the rights or limits thereof of the teachers themselves. This analysis is grounded on case studies of eight such incidents, all of which occurred at the high school level in public school districts. These eight cases are analyzed in terms of the incidents, the teacher’s actions or speech, the consequences, the relevant legal precedents surrounding academic freedom, the parental, student, and community reaction, and the short- and long-term impacts moving forward.