Conflicts over the politics of speech have been a persistent challenge in U.S. higher education. Public narratives portray universities as antagonistic toward conservative speakers, yet empirical evidence remains limited. To address this gap, we analyze the political orientations of 1,875 commencement speakers at 52 universities between 1989 and 2024. Findings indicate a rise in liberal speakers, particularly since 2011, and a higher prevalence of conservative speakers at public institutions and universities with curricular emphases on occupational and professional fields. External environments of universities, including partisan control of state governments, citizen ideology, and disinvitation efforts from both political left and right, also shape speaker selection. Universities strategically navigate ideological landscapes to maintain legitimacy while reflecting organizational values.