Yeshiva University faces a pivotal moment as its president, Rabbi Dr. Ari Berman, is scheduled to deliver a benediction at President-elect Donald Trump's inauguration. This choice raises questions about the values that guide the university today, as Trump's history of divisive rhetoric and actions contradicts YU's ethical and spiritual ideals. While some argue that alliances with imperfection may be necessary for Israel's security and the fight against antisemitism, others believe that this moment is not one for a rabbi, especially considering YU's own moral failures. The juxtaposition of YU's past as a champion of Jewish moral and intellectual leadership and its current willingness to sacrifice its values is troubling. The question remains whether YU will reflect and redirect or continue on its path toward moral bankruptcy.