Literature on philanthropy in higher education is limited, especially concerning the philanthropic behaviors of college and university trustees. We address gaps in the literatures on higher education philanthropy and university trustees through an exploratory comparative case study of donations made by trustees and trustee-affiliated organizations. Drawing on microfoundations theory from neoinstitutionalism, we argue and show that trustees and trustee-affiliated organizations, via their philanthropic behaviors, shape the universities they steward in a myriad of ways. Within our case study, we analyzed donation exchanges across four elite research universities to develop three models of trustee philanthropy (facilitators, supporters and patrons) and two models of trustee-affiliated organizational philanthropy (sponsors and advocates). Differences across institutions highlight the variation across trustees, trustee-affiliated organizations, and universities in how they engage each other in philanthropic relationships. Drawing on these differences, we generate suggestions for practice and future research.