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Knowledge of philanthropy in higher education is limited, particularly concerning the philanthropic engagement of trustees. To address this we explore the philanthropic engagement of all members of the boards of trustees at four elite research universities using a comparative case study that incorporates social networks and qualitative analysis of exchanges. Results show that trustee philanthropy varies widely, ranging from no evidence of engagement to engagement which shapes institutional practices. Furthermore, evidence suggests that trustee philanthropic engagement is a means by which institutions obtain or maintain advantage within the increasingly stratified field of higher education. These findings refine our understanding of trusteeship and philanthropy while also highlighting the need for institutional policies that account for the varied levels of engagement.