Philanthropy does not exist without democracy in civil society in America. Higher education is a major builder of a civil society. The central research question is: What do university presidents need to know about philanthropy to provide relational leadership supportive of the advancement of democracy in American civil society? The study population included four groups (18 participants): five presidents who lead or have lead universities or colleges, five development professionals who serve or have served specifically in the implementation of the philanthropic process in higher education institutions, four philanthropists who have chosen to align themselves with the mission of higher education institutions, and four researchers and thought leaders who pursue the study of the role that philanthropy and democracy play in American civil society. The method of data collection used was the interview. The participants provided understanding of what philanthropy means and how they engage in philanthropy through their history of experiencing it and enacting it. Participants were asked to elaborate on their experiences in making meaning out of the experiences they have encountered. Through relational leadership, what the participants know about philanthropy and how that influences their advancement of democracy in American civil society was investigated. Interviews demonstrated the interdependence (as opposed to independence) of the interview participant's experiences with democracy, philanthropy, civil society and higher education while involved in leading the philanthropic environment in the community in which they are engaged. A small pool in the philanthropist category was a limitation. The majority of interviews were limited to participants living on the west coast. The qualitative research study has identified four primary and two secondary findings. The primary findings are philanthropy is a mission-driven activity, the president and the chief development officer must act as a team, the president is the center of relational leadership of philanthropy at the university, and the president animates the philanthropic culture at the institution. The secondary findings are the president is the primary advocate for the institutional mission in relationships with donors and the university is a philanthropic voice for building democracy in the community. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]