Senior leaders whose job it is to advance the work of public colleges and universities frequently position and leverage the work of their institutions as serving the public good. In doing so, there are frequent references made to the potential role of philanthropy in transforming society by focusing institutional attention on its most daunting challenges. This paper reflects on how transformational giving relates to the expansion of the public university mission and examines how engagement with society in addressing its problems creates new opportunities as well as challenges for giving relationships. It falls to university presidents and senior advancement leaders to pay close attention to the ways that significant gifts set universities on a course of change. The paper challenges traditional approaches to higher education's role in responding to complex societal issues, and helps to clarify two often-used but misunderstood concepts in the advancement profession--transformation and transaction.