There is an uneasy relationship between fundraising for academic programs and intercollegiate athletics. This has little to do with individuals and almost everything to do with circumstances in higher education in the United States that have come into play in recent decades. This chapter identifies issues presidents will confront as they seek funds for academic programs and intercollegiate sports. In spite of difficulties, models for successful practice do exist. Two prevailing models are noted, along with some illustrations of good practice. (Contains 2 tables.)