The College of William and Mary (Williamsburg, Virginia) found itself at a crossroads in 2005. Their long-popular president Timothy J. Sullivan was retiring after 13 years at the helm of the world's second oldest institution of higher education (Petkofsky, 2004). Long known as a bastion of conservatism, William and Mary could now change their future course through their newest presidential appointment. The school heeded this opportunity in their final selection of Gene R. Nichol. Nichol, a liberal democrat and former candidate for political office, won over the students, faculty, and Board of Visitors with his larger-than-life presence and impassioned speeches (Petkofsky, 2005). As expected, Nichol attempted sweeping changes at William and Mary from the very outset of his tenure, but these initiatives were not met with widespread acclaim as many had anticipated. In the end, Nichol served as president for a mere two and a half years (Mahoney, 2008a). His tenure was a time of tumult and upheaval, and the culture and traditions of the college were rocked in many ways. This chapter presents the difficulties inherent in altering campus culture by looking first-hand at Nichol's struggles against institutional norms at William and Mary. Nichol's experiences highlight the necessity of understanding and integrating into an institution's culture and incorporating input from multiple constituencies to affect change successfully.