Roger Di Silvestro was born in Cleveland, Ohio, and raised in Nashville, Tennessee. He received his bachelor’s degree in psychology from the University of Kentucky in 1972. Di Silvestro served as CEO for Athlon Sports Communications, a media company specializing in publishing and sports marketing, and retired in 2006 after 30 years with the company. In 2005, Di Silvestro co-authored "The Art of Constructive Confrontation," a methodological guide to building productive personal and professional relationships with reduced conflict. Today, he spends the majority of his time traveling the world and teaching constructive confrontation.

Di Silvestro was an initial member of the College of Arts and Sciences Dean’s Advisory Board. He is a lifetime member of the UK Alumni Association. In 2004, he created the Di Silvestro Professorship, dedicated to enhancing research excellence within the College of Arts and Sciences. Di Silvestro was instrumental in building the first YMCA Teen Center in Nashville, Tennessee. He has remained devoted to the YMCA “We Build People” program that operates safe and educational childcare programs throughout middle Tennessee. He was recognized by the College of Arts and Sciences in 2004 for his volunteer and philanthropic involvement. Di Silvestro has one son who is scheduled to graduate from UK in 2015.