 In 1969, he graduated from East Longmeadow High School in East Longmeadow, Massachusetts, and received a Bachelor of Science degree from the United States Naval Academy in 1973.He also holds a Master of Science degree in engineering management from Old Dominion University and was a fellow at MIT's Seminar XXI.An F-14 naval aviator, Willard served consecutively in Fighter Squadron 24 (VF-24), Fighter Squadron 124 (VF-124), and Fighter Squadron 2 (VF-2) at NAS Miramar, deploying aboard , , and .