[1] After serving in the Army, Willard returned to his alma mater, St. Dominic High School in Oyster Bay, New York, to be a physical education teacher.
During his tenure there he led his team to the 1980 state championship, posted a 162–89 record, and earned five conference coach of the year honors.
When Willard left Hofstra, he became a member of the Syracuse University staff that appeared in the NCAA national championship game in 1987.
Willard briefly joined Rick Pitino as a member of the staff of the National Basketball Association's New York Knicks.
[2] He held this position until 1999 when he returned to his college alma mater at Holy Cross where he had been a member of the class of 1967 and the captain of the 1966–1967 men's basketball team.
[3] Willard's success at Holy Cross continued as he led the school to two more conference titles and subsequent trips to the NCAA tournament in 2002 and 2003.
During his tenure as the school's head coach, the Crusaders averaged more than 19 victories per season and advanced to the conference tournament championship game six times.
[3] On June 10, 2009, Willard became an associate head coach with the University of Louisville to team once again with longtime personal friend Rick Pitino.