After West Point, Pressler was the head coach at Ohio Wesleyan University (OWU).
After his retirement, Pressler was announced as the head coach for Highland Park High School's lacrosse program.
In his first season at the helm, he led the Scots to a Texas High School Lacrosse League Class AA state championship.
[citation needed] Pressler believed the players were innocent and had argued that the lacrosse season should not be canceled until the DNA test results were returned.
[12] Pressler has written (with co-author Don Yaeger) a book giving his view of the incident, It's Not About the Truth: The Untold Story of the Duke Lacrosse Rape Case and the Lives It Shattered.
[13][14] Then in October 2007, Pressler filed suit against Duke, alleging the university broke the terms of the confidential settlement.
Pressler asserted that Duke broke the terms of the settlement when he was slandered by Duke senior vice president John Burness, who made disparaging comments about him, saying the difference between Pressler and the current lacrosse coach was "night and day."