He is "one of the most prolific authors in the history of the Naval Institute Press in terms of sold books.
[2] Cutler enlisted in the United States Navy in 1965 and rose to become a Gunner's Mate Second Class.
While at the United States Naval Academy, serving between 1981 and 1990, where he was senior lecturer and Executive Assistant to the Chairman of the Seamanship and Navigation Department, and later, Associate Chairman of the History Department, he was awarded the William P. Clements Award for Excellence in Education (military teacher of the year).
[3][2] Cutler founded and served as the first Director of the Walbrook Maritime Academy in Baltimore, also commanding the Naval Junior Reserve Officer Training Corps unit there.
In 1981, he became an associate editor of the United States Naval Institute and rose to become the Institute's Director of Professional Publishing and currently holds the Gordon England Chair of Professional Naval Literature.