The Staples High School community inspires learning, fosters integrity, and nurtures empathy.


James D'Amico

James D’Amico is an educational leader devoted to creating opportunities to thrive for all students. His mission is to transform Staples High School into an emotionally intelligent environment for all students and adults who are part of the Staples community.

James began his career at Staples High School in 2001 as a Social Studies teacher. James was named Chair of the Social Studies Department at Staples in 2005, and became the Grades 6-12 Coordinator of Social Studies in 2009. In 2014 James was appointed Director of Secondary Education for the Westport Public Schools. While he found this work intellectually stimulating and enjoyed working on behalf of all middle and high school students in Westport, he ultimately decided that his calling was to work directly with students, teachers, support staff, and parents, and was thrilled to become Principal of Staples High School in 2016.

James enjoys collaborating with colleagues both in and beyond Westport, and counts having served as a writer and reviewer of the Connecticut Elementary and Secondary Social Studies Frameworks, a member of the Westport 2025 task force, a facilitator for Staples’ Performance Assessment Design Initiative team, co-chair of Staples NEASC accreditation self-study, and currently serves as Westport’s representative to the Connecticut Council of Municipalities Education Policy Committee among his professional contributions.

James is a proud UCONN Husky, earning his Bachelor of Arts, Master of Arts in Secondary Education, and 6th Year Diploma in Education Administration from the University of Connecticut.

James resides in Bethel, Connecticut with his wife Jennifer, a third-grade teacher, and his four sons Benjamin, Samuel, Elijah, and Sebastian. In addition to travelling, enjoying and playing music, and camping with his family, James is a dedicated volunteer for youth programs in Bethel. James earned his Eagle Scout award as a teenager, and is especially happy to serve as a Den Leader and Committee Chair for his sons’ Cub Scout Pack.