New Principal Named At Staples High

After a nationwide search for the next principal of Staples High School, the top candidate turned out to be a very familiar face.

A few minutes ago, the Board of Education approved the selection of James D’Amico. He was one of 3 finalists for the position.

James D'Amico

James D’Amico

D’Amico is intimately familiar with Staples. A highly regarded social studies teacher there from 2001-2009, he also served as grade 6-12 social studies department chair from 2005-2014.

In 2014, D’Amico was named assistant superintendent for secondary education. His office was in Town Hall, but he remained a familiar presence at the high school.

Superintendent of schools Dr. Elliott Landon made the decision after weighing several factors. They included understanding “the very complex culture of Westport”; experience in a large high school with excellent academics, arts, athletics and extracurriculars; experience as a department chair and district administrator, and respect from colleagues.

D’Amico’s “knowledge of our high school is incredible,” Landon said. “And his background and record are exciting. He has intelligence, patience, a reflective mind and an incredible vision for the future.”

Board of Education chair Michael Gordon echoed Landon’s praise.

Staples sealD’Amico is “brilliant academically, but also very human. He has a big heart, is a great listener, and is balanced and thoughtful,” Gordon said. “He’s a strategic thinker, but also willing to make hard decisions. Staples will be lucky to have him, now and for the long term.”

Accepting the position, D’Amico called Staples “our crown jewel. We will do extraordinary things. This is great honor — and responsibility.”

He pledged that the high school will be “a role model for what public education can be.”

D’Amico certainly knows the school he’ll be leading. As a faculty member, he earned high ratings — 4.35 out of a total of 5 — on a sometimes-snarky teacher rating website. Among the comments:

  • Cool teacher. Cool guy.
  • Really cool teacher, lets you be yourself in class and does not attempt to steer the class dynamic….He thinks of really fun activities for the class. He is a good grader and he will always listen to you for your opinions or thoughts.
  • awesome. hes funny, clear, fair grader.
  • Mr. D is AWESOME. hes really funny and a good teacher
  • Mr. D is pretty cool and does fun activities with class
  • HE IS SO AWESOME…really good at explaining things…just sometimes the test questions are tricky
  • He’s really funny and an excellent teacher. Follow directions and you’ll do really well in his class.
  • Mr. D is awesome. Ask him to sing you his song, it rules. AP US is unreal…everyone should take it…

D’Amico majored in educational leadership and administration at the University of Connecticut. He worked in the office of orientation services, as a resident assistant, and was active in the marching band.

After graduating in 1998, D’Amico earned a master’s degree in secondary education and a 6th year in education administration, both also from UConn.

At Staples he was advisor to the Junior Statesman Association. He is also an assistant den leader for his son’s Cub Scout pack.

D’Amico succeeds his former boss, John Dodig, who retired last June after 11 years at Staples’ helm. Mark Karagus has served as interim principal for this school year.

D’Amico assumes his new post on July 1.

In its 132 years, Staples High School has seen many principals. James D'Amico is its newest.

In its 132 years, Staples High School has seen many principals. James D’Amico is its newest.

16 responses to “New Principal Named At Staples High

  1. Tom Haberstroh


  2. Wonderful!

  3. Andrea Moore

    Great news for Staples!

  4. Great news. It’s about time they hired from within.

  5. This “Mr D” sounds like a fantastic torchbearer from my principal, Jim Calkins. I wish him very well in his new post.

  6. Steven Halstead

    Great news!
    A great choice for Staples and Westport.

  7. Stephanie Ostroff

    I had the good fortunate of being one of the founding members of Staples JSA during the 2008-09 school year. I’m confident I speak for everyone who was part of our chapter when I say that Mr. D’Amico was not only an advisor and mentor, but a friend. We all have the utmost respect for him, and I am thrilled with his selection as principal. I look forward to seeing him excel in this role.

  8. Morgan Patrick

    This is fantastic news for Staples — such a wonderful choice!!!

  9. Betsy Pollak

    GREAT news! Made my day 🙂

  10. I do not know Mr. D’Amico, but the praise from his former students speaks volumes and it is about time that the Westport School District looks within, instead of passing over respected and qualified internal candidates.

  11. Amy Schafrann

    Congratulations to Mr. D’Amico! I do remember he was a wonderful teacher for our daughter and had great relationships with his students.

    And Dan, I continue to value you and your blog as all things Westport – covering old and new, good and bad so I am happy to contribute!

  12. Mr D’Amico is a superb choice to be the Principal of Staples High School. He has experience with curriculum development, instruction, use of technology in the classroom, supervision, and much more. Most important to me, however, are his love and respect for students, and great respect for teachers.

  13. Loretta Hallock

    I agree with Dave Eason that it’s about time we hired from within. We have so much talent here and at least we know what we are getting.
    Good luck Mr. D’Amico!!
    Loretta(Staples class of 62)

  14. Michael McGovern


  15. Beverly Breault

    Congratulations Mr. D’Amico. I’m a Graduate of 1952. I know many D’Amico’s. You must be related.. Great people.

  16. Briana DeVito

    Being a 2006 Staples graduate, and having Mr. D’Amico as my social studies teacher back in 2002, assigning him as principal was the right choice. From what I remember, he was a great teacher who not only cared about his students but would always be there to assist faculty with anything they may need. Congratulations Mr. D’Amico, you deserve it!