Phil Rossetti Named High School Assistant Principal of the Year

Phil Rossetti

The students and staff at Windham High School (WHS) in RSU 14 received a surprise morning announcement by Superintendent Chris Howell recently, explaining that the Executive Director of the Maine Principals Association (MPA), Holly Blair was in the building and had good news to share:

“MPA recognizes outstanding high school assistant principals who have succeeded in providing high-quality learning opportunities for their students as well as demonstrating exemplary contributions to the profession,” said Blair during the morning announcement at Windham High School. “After much consideration, MPA has determined that Mr. Rossetti meets those standards and has decided to name him the Secondary School Assistant Principal of 2022.”

Rossetti’s role as assistant principal has made many impacts on the community. Captain William Andrew of the Windham Police Department works closely with Rossetti as a leadership team member for Be The Influence Coalition.

“Phil’s dedication, commitment, and most of all his heart for the betterment of education, the staff, and most importantly the students is what makes this a most deserved award,” said Captain Andrew.

His coworkers enjoy the opportunity to work with Rossetti, including WHS Principal Ryan Caron who has known Rossetti for over twenty years, eight of those years were teaching together at WHS in the social studies department. Rossetti was also one of Caron’s assistant principals at South Portland High School, and now they work together on the administrative team at WHS and have done so for the last four years.

“Phil puts the needs of our students and staff first in all things that he does,” Caron said. “He takes the time to really get to know both students and staff, which allows him to provide support and guidance that is appropriate for the individual while building lasting relationships. When you work with Phil you know that he cares about you and wants the best for you. Students and staff respect his honesty and integrity and believe that he has their best interests at heart.”

Superintendent Howell agrees with Caron and added that Rossetti does a great job mastering the skills and expectations of a vice principal.

“I have known and worked with Phil for close to 20 years,” Howell said. “He is a highly skilled administrator who has a huge heart for meeting the needs of students. Phil has always been able to focus on the big picture as he works to support the students at WHS. I cannot think of a more deserving person for this honor.”

Rossetti said that making a positive change in a student’s life is what motivates him to be the best he can be. “We work to find restorative practices and conversations to turn negative experiences and actions into something positive that create long-term change. People make mistakes and it’s what you do with those mistakes that matters.”

The newly named Assistant Principal of the Year said that his current job is the best job he’s ever had.

Rossetti lives in Raymond with his wife Sara and daughter Maria. When he is not busy at work, Rossetti enjoys golfing and vacationing with his family.