WHS’ Rossetti a finalist for national assistant principal award

Windham Assistant Principal Phil Rossetti 
has been named as a finalist for the
National Assistant Principal of the Year
Award. SUBMITTED PHOTO

The Maine Principals’ Association has announced that Maine Assistant Principal of the Year, Philip Rossetti, Assistant Principal at Windham High School, is a Finalist for the National Assistant Principal of the Year Award.

Rossetti will be honored by the MPA at its annual awards banquet at their Spring Conference on April at the Samoset Resort in Rockport.

The national finalist announcement highlighted Rossetti’s belief that people make mistakes, but it’s what they do after that defines who they are. He’s used this principle to transform how Windham High School manages student behavior, focusing on restorative justice to hold students accountable and repair the harm they caused their school community.

This restorative approach has improved school safety and reshaped school culture, fostering stronger relationships between students and turning mistakes into opportunities to learn.

Reflecting on Rossetti’s selection as a 2022 NASSP Assistant Principal of the Year Finalist, MPA Executive Director Dr. Holly Blair praised Rossetti.

“It is exciting that Mr. Rossetti has been recognized by the National Association of Secondary School Principals (NASSP) as a finalist for the National Assistant Principal of the Year,” Blair said. “This is the first time that Maine has had a finalist in the program. Mr. Rossetti is an exceptional Assistant Principal and very much deserving of this honor. We are very proud of him.”

Rossetti started his educational career as a social studies teacher at Windham High School in 1996. In 2015, he became the Assistant Principal of South Portland High School before returning to Windham High School in 2016 where he continues to serve as Assistant Principal.

During an interview in December, Rossetti said that he had encouraging mentors and loving family members who helped guide him along the way.

“I was lucky to have good teachers and people who cared about education during my high school years,” Rossetti said. “Plus, I had very supportive parents who encouraged me to get an advanced education.”

Rossetti, who lived most of his childhood life in Casco, explained that both of his parents came from a long line of hardworking people, and although his mother and father’s traditional education ended early, they believed in the power of conventional study and held grand hopes of high achievement for their son.

“They believed that the only way to my own success was through education and encouraged me to go to college,” Rossetti said. “They told me they wanted me to have the opportunities that they didn’t have.”

In addition to his parents’ encouragement, Rossetti had a very engaging history teacher at Lakes Region High School where Rossetti’s formative years were created.

“It was the way my history teacher taught classes that made the lessons enjoyable,” Rossetti said. “Plus, he was one of those teachers who really cared about you. He was very encouraging to the students and wanted his students to succeed. This inspired me to follow in his footsteps. I remember thinking to myself one day, ‘I want to be a teacher just like him.’”

He is currently a member of the Maine Principals’ Association (MPA) and the National Association of Secondary School Principals (NASSP) and also serves as an assistant football coach for the school. <