2021 Retirements

Karen Wilkerson, Preschool
Aideen Hunt, Lincoln
Terri McGuire, Lynch
Krissy Greco, Lynch
Liz Christo, Lynch
Chrissy Tarantino, V-O
Jeanine Freimont, V-O
Phyllis Greenspan, McCall
Jane Sheehan, McCall
Dorothy Duff, WHS
Lis Angus, WHS
Tom Haver, WHS
Bob Trakimas, WHS
Gail Texin, WHS
Freda Canavan, District
Pam DiMatteo, District

Each school year we typically pause to recognize district teachers who are retiring this year or plan to retire over the next school year. Below is a summary of each, and you will note that many of our 16 retirees have worked in Winchester schools for decades and have made immeasurable contributions to the lives of countless students and families. We wish them much happiness and good health in the coming years.


Karen Wilkerson,

In her sixteen years as an educator in our integrated preschool, she always managed to strike that balance between nurturing and challenging her students. She supported parents by offering down-to-earth, sensible advice on everything from behavior management to “how-do-I-get-my-child-to-sleep?” She was instrumental in: bringing Winchester High School Spanish students into the preschool to enrich our program; guiding future early childhood educators; and supporting her colleagues with professional development opportunities. Karen brought imagination and energy to her work every day, and did it all with kindness and grace.

Lincoln School

Aideen Hunt worked as a dedicated and skilled grade 5 teacher since 2006 and will be greatly missed by colleagues and families. We wish her much happiness in her retirement.

Lynch School

Terri McGuire has touched the lives of students and families alike with her positive energy, endless dedication, and innovation since 1985! We thank her for 36 years of countless memories, smiles, learnings, and acts of grace which she and “Bumpy” have spread across the school.

Krissy Greco who has spent 33 years calling Winchester Home. Since 1988 Ms. Greco has touched the lives of students at Lynch, Muraco and VO. Her positive energy and attitude will be missed.

Liz Christo has dedicated over a decade to students and families at Lynch. Her creativity and imagination has brought joy and new learning to students and staff alike.

McCall Middle School

Phyllis Greenspan has worked in the Winchester Public Schools as a dedicated and caring adjustment counselor since 2002. Phyllis worked closely with town and community groups to support many children and families during her time in Winchester.

Jane Sheehan was an enthusiastic and skilled math teacher at McCall Middle School for 12 years. She brought energy and caring to this role and will be greatly missed by her colleagues and students.


Chrissy Tarantino started as a substitute teacher in 1986 in Winchester. In September of 1987, she started as a Kindergarten teacher at Vinson Owen. Mrs. Tarantino has shared that she feels so blessed that she’s had the honor of teaching the same grade, in the same school and (essentially) in the same classroom for 34 years.

Jeanine Freimont started teaching in Winchester in 1987. She taught at Lynch, Muraco, Lincoln and then in 1997, she came to V-O and stayed! Mrs. Freimont has taught Kindergarten and Second Grade, but since 1997 she’s been teaching Kindergarten at V-O. She has had many students from the same family and has even taught a few of the younger teachers in the Winchester Schools. Mrs. Freimont shares that the favorite part of her day is sharing stories with her students. The connection between those who share a story is a very special gift.

Winchester High School

Dorothy Duff has been a dedicated Speech and Language Pathologist working with many special education students Grade 9 through the Post Grad Program at WHS. Dorothy has been a cornerstone in the special education department, helped to establish the PACCES program for social pragmatics/communication students, and has been a champion for so many students throughout the district. We wish Dorothy the best in retirement.

Lis Angus is a 30 year veteran teacher of Physics. Her dedication to high standards and to helping students reach those high standards helped build the reputation of

excellence that is Winchester High School. A lot of students found a kindred spirit in Lis, and they learned more Physics because of that connection. What you may not know about Lis is that she is a very talented musician and she hopes to play keyboard and sing in her well-earned retirement. As Lis would say, “Just Ride the Wave!”

Tom Haver served as the math director from 2004 to 2019 and as a teacher for the past two years. Under Tom’s leadership as the director, the Math Department expanded its course offerings to include AP Stats, AP Computer Science Principles and AP Java, among other courses. He also led the department in the development of integrated courses for grades 9 and 10. Tom led many conversations about the accuracy of the presidential polling and the significance of the electoral college.

Bob Trakimas is best known for his love for teaching Honors Precalculus and his ability to make connections with students. He challenged students to reach their potential and incorporated real life math applications into his lessons. He especially liked teaching bearings and probability as well as preparing the students for the SAT II subject tests. Bob has his golf clubs ready to go!

Gail Texin taught a wide variety of 9th and 10 courses over the past twenty years. She enjoyed working with students and encouraged them to think mathematically. She spent considerable time making sure her lessons were accessible and always brought her enjoyment of math to the classroom. Gail is looking forward to spending more time with her children and grandchildren. Rumor has it she has a one-way ticket to California.


Pam DiMatteo worked as a dedicated speech and language pathologist in the district since 2005. In this crucial role she supported teachers and special educators to help students gain essential skills. Her focus on meeting the needs of individual students and families made a great difference for so many students in helping them meet with success.

Freda Canavan, long-time assistant to the superintendent, will retire later this year. Freda started working as a lunchroom supervisor at the Lynch School in 1990, then worked as a secretary in the early childhood and special education office. She has been the School Committee secretary for many years and moved to the superintendent’s office in 1996. Freda has enjoyed working with five superintendents and is known for her empathy and attention to customer service.