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Winchester School Committee chair Tim Matthews honored with inaugural Commonwealth Pride Award

Supporters say his advocacy in Winchester extends beyond schools, including work tied to the town’s Human Rights Commission.

From left, Timothy J. Matthews holds his daughter, Rose Matthews-Sawicki, alongside his son, Jacob Matthews-Sawicki, and his husband, Dr. Greg Sawicki, in the Massachusetts Senate Chamber at the State House in Boston on Wednesday, June 17, after Matthews received one of the first Commonwealth Pride Awards from the Massachusetts LGBTQ+ Legislative Caucus. COURTESY PHOTO / TIM MATTHEWS

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Timothy J. Matthews was honored at the State House for being visible. He used the moment to talk about being erased.

Matthews, the openly gay chair of the Winchester School Committee, was named to the first class of Commonwealth Pride Award recipients on June 17, an honor created this year by the Massachusetts LGBTQ+ Legislative Caucus.

State Rep. Mike Day nominated him; by Matthews’ own account, the ceremony arrived less as a celebration than as a charge.

“For myself and my family, joining with progressive leaders and legislators from across the Commonwealth was an inspiring reminder of why the vital work we do to advance equity and inclusion for all is essential, particularly while efforts to silence our voices and erase our impact are underway at the federal level and across the United States,” Matthews said.

He said it as a school leader and as a father, putting his family at the center of his remarks.

Timothy J. Matthews stands beside a ‘MA Proud’ banner at the Massachusetts State House on Wednesday, June 17, where the Massachusetts LGBTQ+ Legislative Caucus presented him with a Commonwealth Pride Award. COURTESY PHOTO / TIM MATTHEWS

Day said the choice was about character as much as title.

“I nominated Tim because he personifies what Pride Month is about: making everyone in our community feel welcome, valued and safe,” Day said.

Day credited Matthews’ visibility and voice with reassuring children and parents, day-to-day, that the district’s diversity is a strength and that the town is better for celebrating it.

“We could all do well with a little more kindness in our lives, and Tim brings that to us with his words and with his actions here in Winchester,” Day said.

The recognition lands as Matthews holds two roles that do not always sit easily together: the chair steering a school system through tight budgets, and one of the most visible LGBTQ+ officials in his town.

His standing in Winchester was built first on reading, not Pride. Matthews won his seat on the committee for the 2024-2027 term, and he came to it as a psychologist and literacy researcher: he co-authored a 2016 article, “Reading and Language in the Early Grades,” in the journal Future of Children with Harvard professor Catherine Snow, examining how literacy develops in young children and which practices help them learn to read.

In 2024, pressing the district to move faster on curriculum, he argued that Winchester children should have “updated, evidence-based, cutting-edge curricular supports.”

He took the gavel this spring and said the committee would work “with urgency and transparency” through the hard choices ahead. He runs the board with Vice Chair Stefanie Mnayarji, who works closely with him.

His equity work, supporters say, predates the recognition.

Anthea Brady, chair of the Winchester Select Board, worked with Matthews on the effort to create a town Human Rights Commission and described him as a steadfast supporter of human rights and social justice. She said he spoke up for the commission as the town built it and guided others to voice their own advocacy.

“Tim is unfailing in speaking truth to power and sharing his lived experience to issues that unfold in town,” Brady said.

Timothy J. Matthews, chair of the Winchester School Committee, stands in the Massachusetts Senate Chamber on after being named to the inaugural class of Commonwealth Pride Award recipients. COURTESY PHOTO / TIM MATTHEWS

Brady, who led the Human Rights Commission effort before taking the Select Board’s gavel, said the town is fortunate to count Matthews, his husband and their children as residents.

Matthews is married to Dr. Greg Sawicki, a physician and member of the Winchester Board of Health who chaired that body until this spring and now serves as a regular member. Their children are Jacob Matthews-Sawicki and Rose Matthews-Sawicki.

Their public lives have run on parallel tracks: Sawicki stepped back from the Board of Health chair this spring, the same season Matthews stepped up to lead the schools.

The caucus, a group of state lawmakers, created the award this year and drew its first class from across Massachusetts. Matthews was recognized during Pride Month, in June.

The honor changes nothing about the fight Matthews named. He goes back to the School Committee, the advocacy and the family he put first when he accepted it — his husband and their two children — Jacob and Rose.

Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He is also the founder and editor of The Marblehead Independent, a reader-funded digital newsroom.

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter. Copyright 2026 Winchester News Group, Inc. Copying and sharing with written permission only.

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