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Sen. Jason Lewis says he’s looking forward to new challenges, new opportunities after retirement

Education has been at the top of Sen. Jason Lewis’ public service, from his initial run for the House of Representatives in 2008 to his current chairmanship of the Education Committee in the Senate. On Feb. 24, Lewis announced he would not be seeking re-election in the fall of 2026. COURTESY PHOTO/OFFICE OF SEN. JASON LEWIS

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Winchester will have two new senators come January 2027. First, Sen. Pat Jehlen decided not to seek re-election in the 2nd Middlesex District. And now, Sen. Jason Lewis.

“It’s not a decision to be made lightly,” Lewis says on Feb. 24, just hours after releasing news he will also not be seeking re-election this fall. “I’ve been thinking about it for a while. I’ve been so grateful to have had this opportunity, serving my constituents and improving the Commonwealth. I don’t believe in term limits, but I thought it was just time.”

Sen. Jason Lewis speaks outside the State House on educational issues facing the state. COURTESY PHOTO/OFFICE OF SEN. JASON LEWIS

Lewis represents the 5th Middlesex District, which encompasses Malden, Melrose, Reading, Stoneham, and Wakefield and Precincts 1, 2, 3, and 8, in Winchester.

He says there was no one factor in his decision, calling the choice to serve “a very personal decision.”

“There are a lot of expectations and responsibilities, and there should be, but you have to give it your all,” Lewis says. “For me, this felt like the right time to start a new chapter.”

Picking up the mantle

Lewis has been in office since 2008 when he ran in the 31st Middlesex District, the seat currently held by Rep. Michael S. Day. He had already served on the Winchester Finance Committee during the ‘90s.

But two issues on the state level drew his attention in 2007 and Lewis knew he had to throw his hat into the ring when Rep. Paul Casey left after 20 years.

“It was a time when there were cuts in Chapter 70 funds and in Winchester, that meant the schools had to lay off school librarians,” Lewis recalls. “The district asked for parent volunteers to help keep the school libraries open. That shocked me and my wife.”

Lewis calls the experience “eye-opening.”

Sen. Jason Lewis speaks before colleagues in the Senate about childhood literacy. COURTESY PHOTO/OFFICE OF SEN. JASON LEWIS

The other issue that drew him was the issue of marriage equality.

“There was a lot of debate at the time about whether Massachusetts would continue to embrace that,” Lewis says.

His interest in civil rights went back to having been born and spending some of his childhood in South Africa during Apartheid before his family came to the U.S. in 1980.

“I saw the cruelty and the impact it had on people of color,” Lewis says, adding that led to his activism in civil rights. “It motivated me to seek public office.”

Lewis knocked on thousands of doors in both Winchester and Stoneham, where he says he not only met a lot of people, but learned so much about the district.

After his win, he was sworn into office at the House of Representatives in January 2009.

“It was a shock for my family,” Lewis recalls, with a laugh. “I had never thought of running for public office. No one in my family had run for public office. It was a big change.”

It is not always about being serious. Here, Sen. Jason Lewis takes time out for a selfie. COURTESY PHOTO/OFFICE OF SEN. JASON LEWIS

Switching houses

 It will come as no surprise to anyone who knows him or his record, but Lewis threw himself into his House duties. But the resignation of Hillary Clinton as secretary of state in February 2013 set off a chain reaction that reached down through the Massachusetts political structure — and offered him an opportunity.

It was like musical chairs.

Clinton’s leaving caused then Sen. John Kerry to be appointed to the secretary of state position, leaving his seat open.

Long-time Congressman Edward Markey ran for and won Kerry’s former seat, leaving his job open.

That gave then state Sen. Katherine Clark, of Melrose, the opportunity to run for Markey’s former job, which she then won.

With us so far?

Sen. Jason Lewis speaks to residents following a Veterans Day event. COURTESY PHOTO/OFFICE OF SEN. JASON LEWIS

Lewis says it was a great opportunity to make the jump from the House to the Senate.

“I loved serving in the House, but the Senate had an appeal,” he explains. “The benefits are that it’s a smaller body so there’s more respect and influence. Plus all the senators have a committee chairmanship from day one.”

From day one, Lewis was assigned as the chair of public health, then Labor & Workforce Development where he helped negotiate the Grand Bargain in 2018, and then to his current position as head of the Education Committee. The last one led him to get the Student Opportunity Act passed.

What’s next?

The Student Opportunity Act is one of two issues Lewis plans on pursuing throughout the rest of his tenure in office. His last day will be Dec. 31, 2026.

“There’s are so many things that I still need to focus on,” he says. “I still plan to serve out my time and serve the constituents.”

But if he had to pick? Yes, Lewis admits, he wants to continue pushing for adequate funding for the education in the state.

He says the Student Opportunity Act, which he was instrumental in writing and helping pass in 2019, will have its final implementation during the 2027 state budget.

“The question is what comes next?” Lewis says, of education funding. “The plan is to fund every [community] and providing high quality education to every student.”

Civil rights for everyone is something Sen. Jason Lewis has always championed. Here, he speaks at Winchester PRIDEfest in October 2025. WINCHESTER NEWS FILE PHOTO

And his other issue?

“We really need to address single-use plastics,” Lewis says. “That has increased tremendously over the years.”

He calls it “a plague” on the environment and public health.

“Last session, the Senate passed a bill that I helped put together that addressed single-use plastics,” he says. “The bill didn’t make it all the way through the legislative process, but I want to continue to push for it.”

With all these issues still on his plate, you would think it would be difficult for Lewis to whittle down all his accomplishments to one issue that defines him as a legislator.

“Can I pick two?” he asks, laughing. “I think there are two policy areas that I’m most proud of because they not only improve the lives of the people in my district, but also across Massachusetts.”

The first is the passage of paid family and medical leave, which allows residents to take time off their jobs to tend to health issues while still being paid a salary and without losing their jobs.

The second is the Fair Share Amendment, more commonly referred to as the “millionaire’s tax,” which was passed by Massachusetts voters in 2022.

“I was the lead Senate sponsor,” Lewis says. “I worked on that for about 10 years.”

Because of the amendment’s passing, Lewis says the state has been able to provide universal meals for kids in grades K-12, make community college education free for students and put funding towards infrastructure projects, such as improving the MBTA.

It’s quite the list. But Lewis could talk about all the accomplishments and changes he’s helped make in the state during his tenure.

Sounds like he’s going to miss it all.

“Of course!” he says, when asked. “I love what I do!”

But it’s a lot. And Lewis says while he’s enjoyed the experience of public service, it’s a weighty responsibility.

“You represent about 180,000 people,” he says. “And I do my best to serve the needs of my constituents.”

But again, it’s just time to go.

“It’s an exciting job to have,” Lewis admits. “And there’s really a lot to miss about it, but I’ve had a good run and I’ve enjoyed the time I’ve had.”

As the news of his retirement decision spreads throughout Winchester, Lewis says he’s had a lot of people reach out via telephone, text, email and social media.

“People are definitely surprised,” he says. “They have been very gracious, thanking me for my public service. I’m feeling very touched by that.”

Gov. Maura Healey visited Winchester in August 2025 to announce statewide funding for affordable housing projects throughout the state, including in Winchester. Sen. Jason Lewis was among the speakers at the event. WINCHESTER NEWS FILE PHOTO

What does he plan to do once it’s all over and he moves into 2027 as a private citizen?

“I have no definitive plans, but I’m excited about all the different possibilities,” Lewis says. “Maybe I’ll do some teaching and youth mentoring. I’d like to be involved with more of the local non-profits in town and offer ways to support their work.”

But he does have one very personal goal.

“It’s a high goal,” Lewis laughs. “I want to complete an Ironman before I’m 60!”

Nell Escobar Coakley has been a journalist for more than 30 years. She is co-founder and editor-in-chief of Gotta Know Medford and editor of Winchester News. She can be reached at editor@winchesternews.org.

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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