Winston Daley Makes Milton History with Select Board Win
Winston Daley now holds a seat on the Milton Select Board — the town’s top leadership group. He’s the first Black person ever elected to this role in Milton’s 365-year history.
“Sometimes walking in, I can’t believe I get to do this,” Daley shared. “I think I’m still kind of shocked. But once I get into the meetings, I’m good.”
His election was part of a competitive local race in April, where he joined newcomer Meghan Haggerty as a winning candidate. Now, Daley sits at the decision-making table, ready to serve the people who trusted him with their vote.
A Journey from Jamaica to Massachusetts
Daley’s road to public service began thousands of miles away in rural Jamaica. His mother left behind a stable career as a bank manager to start fresh in America with him and his sister.
“My mom wanted to move us here just for opportunity,” he said. She took night classes to learn computers and worked as many shifts as she could. Daley remembers attending those classes with her, watching her adapt to a new life.
Back then, Jamaica only had one TV channel. Now, decades later, Daley leads in a town once unfamiliar with someone of his background sitting in such a high office.
Education and Hard Work Built His Path
Daley arrived in Boston at age 10 and grew up in the Allston-Brighton neighborhood. He went to Alexander Hamilton and Thomas Edison elementary schools, not knowing much about their namesakes at the time — only that he loved to learn.
He worked hard and made a name for himself as a strong student. His family, including his mom and relatives, all found jobs at the Woolworths in downtown Boston, a place that “had everything,” he recalled with a smile.
That foundation of grit and community pride helped shape the leader he is today.
Representation and Responsibility Matter
Daley understands that his win means more than a seat at the table. It signals a shift for a town with centuries of tradition. He sees it as a moment of deep meaning for people who rarely see themselves reflected in local government.
“I’m not from a lot of people who feel they are worthy of or should ask for positions like this,” Daley admitted. “To me, it’s a really big deal… to have people vote for and entrust me with their support. It’s not something I take lightly.”
His election is not just about change — it’s about possibility. He hopes to show others that civic leadership is within reach, no matter where you start.
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