Support Winston Daley for Milton Select Board: A Leader for All

Milton’s town elections are fast approaching, and as candidates step forward, one name stands out for his consistent dedication and heart—Winston Daley. His candidacy for the Milton Select Board is more than a political decision; it reflects years of service, integrity, and deep love for our town and its people.

A Leader Who Shows Up for Milton

For over a decade, Winston has been deeply engaged in Milton’s civic life. Whether coaching youth sports, launching programs at Tucker Elementary, or serving on town committees, he leads by example. His leadership is rooted in action, reliability, and showing up, time and again.

Winston has helped strengthen youth programs, served on the Milton Foundation for Education, and currently holds roles as a Parks and Recreation Commissioner and Town Meeting Member. He has never sought attention; instead, he has focused on uplifting others and helping to build a better Milton.

A Vote for Winston Is a Vote for Milton’s Future

Too often, decisions in Milton have been made behind closed doors, without transparency or real community input. Winston offers something different: honest, collaborative leadership grounded in fairness and inclusion. He’s not here for personal gain, partisanship, or privilege. He’s here to move Milton forward—for everyone.

As Winston puts it, “I will find common ground with anyone.” He believes the Select Board sets the tone for how Milton operates—and how we treat one another. It’s time to move past zero-sum politics and division. We need unity, progress, and leadership with heart.

Professional Experience That Matters—Now More Than Ever

Winston brings valuable experience in finance, investment, education, and nonprofit leadership. With over a decade of experience in financial services at State Street, BNY Mellon, and Brown Brothers Harriman, he has developed expertise in long-term planning, budgeting, and risk management. He later launched a startup to diversify the education workforce and remains active in tech and investment circles today.

This unique combination of financial insight, entrepreneurial spirit, and community dedication is exactly what Milton needs. As we work to recover from recent instability and damage caused by leadership missteps in the Select Board and other committees, we can’t afford the status quo. In these turbulent times, Milton needs leaders who are both competent and compassionate, and who are accessible to their constituents. Winston is that leader. 

Fresh Energy, Real Experience

Milton is filled with talent—educators, healthcare workers, technologists, tradespeople, parents, and community builders. For the past few years, we have been trapped by outdated ideas and have continued to face negative results, including a fiscal mess, a divided culture, and unnecessary partisanship in our cherished town. Now, more than ever, we need leaders who combine personal excellence with experience to inspire and rejuvenate our sense of collective responsibility and engagement.

Winston brings new energy and lived experience in finance, nonprofits, education, and the startup sector. As a father and a homeowner, he understands what’s at stake. Every decision we make now affects the future of our children and our community. Winston is ready to lead with vision, humility, and boldness.

A Call to Action

This election is bigger than one vote—it’s about the kind of Milton we want to be. Winston Daley has the courage, experience, and heart to help us move forward. He’s already proven his dedication to our town. Now it’s time for us to stand with him.

Let’s come together and elect Winston Daley to the Milton Select Board. Let’s build a Milton that listens, includes, and grows together.

Disclaimer: The views expressed here are solely my own. I have not been paid or influenced by Winston Daley or his campaign. This is an independent and genuine expression of support, rooted in Winston’s long-standing commitment to our community.

— “Uncle” Bou Ba Cardieme

Community Advocate & Resident

This is a promotional sponsored story.  

The views expressed in this piece are those of the author/advertiser and do not necessarily reflect the views of The Milton Scene.