Benjamin Reif-Caplan

Benjamin ("Ben") Reif-Caplan is honored to serve the Monterey community and is committed to helping the town navigate its future thoughtfully, collaboratively, and responsibly.

Ben's connection to Monterey runs deep. His ties to the town come through his wife, Jessica, whose mother and stepfather, Elliot and Ika Reif Small, were longtime, proud members of the community. Jessica introduced Ben to Monterey over 25 years ago, and he's been sharing in that pride ever since.

Today, Monterey is a central part of Ben and Jessica's family life. Their children, Moshe and Mina, have been coming to the Berkshires since they were born: ski school in the winters at Otis Ridge, summers at Kutshers with afternoons on the lake, and springs and falls spent enjoying the beautiful countryside and incredible hiking trails. These experiences have helped shape their family's strong connection to the region and to the Monterey community.

Ben has also been actively involved in town affairs through his work on the Monterey Housing Committee, where he has contributed to discussions and research focused on housing availability and the long-term sustainability of the community. In a time when housing costs are high and rising, he believes it is important for towns like Monterey to thoughtfully explore ways to keep housing attainable for the people who live and work in the community.

Ben believes that Monterey's long-term strength depends on maintaining a vibrant year-round community. He cares deeply about supporting full-time residents and preserving the character of the town while thoughtfully managing change. He believes it is important to ensure that Monterey does not gradually become a town dominated by short-term rentals, but instead remains a balanced community that welcomes both year-round residents and part-time homeowners.

Professionally, Ben brings significant leadership experience to public service. Through his career as an engineer and manager, he has experience leading teams, managing complex budgets, tackling challenging problems, navigating difficult decisions, and working collaboratively with people who hold different perspectives. These are skills that translate well to the work of the Select Board. His professional background has also instilled in him a mindset of continuous learning and improvement, approaching challenges with curiosity, asking questions, and working to understand problems deeply before proposing solutions. Ben believes this mindset is particularly valuable in public service, where listening to the community and learning from the people who know the town best is essential.

Ben understands that there is always more to learn about a community as unique as Monterey, and he approaches the role with openness and a commitment to listening. He believes that good decision-making starts with hearing directly from residents and drawing on the deep knowledge and experience that exists within the community, and would combine that with data and other information to drive decisions.

Ben believes that addressing Monterey's challenges requires careful stewardship of town resources while preserving the qualities that make the community special.

Ben believes that strong schools are an essential part of Monterey's community and future, supporting both local families and the town's long-term vitality. He is committed to ensuring that Monterey students have access to high-quality education while also approaching school funding with a long-term perspective, working collaboratively to balance educational excellence with long-term financial sustainability.

While Ben and his family split their time between Monterey and Newton, Monterey has long been an important part of their lives. Ben believes that strong communities are built through participation, listening, and shared responsibility, and he is committed to doing the work necessary to serve the town thoughtfully and effectively.

Ben approaches public service with humility, openness, and a deep respect for the people who make Monterey such a special place.

Ben is grateful for the opportunity to continue serving a community that has meant so much to his family, and looks forward to contributing in a broader way to Monterey's future.