WILBRAHAM — With the May 16 town election approaching quickly in Wilbraham, Reminder Publishing sent questions to the candidates for the contested Select Board race.
Current Select Board Chair Michael Squindo is seeking reelection for a second three-year term, with newcomer Ryan Costello looking to fill the seat as well. Squindo joined the Select Board in 2023 after winning his race against incumbent Carmela Blair by 28 votes. The questions slightly vary per candidate as Costello is running for the the first time and Squindo is up for reelection.
Q: What are your general thoughts or feelings going into election season?
Squindo: Election season is an energetic and exciting time of year for me. It’s an opportunity for residents to share their priorities for the future while thoughtfully evaluating the candidates they will choose to carry those priorities forward. I value the conversations that come with hearing directly from residents about their concerns, ideas, and hopes for the community. It is an important exchange which helps to ensure we’re moving in the right direction together.
Costello: I’m feeling positive and energized. I think the current Select Board has done a good job tackling some complex issues, and it’s encouraging to see that progress. At the same time, I think there’s an opportunity to build on that – especially when it comes to transparency, communication and making sure residents feel more connected to the decision-making process. I’m really looking forward to getting out, talking with people and hearing what matters most to them.
Q: Is there anything you’d like voters to know in specific, or why would you hope to get their vote?
Costello: At the heart of my campaign is the idea of “One Wilbraham” — bringing people together around a shared vision for the town. I’ll bring experience, a practical approach and a real commitment to listening. My goal is simple: to make thoughtful decisions that reflect the community and help position Wilbraham for the future. I’d be honored to earn people’s support to that end.
Squindo: Over the past three years, I’ve worked to bring a focused, thoughtful and collaborative approach to the Select Board – helping move important priorities forward while strengthening transparency and accountability. I’m proud of the progress we’ve made, but there is still important work ahead. I’m running for reelection because I care about the future of this community and I believe in doing the work the right way – setting clear priorities, making informed decisions and ensuring every voice is heard. Whether it’s long-term planning, fiscal responsibility or improving the quality of life in Wilbraham, I’m committed to delivering results that reflect the needs and values of our residents. I would be honored to earn your vote again and continue working on your behalf. Please visit www.electmikesquindo.com or email me at electmikesquindo@gmail.com to learn more. Thank you for your support, and I respectfully ask for your vote on May 16, 2026.
Q: Can you tell me about your background and what inspired you to run for this position?
Costello: I’m a Hampden/Wilbraham native and a 1999 graduate of Minnechaug. After spending many years living and working abroad in Italy, I was thrilled to move back to town in 2025. Professionally, I’ve spent over 20 years as an international lawyer, executive and board member. My work has focused on navigating complex legal and corporate challenges, balancing competing business priorities and helping organizations make clear, data-driven decisions. I’ve also served on nonprofit boards and supported community initiatives, which has given me hands-on experience in governance, collaboration and leadership. All that said, though, I’m most proud of my role as a proud father to three absolutely amazing kids. Wilbraham is home, and coming back really reinforced how much this community means to me. I felt a strong pull to give back in a meaningful way. There are some important decisions ahead for the town — around infrastructure, schools and economic development — and I want to be part of helping guide those conversations in a thoughtful, practical way. That’s really what motivated me to run.
Q: Is there something that stands out as your favorite part of being on the Select Board?
Squindo: My favorite part of serving on the Select Board is being a small part of the success that comes when our community works together toward a common goal. One example is the effort to locate the pickleball courts at Memorial School. Through the dedication of the Playground and Recreation Commission, the Parks and Recreation Department and strong support from the pickleball community, these courts are now a valuable addition to our town’s recreational programming. Another example is the progress on sidewalk improvements, including the intersection of Springfield Street and Stony Hill Road and the final install of sidewalks at the intersection of Stony Hill Road and Boston Road. With the support of the Annual Town Meeting on May 11, 2026, these projects are positioned to move forward and become a reality. They reflect consistent advocacy from residents for improved safety and walkability. These projects also reflect and are a result of the leadership of our DPW director and her team in guiding us in becoming a Complete Streets community, opening the door to additional funding to support this work. While the process can be long, seeing that collaboration turn into real results is what I value most – and it’s why I’m proud to serve.
Q: Is there anything that you have your eyes set on to accomplish within the Select Board that hasn’t been done yet or you think could be improved on?
Costello: There are a few areas I’d focus on. First, continuing to move forward on key sidewalk projects, like the Stony Hill School connection and improvements near Town Hall. These are the kinds of projects that improve safety and really bring the community together. Second, supporting thoughtful economic development – especially in the town center – so we can strengthen the local economy while still preserving what makes Wilbraham special. Third, improving transparency and engagement. I think there’s a real opportunity to communicate more clearly and give residents more meaningful ways to be part of the process.
Q: Do you have anything on your mind that you would still like to accomplish with the Select Board in the case you’re reelected?
Squindo: If reelected, there are three major areas I would like the town to focus on over the next three years. First, after more than a decade of study and discussion, the town must move forward with a clear, actionable plan for Memorial School. At the 2022 Annual Town Meeting, Wilbraham supported a non-binding resolution to relocate Parks and Recreation to Memorial School. The Select Board should ensure that a comprehensive plan is ready for consideration by Annual Town Meeting in spring 2027, following the final review and recommendations of the Building Utilization Committee. Second, Wilbraham must continue working collaboratively with Hampden, the School Committee and our regional partners to address long-term challenges facing our school district. Both communities’ Select Boards are actively engaged in discussions about the future of the middle school, including near-term improvements and the potential for a full renovation or new construction project likely to exceed $100 million, with partial state reimbursement. In addition, the Select Board must continue advocating at the state level to address chronic underfunding of public education. Finally, Wilbraham should take a more proactive approach to housing and affordability. The town currently falls below the state benchmark for affordable housing under Chapter 40B. We need to develop a Housing Production Plan to address that gap while building community support. This is important not only for compliance, but to ensure that residents who grew up in Wilbraham — or hope to move here — can afford to stay. We should also explore targeted measures such as increasing the Senior Work-Off Program abatement from $1,500 to $2,000, providing property tax relief in exchange for volunteer service. Additional solutions may require home-rule petitions or state legislative action, and I look forward to engaging residents and advancing practical proposals. These are complex challenges, but they are achievable with clear direction, collaboration and consistent follow-through.
