Survey Questions – Ward 5 Candidates
Inform Your Vote
Ward 5 Councillor Candidates for the 2026 Municipal Election Share Their Insights
Q & As
1. If elected to Council, what would be your top priority, and how will you address it?
Anthony Caputo: My top priority would be managing growth responsibly while protecting the quality of life in Bolton Ward 5. Growth must be matched with the roads, traffic solutions, infrastructure, parks and services our community needs. If elected, I will advocate for responsible development, careful management of taxpayers’ dollars, and practical solutions to congestion and infrastructure pressures. Most importantly, I will listen to residents, keep them informed, and ensure their voices are heard in Council decisions. My goal is smart growth, responsible spending, and a stronger Bolton.
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Diana Mollicone: Truck traffic – both illegal land use and the pressure growth is putting on our roads. Warehousing and logistics have grown quickly, but our infrastructure hasn’t kept pace. I’ll push to get critical road upgrades moving faster while continuing to strengthen enforcement against illegal operators. That means using every tool available to the Town, including entrance blocking and administrative penalties that don’t require us to wait years for a court outcome.
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John Muir:
2. How have your education, skills and experiences prepared you for the role of Councillor?
Anthony Caputo: My education, professional experience, and involvement in the community have prepared me to understand complex issues, evaluate information, and make practical, responsible decisions. I bring strong communication, problem-solving, leadership, and relationship-building skills, along with the ability to listen to different perspectives and find common ground. I understand the importance of fiscal responsibility, accountable governance, and planning for sustainable growth. As Area Councillor, I would bring a practical, collaborative approach focused on representing residents and delivering results.
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Diana Mollicone: I’m a Professional Engineer with a Master’s degree and 10 years of experience managing design-build and construction projects. I’m used to solving problems, managing resources (internal and third-party), working under pressure and figuring out how to actually get things done. Owning Coffee Time has taught me a completely different side of leadership – employees, customers, budgets and community. I think combination will give Caledon a unique perspective at the table.
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John Muir:
3. How does the use of Strong Mayor Powers impact the role of Council? How will you move your priorities forward in a Strong Mayor environment?
Anthony Caputo: Strong Mayor Powers change how decisions are made, but Council remains essential in representing residents, providing oversight, and holding municipal leadership accountable. I would use my role to ensure my constituents’ priorities are heard early and consistently. By building strong working relationships with the Mayor, Council, staff, and community, I would advocate for practical solutions on issues such as responsible growth, infrastructure, roads, services, and community safety. Strong Mayor Powers make collaboration and accountability even more important, not less. My commitment is to listen, advocate, and deliver results for the residents I represent.
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Diana Mollicone: Strong Mayor Powers move some decision-making away from Council, which means individual councillors need to work harder to get their priorities heard. I’ll keep Bolton’s needs front and centre, come prepared with facts and workable solutions, and do the work needed to build support around the Council table.
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John Muir:
4. How will you balance the needs of your own ward(s) with the needs of the Town as a whole?
Anthony Caputo: My responsibility is to represent my ward while recognizing that every decision affects the Town as a whole. I would listen closely to local concerns and advocate strongly for my constituents, while evaluating each issue through the lens of fairness, long-term sustainability, and the broader community interest. I believe strong municipalities are built through collaboration, not competing interests. My goal would be to find practical solutions that address local needs while strengthening Caledon as a whole.
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Diana Mollicone: Different areas of Caledon have different priorities, and they all deserve attention. Illegal truck yards may be concentrated around Bolton, but those trucks travel Highway 10 and on roads across the Town. Ward 5 is also the most densely populated and home to a significant share of Caledon’s business community. Supporting its infrastructure and economy benefits all of Caledon. I intend to bring that same perspective to issues affecting every ward.
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John Muir:
5. How will you balance maintaining affordable property taxes while investing in the services and infrastructure residents rely on?
Anthony Caputo: I believe residents deserve both responsible property taxes and reliable municipal services. I would prioritize essential services, infrastructure, and long-term asset management while ensuring every tax dollar is spent efficiently. That means reviewing spending, identifying savings, seeking appropriate grants and partnerships, and prioritizing projects based on need and value. Growth should also help pay for the infrastructure it requires. My approach would be fiscally responsible, transparent, and focused on delivering the best value for residents.
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Diana Mollicone: Keeping taxes affordable doesn’t have to mean cutting services. It means spending smarter. I’ll prioritize infrastructure based on actual need, chase every available dollar from other levels of government and make sure growth pays its fair share instead of leaving existing residents with the bill. We also need to support and grow our commercial tax base. I run a “2$ drip coffee” business – I know you can’t spend money you don’t have.
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John Muir:
6. How will you manage growth while protecting Caledon’s agricultural lands, natural environment and water table?
Anthony Caputo: Caledon’s growth must be carefully planned, sustainable, and respectful of what makes our community unique. I would support responsible development in appropriate areas while protecting prime agricultural lands, natural heritage, and our water resources. New growth must be supported by proper infrastructure and should not place unnecessary pressure on existing residents or the environment. I would advocate for evidence-based planning, strong environmental protections, and meaningful community input to ensure growth strengthens Caledon without compromising the land and resources future generations depend on.
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Diana Mollicone: We know growth is coming, so I’ll push to direct growth toward already planned settlement areas, protect prime agricultural lands and sensitive natural areas, and implement phasing so development doesn’t outpace roads, water, wastewater and other critical infrastructure. I’ll also push for stronger consideration of groundwater and surrounding impacts when major developments are reviewed.
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John Muir:
7. How will you keep residents informed and engaged, ensuring transparency and accountability at Town Hall?
Anthony Caputo: I believe residents deserve clear, timely information and meaningful opportunities to be heard. I would provide regular updates on Council decisions, spending, projects, and issues affecting our community, while making myself accessible through community meetings, email, and other channels. I would encourage residents to ask questions, share concerns, and participate before major decisions are made. Transparency also means being accountable for my decisions and clearly explaining both what we can accomplish and where challenges remain.
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Diana Mollicone: I’ll use social media to break down important Town decisions into plain language and hold local town halls where people can actually ask questions comfortably. Residents may not always agree with every decision I make, but they deserve to understand how I got there, feel like they were heard and know they can reach me.
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John Muir:
8. What is one challenge facing Caledon that you believe deserves more attention? How will you move this forward?
Anthony Caputo: One challenge that deserves more attention is ensuring infrastructure keeps pace with Caledon’s rapid growth. Roads, water, wastewater, recreation, and other services must grow alongside our communities. I would push for better long-term planning, clear infrastructure priorities, and development that pays its fair share of growth-related costs. I would also work with the Region and other levels of government to secure funding and accelerate projects. Growth should bring opportunity, but it must be supported by the infrastructure residents need today and in the future.
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Diana Mollicone: Our youth. We talk a lot about building communities for families, but there isn’t enough here for kids once they get older, and finding that first job is getting harder. I’ve hired 31 local youth in five years at Coffee Time, and many have come back for multiple summers or stayed while pursuing other careers. I’d like to see Caledon do more with co-op, mentorship and job-ready skills while connecting willing local employers with young people looking for that first opportunity.
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John Muir:
9. How will residents know whether you have been successful at the end of your four-year term?
Anthony Caputo: Residents should judge me by results, not promises. At the end of four years, I want residents to see progress on infrastructure, responsible growth, roads, services, fiscal responsibility, and protecting Caledon’s character. They should also be able to say that I was accessible, listened to their concerns, communicated openly, and followed through. I would provide regular updates on priorities and decisions so residents can measure my performance for themselves. Success means making Caledon stronger while delivering value for taxpayers.
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Diana Mollicone: Don’t judge me by what I promise in 2026. Judge me by what I can show you in 2030. I want residents to be able to point to things that are genuinely better, but I also want to be held accountable to what I didn’t accomplish. I don’t think success is measured by how many motions I bring forward. It’s whether Ward 5 residents feel better served at the end of four years than they did at the beginning.
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John Muir:
10. Is there anything else that you would like voters to know about you or your priorities for Caledon?
Anthony Caputo: I am committed to putting residents first and making decisions based on what is best for Caledon today and for future generations. My priorities are responsible growth, fiscal accountability, infrastructure that keeps pace with development, and protecting our agricultural lands, natural environment, and community character. I believe in listening, working collaboratively, and being accountable for results. I will bring a practical, common-sense approach to Council and work hard to ensure Caledon remains a great place to live, work, raise a family, and build a future.
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Diana Mollicone: I’m not running to become involved in this community; I already am. I’m running because I think I can take what I’ve learned as an engineer, business owner, employer, volunteer, and sponsor and put it to work on a bigger platform. I’ll do my homework, ask questions, work with people I don’t always agree with and speak up when something doesn’t make sense. All of that with respect, courtesy and integrity. My commitment to the community is here – before, during, and beyond elections.
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John Muir: