Before the Ballot: Questions for Hamilton's Next Mayor

The Hamiltonian is launching a new feature titled Before the Ballot: Questions for Hamilton’s Next Mayor.

As the municipal election approaches, we will be putting a consistent series of focused questions to all declared and prospective mayoral candidates. Responses will be published in full, providing readers with a clear and fair basis to compare positions over time. Where a candidate chooses not to respond, that will be noted for transparency.

We believe Hamiltonians are best served when they have the opportunity to consider the views of all those seeking to lead the city.

Our first instalment features potential mayoral candidate Scarlett Gillespie. This set of questions has been circulated to all known potential candidates.

We invite you to read our conversation with Ms. Gillespie.

Jackson Square was once envisioned as a “people place” at the heart of Hamilton’s downtown. Today, it reflects mounting pressures tied to safety concerns, disorder, and declining commercial activity.

Do you believe Hamilton’s downtown—beginning with areas like Jackson Square—requires fundamental transformation? If so, what specific, actionable plan would you lead to restore safety, economic viability, and public confidence? How would your plan be different from others attempts Hamiltonians have seen in the past? 

If you are in support of a concerted effort to transform Hamilton’s s downtown, what do you say to those who would argue that such an effort would take away from other priority issues in other parts of the city?

Ms. Gillespie's reply is as follows:

I think the premise of the question is flawed, because it treats Jackson Square as a failed space that needs to be “fixed,” rather than a complex, functioning part of our downtown that has been misunderstood and mismanaged. 

Jackson Square isn’t just a mall: it’s a civic hub. It connects office workers, small businesses, the library, the farmers’ market, transit, and people seeking shelter or services. It brings together all walks of life in one place. So the issue isn’t whether we “transform” it. The issue is whether we finally take responsibility for how it’s governed.

Right now, the conversation is being framed as if the City can simply redesign or “fix” the site. That’s not accurate. The City of Hamilton owns the land under Jackson Square, but the mall itself is privately controlled through a series of long-term 99-year leases held by Yale Properties, with approximately 56 years remaining on that term. And for years, we’ve had that leverage - and we haven’t used it well. At times, we’ve even considered selling it off entirely; in 2024, Yale Properties tried to renegotiate their lease to add an additional 50 years to their existing 99-year term. They expressed that they would consider purchasing the property (land) all together if given this extension as they represented that they needed to justify and defray the cost of any future capital expenses like renovations.  

So before we talk about transformation, we need to be honest about governance. For decades, the City has had leverage and hasn’t used it effectively.  That means any meaningful transformation requires political will, leverage, and renegotiation - not just vision statements.

Do I believe downtown needs better leadership? Yes. But not the kind of transformation that starts with blaming “disorder” or treating Jackson Square as a security problem which often responds with inadequate surface-level fixes. What people are calling “disorder” is often just visibility of poverty, mental health struggles, and addiction. Jackson Square reflects the realities of our city - it doesn't create them. Real safety comes from activity, inclusion, and design, not displacement.

The real issue is structural: Jackson Square was designed to be insulated; it cuts itself off from the city instead of contributing to it.  . The mall cuts off streets, limiting entrances and pedestrian flow, ultimately disconnecting itself from the surrounding city instead of contributing to the quality of public life in Hamilton. My plan would start there: with structure, not stigma. My plan focuses on that root problem.

First, I would use the City’s position as landowner to renegotiate the terms of that lease in the public interest. Any extension or amendment of the lease needs to be tied to enforceable requirements: opening the building to the street, increasing entrances, activating dead frontages, and restoring access, integration, and therefore walkability within the surrounding neighbourhood.

Second, we stop treating Jackson Square as an isolated problem; the mall is a part of a larger civic district and should be planned together as part of downtown: The FirstOntario Centre, the Convention Centre, the former City Centre lands, and surrounding streets. Right now, we’re redeveloping pieces in isolation, when what we need is a coordinated master plan for the largest employment and civic hub in the city.

Third, we shift the conversation on safety. Safety doesn’t come from over-policing or pushing people out: it comes from activity, visibility, and inclusion. Safety follows activity. That means:

• attracting customers at different times of day (arts, food, services, community uses)
• increased cultural programming
• supporting small, local businesses; not just large anchor tenants
• making space for the communities already there, instead of trying to displace them
• designing spaces people actually want to be in

We’ve known for decades that breaking up superblocks and restoring street-level connections would improve this site, but previous plans were never implemented. If I become Mayor, I would tie approvals and negotiations to actually delivering those changes.

What makes this different from past attempts is simple: accountability. Since the City owns the land, we need to stop negotiating passively like we are a bystander. The city has power it can leverage to improve the quality of life for every Hamiltonian, which it has failed to do thus far. 

Finally, to those who say focusing on downtown takes away from other parts of the city - I would say the opposite is true. A functioning downtown generates economic activity, jobs, and tax revenue that supports the entire city's services and programs. When it works, it supports services and investment across every ward.   Treating Jackson Square as a “special project” instead of critical infrastructure is exactly how we got here.

Hamilton doesn’t need another cosmetic revitalization plan. It needs to use the power it already has - and to stop squandering that power towards the benefit of all Hamiltonians. 

Sincerely,

Scarlett Gillespie

Thank-you Ms. Gillespie for engaging with Hamiltonians in The Hamiltonian. To read a prior piece featuring  Ms. Gillespie, click here. 

The Hamiltonian Analysis: Downtown Strategy — Vision Strong, Execution Uncertain

Assuming you may not have the time to read and consider a 17 page report on how to revitalize Hamilton's downtown, we did the reading  for you. Here are our observations: 

Hamilton’s newly proposed 10-Year Downtown Revitalization Strategy is ambitious, structured, and politically careful. It acknowledges long-standing concerns about the downtown core while attempting to chart a path forward without asking taxpayers for significant new funding upfront. 

But beneath the language of “activation,” “placemaking,” and “coordination,” key questions remain about whether this plan is transformational—or simply another iteration of past efforts.--

Where the Strategy Is Strong

1. Realistic Focus on Early Wins

The plan prioritizes “quick wins” in the first 1–3 years—cleanliness, lighting, maintenance, and visible improvements. This is a practical acknowledgment that perception drives confidence in downtowns. 

2. Cross-Department Coordination (At Least in Theory)

There is a clear recognition that fragmented governance has hindered past efforts. The commitment to a governance review and interim centralized leadership through Economic Development is a step in the right direction. 

3. Activation Strategy Built Around Existing Assets

Initiatives like:

• James Street North festival infrastructure
• King William pedestrianization
•  Farmers’ Market activation
• TD Coliseum entertainment district

…show a strategy built on leveraging what already works rather than reinventing the wheel.

4. Fiscal Restraint Messaging

By relying primarily on reallocating existing resources and a baseline $1 million annual allocation, the City avoids immediate political backlash tied to new spending. 

 Where the Strategy Is Weak

1. No New Money Is Also “No New Capacity

The report repeatedly emphasizes implementation through existing resources. This is the central vulnerability, although an argument can be made that inventing a new Downtown Office will amount to a waste of taxpayer money- as the problem is not at the staff level. 

Downtown Hamilton’s challenges—safety, cleanliness, homelessness, infrastructure decay—are not minor. Reallocating existing budgets risks spreading already thin services even thinner.

2. Governance Review Delayed Until 2027

The strategy acknowledges structural inefficiencies—but delays meaningful reform for up to a year. That raises a fundamental concern: How can a complex, multi-department strategy succeed when the governance model needed to deliver it is still undefined?

3. Heavy Reliance on Pilot Projects

Pilot programs (York Boulevard, parks, wayfinding) dominate the early action plan.

Pilots are useful—but Hamilton has piloted downtown revitalization ideas for over a decade. The concern is whether this becomes another cycle of testing without scaling.

4. Vague Accountability Metrics

While the report references “measurement frameworks” and annual updates, it lacks:

•  Specific KPIs
•  Defined targets
•  Timelines tied to outcomes (not just actions)
• Without these, Council and the public will struggle to measure success objectively.

5. Avoidance of Root Issues

The strategy focuses heavily on physical space and activation—but is notably cautious around:

•  Public safety realities
•  Mental health and addiction impacts
• *Chronic homelessness

These are acknowledged indirectly but not confronted as central drivers of downtown decline.

6. Historical Context Raises Red Flags

The report itself notes that past renewal efforts (1970s–1980s) are now aging and underperforming. This underscores a deeper concern: Hamilton has had “revitalization strategies” before—why will this one be different?

 Key Questions Councillors Should Be Asking

Governance & Accountability

•  Who is ultimately accountable for results if multiple departments are involved?
•  Why is the governance review not completed before implementation begins?
•  What happens if departments fail to align?

Financial Reality

•  Is $1 million annually sufficient for a city the size of Hamilton?
• What services are being deprioritized to fund this?
•  When will Council see the first request for additional funding?

Measurement & Transparency

What are the specific, measurable targets for:

•    Cleanliness?
•    Safety perception?
•    Business occupancy?
•    Foot traffic?

What constitutes failure—and what is the corrective mechanism?

Execution Risk

•  How many past downtown strategies relied on “pilot projects” that never scaled?
•  What guarantees exist that successful pilots will be permanently funded?

Public Safety & Social Conditions

•  How does this strategy integrate with homelessness, addiction, and mental health strategies?
•  Can “activation” succeed without first stabilizing these underlying conditions?

Economic Impact

•  What is the expected ROI of this strategy?
• How will success be measured in terms of private investment and tax base growth?

Equity Across the City

• If this becomes a model for other neighbourhoods, how will resources be distributed?
•  Will downtown continue to receive disproportionate focus?

Bottom Line

This strategy is not without merit—it is structured, grounded in consultation, and politically pragmatic.

But it is also cautious to a fault.

Hamilton is not suffering from a lack of plans. It is suffering from a lack of execution, coordination, and sustained investment. It is blind to the brand and dosage of leadership that is required to transform. 

Unless Council addresses those structural gaps head-on and understands the brand of leadership required  and dosage, this strategy risks becoming what many before it have been:

A well-written document… that doesn’t fundamentally change outcomes.

Hamilton at a Crossroads: Why Farmland Must Not Be the Price of Growth

Hamilton is once again being pulled into a familiar and consequential battle — one that will define not only how the city grows, but what kind of city it ultimately becomes.

At the center of the latest dispute is a high-stakes hearing before the Ontario Land Tribunal, where developers are pushing to expand Hamilton’s urban boundary by nearly 1,700 hectares of rural land. Their vision: tens of thousands of new homes, sprawling outward into farmland that has long been part of the region’s agricultural backbone.

The city, to its credit, is holding the line — at least for now.

Hamilton’s legal position is clear: no expansion is necessary. Instead, the city continues to advocate for a fixed boundary approach, focusing growth inward through intensification, smarter land use, and more efficient infrastructure planning. 

This is not simply a planning debate. It is a defining test of priorities.

The Illusion of “Necessary” Expansion

Developers argue that expansion is essential to meet housing demand, projecting over 50,000 units and more than 150,000 residents across proposed developments like Elfrida. On the surface, that sounds like a solution to the housing crisis.

But it isn’t.

What is being proposed is not a new model of affordability or sustainable housing — it is a continuation of the same low-density, car-dependent growth pattern that has driven costs higher and infrastructure deeper into deficit for decades. 

Even the city’s own analysis suggests that these projections rely on outdated assumptions — particularly the continued dominance of single-detached housing. That model is increasingly incompatible with modern economic realities, environmental constraints, and shifting demographic needs.

Simply put: building outward is not the same as building smart.

The True Cost of Sprawl

Every hectare of farmland lost is not just a change in land use — it is a permanent loss.

Prime agricultural land, once developed, is gone forever. In a time of growing food insecurity, climate instability, and supply chain vulnerability, that should give policymakers pause.

But the cost goes further.

Urban expansion brings with it a cascade of infrastructure demands: roads, sewers, transit, emergency services — all stretched further and funded by taxpayers. Residents in newer, low-density areas often pay less than the true cost of servicing those communities, leaving existing urban taxpayers to subsidize the gap.

And then there is the environmental toll. 

More pavement means more runoff, more strain on stormwater systems, and increased flood risk — concerns already raised by local residents near proposed expansion zones. The pattern is well known: sprawl amplifies the very infrastructure and climate challenges municipalities are struggling to manage.

A Better Path Already Exists

Hamilton has already made its choice — twice.

In 2021, and again under a subsequent council, the city embraced a fixed urban boundary, aligning itself with the widely supported “Stop Sprawl” movement. That decision was rooted in a forward-looking strategy: intensify where infrastructure already exists, revitalize underused land, and build complete communities within the current footprint.

This is not anti-growth.

It is pro-responsible growth.

Cities across North America are increasingly recognizing that density — when done well — supports affordability, vibrancy, and long-term fiscal sustainability. Hamilton has the opportunity to be part of that shift rather than reverting to outdated expansion models.

The Line That Must Hold

Even some local leaders acknowledge the risks. Councillor Mark Tadeson has pointed out that certain proposals amount to “leapfrogging” development — bypassing more appropriate, less disruptive areas closer to the existing boundary. That observation underscores a critical point: this is not a binary choice between growth and no growth.

It is a choice between disciplined, strategic development and unchecked sprawl. 

Hamilton stands at a crossroads. The decisions made through this tribunal process will reverberate for generations — shaping the city’s landscape, economy, and environmental resilience.

Growth is necessary. Housing is urgent.

But sacrificing irreplaceable farmland is neither necessary nor wise.

If Hamilton is serious about its future, the line it drew around its urban boundary must not just be defended — it must be respected. 

Hamilton’s Downtown: 15 Years of Plans, Progress—and Persistent Problems

For more than a decade, downtown Hamilton has been the subject of plans, promises, and periodic optimism. Yet for many residents and observers, the central question remains unchanged: is the core truly revitalizing, or simply evolving in uneven and incomplete ways?

Since roughly 2011, the city has laid a substantial policy and investment foundation. Updated planning frameworks, including a modernized Downtown Secondary Plan and a series of Community Improvement Plans, have aimed to attract private investment while preserving heritage and enhancing public space. Financial incentives—grants, tax rebates, and redevelopment programs—have lowered barriers for developers and encouraged adaptive reuse.

There have been tangible wins. Office vacancy dropped to just under 12 percent by 2019, retail vacancies improved, and billions in assessment value flowed into the core. Landmark projects like the Lister Block restoration, the McMaster downtown health campus, and the ongoing half-billion-dollar entertainment precinct redevelopment demonstrated what coordinated public-private investment can achieve. Thousands of new residential units, many tied to heritage buildings, have added density and helped reintroduce life to the downtown.

But the story is far from a clean success.

Major structural challenges—homelessness, affordability, and public safety—have not only persisted, they have intensified. Encampments, strained social services, and rising housing costs have reshaped the downtown experience. Businesses and residents alike continue to raise concerns about safety and vibrancy, particularly in the post-pandemic environment where office patterns and retail dynamics have shifted.

Critically, not all strategies have delivered. Large-scale, top-down redevelopment efforts have historically struggled, sometimes draining street-level vitality rather than enhancing it. Several high-profile proposals have stalled or been abandoned entirely. The lesson emerging from the past 15 years is clear: incremental, coordinated, and community-informed development works better than grand, isolated schemes; at least, where Hamilton is at.

Today, the city finds itself at another turning point.

Councillor Cameron Kroetsch’s push for a more structured downtown revitalization approach—including clearer recommendations, dedicated attention, and potentially a centralized downtown office—signals renewed political will- at least on the part of the responsible Councillor-we’ll see about the others. . But vision alone will not be enough. Without a realistic understanding of costs, sustained funding, and measurable outcomes, the risk is repeating a familiar cycle of ambition without execution.

The city’s new 10-year Downtown Revitalization Strategy (2025–2035) acknowledges this reality. Early direction points toward integrated solutions: more affordable housing, stronger social supports, improved safety, and continued economic diversification. The emphasis is no longer just on buildings and investment—but on livability.

That shift may be the most important development of all.

Downtown Hamilton has not failed—but it has not fully succeeded either. It has stabilized, grown in pockets, and attracted investment. At the same time, it continues to struggle with the very issues that define whether a downtown truly thrives: safety, inclusivity, and everyday vibrancy.

The next decade will determine whether Hamilton can move beyond incremental progress and deliver a cohesive, confident urban core—or whether revitalization remains, as it has for years, a work perpetually in progress.

The secret sauce has always been aggressive bold leadership, coupled with know-how; which remains elusive in Hamilton.

Hamilton’s Sunday Parking Shift: A Small Change with Big Urban Implications

A seemingly modest policy change is quietly signaling a more significant evolution in how Hamilton manages its streets.

The City has begun enforcing Sunday parking rules under a pilot program. While on-street parking remains free, the introduction of enforcement—where historically there was little to none—marks a shift toward a more structured, intentional approach to curbside management.

At first glance, this may appear administrative. In reality, it places Hamilton squarely in line with how comparable municipalities across Canada and beyond are rethinking urban space, congestion, and fairness.

What Other Cities Are Doing

Across Ontario, Sunday parking policies have already undergone similar transitions.

In Toronto, Sunday enforcement has long been standard in high-demand areas. While some residential streets remain more flexible, commercial corridors enforce time limits consistently seven days a week. The rationale is straightforward: turnover. Retail districts depend on it, and unrestricted parking—even if free—can suppress economic activity by allowing vehicles to occupy spaces indefinitely.

Ottawa follows a hybrid model. In its downtown core and ByWard Market, Sunday enforcement is active, though often paired with reduced rates or time allowances. The policy balances accessibility with mobility—encouraging visitation while preventing stagnation.

Meanwhile, Mississauga and Burlington have gradually expanded enforcement into weekends, particularly in revitalized downtown areas. Their approach reflects a broader planning principle: streets are not static storage zones—they are dynamic assets that must serve multiple users.

Beyond Ontario, cities like Vancouver and Calgary enforce parking regulations seven days a week in most urban centres. The consistency eliminates ambiguity and supports transit integration, pedestrian flow, and commercial vitality.

Why Sunday Matters More Than It Seems

Historically, Sunday has been treated as an exception—quieter, slower, less regulated. That assumption is increasingly outdated.

Urban planners now recognize Sunday as a high-activity day. Restaurants, cultural venues, waterfronts, and retail districts often see peak foot traffic. Without enforcement, prime parking spaces can be occupied for hours—or all day—by a single vehicle. This reduces accessibility for others and can unintentionally discourage economic participation.

Hamilton’s move suggests an acknowledgment of this reality.

Importantly, the City has not introduced Sunday parking fees—only enforcement. That distinction matters. It positions the policy less as a revenue mechanism and more as a behavioural one: encouraging turnover, fairness, and compliance without imposing additional cost barriers.

The Policy Signal Behind the Pilot

Pilot programs are rarely just about testing logistics. They are about gauging public tolerance and measuring downstream effects.

In Hamilton’s case, several strategic objectives are likely in play:

First, improving parking availability in busy corridors without expanding infrastructure. Building new parking is costly and land-intensive; managing existing supply is far more efficient.

Second, aligning with broader transportation goals. Consistent enforcement supports transit use, active transportation, and reduced congestion—all priorities in modern municipal planning.

Third, standardizing expectations. When rules apply inconsistently—weekday versus weekend, enforced versus unenforced—compliance drops. Predictability improves adherence.

The introduction of Sunday enforcement, even without fees, moves Hamilton toward that consistency.

What Comes Next

If the pilot proves successful, the City will face a familiar decision point seen in other municipalities: whether to maintain enforcement-only, introduce Sunday fees, or refine the model based on zone-specific demand.

Toronto and Vancouver, for example, ultimately moved toward paid Sunday parking in high-demand areas after initial enforcement-only phases demonstrated strong utilization and turnover benefits.

Hamilton may or may not follow that path—but the trajectory is clear. This is not an isolated adjustment. It is part of a broader re-calibration of how urban space is allocated.

The Bottom Line

Hamilton’s Sunday parking enforcement pilot is less about tickets and more about philosophy.

It reflects a shift from passive to active management of public space—recognizing that streets serve economic, social, and mobility functions that extend well beyond Monday to Saturday.

For residents, the change may feel subtle. For the City, it represents a step toward a more modern, data-driven approach to urban planning.

And as comparable municipalities have already demonstrated, once that shift begins, it rarely stops at Sunday.

Media Release: Harry Howell Twin Pad Arena selected as training facility as City welcomes AHL team

HAMILTON, ON – The City of Hamilton announced today that the New York Islanders and Oak View Group have selected Harry Howell Twin Pad Arena as the practice and training facility for the Islanders’ American Hockey League (AHL) affiliate. The AHL Board of Governors unanimously approved the relocation of the team to Hamilton on Tuesday March 31, 2026.

“We are so excited for the AHL to practice and train in our very own facility - Harry Howell Twin Pad Arena. This collaboration between the City of Hamilton, the AHL team and Oak View Group (OVG), solidifies our continued partnership as we look ahead to achieving more milestones for the city as a whole,” said Mayor Andrea Horwath. “We are investing in new and upgraded infrastructure, and through partnerships such as this, we see Hamilton continue to grow into a vibrant community where youth, residents and members of our community thrive.”

Construction is set to begin at Harry Howell Arena soon. This partnership between the City of Hamilton and New York Islanders puts the community first while securing a practice facility for the AHL team. The deal will see the team use the City-owned arena as its practice rink and build a state-of-the-art training facility, while also committing to giving back to the community it will call home.

“Harry Howell Twin Pad Arena has become a community hub for youth, adult and recreational hockey players alike,” said City Manager Marnie Cluckie. “We are proud and excited to welcome a professional hockey team into a space that has served the Flamborough community since 2012. Residents can be assured that the City will continue to deliver the high level of customer service they have come to expect from Harry Howell staff, while also benefiting from new opportunities to connect with professional hockey in their community.”

“We are excited to be a part of the Hamilton community and practice at The Harry Howell Twin Pad Arena,” said Mathieu Darche, Islanders General Manager and Executive Vice President. “The Harry Howell Twin Pad Arena provides our prospects everything they need to develop their game and become New York Islanders."

Harry Howell Twin Pad Arena, located at 27 Highway 5 West in Hamilton, will undergo a transformation, including the construction of a two-level AHL-exclusive training facility integrated into the existing arena. Throughout construction and beyond, the City will maintain current service levels for recreation users, residents and visitors. This milestone marks an exciting step forward in strengthening Hamilton’s position as a destination for sport, entertainment, and community activity.

“We’re excited to welcome professional hockey to TD Coliseum,” said Nick DeLuco, Senior Vice President and General Manager of TD Coliseum. “Beyond the impact on the ice, this project represents an important investment in the Hamilton community by supporting local engagement and bringing fans together. A dedicated, high-performance training environment is essential to the team’s success, and we thank the City of Hamilton for its partnership in making this facility a reality.”

Community Impact

Economic growth remains a key priority for the City, and this investment in infrastructure further strengthens Hamilton’s position as a hub for culture, sport and tourism.

Community-focused opportunities, such as open practices and developmental clinics, will be hosted at the arena, creating a valuable opportunity for the public to connect with the team and the sport. The City looks forward to welcoming the Islanders and its players to Harry Howell Twin Pad Arena, where residents of all ages can engage with the game and be part of this exciting new chapter.

Additional Resources:Web Page: City of Hamilton Harry Howell Arena Project
Media Release: Islanders to move AHL affiliate to Hamilton | March 31, 2026
Media Release: New York Islanders to Relocate AHL Affiliate to Hamilton, Ontario | March 19, 2026