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.