If you followed only Mayor Donna Deegan's campaign communications, you might come away with one picture of Jacksonville: a city moving forward through new investments, infrastructure improvements, public safety initiatives, Downtown development, parks, affordable housing, community events and smiling residents gathered around the latest example of progress.

Follow Republican mayoral challenger Ron Armstrong, and you can encounter a noticeably different Jacksonville. There are smiling residents and business owners there, too. There are community events, supporters and plenty of optimism. But there are also potholes, trash, blight, homeless encampments, neglected neighborhoods and other visible problems that don't normally make particularly attractive political photographs.

Welcome to Two Jacksonvilles.

As Jacksonville's 2027 mayoral campaign begins taking shape, Deegan and Armstrong aren't simply offering voters different candidates. They're increasingly offering different ways of looking at the same city. And that raises a fascinating political question: When you're running for mayor, is it better to show voters what's going right—or what still needs to be fixed?

Deegan: Getting Things Done

Mayor Deegan doesn't hide the premise of her reelection campaign. Her campaign website "Re-elect Mayor Donna Deegan" puts it right at the top: “Getting Things Done.” The campaign presents her first term as one of tangible progress, emphasizing major infrastructure and neighborhood investments, public safety, city services, affordable housing, youth programs, health care, Downtown economic development and making government more accessible.

When Deegan formally launched her reelection campaign in April, the message was similar. She pointed to investments in infrastructure, health care, literacy and affordable housing, along with raises for police and firefighters, new Downtown riverfront parks and the cranes visible over Downtown development. The underlying political message isn't difficult to understand: Jacksonville is making progress. Keep the momentum going.

For an incumbent mayor, it makes perfect sense. Every completed project becomes evidence. Every ribbon cutting becomes evidence. Every new park, road project, business announcement and community investment potentially becomes another reason voters should leave the person already sitting in the mayor's office right where she is. It's progress-and-people campaigning.

Armstrong: Look at What Still Needs Fixing

Armstrong approaches Jacksonville from almost the opposite direction. His campaign website, "Ron Armstrong for Mayor of Jacksonville," tells voters that Jacksonville needs leadership that has been “in the trenches” and understands the needs of communities. His People's Plan includes road conditions and flooding, development beyond Downtown, reducing permitting times, restoring neighborhood rights, advocating for small businesses and conducting an audit of city government.

Perhaps the clearest representation of his campaign philosophy is a feature on his website called “Tell Ron!” It invites residents to tell Armstrong about issues they see around Jacksonville. That's more than a contact form. It captures the premise of his campaign: Show me what's wrong.

Armstrong's social-media presence reflects that approach. He doesn't limit his imagery to the Jacksonville that photographs well. He has been willing to stand alongside visible community problems—trash and debris, troubled streets, homelessness and other conditions—and incorporate them into his argument that government needs to pay more attention to people where they actually live.

That creates a fundamentally different political message: Jacksonville has made progress, but look at what we're leaving behind. Call it problem-and-people campaigning.

Armstrong Isn't Simply Running a Negative Campaign

That's an important distinction. Armstrong also regularly presents the positive side of Jacksonville: residents, businesses, community organizations, supporters and people working to improve their neighborhoods. His campaign website is filled with similar themes.

So the contrast isn't simply positive Deegan versus negative Armstrong. It's subtler. Deegan's political imagery overwhelmingly supports the proposition that progress is occurring. Armstrong's approach attempts to combine optimism about Jacksonville's people with dissatisfaction about some of Jacksonville's conditions.

One says, Look at what we're accomplishing. The other says, Look at what we still need to accomplish. Both can be true.

Even Problems Can Be Presented Positively

Deegan certainly discusses homelessness, infrastructure deficiencies, crime, affordable housing and other challenges. Her campaign website specifically says her administration is working to reduce homelessness and invest in under-resourced communities.

But politically, an incumbent has a powerful incentive to present problems in the context of government doing something about them. The visual story becomes: Here was the problem. Here's what we're doing. That's very different from a challenger standing beside the unresolved problem and essentially asking: Why hasn't this been fixed?

The same pothole can tell two completely different political stories. For Deegan, a newly resurfaced road can demonstrate the government at work. For Armstrong, the deteriorating road two neighborhoods away can demonstrate how much remains undone. Neither photograph necessarily lies. The camera is simply pointed in a different direction.

The Advantages of Being Mayor

There is also an enormous structural difference between these candidates. Deegan is mayor. Armstrong wants to be mayor.

That means Deegan occupies a position that generates positive political imagery almost every day without her campaign having to manufacture an event. Mayors announce projects, cut ribbons, present awards, visit businesses, announce grants, tour construction projects and appear alongside police officers, firefighters, children, neighborhood leaders and business executives.

The office itself is a content machine.

That doesn't make the resulting communication inappropriate. Public officials are expected to communicate what government is doing. But politically, there is undeniable value in being the person standing in the middle of the photograph.

Armstrong doesn't possess that advantage. His campaign has to find another reason for people to look. Jacksonville's unresolved problems provide one.

The Challenger's Cheap Content Advantage

There is an interesting economic component to Armstrong's approach as well. Set campaign advertising budgets aside for a moment. Showing problems can be remarkably inexpensive political communication.

A pothole supplies its own production value. So does illegal dumping. A flooded street doesn't require sophisticated graphics to communicate that something is wrong. Armstrong can travel to a neighborhood, record what residents are experiencing and distribute it directly through social media.

The implicit message becomes: I'm here. I see it. I'm listening.

For a challenger facing an incumbent with greater name recognition, fundraising capacity and the visibility of the mayor's office itself, that's potentially valuable. Deegan has the communications advantage of governing. Armstrong has the communications opportunity of documenting what government hasn't finished.

But Both Strategies Carry Risk

Armstrong has to be careful. Show voters enough garbage, deteriorated roads, homelessness and dysfunction and eventually they may wonder whether the candidate sees anything good about Jacksonville at all. A campaign about problems can become a campaign that simply feels negative.

That's why his positive interactions with residents and businesses matter. They provide the other half of the story: These are the people and places worth fighting for.

Deegan faces the opposite danger. If political communication becomes an uninterrupted stream of smiling people, celebrations, announcements and accomplishments, residents experiencing a very different Jacksonville may eventually wonder: Where is my Jacksonville in all these pictures?

Someone whose street floods doesn't experience an infrastructure announcement the same way as someone whose drainage project has just been completed. Someone driving over deteriorating roads may not experience City Hall's definition of progress the same way as someone attending a Downtown ribbon cutting. And someone encountering homelessness, blight or illegal dumping every day may reasonably wonder why those images appear so rarely in the optimistic portrait politicians naturally prefer to present.

That's the danger of what might be called the Instagram city—a place that can be entirely real while still being incomplete.

Republican vs. Democrat?

There is an obvious temptation to attribute the difference to party. Deegan is a Democrat. Armstrong is a Republican. Their policy language certainly reflects some traditional differences.

Armstrong talks about reducing government overreach, lowering property taxes, auditing city government and restoring neighborhood authority. Deegan emphasizes government investment in infrastructure, housing, health care, public safety and underserved communities.

But party may not be the most important explanation for their communications strategies. Their positions in the race may matter more.

One is the incumbent. The other is the challenger.

Imagine Armstrong campaigning every day about how wonderfully Jacksonville is doing. Eventually voters might reasonably ask: Then why should we replace the mayor?

Now imagine Deegan spending every day photographing deteriorating streets, trash piles, homelessness and neglected neighborhoods. Voters could ask an equally obvious question: You've been mayor since 2023. Why haven't you fixed it?

Political circumstance practically demands different cameras.

Two Jacksonvilles Can Both Be Real

That's what makes this campaign worth watching beyond the candidates themselves. Jacksonville can be experiencing extraordinary investment while a neighborhood five miles away struggles with illegal dumping. Downtown can celebrate a major new development while someone elsewhere drives home over a deteriorating street.

City government can announce millions of dollars in infrastructure spending while residents wait years for projects to reach their neighborhoods. A business owner can be optimistic about Jacksonville's future while a resident remains frustrated with basic city services.

Those aren't contradictions. They're Jacksonville.

And that may ultimately be the most interesting thing about the emerging Deegan-Armstrong campaign. Political campaigns don't necessarily have to lie to create competing realities.

Sometimes they simply decide which truths to photograph.

In Part 2 of Two Jacksonvilles, we'll turn the camera toward the incumbent and examine why portraying a city moving forward isn't simply good politics for Donna Deegan—it may be one of the most powerful advantages that comes with already occupying the mayor's office.