In Mayor's Office Parts I and II, we followed the money inside City government. Part I found that Mayor Donna Deegan entered office with the same 18-member executive staff as outgoing Mayor Lenny Curry — but at roughly $590,000 more in annual salaries, an increase of about 23%. Since then, Deegan has expanded the executive operation further, bringing its annual salary cost to roughly $5 million.

Part II asked where Jacksonville concentrates those salary dollars. We found that the Mayor’s Office averages roughly $161,000 per authorized position, compared with about $50,000 in Public Works, $79,000 in Parks, $89,000 in Planning, $96,000 in Finance and $102,000 in Technology.

In Parts I and II, we called that “salary concentration.” Put more simply, it’s the average salary per position, and we’ll use average from here forward.

Who Cares How Much They Make?

Fair question. If Jacksonville needs exceptional people to help run a $2 billion-plus government, paying competitive salaries can be a very good investment. A $200,000 employee who saves taxpayers millions, improves services or makes an operation substantially more productive could be a bargain.

But most of the people paying those salaries — and most of the people working for Jacksonville — don’t earn anything close to them. The average Jacksonville-area worker earns roughly $66,000 a year. Jacksonville itself has advertised some jobs at $15 an hour, while Public Works positions we've examined have started in roughly the $33,000-to-$43,000 range.

Now consider a number that appears repeatedly in Deegan’s original executive payroll: $185,000. That’s nearly three times the average Jacksonville-area wage.

That doesn’t make $185,000 excessive. It makes it consequential. For most Jacksonville residents, $185,000 is executive compensation, and taxpayers and City employees can reasonably expect executive-level responsibility, expertise and results in return.

City Employees Have a Stake in This, Too

Private-sector workers routinely compare employers based on pay, advancement, job security and how companies reward experience. People working for Jacksonville — or considering working for Jacksonville — can make the same calculations.

An engineer, planner, accountant, technology specialist or longtime City employee can reasonably ask where Jacksonville places its greatest value. Does it reward technical expertise, institutional knowledge, managing hundreds of employees, improving productivity, running capital projects, developing policy, communicating with the public — or proximity to executive decision-making?

Those aren’t merely political questions. They’re workforce and management questions.

Technology, automation and artificial intelligence make that issue increasingly important. If an engineer manages more projects, a planner processes work faster or a technology specialist automates an expensive manual process, those employees create additional taxpayer value.

Government ROI shouldn’t simply mean employing fewer people. It should mean getting more public value from every dollar — and recognizing the people who produce it.

Political Appointments Carry a Different Risk

There’s a legitimate argument for paying some political and executive appointees more. Someone leaving an established career to join an elected administration may reasonably expect the job to last only four or eight years — perhaps less. Jacksonville may need to pay a premium to attract accomplished people to positions with that uncertainty.

But employment risk only explains part of the equation. Department directors can also face leadership changes when administrations turn over, while some Mayor’s appointees already had government careers and others possess skills readily transferable to the private sector.

So political risk may justify some premium. It doesn’t automatically establish how large that premium should be.

What Does Jacksonville Get for What It Pays?

That brings us to Part III. If the Mayor’s Office carries a substantially higher average salary than departments performing much of Jacksonville’s day-to-day work, how do those salaries compare with what Jacksonville pays people responsible for running entire City departments?

We aren’t starting with the assumption that high salaries are bad. We’re asking whether compensation reflects talent, responsibility, productivity and results.

Deegan herself has given taxpayers a standard. In her FY2026-27 budget address, she said:

She also said each dollar invested should deliver a positive return for citizens. That’s a businesslike principle applied to government. So let’s apply it to the government's own payroll.

First, an Important Distinction

Not everyone who ultimately reports through Jacksonville’s executive branch works in the Mayor’s immediate office. The Chief Administrative Officer holds a citywide executive-management position, while departments such as Technology Solutions, Public Works, Planning, Parks and Finance have their own operating leadership. For this comparison, we therefore distinguish among Mayor’s executive, policy and communications staff; citywide executive administration; and directors responsible for major City departments and operating functions. That distinction makes the comparison more precise.

Start With the Same Year

Salary comparisons can mislead when the years don’t match. Comparing a department director’s 2023 salary with a Mayor’s Office employee’s 2026 salary could exaggerate the difference. So wherever the records allow, we compare 2023 with 2023 and 2024 with 2024, then look at where compensation stands today.

2023: The Higher Average Started on Day One

Deegan entered office in July 2023 with an 18-person executive team carrying approximately $3.18 million in annual salaries. Curry’s departing 18-person team cost approximately $2.59 million. Same number of people. About $590,000 more — a 23% increase. That doesn’t prove Deegan overpaid anyone. Different mayors organize administrations differently and compete for different talent. But it establishes something important: much of the higher average was built into Deegan’s staffing structure from the beginning. Several appointees started around $185,000.

Mayor’s Executive / Policy Staff — 2023

Ahmed's 2023 title is shown historically. His current title is Chief of Analytics.

Citywide Executive Administration — 2023

We separate the CAO because that position carries broad administrative responsibility across City government and isn't directly comparable to a communications, policy or initiative position.

Department and Operating Leadership — 2023

We removed the previously listed Michael Weinstein/$250,000 CFO entry from the 2023 comparison rather than carry forward a classification and salary combination that requires additional reconciliation.

The revealing part of the comparison remains the cluster around $185,000. Jacksonville valued Communications, Strategic Initiatives, Diversity & Inclusion and Public Safety at approximately $185,000 each — essentially matching the salary for running Public Works and exceeding the documented salaries for the Parks and Employee Services directors.

2024 Makes the Comparison Clearer

By 2024, several salaries that started at $185,000 had risen to approximately $189,625. Public Works Director Nina Sickler also earned approximately $189,625.

Now the comparison becomes easy to see.

Same government. Same year. Same compensation tier. Very different responsibilities.

Deegan Chose Nina Sickler, Too

Deegan selected Nina Sickler as Public Works director in 2023. Her administration highlighted more than 30 years of design, management and leadership experience delivering government infrastructure programs, including extensive work on Jacksonville projects.

So Sickler wasn’t simply a director Deegan inherited. Deegan chose her. That means the administration placed the person running Public Works and several people in the Mayor’s executive operation at nearly identical salaries. That doesn't establish which person deserves more; it shows how Jacksonville valued dramatically different responsibilities.

Public Works handles streets, drainage, facilities, engineering, contracts, equipment and capital infrastructure. Even modest improvements in an operation of that scale can produce substantial taxpayer value. A department director isn’t simply a figurehead. Strong leadership can materially change the return taxpayers receive from an entire operation.

Helena Parola Adds Another Dimension: Time

Planning Director Helena Parola joined Jacksonville’s Planning Department in 1998 as an assistant planner and spent roughly 27 years advancing through professional, supervisory and management positions before Deegan appointed her director. Her appointment salary was approximately $190,550. Several Mayor’s executive positions sit around $195,000.

That comparison adds another consideration: institutional experience. A career employee can spend decades learning not only a profession but Jacksonville itself — its systems, regulations, personnel, infrastructure and institutional history. Longevity alone doesn’t determine value. But taxpayers and City employees can reasonably ask what expertise, responsibility and results justify valuing very different career paths at roughly the same salary.

Experience Also Supports Many Deegan Appointments

Deegan’s staff shouldn't be characterized as a collection of inexperienced political hires. The evidence doesn't support that. Kelli O’Leary brought previous City and transportation-agency executive experience. Joe Inderhees brought extensive television-newsroom leadership. Lynn Sherman brought decades of health-care experience. Garrett Dennis served on City Council and worked for the Supervisor of Elections. Parvez Ahmed brought finance, quantitative-analysis and civic experience, while Phil Perry brought strategic and political communications experience. Those facts support Deegan’s hiring decisions. Qualifications matter.

But qualifications establish what Jacksonville bought. Results tell us what Jacksonville got.

There’s Also a Media Connection

Deegan spent decades in broadcast journalism before entering politics, and several people she selected also came from media, broadcasting or communications. Melissa Ross had a long broadcasting and journalism career; Joe Inderhees brought television-newsroom leadership; Phil Perry came from strategic and political communications; and Brittany Norris brought communications and digital-media experience along with municipal elected experience.

None of that establishes anything improper. Executives frequently recruit people from professional worlds they know. A mayor from banking might recruit heavily from finance; one from insurance might bring more corporate or insurance experience. Deegan came from broadcasting, communications and public engagement. It’s reasonable to examine how that background shaped the expertise she chose to emphasize at City Hall. The relevant question isn't where someone worked before City Hall. It's what Jacksonville bought with that experience — and what it produced.

Some Returns Are Easier to See Than Others

Public Works can measure roads, drainage projects, construction schedules, contracts and capital costs. Planning can measure applications and processing times. Technology can measure system performance and automation. Finance can measure budgets, debt, audits and financial controls.

Strategic Initiatives, Community Initiatives, analytics, communications and intergovernmental affairs can also create substantial value, but taxpayers may have a harder time measuring that value independently.

What did an initiative cost? What changed because of it? What savings did analytics identify? What measurable benefit did communications produce? What outside dollars did intergovernmental work secure?

The less tangible the function, the more important transparent performance measures become.

Melissa Ross Shows Why Nuance Matters

Reducing Melissa Ross’s résumé to “radio host gets $195,000” would misrepresent her experience. She brought decades of journalism and broadcasting experience and substantial familiarity with Jacksonville civic affairs. The more useful question concerns the broader Strategic Initiatives function: What initiatives? What measurable outcomes? What public benefit? What return? Those aren't attacks on her qualifications. They're the questions any organization serious about ROI should ask about a highly compensated position.

Technology Changes the Salary Conversation

Technology, automation and AI can reduce repetitive work and allow employees to manage more projects and serve more residents. Jacksonville is already pursuing technology-driven efficiencies in areas such as permitting and digital processes. But success shouldn't simply mean eliminating positions. Jacksonville should measure how much additional value its workforce produces.

If an experienced employee uses technology to accomplish more work, reduce consulting costs or shorten processing times, Jacksonville has created value. If competitive compensation helps retain that employee, the additional compensation can itself produce a return. The Salary Pyramid isn't simply about finding the highest paycheck. It's about whether Jacksonville rewards the people and positions producing the greatest public value.

What Does Jacksonville Get for $195,000?

If Jacksonville pays approximately $195,000 for analytics, what did the analytics produce? If it pays approximately $195,000 for strategic initiatives, what initiatives reached completion? If communications commands department-director-level compensation, what measurable public value did it create?

The answers could strongly support Deegan. If analytics identifies millions in savings, $195,000 could be an exceptional investment. If strategic initiatives attract outside money or solve expensive problems, document it.

A high salary doesn't prove poor ROI. An impressive résumé doesn't prove good ROI. Performance does.

What About City Council?

One recurring response to Parts I and II has been: “City Council approved the money.”

Correct. Deegan proposes the budget, while Council reviews, amends and ultimately approves the appropriation. Council therefore shares responsibility for funding the Mayor’s executive operation.

But approving an overall budget isn't the same as selecting individual Mayor’s Office employees. Within the authorized budget and personnel structure, the Mayor exercises broad discretion over her executive staff.

Put simply: Council approves the money. The Mayor chooses how to staff her executive operation within that framework. Council approval therefore doesn't eliminate the ROI question. It expands who should answer it.

Department Directors Face Another Layer of Accountability

Department leadership works differently. The Mayor selects department directors, and City Council generally confirms those appointments. For the Mayor’s immediate staff, the Mayor selects the personnel and Council approves the overall funding. For department directors, the Mayor selects the candidate, Council confirms the appointment and Council approves the funding. Deegan chose Sickler. Council confirmed her. Both branches carry responsibility — just in different ways.

Deegan Didn’t Simply Inherit the Department Heads

Jacksonville mayors have considerable ability to reshape departmental leadership, and Deegan has exercised that authority. She selected Sickler for Public Works and later appointed Parola to lead Planning.

Retaining an existing director also represents a leadership decision. So we can't simply dismiss these comparisons by saying “Deegan inherited those salaries.”

In several important cases, she didn't. That makes the comparison more direct: How does the administration value one kind of executive responsibility versus another?

The Raises Aren’t the Main Story

Several $185,000 Mayor’s executive salaries rose to approximately $189,625 — about 2.5%. O’Leary’s approximately $200,000 became $205,000, also about 2.5%, while Library Director Timothy Rogers’ compensation increased by a similar percentage.

That doesn't support a sweeping claim that Deegan handed her aides extraordinary raises while department directors fell behind.

The evidence points somewhere more interesting: Deegan built an executive operation that valued several positions at department-director compensation levels from the beginning — and subsequent increases largely preserved that relationship.

So, Who Makes More Than the Boss?

The title is deliberately provocative. A department director isn't literally the boss of someone in the Mayor’s executive operation, and the evidence cuts both ways.

Technology leadership has commanded high compensation. The CAO carries broad citywide responsibilities. Several Deegan staff members bring decades of relevant professional or government experience. Political appointments can carry employment risk, while some department directors came from outside government because Jacksonville needed specialized expertise. But the central finding remains:

Jacksonville has repeatedly paid several policy, communications and initiative positions surrounding the Mayor about what it pays people to run major operating departments — and sometimes more.

In some cases, Deegan selected both sides of the comparison. That doesn't prove the salaries are excessive.

It makes the business question more important.

What Does Jacksonville Get for What It Pays?

Jacksonville isn't a private corporation, and essential government services can't always be valued on a balance sheet. But Jacksonville still employs thousands of people, buys technology, manages billions of dollars, awards contracts, builds infrastructure and competes for talent.

Those are management decisions, and good management asks what each investment produces.

That standard should apply to an engineer, planner, technology specialist, department director, political appointee — and someone working immediately beside the Mayor.

So if Jacksonville receives extraordinary value from a $195,000 executive position, show it. If analytics generates millions in savings, show it. If strategic initiatives produce measurable improvements, identify them. If technology makes career employees more productive, recognize the value they create. If strong department leadership reduces project costs, account for that return too. This isn't an argument for paying everyone less. It's an argument for connecting compensation to talent, responsibility, productivity and results.

The real question behind Jacksonville’s Salary Pyramid isn't simply who gets paid the most?

It's: Who creates the value — and does Jacksonville’s salary structure reflect it?

By Deegan’s own standard, taxpayers shouldn't have to assume the return exists.

They should see the proof.

The Mayors Office Part IX

The Mayors Office Part VIII

The Mayors Office Part VII

The Mayors Office Part VI

Donna The Mayors Office Part V

The Mayors Office Part IV

The Mayors Office Part III

The Mayors Office Part II

The Mayor's Office Part I