OPINION: City Manager’s Annual Report Highlights Progress, Avoids Core Issues
Accountability, governance and more glossed over in 42 pages.
The City of Key West’s 2024–2025 Manager’s annual report is polished, photo-heavy and expansive.
It highlights capital projects, departmental activity and infrastructure work across city government. What it does not do is confront several of the most consequential issues facing the island city.
A public annual report is not required to be critical.
It is expected, however, to be complete. Looking back is not the problem. Cities should take stock of what they have accomplished.
What is harder to justify is glossing over unresolved challenges without charting a viable path — and plan — forward. In several key areas, the omissions are asunderous.
Grand Jury Findings and Ongoing Corruption Case
The report contains no meaningful update on the city’s response — or lack thereof — to the grand jury findings that preceded indictments tied to what has become known locally as the “Bubba Bozo Trio.” That investigation has produced 27 felony counts across multiple defendants, with additional charges possible as investigators continue to follow financial records.
The case has been widely described as the most significant corruption scandal to affect the Southernmost City in decades. The last episode of comparable civic impact dates to the 1970s, when former Key West Fire Chief Joseph “Bum” Farto was convicted in federal court of racketeering and cocaine trafficking before disappearing prior to sentencing.
The current city manager has circulated spreadsheets tracking implementation of grand jury recommendations. Several items are listed as “100 percent complete.” The grand jury recommended that City Commissioner Lissette Carey resign from office. That item is marked complete. Carey remains on the dais and has been rumored to be considering a run for higher office. She also played a central role in the public ouster of former City Manager Al Childress following the Corradino report controversy.
That firing was what kicked off the entire Bubba Bozo Trio corruption investigation in the first place.
Another recommendation called for Assistant City Manager Todd Stoughton to lose his position. That item is also listed as complete.
Technically, he did lose his position as assistant city manager. But as those inside the city often do, Stoughton landed softly across the hall with a promotion, now overseeing legislative and lobbying efforts for the City in both Tallahassee and Washington.
The gap between the grand jury’s recommendations and the resulting reality has fueled discontent among residents and voters and the Monroe County District Attorney who famously told the media “I can’t tell them what to do, but I can make them follow the law.”
As was mentioned, the investigation is on going and more indictments reaching further into city hall would not seem unreasonable.
Legal Representation and Governance
The city continues to rely on contracted outside legal counsel after struggling to attract applicants willing to serve as full-time city attorney.
The outside city attorney — high-powered Orlando freelancer Mayanne Downs — bills the residents of Key West $499 an hour, ostensibly to obtain more outside counsel at rates reportedly ranging from $350 to $500 an hour.
Since being retained by Mayor Danise Henriquez, Downs has missed at least two City Commission meetings, failing to even attend by ZOOM. Instead, she sends fledgling in-house staff counsel in her stead.
The result? Commissioners routinely struggle to obtain clear answers to routine legal questions often leaving to ask “Exactly what are our constituents getting for their money?”
The annual report does not address recruitment challenges, legal expenditures (Downs provides itemized invoices but none have been produced by other outside attorneys on behalf of the city) or long-term plans to stabilize the department.
City Workforce, Payroll and Fiscal Exposure
The City Commission has previously directed staff to reduce payroll through attrition and consolidation. The annual report provides staffing summaries but does not clearly address whether those reductions have occurred.
Instead, new positions appear to have been added in several departments without prominent public discussion.
For a city with a year-round population of roughly 25,000 residents, staffing levels remain high compared with similarly sized seasonal Florida municipalities.
Key West employs roughly 550 full-time workers across departments on a roughly 5.6-square-mile island with a FY 2024-25 budget of $262.5 million working out to approximately $10,500 per resident.
By comparison:
Naples (Heavy snowbird,) population approximately 22,000, employs roughly 500 with a footprint of roughly 13 square miles. ~$335 million ~$15,200 per resident.
St. Augustine (Heavy tourism,) population approximately 15,000 with significant tourism, employs roughly 450 to 500 in a city with approximately 12.9 miles of acreage. ~$195 million — ~$12,600 per resident.
Marathon (Heavy snowbird,) population approximately 8,500, operates with roughly 300 employees in 8.6 square miles. ~$112 million — ~$13,000 per resident.
Cocoa Beach (heavy snowbird and tourism,) population approximately 12,000, employees 90 over a 4.9 square mile area. ~$65 million — ~$5,700 per resident.
While Key West serves a large visitor population and a dense island footprint, its administrative structure has grown increasingly layered, with expanded senior management and departmental staffing.
This expansion has occurred alongside rising executive compensation. The city manager received a substantial salary increase in the most recent contract revision, and at least one department manager received a pay increase of roughly 10 percent following a reclassification. In addition, at least one position was created that critics have described as tailored for a family member of a city official.
Granted, all of this happened after the report. But it still appears to directly fly in the face of direction from a dais that likes to tout itself as fiscally conservative.
All of these staffing and compensation decisions come at a moment of fiscal uncertainty. The City of Key West increased property taxes by 5 percent — the only municipal authority in Monroe County to do so — even as cities and counties across Florida face the prospect of significant property tax restructuring or reductions from the Legislature in Tallahassee. For cities that rely heavily on ad valorem revenue, potential state action represents a structural risk.
The annual report does not meaningfully address how current staffing levels, payroll growth and management expansion would be sustained if property tax revenues were reduced or capped further. It also fails to address commissioner’s directions to reduce staff.
Transportation
Transportation planning receives limited treatment despite being one of the most persistent concerns raised by residents, workers and business owners.
The city frequently cites nearly $1 billion in assets and no bonded liabilities, yet has not committed to a coherent, fully funded mass transit plan. The Duval Loop continues to rely heavily on uncertain state funding. No long-term replacement funding strategy is outlined.
The collapse of Conch Connect — the Monroe County-run microtransit system launched in partnership with Freebee — left a gap that has not been meaningfully addressed. The program proved popular but ended after Monroe County dismantled its transit department. Freebee continues to operate in other Florida municipalities, including Islamorada, but no comparable replacement was implemented in Key West.
Key West Rides has improved since its rollout but ends service at 8 p.m. and lacks sufficient capacity during peak commuting periods.
Comparable tourist-driven Florida cities of similar size operate more robust transit systems. St. Augustine maintains a municipal trolley and shuttle system with extended evening hours. Naples operates Collier Area Transit routes supplemented by seasonal circulators. Other coastal communities deploy fixed-route buses, seasonal trolleys and barrier-island shuttles designed to reduce congestion in tourist corridors.
The annual report does not outline a comprehensive plan to replace Conch Connect, expand service hours or create a dedicated city-funded circulator system.
Environmental and Water Quality Issues
The report references environmental initiatives but gives limited attention to nearshore water quality.
After months of discussion about formalizing water-quality monitoring, a redlined version of proposed testing procedures was presented publicly to city staff and commissioners by an attorney who also owns a private wastewater treatment facility in Key West. That redline document was incorporated into the final framework.
The revisions removed turbidity testing in Key West Harbor and eliminated broader nearshore testing provisions included in earlier drafts, narrowing the scope and geographic reach of monitoring.
Negotiations surrounding the final language were pushed by the city’s contracted outside legal counsel, Mayanne Downs, during the drafting process. Critics argue the resulting framework benefits private stakeholders with waterfront and wastewater interests while reducing scrutiny of harbor and nearshore waters.
The privately owned wastewater facility associated with the attorney operates shallow injection wells permitted under state regulation. Environmental advocates have long raised concerns about the potential migration of treated effluent from shallow injection systems into nearshore waters.
Nearshore areas critical to tourism have experienced repeated health advisories and closures issued by the Monroe County Health Department because of elevated bacteria levels. The annual report does not address the elimination of turbidity testing, the narrowing of sampling locations or a long-term mitigation strategy.
For a tourism and commercial fishing community built on its surrounding waters, the absence of a detailed explanation of monitoring standards and remediation plans is significant.
Housing and the Loss of Assisted Living at Poinciana Gardens
Another year has passed without adoption of an inclusionary housing ordinance requiring developers to include affordable or workforce units in major projects.
At the same time, the city has lost its last assisted-living facility for low-income seniors. Assisted-living operations at Poinciana Gardens were discontinued after the Key West Housing Authority determined the program cost too much to maintain. Residents who had been able to age in place in Key West were relocated off island.
The closure leaves a significant unanswered question for the broader community: what happens to residents who may one day require assisted-living services that are no longer available in Key West.
It yet again reflects a city with considerable resources and limited debt that has opted not to maintain support for its most vulnerable residents, despite those services being paid for and never free.
Culture and Economic Diversification
Key West’s bid for UNESCO Creative City designation was unsuccessful, thanks to the myopic vision of a group of commissioners that wouldn’t know what culture was if it bit them in the ass. It didn’t even come to a vote, and instead Key West lost out to New Orleans despite an artistic and literary history second to none. The annual report does not reference the effort or its outcome.
The next chance comes in 2030.
The “report” also fails to highlight the completion and reopening of the renovated Key West International Airport, which continues to report record passenger levels and the additional accompanying challenges.
EYW is owned and operated by Monroe County, not the City of Key West. As passenger numbers rise, so do the pressures on city roads, utilities, housing and public safety — even though the city receives no direct operating revenue from the county-run airport system. It fails to address how the city intends to absorb the added strain on infrastructure and quality of life.
An annual report should reflect both accomplishments and unresolved challenges. Without fully acknowledging the latter, or outlining a clear strategy for navigating fiscal uncertainty and growth pressures, it risks appearing incomplete at a time when public confidence in local governance remains fragile.
Again, it just seems to reinforce the idea that the only place there is transparency is through the windows in the front door at 1300 White Street.
In the end, it seems like a glossy, slick re-election brochure paid for with taxpayer money.
We’ll find out more about that when the Mayor gives her annual State of the City address.
But regardless, the people of Key West — and visitors — deserve better than that.