MORE DETAILS: Key West to Set Rules for Filling District 5 Vacancy

Resolution outlines application window and selection process as city moves to replace late Commissioner Mary Lou Hoover; outside counsel unavailable to attend.

The Key West City Commission will convene a special meeting Monday to establish the formal procedure for selecting an interim District 5 commissioner, just days after the death of Commissioner Mary Lou Hoover created a sudden vacancy on the seven-member body.

The meeting is set for 2 p.m. Monday, Nov. 24, at City Hall, 1300 White Street, and will be streamed live on the city’s website.

The session is expected to be one of the most consequential special meetings the commission has held in the last five years.

Outside City Counsel Mayanne Downs has informed city staff that she will be unable to attend, according to city officials. Assistant Chief City Attorney Kendal Harden will sit in her stead, advising the commission through a legally sensitive and time-compressed appointment process governed by the City Charter.

A draft resolution released Friday morning outlines the steps the commission must adopt under Section 2-31 of the City Code, which requires the board to fill any permanent vacancy within 15 days.

Under the proposed rules, the City Clerk will immediately open an application period for any eligible District 5 resident seeking appointment. Applications — including a required Affidavit of Residency — would be accepted until 5 p.m. on Nov. 28. The clerk and City Manager would be required to publicly post notice of the application window on the city’s website and through “any additional reasonable means.”

Once the filing window closes, all submitted applications will be distributed to commissioners for review.

The resolution sets the formal nomination process for the Dec. 2 morning session of the regular City Commission meeting. Each commissioner may nominate one or more eligible candidates, and nominations do not have to come from the applicant pool. No second would be required.

Commissioners and Mayor Danise Henriquez are “encouraged” to interview applicants before Dec. 2, although interviews are not required.

Before nominations begin, the mayor must ensure that all applicants — and any member of the public — are given three minutes each to address the commission.

However, critics are concerned that scheduling the selection for the morning session of the regular December meeting thwarts transparency and potentially limits public participation and comment.

The final selection process will follow rules outlined in Resolution 95-517, which governs how commissioners vote when filling a vacancy.

If approved Monday, the resolution would take effect immediately. The appointed District 5 commissioner will serve until an election is held or until the end of the term, depending on the city’s electoral calendar.

How Key West Fills a City Commission Vacancy

Section 2-31 of the City Code outlines a tight 15-day timeline

Under Section 2-31(b) of the Key West Code of Ordinances:

• The City Commission must fill a permanent vacancy within 15 days.

• Commissioners must first adopt a resolution establishing the nomination and selection procedure.

• The City Clerk may accept applications, but commissioners may nominate any eligible resident, even if they did not apply.

• Before nominations, the mayor must allow three minutes of public comment for both applicants and any member of the public.

• All nominations and votes must occur in open session and be broadcast publicly.

• The appointed commissioner serves until an election is held or until the end of the term.

The Political Stakes Behind the District 5 Appointment

The appointment to fill the late Commissioner Mary Lou Hoover’s District 5 seat may last only months, but it carries significant political weight for both candidates and commissioners.

Two declared candidates — Chris Massicotte and Harry Russell — have already filed for the 2026 District 5 race.

Massicotte has publicly stated that he would recuse himself from consideration as long as Russell does the same, arguing that neither candidate should receive the advantage of incumbency heading into next year’s election.

Mayor Danise Henriquez told Joe Moore on 104.1 US 1’s Morning Magazine, that the appointment will either be available to everyone, or exclude the two filed candidates.

The vacancy also arrives during a period of heightened sensitivity for Key West City Hall. After a year marked by corruption indictments, administrative turnover, and ongoing reform discussions, city officials are aware that the appointment process will be viewed as a test of fairness, transparency, and commitment to Sunshine principles.

Significant fiscal and policy decisions await the commission in the coming weeks — including Historic Key West Bight negotiations on things like Jimmy Buffett’s Shrimp Boat Sound, the possibility of allowing larger cruise ships back in to Key West owned docks, Bayview Park planning, and capital-project authorizations — meaning the District 5 appointee will immediately step into meaningful votes.

Behind the scenes, political alliances and neighborhood loyalties are expected to influence how commissioners approach the appointment. Whether the board opts for a placeholder or someone who may emerge as a future candidate will signal how city leaders view District 5’s role in a shifting political landscape.

This is an evolving story. Watch this space for updates.