The city of Key West is acting quickly to fill the District 5 city commission seat that Mary Lou Hoover occupied from 2018 until her passing on Nov. 19.
The city commission will appoint an interim commissioner at their Dec. 2 meeting. That person will serve until the Aug. 18 election, when Hoover’s term would have ended. She had already decided not to seek reelection and two candidates — Chris Massicotte and Harry Russell — are running for the District 5 seat.
What’s the application process?
Applications are being accepted through 5 p.m. on Friday, Nov. 28. Anyone interested must live in District 5 and must have been a full-time resident of Key West for at least the past year. Applications are available at cityofkeywest-fl.gov. City commissioners and the mayor “are encouraged to conduct applicant interviews, at their discretion, prior to the Dec. 2 commission meeting,” states the resolution that was approved at a Nov. 24 special meeting to finalize the appointment process.
“All applications received will be added to the Dec. 2 agenda and published on a daily basis,” the city clerk’s office told the Keys Weekly in response to a Nov. 24 public record request for applications. As of 2:53 p.m. on Monday, Nov. 24, the clerk’s office reported, “We currently do not have any applications. … You can submit a daily request for records or check the city’s website for the updated activity.” (Due to early holiday print deadlines, applications are likely to have been posted to the city’s website by the time of publication.)
The application asks for three references and asks candidates to list their relevant professional experience, community involvement/volunteer experience, prior public service and why they’re seeking the appointment.
The application also asks, “Do you or any immediate family member have any financial, contractual or organizational interests involving the city of Key West that could present a conflict? If yes, please explain.”
Who might it be?
Commissioner Sam Kaufman, at the Nov. 24 meeting, said he would like to see former commissioners apply for the interim position, given their experience, particularly with the city’s budget process that takes place in July and August.
Commissioners Kaufman, Monica Haskell and Donie Lee as well as Mayor Dee Dee Henriquez indicated they were not inclined to appoint one of the declared candidates — Massicotte and Russell — for the seat in the interest of maintaining a level playing field in the race.
Immediately following Hoover’s death, Massicotte urged the commissioners not to appoint him or Russell to the interim post.
“Giving any declared candidate an appointed incumbency would tilt the playing field and raise serious concerns about fairness,” Massicotte said on Nov. 20. “District 5 deserves a process that voters can trust. I am willing to recuse myself from consideration for appointment to this vacancy if the commission also commits that the other declared candidate, Harry Russell, will not be considered. No candidate should get an unfair advantage. The fairest path is to appoint a caretaker who will not run for the seat and will simply serve until the voters decide.”
A few days later, Russell had a different take. Shortly after the Nov. 24 meeting, Russell told the Keys Weekly — and posted on social media — “I will absolutely be applying for the appointment and welcome the vetting process. My leadership experience and commitment to service would be an asset to the city of Key West. I have been asking the residents of District 5 since April for the job. I am ready to get to work.”
Massicotte followed that up with a statement urging the commission to “protect the integrity of the process and the trust of District 5 voters.”
“The voters of District 5 do not get to choose this interim commissioner,” Massicotte wrote. “Six people, none of whom will be able to vote in the 2026 District 5 election (as they do not live in the district) will be making this decision. … I immediately said I would not pursue this because it would give any candidate an unfair advantage. That is not how you earn trust. That is how you damage it.
“During today’s meeting, commissioners Haskell, Kaufman,and Lee, along with Mayor Henriquez publicly stated they do not support appointing either candidate. …These elected leaders deserve credit for taking a principled stand. They recognize that turning this into a political opportunity for any candidate would dishonor the process and commissioner Hoover’s legacy. … Pushing for an unelected incumbency in a moment of community grief is especially troubling.”
So … who else?
Assuming the city commission remains neutral and appoints an interim commissioner who is not running for the same office, who might be on the list?
Former District 5 commissioner and watchdog Margaret Romero, who attends nearly all city meetings, told the Keys Weekly on Nov. 24 that she will apply, saying, “I think I’m the most qualified for the position.” Romero represented District 5 on the commission from 2015 to 2019 and has been a candidate for mayor.
Former city manager Greg Veliz, who is the director of Florida Keys Aqueduct Authority, has also been mentioned. The Keys Weekly asked Veliz on Nov. 24, “Any truth to the rumors that you’ll apply?”
Veliz replied, “I’ve heard the same rumors. I’m spending Thanksgiving with the kids and grandkids in North Florida. I’m sure we will have some discussions during the holiday. Have a great Thanksgiving.”
There will surely be other applicants. So stay tuned to keysweekly.com and cityofkeywest-fl.gov as the applications are filed and posted online.
