There are no pending indictments or upcoming trials involving any candidates in the Key West city elections, but the local races nevertheless are drawing plenty of attention and speculation.

Will Mayor Teri Johnston seek her final term? And if so, can she defeat former Monroe County tax collector Danise “Dee Dee” Henriquez, who announced her candidacy last year and already has raised more than $11,000? Is Commissioner Sam Kaufman considering a run for mayor? Would he run against Johnston, or only if she doesn’t run? And is former city commissioner and downtown bar owner Mark Rossi eyeing Kaufman’s current District II commission seat in the event that Kaufman has to give up that seat to run for mayor?

The Keys Weekly got answers to many of the above questions.

Johnston said she will decide “probably within the month” whether she will seek her final term in office. 

“My first conversation is always with Dar, and then with my campaign team, asking them all, ‘Do you have another one in you?’” Johnston told the Keys Weekly on Jan. 10. “That’s where we are now in that process. Whatever decision we make will be in the best interest of the community.”

Kaufman said he would only consider a mayoral campaign if Johnston decides not to run.

“I support Mayor Johnston 1,000% and would never run against her,” Kaufman said on Jan. 9. “I fully hope she chooses to run again. I think she’s a shoo-in for another term and that would give our new city manager more time to make continuing progress.”

If Johnston decides not to run, and Kaufman indeed challenges Henriquez for mayor, Florida rules require Kaufman to resign his commission seat.

“I can declare my candidacy for mayor, but then I’d have to resign my commission seat a week before qualifying occurs in the mayor’s race in June,” Kaufman said, adding that even if he lost the mayoral bid, he would still have abandoned his commission seat in District II.

Such a move — Johnston stepping back and Kaufman running for mayor — would open the door for Rossi to seek Kaufman’s seat, which Rossi occupied from 2004 to 2016.

Rossi told the Keys Weekly in December he “would neither confirm nor deny” conversations he had had about supporting Kaufman for mayor if Kaufman supports Rossi for the District II seat.

Speaking of city commission seats, Key West voters will choose three new commissioners this year.

Commissioners Clayton Lopez (District VI),  Billy Wardlow (District III) and Jimmy Weekley (District I) cannot seek reelection due to term limits.

Thaddeus Cohen, a former Key West planning director who last year applied for the city manager position, is running for Lopez’s seat in District VI, which includes most of Bahama Village and parts of Old Town.

Former Key West police chief Donie Lee, who served in the post from 2008-2018, told the Keys Weekly on Jan. 10 he expects to file his paperwork to run for the District III seat being vacated by Wardlow this week.

No one had filed for Weekley’s District I seat as of Jan. 10.

The Key West city races are nonpartisan. Commissioners are elected only by voters in their city districts, while the whole town votes for the mayor. City races will be decided in the Aug. 20 primary if and only if a candidate receives more than 50% of the vote. If no one earns that majority, then the top two candidates for the seat will head to a runoff election on Nov. 5. 

For a full rundown of announced candidates and races, visit keyselections.org, where voters also can check their vote-by-mail status if they want to receive a ballot by mail for the 2024 elections.

2024 Election Dates:
Primary election: Aug. 20
General election: Nov. 5

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.