WHO’S RUNNING FOR WHAT? AN EARLY LOOK AT FLORIDA KEYS ELECTIONS

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Candidates every few years kicks off election season in the Florida Keys.

This year was no different and more than 200 people filled Salute restaurant in Key West on March 9 to hear from more than a dozen city, county and statewide candidates.

With four Key West leadership seats up for grabs in the Aug. 18 primary, the politics and priorities of the city commission could see a shift, said Todd German, president of the nonprofit voter education group Hometown, which hosted the March 9 Call for Candidates.

In the coming weeks and months, the Keys Weekly will dive into each race with analyses of campaign contributions and questions posed to all candidates, whose answers will be printed in their entirety.

But with the primary election still five months away, here’s an overview of who’s running for what position.

Key West mayor

Incumbent Mayor Dee Dee Henriquez, who previously served as the county’s longtime elected tax collector, ran unopposed for mayor two years ago and handily won her first term. 

She now faces a challenge from current District II city commissioner Sam Kaufman, who has been on the commission for 10 years and now wants the center seat, the final vote on city matters and the mayor’s gavel.

Henriquez: “When I was sworn in, I inherited a number of challenges. We are continuing to move forward and with a positive attitude. I am very proud of what we have done and we will continue to do in the future.”

Kaufman: “No more backroom deals. We’ve got a lot of things to change, but it starts with open access, open meetings and encouraging public participation.”

City commission, District II

Kaufman’s entry into the mayor’s race will leave his District II city commission seat vacant. Two men are vying to occupy it. 

Bobi Lore is the owner of Island House guesthouse.

“Key West is special and we need to keep it that way,” he told the Hometown audience, vowing to listen to and represent the residents. 

Mark Rossi previously held the District II seat. He owns Rick’s and Durty Harry’s bar and entertainment complex on Duval Street, and emphasized his “proven leadership” that helped build Truman Waterfront Park and the current city hall building.

City commission, District IV

In District IV, current commissioner Lissette Carey had not filed for reelection, leading to a three-way race among Sarah Compton, Juan Llera and Wayne Garcia. 

Compton: “My instinct is always the same. Bring everything into the sunshine. If something can’t handle public scrutiny, then we probably need to ask why.”

Llera: “I’m a retired veteran and former law enforcement officer. I’m also a voter and it was great to hear from all the candidates today. Their qualifications, their community involvements and the things they’ve supported are the things we need to know before we go vote.”

Garcia: This island is my heart. It’s my passion. There’s things we have to address, but I know what I feel about this island.”

City commission, District V

In District V, commissioner Greg Veliz was appointed to fulfill the term of the late Mary Lou Hoover, but Veliz has not filed to run for the seat. Chris Massicotte and Greg Sullivan are running to represent District V.

Massicotte: “Make city hall make sense. Make fiscally responsible decisions and ask hard questions. Tallahassee shouldn’t get to decide who or what we celebrate. Not on my watch.”

Sullivan: “I’ve been here 31 years and I want to bring my skills in maintenance to the city of Key West.”

Keys Weekly will evaluate the other races in the coming weeks, including county commission, school board, mosquito control, judicial races and statewide races. 

Here’s a look at a few other candidates who attended the Hometown event on March 9.

County commission District 4

Monroe County Commissioner Michelle Lincoln is seeking reelection and is thus far unopposed.

County commission District 5 

County Commissioner David Rice is seeking reelection and is thus far unopposed. 

School board District 1

Incumbent Darren Horan seeks reelection

Former superintendent Theresa Axford has said she intends to run, but has not officially filed.

Luis Gonzalez spoke on March 9, but has not officially filed. 

School board District 5

Incumbent Sue Woltanski is seeking reelection and has a challenger in Chelyn Shaw.

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.

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