Key West’s leadership will change in the coming months, when voters elect a mayor and three new city commissioners in Districts II, IV and V.
The nine candidates in the four Key West races introduced themselves to voters at Hometown’s June 12 Meet the Candidates event, which also included candidates for county commission, school board, mosquito control, judge, utility board and the U.S. House of Representatives.
In Key West, three of the four nonpartisan races will be decided in the Aug. 18 primary. In District IV, three candidates want to succeed commissioner Lissette Carey, who is not seeking reelection. If none of the three secures more than 50% of the votes, the top two will head to a November runoff.
The comments here are excerpts taken directly from each candidate’s introduction.
(Scan the QR code on this page or visit hometownkeywest.com to watch the full video. See page 19 for the county commission and school board candidates. And stay tuned to Keys Weekly for coverage of the races for judge, utility board, mosquito control and more.)
MAYOR
Sam Kaufman
“We need city hall to change. We need more communication, more accountability. We need a better process for making decisions, whether it’s water quality testing, which we haven’t had for two years; a strategic plan, which we haven’t had in two years; or increased taxes over the last two years, which was not a good decision.
“We need a better commitment to One Human Family. We have to stand together. … We have to stand up for home rule … and we have to have fairness in city hall. We want to have confidence back in our city government.
“We need a new mayor and we need a new city commission.”
Dee Dee Henriquez
“When I took office in 2024, I inherited some of the most difficult challenges our city has faced in recent years. Leadership is not about making the easy choice. It is about making the right choice. As mayor, I represent every resident. … My responsibility has always been to do what is best for the entire community even when those decisions are difficult.
“This election is about more than just projects. It’s about leadership. It’s about choosing someone who has proven they have navigated difficult times, made tough decisions and always put the interests of the entire city first.”
CITY COMMISSION, DISTRICT II
Mark Rossi
“I was vice mayor for over 11 years. I know how it works. I have proven leadership. I’ve been a business owner on Duval Street for over 43 years. … I have over 115 employees and I own workforce housing. I know the challenges and I listen.
“I will not raise tax dollars for anyone. I think it’s too much right now to be honest. There’s a lot of waste.
“I care about this community. I love it. I’ve been one of the longest business owners on Duval Street. I live and I die and I breathe Key West. Is anything perfect? No, but we will sure try.”
Bobi Lore
“I’m motivated by a sense of urgency that we’re at a historical crossroads and we have an opportunity for change.
“I’ve been in Key West for over 10 years, and I’m a business owner that treats his employees with kindness and respect. I bought a property adjacent to my business and turned that into workforce housing. I’ll be a champion for working families that make this island function.
“Key West has always stood for diversity and our One Human Family ethic, where we all can feel welcome. I care about this town with all my heart and I will foster an open and trusting government that works for all of us.”
CITY COMMISSION, DISTRICT IV
Sarah Compton
“When there’s an issue, I’ll explain not only what I’m supporting, but why.
“People deserve honesty even when the answers aren’t easy. People want to know someone is paying attention. That’s the kind of commissioner I will be.
“I’ll ask hard questions. I’ll respect the expertise of our city staff. I’ll work with fellow commissioners even when we disagree. I’ll keep learning, keep listening, and keep showing up. “This job is about earning trust. Most of us want the same things — solutions to flooding, responsible spending, thriving local businesses. And we want to preserve what makes Key West so special.”
Wayne Garcia
“I’ve spent my whole life here cultivating friendships and experiences to prepare me for this. I want to preserve some of what Key West was and promote what Key West can be.
“Key West means the world to me. By us finding one common thing that we can all work together on to start with, we can unite this city that’s divided.
“I know people from the construction industry to the art community and everywhere in between. One thing I always see in people is their love of this island. We’re all Key Westers whether you’ve been here a month, a year, 50 years. … We can make this island even greater. Let’s do that together.”
Juan Llera
“My entire life has been public service — the military for over two decades, then 13 years in law enforcement.
“We’re in a very unique situation, not only at the local level, at the national level. We need to vote.
“Just like Wayne and Sarah, I want to preserve our values. Certainly we need transparency and leadership. I’ve prepared my entire life for this opportunity — from community college to Harvard Business School in educational leadership programs. So this is a great opportunity to give back to my community.
“As a 10-year-old coming from Cuba, I made a promise to serve this great nation. Thank you for the opportunity.”
CITY COMMISSION, DISTRICT V
Greg Sullivan
“I’ve been a Rotarian here for 28 years. I believe in giving back.
“I want to see where we can save money to have the highest level of service with the lowest tax rate. I hear chatter about the planning and the building departments, that it’s confusing to navigate. I want to sit down with the city manager, bring the departments together and make them user friendly.
“You should be able to go into city hall, ask questions and leave with answers. I hear that’s a problem.
“I also believe Higgs Beach can be a gem for all of us, and I will advocate for free parking for all residents at Higgs Beach.”
Chris Massicotte
“Key West is a wonderful place to live, but it’s a government that can do better. I was a political consultant and learned local government matters so much more than Washington or Tallahassee. We need to focus here at home.
“I’ve been president of Keys Last Stand advocating for clean water, responsible development, protecting what makes Key West special.
“I often come away from commission meetings saying, ‘That doesn’t make sense.’ So my campaign slogan is, ‘Make city hall make sense.’
“It feels like we are favoring insiders over everyday residents. The trust has been broken. But we can fix this. We need a change, and I’m going to be there for it.”
