Henriquez Is Betting Key West Wants Results

Mayor Danise "DeeDee" Henriquez faces a very different political arena from when she was first elected unopposed in 2024 having previously been the county's longtime Tax Collector. Now, she is fending off what many regard as a strong challenge by City Commissioner Sam Kaufman in what has become one of the island's most intensely discussed elections in recent memory.

Palm and Prejudice invited both candidates for a brief conversation to discuss the state of the race, undecided voters, and what they believe will ultimately swing the election. Commissioner Kaufman was first to respond and his remarks were previously published.

In the following lightly edited conversation, Mayor Henriquez laid out what she believes were significant economic victories in her first term, responded to criticisms of her leadership style, clarified the Casa Marina vote, and made a case to voters who she thinks will value the relationships she has rebuilt with the city and state.

Mayor, now that we are very close to election day, how does the race feel to you at this point?

Henriquez: I will tell you, Kevin, I am very excited about the last 19 days of this election. There's a lot of momentum. There's a lot of excitement. We're going door to door every day. We have our teams and we're getting out there and reaching out to the people. And so, I'm very, very excited about the last 19 days.

I feel like I might know the answer to this, but does the whole campaign experience feel different from what you expected when you first decided to seek another term?

Henriquez: I'm not doing anything differently than when I ran the first time for mayor. I am very hands on and participate in everything that I can that involves our city, involves City Hall, participate in all the meetings. Everything that I have done in my first campaign versus [this] campaign, I'm not doing anything differently. It's always been about the people.

And so I will tell you, when I first ran for office in 1999, there was a young lady that told me something that has stuck with me for 30-something years. And it was that when you run for office and you win, you participate in everything every single day. And whether your term is two years or whether your term is four years, that you go out every day and like I said, participate in everything that you can. You don't want to show the people that you are only going out there during election time.

That's always stuck with me. So I don't go out just during election time to go meet the people and talk with the people. I do it every single day, whether it's a two-year term or a four-year term. And that has always stuck with me.

In going out there and meeting all these people, not just for the campaign, but through your role as mayor, who do you think is out there still making up their mind? How would you describe, if at all, the state of undecided voters in Key West?

Henriquez: Walking door to door, it has been a huge impact because there have been undecided voters. And because I've been able to meet them face to face and asking me all kinds of questions or concerns that they had that may make that decision, that has been my opportunity to reach out to them. So going door to door has been very, very impactful for me to be able to meet with them and let them ask me any questions that they may have.

When voters ask you why you think you should stay in there for another term, why you deserve another term, what accomplishment or decision from this first term do you point to the most?

Henriquez: So good question. There was a household that I knocked on the door. It was a Saturday morning. And one of the questions they asked me was, "What is the difference between you and your opponent?" The first thing that I had responded to was what I have accomplished in 23 months being in office, my opponent hasn't accomplished in 10 years. It's all about building those partnerships and relationships because we didn't have that when I first ran two years ago. And those partnerships and relationships with our community, with our municipalities, the county, the state, the federal level, even the Monroe County School Board, Keys Energy – there was a lot of broken partnerships. And so my goal was to try and bridge those gaps and build those partnerships back with all of our legislation and all of our municipalities and the leadership. And that's exactly what I've done.

Just in a matter of 23 months, I mean, look what we did with the State in Tallahassee, bringing back $5.5M in revenue, which the city hasn't done in 10 years. Why hasn't my opponent gone to Tallahassee or Washington as Vice Mayor and try and build those partnerships and bring money back that will help reduce taxpayers' dollars in our budget and help get some of these projects accomplished?

Then what do you think would be at the top of the list of your accomplishments when it comes to looking at what has concretely changed for Key West residents because you've been the mayor?

Henriquez: So some of my accomplishments, like I had just said, was bringing back $5.5M to the City of Key West because we didn't even get the veto pen where the county, the college, Miami-Dade, Broward, West Palm Beach, they all received the veto pen from our governor.

What's a veto pen?

Henriquez: Meaning when they veto our bills. So when all the bills go through the [Florida] House and the Senate, then it goes to the governor for approval. And he will either approve or he will veto. And all of our projects that we received and more – they were never vetoed by the governor. And that's a huge accomplishment because like I said, what we have brought back in one year, our city hadn't done in 10 years.

Do you think that that could explain why there seems to be more businesses or business-minded individuals who are publicly backing you, donating to your campaign? Do you feel like Mayor Henriquez is good for business?

Henriquez: Well, I will tell you that part of that $5.5M, it was $750,000 for the wastewater treatment facility project. There was $750,000 for the College Road Outfalls Project. A million dollars for the Duval Street pump station design where we've had flooding at both ends of Duval Street. And they've been talking about Duval revitalization for years. Well, you know what? With us building those partnerships back with our delegation in Tallahassee, with our representative, with our senator, we're going to start designing the pump station to be able to help the flooding at the end of Duval Street. And another $3M for the Stock Island Landfill, the remediation feasibility study. That's been sitting there. They call it Mount Trashmore. That's been sitting there for years and years and years. And now we were able to receive $3M to start a study for that. So in reference to businesses, I mean, we are very business oriented and I would love to see all of – I will fight for them.

Matter of fact, I'm building a partnership. Here we go again. I've already had a partnership, building a relationship back with our Realtors Association, having a roundtable luncheon to be able to communicate with the Realtors Association and our city staff to be able to put a name with the faces and be able to be hands on and [answer] any questions that they may have. Well, we're getting ready to do this now August 4th with the business community and have them have the opportunity to be able to sit down and have lunch and be able to ask [questions]. And they've already submitted some questions so our staff could be prepared and be able to put a name and a face with the business community and have their questions answered. It's all about communication and transparency.

My opponent talks about how we don't have it in City Hall. Well, maybe if he would come to City Hall more often, then he would be able to see actually all the good stuff that's going on in City Hall. All he talks about is corruption and backdoor deals. He needs to come to City Hall, get involved with his staff and the employees, but we haven't seen him in over a year.

[Author's note: The Mayor later clarified that while she acknowledged Commissioner Kaufman was present for meetings and workshops in the past year, her comments were directed in general at his level of engagement with staff and accumulated mail at City Hall.]

And so Mayor, you brought up your opponent. His fundamental argument has been that City Hall needs more openness, accountability and communication. What do you think is fair in that criticism and what do you think he gets wrong?

Henriquez: Well, I don't think it's fair. Like I said, Kevin, if he would come to City Hall and see all the great stuff that our staff – I say our because it's his staff as well – our staff and our community and see what's actually going on in City Hall, maybe he would see all the good stuff. We just had a strategic plan workshop yesterday and people were watching it online. The phone calls that I received afterwards was, they were so impressed with the staff and the knowledge and to be able to show all the good stuff that we are doing in City Hall. And we're letting our community come in. Like I said, we're having all these workshops. We're open. Everything's online. It's transparent. So I just think if he would come to City Hall more often, he would know what's going on.

Now, some of your own voters have told me that they really want to hear you explain your votes and the reasoning behind City Hall decisions more often. Do you think your leadership style has sometimes been quieter than the moment required?

Henriquez: I'm glad you asked that question because honesty is always the best policy with me. And you know what? If I had to grade myself in all these questions that you're asking me, if there's something that I probably need to work on a lot better, it would probably be explaining myself and why I voted the way I voted. Because I have heard that as well. And they would tell me, "Mayor, you're doing a phenomenal job, what you're doing and how you're changing our city and moving our city forward. But we would like to hear a little bit more on the reasons why you voted the way you voted." I have to agree with them. And everybody has strengths, everybody has weaknesses, and that's one that I do need to improve.

Is there one vote in particular that you wish you could go back in time and maybe explain what was going on behind the scenes better?

Henriquez: Let me think about that for a second. So I would probably say, I know that Casa Marina was a vote that I probably didn't explain myself more of why I supported. And so that would probably be one of them, was the Casa Marina vote.

And what was the nature of that vote?

Henriquez: The reason why I supported yes, because my opponent talks a lot about workforce housing. As far as workforce housing, we were able to celebrate the [Lofts At Bahama Village], which was I believe, 99 units. We were able to partner with and help move forward with the Monroe County School Board – 150 units of workforce housing. We were at the groundbreaking for the Housing Authority of another 54 units, which my opponent never shows up to. And so, we are chipping away little by little in reference to the housing. Every opportunity that we can partner with someone and be able to help our community, that's what we're doing. We are chipping away one housing unit at a time. The Casa Marina, not only was it not going to cost taxpayers dollars, but the Casa Marina was willing to invest $80 million to improve that property that has been sitting there since 2005 during Hurricane Wilma.

In the beginning, I will tell you, in the beginning, I was opposed prior to [being] mayor. I was going to those meetings, to every single one of those meetings. And in the beginning, I was opposed. But you know what? They kept listening to the people. And every time that we went back to those meetings, they had adjusted what they felt that they could adjust because they were listening to the people. At first there was no housing part of that project. And then there was going to be housing for the police, the firefighters, their workers. That would have been more housing units that we would have had that we were able to chip away. The property taxes, the values and properties would have gone up. There were just so many opportunities that we had for that Casa Marina project that unfortunately was voted against.

So I was in support of it. And if it had to come before us again, I would support it again.

Now, your experience and your ability to build relationships as you've explained throughout this conversation are some of your strongest arguments. So how do you feel when you encounter voters or islanders who might say, "You know what? You did a decent enough job," but they just want to affect change. Do you think that is a valid reason for someone to cast their vote this August?

Henriquez: If it was a change for better, I would say yes. But it is not a change for better. And I did say this in a forum. If [Kaufman] does become mayor, what he will destroy in two years, it'll take somebody years to fix it. And when I first became mayor, there was $4.3 million dollars [worth of studies and consultants reports] "sitting on a shelf." And I tell everybody, I didn't come there to dust the shelves. I came there to move those projects off the shelves. They had been sitting there for years. Why are we going to do studies and have consultants and pay $4.3 million for it just to sit on the shelf? So what we have done in my 23 months is we started moving those projects off the shelf. Look at what happened with Mallory Square. When I first became mayor, I sat down and I spoke to all the different directors.

We had a grant with TDC for $2M prior to me being there to redo the bathrooms, have shade structures. And guess what? They didn't do anything with that $2M. It sat there for two years. And guess what? They had to return that $2M back to TDC.

That's embarrassing. But you know what? Now we have I think $4.2M or $4.3M that we have been awarded for the Mallory Square Project. It has to be approved by the Board of County Commissioners, and I hope it gets approved in the next couple months. And then guess what? We're ready to hit the ground running.

We're ready to redo those bathrooms and put shade structures and trees and furniture and really enhance Mallory Square. That was one of my commitments, to get Mallory Square moving forward, to get Duval Street moving forward. We were able to finish the John Jones Navigation Center. We were able to finish the Frederick Douglas Community Center, Clinton Place. I mean, we're just getting projects and we're able to get money from Tallahassee and continue to move these projects forward. And that's what I've done in 23 months.

You've probably spoken with more voters, I would think, across the city during this campaign than probably any other point in your public career. What are voters bringing up to you that isn't receiving enough attention in the forums or in the press?

Henriquez: Let's see. I mean, there's been all types of communication. Mostly in the conversations that I've been having with people throughout the City of Key West has been that it's been very refreshing to see what I have done and what I have accomplished in the short period of time than what my opponent has in all the years that he's been there. He's always the minority and not the majority, and people question why.

What do you think at the end of the day is the fundamental choice voters are making between you and Commissioner Kaufman?

Henriquez: Like I said, going door to door and listening to the people and how excited they are and just the excitement for me to be able to continue to move our city forward.

Whatever happens in August, what has running for reelection as mayor taught you about Key West that serving as mayor or serving as tax collector previously did not?

Henriquez: Well, that's a good question, Kevin. So I've been in public service for 30 years, a little over now 30 years in public service. And even today, people will come to me and ask me questions that doesn't even have anything to do with City Hall or even as mayor. It could be as simple as a question on their property tax bill.

And I will tell you, that happened to me one time when I was walking door to door. And she was very undecided on who she was going to vote for. And she talked to me about property taxes. And I told her, I said, listen. I explained to her what would happen if in the event that property taxes were taken away. And I told her, I said, "You call me the moment that we see what's on the ballot and what the verbiage is going to be in reference to the referendum.

So that's going to be on the ballot in November. And I'm going to go there and I'm going to look at her bill. And on each of those items that she's going to vote on, I'm going to let her know how it would affect her. And she's like, "You would do that for me?" And I'm like, "This is my job. I am here to serve. No matter as a mayor, as DeeDee Henriquez, or even as your previous tax collector, no matter what anyone has a question for, I am always here to help them. If I don't know the answer, I will get them the answer. But that's what I'm here to do. I am here to serve our community.

Do you have any predictions for your race or the others citywide. Well, not citywide, but the other city specific races that are happening at the same time?

Henriquez: I don't have a prediction for any of the other races, but I will tell you this. I congratulate each and every one of them that are running for any elected position, whether it's in the City of Key West or throughout Monroe County. And running for Monroe County is a lot harder than it is to run for the City of Key West because of the amount of miles that they have to cover in a course of a day between Key West all the way to Ocean Reef. But like I said, I don't have a prediction, but I do want to say congratulations to each and every one of them for running, putting themselves out there in the public. It's not easy. It's not easy. It's not easy talking, going up to people that you don't know, introducing yourself, speaking in front of everyone. So again, I would just like to say congratulations to everyone out there that put their name in the hat.

Mayor, thank you for your time.

Henriquez: You are very welcome.