Chris Massicotte Wants City Hall to Make Sense

Multiple open races across Key West have made this summer one of the city’s most watched off-year election cycles in recent memory. That is especially true in District V, where the death of former Commissioner Mary Lou Hoover last year left a vacancy later filled by Gregory Veliz, who was appointed to serve until the upcoming August election.

Veliz is not running, leaving District V without an incumbent on the ballot. The race comes down to Chris Massicotte, a former political consultant, and Greg Sullivan, a senior district manager for Waste Management.

Both candidates were invited to discuss the final weeks of the campaign, the issues they believe should take priority for District V, and how they see the race taking shape before voters make their choice. As of publication, Massicotte was the only candidate to respond.

Below is a lightly edited conversation with him.

Chris, we're in the final weeks of the race. What does the campaign feel like to you at this point and what are you hearing the most from District V voters?

Massicotte: Yeah, so I think that I'm feeling pretty good about the race because I've been talking to voters over the last year and I ran for county commissioner, so I've been talking to Key West and District Five voters for two years. And I joke, because this district is so small and because our Key West districts are so small, I'm probably going to know 75% of the people that vote for me. And we've just been identifying voters and we're just making sure that they get out and vote. And my favorite time of the day is when the supervisor of elections releases the names of the people who have voted that day. So we've got 22 days to go.

And Chris, this has been, correct me if I'm wrong, this has been your address for a long time in Key West. This is just how it worked out. You were already living in District V.

Massicotte: Yes. So the first place I lived when I was renting a home was on White Street in District One. And then when I decided that I was never leaving this place, I bought a house in Midtown. And yeah, so I bought that house in 2019. And it was not with the intention of running for city commissioner. It was just by coincidence.

And for people who may not be as familiar, can you explain what has happened more recently with that seat within the last year or so?

Massicotte: So our commissioner who was first elected in 2018, Mary Lou Hoover, she passed away in November. And the city commission could have gone in one of two ways. They could either have called a special election for it, but because we were so close to the actual election, they decided to appoint a caretaker to it, somebody who they had expressed a desire for them not to run for a full term. And that was the Aqueduct Authority head, Greg Veliz. And he has been occupying that seat for the last seven months. His last city commission meeting will be a week from today in August, and whoever wins the District Five race will take office in [August].

Was there ever a part of you that was anxiously waiting to see what the current City Commissioner was going to do? Because obviously you can promise not to do something and then do it anyway. There's no legally binding element to that. So did you think that it would always come down to you and one other candidate or were you expecting other people to jump in?

Massicotte: That's an interesting question. And I will say that at first I was not thinking that Greg Veliz would get into the race just because he had expressed that he didn't want to, and he had a full-time job at the Aqueduct Authority that consumes quite a bit of time. But then over the course of the next couple of meetings, he clearly was engaged and he was really involved in the city government and in fulfilling his role. So I thought that there might've been a chance that he would, but when my current opponent, Greg Sullivan, decided to get into the race, I kind of figured that there would only be two of us. And it's good because we will at least know who's going to be our commissioner in August.

Right. And so when you talk to District Five voters as you have been since you've been campaigning, what concerns are coming up the most and what are you realistically planning to do about it?

Massicotte: The biggest thing that I think District Five voters are looking at is change. And we've been through so much over the last two years with the firing of Al Childress [former City Manager], with these indictments, and grand jury reports. And it seems that most of the news in Key West coming out was about City Hall and not news coming from City Hall about improvements and things. So people just want their commission to get back to work and to start making real decisions in improving Key West for the future. And that's pretty much what I intend to do. I have a slogan called "Make City Hall Make Sense" because so many decisions just don't seem to make sense when they come down to it. And one thing that you would think of that makes perfect sense, they go in the opposite direction. So that's what I'm hearing from voters that just want to get back to the business of running the city.

Now your campaign has talked a lot about accountability and fiscal responsibility. What's one specific part of City Hall that you think needs more scrutiny or explanation?

Massicotte: I think our land development regulations could do with a good overhaul. In the grand jury report, they specifically cited our LDRs as being antiquated, as being too complicated. And what that ends up doing in real terms is that when you want to do anything to your home or to your property or your commercial property, you've got to sift through all of these different codes and regulations. And sometimes they contradict each other and they don't know what kind of license or permits to issue. So I think that we can do better in the building department and the licensing departments so that it's easier and that people don't have to spend so much time and money just to get the necessary permits here because it's really unnecessary to have so many complicated land development regulations. So that's pretty much where I would go first to helping City Hall work better.

In recent weeks, there have been critics who have put your background in political consulting under a magnifying glass, so to speak, although I'm not sure how deeply they've dug into anything. But [how] do you feel [about] anyone concerned about you bringing a more partisan campaign style approach into a non-partisan local race? Is that fair? How do you respond to voters who have concerns about what you did before you even came to Key West as a full-time resident?

Massicotte: Oh, that's a very good question. Thank you for that. So I was a political consultant for almost 20 years and I worked mostly in political technology, but it was partisan. I am a Democrat and I ran as a Democrat, which is a partisan race, for county commissioner. This race is non-partisan, but for whatever reason, there are folks that are trying to make it partisan by highlighting the past work that I've done. And I'm proud of that work. I've seen local governments all over the country. I've seen what works. I've seen what doesn't. And the best run cities are ones that are run by elected officials that are independent, that aren't funded by people who have city contracts, that aren't having city contracts of their own, that they are fully independent and they are working for the people. And they're trying to make this a partisan race.

I am an unapologetic Democrat. My opponent does happen to be a Republican. And if that matters to people in a nonpartisan race, then they can find out what party we belong to. But to me, it's all about the ideas that you have and the background that you have when you're coming in to a nonpartisan race. I'm a very big fiscal conservative. I don't love public debt, even though I did vote for two of the bond funding referendums because I feel very strongly about public safety and resiliency. But otherwise, I'm a very strong fiscal conservative and I don't like when municipalities go into debt that they have to pay back over 30 years.

And Chris, another thing people pointed out – continue to point out – is that you're part of a broader group of candidates who could potentially vote together or shift the commission as a bloc, which I think is how most politicians operate anyway. But are you running as part of a slate or should voters see you as fully independent?

Massicotte: Well, you can't really run as a slate in Key West. We don't have that kind of form of government. There are four candidates that do share similar values. But I'll tell you that if we get elected or if I get elected in particular, I'm going to take those Sunshine Laws very seriously because it is so important for folks to have a comfort level to know that they can trust City Hall. And the best way to do that is to communicate with the other commissioners in public. Interviews like this, Kevin, are so important because this is a public setting that you're going to publish to everybody. And I can say that I'm for or against a particular issue in public so that when we get to a commission meeting and we discuss it, we have an understanding. But we're not running particularly as a slate, but we do share a lot of the same values and the same hopes for Key West.

I don't know if you consider some of these other candidates to be friends or just working allies, but how would you feel if you hypothetically ended up being the only candidate to successfully emerge from this group of four?

Massicotte: That's another good question. And I haven't really considered that. I would just do the job as I've been campaigning on. And if the other commissioners who were elected disagree, then that's how it would go. I am running my own campaign. I have my own ideas and my own thoughts for the future of Key West, but if the majority of the commission doesn't agree with me, then we can only – the best part about the Sunshine Laws is that we do have to have these discussions on the dias and not in private. And I think that we can do some persuading and have some opposing views. I think that's actually a positive thing.

Now, people who are supporting Greg Sullivan, your opponent, they present him as this sort of long time nuts and bolts Key West figure who's focused on infrastructure and maintenance and more practical city services. Where do you think voters should see the clearest difference between you and Mr. Sullivan?

Massicotte: I have a tremendous amount of respect for Greg Sullivan. He has been here for 30 years. He has been head of Waste Management for quite some time. He has been involved in so many different aspects of our community. But the biggest difference between he and I is that he's the head of Waste Management, which is the largest single recurring contract that the city has. I believe that creates an incredible conflict of interest. And then we also have campaign donations from other city contractors donating to him, to his campaign. And I'm not taking any money from anybody who has a contract or a lease with the city to remain independent so that people will know that I'm only working for them. You have a choice. You can [be] a commissioner and you can work for the city, or you can be a vendor and a contractor and you are responsible to your company.

I don't think you can do both. And part of my political work over the last 20 years has been also trying to get dark money and corporate money and corporate influence out of our politics so that people can know that their elected officials are working for them. And I think that's really the biggest difference in our candidacies. And I too am a very big proponent of improving our infrastructure and planning long-term for the future.

And finally, Chris, given that your background at some point must have involved polling. If you look into your data, if you're reading the room in the way that I think you would've as somebody who's pretty involved in the community, what's your prediction for how these races are going to shake out in August?

Massicotte: I am hopeful that I will be elected. I have been identifying voters and I am guessing about 1,200 to 1,300 people will vote in District Five. I think about 6.000 to 6,500 people will vote citywide. And I think that we have identified enough people to feel comfortable that we will be able to get over 50%. The one race that I cannot predict is District Four. The joke is that that campaign is really boring because everybody is so nice to each other. But I just don't know how that three-way race will turn out. And I can tell you that all of those candidates are working very hard to get their message out to voters.