Naples sets Feb. 2 special election for vacant council seat

The city of Naples will hold a special election Feb. 2, 2027, to fill the seat held by longtime council member, vice mayor and Community Redevelopment Agency Chair Linda Penniman, who resigned last month after her husband died. 

City Attorney Matthew McConnell told Naples City Council on Oct. 7 that the date is the earliest Collier County Supervisor of Elections Melissa Blazier can hold a special election. Although the city charter says an election must be held within 60 days of a resignation, he said Blazier can’t hold it before then because of the Nov. 3 general election. As a result, Dec. 4-14 will be the candidate qualifying period, and there will be no early voting due to cost considerations. 

“As Linda steps away from City Council, I just want to again express our profound gratitude for her many years of service to the city and the people of the city and Naples in general,” Mayor Teresa Heitmann said before a series of votes involving the special election. “Linda has given her heart and soul to our community, and our hearts are with her and her family at this difficult time.” 

Penniman, 83, resigned Sept. 29, the day her 88-year-old husband, Nick, died after battling cancer. In her resignation letter, she said, “it will be incumbent upon me to address myself fully to personal matters.” In an interview later that week, she said stepping down was “only fair to the city because I wasn’t giving it my all — at least for a protracted period of time.” 

“So, let’s see if there isn’t somebody else out there that would like to take a seat on the City Council,” Penniman added. “And, you know, quite frankly, if they turn out to be duds, I’ll run again.” 

Penniman first won election in February 2014, served as vice mayor from 2016 to 2018 and was reelected in 2018 as the top vote-getter in a four-way race for three seats. She resigned in January 2019 to care for her husband. In 2024, Penniman ran again and was elected in a heated six-way race for three council seats that ended in a recount. The mayor also was reelected in a three-way race. 

At this week’s meeting, Vice Mayor Ted Blankenship raised concerns about the possibility of tie votes with just six council members, seasonal residents returning shortly before the election and the ability to hold several candidate forums “so that we have an informed electorate making wise decisions. … It seems like a two-week cycle to squeeze in forums.” 

He noted a new state law says all requests for mail-in ballots expire Dec. 31 each year, so residents who want a mail-in ballot would have to request one again. 

“For people coming back in January, finding out there’s an election, they don’t realize they need to request a mail-in ballot,” Blankenship added, noting there won’t be early voting. “They may not be here Feb. 2. It sounds like it’s a recipe for the lowest turnout ever in our history for a special election.” 

He asked whether there was a communication plan to ensure voters are informed and engaged, including notifying those who will be away that they must request mail-in ballots. City Clerk Patricia Rambosk said the timing of the special election provides enough time to inform voters. 

“We can do social media, we can do e-mail blasts, we can put it in the newsletters so we can get the information out to the public,” Rambosk said. “I don’t believe that that’s going to be a negative.” 

She said residents can request mail-in ballots in late October or early November, but they won’t be mailed until after Dec. 31. However, she acknowledged that special elections typically draw low turnout. 

“That’s just the way it is,” she said. “If we proceed, we do have enough time. The last time we had a special election, we did it in 69 days. … It took a lot of coordination with the Supervisor of Elections, our staff, the city attorney, the city manager, the mayor … so we were all working behind the scenes putting this together as fast as we could.” 

That occurred when Penniman previously resigned. Council member Bill Kramer said it’s up to candidates and their advocates to get residents energized. 

“If people don’t want to vote, they’re not going to vote,” he said. “Unfortunately, when you live in the best hometown in America, the vast, vast majority of citizens are really, really happy with how everything’s going and don’t pay much attention and there’s a handful of folks who aren’t happy with how things are going in any given time, and they’re the ones that typically are active.” 

Council approved the special election date, designated Rambosk as the city’s chief election official, appointed Collier Circuit Judge Christine Greider, a city resident, to the Canvassing Board and approved an interlocal agreement to use county Supervisor of Elections equipment and ballots. 

Council member Scott Schultz, the Community Redevelopment Agency’s vice chair, assumed Penniman’s position as chair, and Council voted to name council member Berne Barton vice chair. After Schultz offered to take over Penniman’s seat on the county Coastal Advisory Committee, Council approved that appointment. 

Hours later, former Vice Mayor Terry Hutchison, who already had expressed his intent to run, formally announced his candidacy. 

“My decision to run is about the future of Naples — protecting what makes our city special while preparing responsibly for the challenges ahead,” Hutchison said after attending the meeting. “Naples does not have to choose between a healthy economy and strong neighborhoods, or between preparing for the future and preserving what we value today. Good government requires us to do both.” 

Hutchison’s term ended in March after he served two four-year terms. He said he plans to focus on maintaining the city’s small-town character, resilience, economic vitality, defending “home rule,” ensuring rules are predictable, listening and being accountable.