Flagler School Board’s Colleen Conklin and Cheryl Massaro Will Not Run for Re-Election in 2024

“I could have said it’s time to retire and I’m going going to ride into the sunset,” Conklin said, “but the reality is, it’s gotten to a level where it’s gotten so nasty that if I ever wanted to do anything in the future, I don’t want to be part of this new type of campaigning. I refuse to get in the mud and play with pigs. I will not do that. And I will do my very best to support a candidate that I believe will always put what is good for kids first.”

Their decision will have far-reaching consequences. When the 2024 board is sworn in, its members will have the shortest combined experience on the board in at least two decades and a half. Three members will have served two years, assuming they all make it that far. Two will be rookies, assuming a former school board member doesn’t opt to run and win.

The institutional memory that Conklin’s 22 years of service brings to the board will be gone, a loss the top administrative staff can only compensate in part, since much of it is of shorter memory, too. The exception is Board attorney Kristy Gavin, who survived attacks and attempted firings by two board members who lost in 2022, and may yet again be in cross-hairs after 2024, depending on the outcome. The board hired Superintendent Cathy Mittelstadt three years ago. That contract is up for renewal in April.

Board member Sally Hunt on Tuesday unwittingly alluded to just that institutional memory during a discussion about student enrollment: “I don’t want for Colleen to be one of the only people in this county other than you guys who really understand what all of this is saying,” Hunt told administrators, asking for more accessible information on the subject. Neither she nor the staff have any idea what’s ahead in two years, without Conklin, and there won’t be much either could do about it short of a two-year crash course.

The current 3-2 majority of right-of-center progressivism that carried over from the previous two years will be in jeopardy of switching to a majority of the hard-right, ideological conservatism represented by newcomers Christy Chong and Will Furry, whose campaigns were largely stage-managed by the likes of Jearlyn Dennie, a local GOP operative, bankrolled by conservative political action committees, and themed around culture-war issues and disinformation. There is little doubt that the 2024 cycle, a presidential-election year that once again includes Donald Trump and will likely include the candidacy of Gov. Ron DeSantis will further amplify the acrid tone of the 2022 campaign–the very tone Conklin cites as a reason to bow out.




Conklin is more adamant than Massaro that she will not run. Massaro still leaves a very small possibility that she could change her mind–as Trevor Tucker did after deciding not to run for re-election in 2022. He lost to Chong, after barely campaigning.

“I will be very transparent and honest,” Conklin said. “In watching how this last election cycle went, I have served Flagler County for 22 years, respectfully, without any major ethical issues and controversies. I understand sometimes I can be a lightning rod for some of the positions I take. But for 22 years, I have done my very, very best with full integrity and an ethical compass, to best serve students, staff and our families. I know there are individuals out there that will spend an endless amount of money to do everything and anything they can do to destroy that reputation. I have worked too hard and too long to allow that to be a distraction and take away the focus on student achievement. If it means I have to step aside so that someone who may not be as controversial can step into that role and continue to force the focus to be on students achievement, then I’ll be honored to step aside in that manner. I don’t know if that makes sense, but people who love me know my heart is in serving this community but also recognize the absolute destruction that would come my way.”

Conklin is in her sixth term on the board and is the longest-serving elected official in the county, by consecutive years. Bunnell Mayor Catherine Robinson exceeds Conklin’s service by four years, her consecutive streak interrupted only by her decision to step away from public service for two years at the turn of the century. State law changed earlier this year, imposing consecutive 12-year term limits on school board members. The law does not affect past tenure. The clock started with the 2022 election. It’s in effect for current board members. It would not start for Conklin and Massaro until the 2024 cycle, giving them yet 12 more years to serve if they chose.




Massaro says she ran in 2020 with the intention of serving one term. “I’m almost 70, so I would like to retire at some point,” Massaro said. “People keep asking me. I’m hoping we have viable candidates, and if we have viable candidates, that makes that decision easier. But that’s where I am at this point. That’s true. I know. There’s a lot of people unhappy. But we’ve got to give this board a chance.”

Last week, for the first time in memory, all five school board members sat down for a meal together, unrelated to business–they are barred by the Sunshine law from discussing pending school issues–at the Grand Hyatt Hotel in Tampa Bay, where they were all attending the Florida School Board Association conference. They talked about their families, their children, their hobbies, and got to know each other a little outside the stresses of formal meetings. It gave Massaro and Conklin hope.

“I don’t see any animosity,” Massaro said as a consequence, a term that could easily have applied to many meetings of the board before the election, when Janet McDonald and Jill Woolbright were members, when trust between Massaro and Conklin on one side and Woolbright and McDonald on the other was non-existent and Woolbright likened her colleagues to Satan.




“I’m optimistic, but there’s always a chance, I’m not going to say outright no. There’s always a chance I could change my mind,” Massaro said. She is concerned about the long learning curve her colleagues face, and the fact that all three have no background in education. With her departure, and Conklin’s, the board could be left without a single educator. That could play into her decision.

“In today’s environment you don’t know who’s going to be willing to take that shot. Running a political campaign as we saw in the last campaign is not fun, and it’s not pretty,” Massaro said. “I am the oldest person on that board and I think it’s time to let new blood in, and I’d like to take care of my family, because it’s a team effort. I would prefer not to carry that mantle for another four years. A lot of people are disappointed, I can tell you that. They tell me ‘you need to run, you need to run.’ That’s not what I’m planning to do.”

Conklin was heartened by the meal the five board members shared (the superintendent was at a meeting, but joined them the next day at breakfast), calling it “lovely.”

“I have great hope that our board is starting off on the right foot,” Conklin said. “I truly believe that while we may have our differences, each person is there with hopefully the intention of focusing on student achievement and what’s best for kids.” She called the new board “a new day in Flagler County,” off to a good start. “Anything has got to be better than where we were.” The board will be holding a pair of retreats in the new year to foster better mutual understanding, and presumably avoid the disaster of the last such attempt, when the room crackled with accusations, name-calling and lies, and even an attempt to stop media or anyone else from recording. The attempt was not successful (it would have been illegal.)

Nevertheless, Conklin has no illusions about what would be ahead of her if she ran again.

“People are not fighting fair. I’ve never in my life seen the level of dark, shady money coming into races, I’ve never seen fake mailers, I’ve never seen some of the tactics utilized before,” Conklin said, all references to the campaigns two of her new colleagues (Furry and Chong) ran, but of course not just them. Conklin did not name names. She had become disillusioned with the increasingly rabid tenor of campaigns even in 2020, when she had long hesitated before deciding to run again.

The simple fact that school boards are non-partisan is a direct intent for us to all remain on student achievement and not get into state political, cultural wars and some of the nonsense that’s been going on for the last several years.”

School board elections have been non-partisan since voters approved that initiative in 1998 Florida’s GOP-majority legislature attempted to undo that last year, and is attempting to do so again.

“My point exactly,” said Conklin, who’s been the board’s legislative liaison, and is one of only five registered Democrats still serving among the county’s 34 elected officials (two of them on the mosquito board; the 34 seats don’t include Marineland and Beverly Beach town boards or community development districts). “Why do that? What’s the true intention of that? Is it to remain focused on students? Because guess what: I don’t represent Democrat families or Republican families. We represent all children, as it should be. Partisan politics has no place in education, and that’s just an example, and it’s two years from now.”