School Board’s Cheryl Massaro Will Run Again, Saying Reign of Rookies Scares Her

When Cheryl Massaro was elected to the Flagler County School Board a little over three years ago, she intended to serve one term. The past year’s aberrations on the board by its three rookies and constituents’ pressures on her not to retire in the face of those aberrations changed her mind. Massaro is running again.

Colleen Conklin, who was elected in 2000 and has not lost an election since, has opted not to run again. Her decision is final. Christy Chong, Will Furry and Sally Hunt were elected in 2022 but had no prior experience either in public office or in public organizations.




“The fact that they have no educational background in how to operate and work within Flagler County Schools, that’s the weakness,” Massaro said. Without referring to any of them by name, Massaro said she sees some efforts to learn on the part of two of them, but not the third. She was clearly referring to Hunt, who has been the most disengaged and is often a no-show at district events (including last may’s high school graduations) or her liaison responsibilities in schools.

Superintendent LaShakia More is in her rookie year. Her top administration is similarly thin on experience, with two of the longest-serving members of her top staff–Board Attorney Kristy Gavin and Jason Wheeler, who’s been in charge of communications–are on their way out.

“If she leaves and I leave, that board will have absolutely no historical knowledge,” Massaro said, “which scares me tremendously.”

“We have a brand new superintendent. We have an administrative office that has only one person and that’s Tommy Wooleyhan, that has experienced over a year,” Massaro said, referring to the district’s safety coordinator. “How do you function and drive the school board when missing all those major parts? So I think that is the main reason. I believe that I can help guide the board.” (A few others have solid administrative experience, among them Dave Freeman, who is in charge of operational services.)




On Tuesday, Massaro drove to the Supervisor of Elections’ office in Bunnell and filed the required papers. Not long afterward, AsFlagler’s Chris Gollon–who first reported her candidacy–was calling her.

“I am thrilled to know that Cheryl is running for another term,” Conklin said today. “I think now more than ever the board needs some stability and historical institutional knowledge.”

So far Massaro is the only candidate who’s filed for the District 5 seats. Two candidates have filed for Conklin’s District 3 seat, Paul Mucciolo and Nicole Durenberger, though Durenberger has reportedly said on Facebook that she was withdrawing. Her candidacy is still active, as far as the elections supervisor is concerned. The three other seats on the board are not up until 2026, so the election’s outcome will not change the majority’s orientation.

While Massaro says that public pressure to run tipped her over, several other issues were also key in her decision, not least the way–the bad way–the negotiations aimed at saving Gavin’s job in the last few weeks have gone, and the way the rookie majority got rid of Cathy Mittlestadt, the former superintendent. “That was the start,” Massaro said. “And it probably has gone right on through and this whole situation with our school board attorney.”




Massaro and Conklin saw no reason for getting rid of Mittlestadt anymore than they see any reason to fire Gavin. Though they have not cited specific causes other than obvious antipathies, the other three board members are disenchanted with her and want her gone. “They don’t have just cause and it’s setting this district up for an unbelievable lawsuit,” Massaro said.

“They’re willing to take that chance, as well as being told that she should break the law to protect the children. That scares me too. And we can’t function like that. We have to follow rules and regulations.” (Furry argued at a board meeting that Gavin should have censored public records regardless of whether it violated the law, and deal with a challenge if it arose.)

Supporters who are urging Massaro to run also want to see the district led by a board more focused on students than on peripheral issues, and one that would make it a priority to lift the district’s grade back to an A, after scoring a B in nine of the past 10 years, including this year. The board’s focus over the past year has been more on settling accounts, firings, skirmishing over culture-war issues, or micromanaging district operations.




The district’s finances are also a concern. Massaro said the district’s finances are not on as solid a footing as they should be, with reserves below the recommended minimum, and with the recent loss of $726,000 from construction funds, to a common scam. (The construction money is drawn largely from development impact fee revenue rather than the general fund.)

Massaro is a registered Republican, as are all the other members of the school board except Conklin, a rare remaining Democrat in elected office. The race is ostensibly non-partisan, though in fact the local parties and many voters pay attention to candidates’ affiliations.

Massaro considers her re-election chances solid, assuming she draws opposition. “At this point, if we held an election tomorrow, I believe that Dr. Conklin and I would be renewed and I don’t think the other three would be,” Massaro said, “that’s what I hear out in the general public.”