School Board Will Decide Superintendent’s Fate in April as Back-Channel Jockeying Intensifies

By the April 4 workshop, Mittlestadt will have filed her self-evaluation (that’s due on March 17). The school board members will have each filed their own evaluations of the superintendent. They will have met with her, one-on-one. Their discussion at that workshop should “create a great deal of clarity,” in the school board attorney’s words, so that the wording of the April 18 agenda item may be decided on April 4.

The board’s vote at the April 18 meeting is more likely to be a ratification than a surprise, unless the evaluations are so opaque as to create further uncertainty. “Stranger things have happened,” Board attorney Kristy Gavin said.

Board member Sally Hunt was ready to have the evaluations and a vote conducted in a special meeting on April 4.

“I don’t want anybody to feel that rushed,” Board member Christy Chong said. “We need to come to a decision soon, but we don’t have to ram it through.”




Meanwhile, positioning, backgrounding, behind-the-scenes meetings and perhaps not a small dose of machinations continue.

The school board set that timeline on Tuesday as Hunt again brought up Mittlestadt’s contract, against a backdrop of public comments that appeared clearly directed at her, and that reflect the posturing taking place behind the choice for superintendent.

Hunt was elected on the strength of a push against Jill Woolbright, the more reactionary board member she replaced, and on the assumption that Hunt would be more of a centrist. Woolbright was not fond of Mittlestadt (against whom she’d filed a criminal complaint at one point). She was one of the people who addressed the board on Tuesday, criticizing two board members who have already spoken their support for Mittlestadt, without naming them (Cheryl Massaro and Colleen Conklin) and praising Hunt, whom she’d also portrayed as a criminal during the campaign. “So do not give away how you’re going to vote to anyone,” she said, words usually spoken only in preface to a change, never as an endorsement for continuity.

Hunt had previously spoken glowingly of the superintendent. That changed in recent months, perhaps not coincidentally, after her conversations with Paul Peacock, the principal at Wadsworth Elementary. Hunt is assigned to Wadsworth as that school’s liaison (each board member represents one or two schools), and in such roles, board members meet regularly with their schools’ principals.




Peacock is embittered against Mittlestadt, and is currently in the middle of a grievance against the administration. The board is hearing the grievance later this month. How the board votes on the grievance may also be a preview of its vote on Mittlestadt. How Hunt has been positioning herself with regards to the superintendent may be a reflection of her conversations with Peacock and his allies. (Peacock did not respond to an email asking him about his intentions.)

Mittlestadt in June 2022 demoted Peacock from his post as chief of operational services–a role similar to assistant superintendent–a year after elevating him to the post. She also removed him as chief negotiator on the district’s collective bargaining team. His removal from the team was a result of a breakdown in negotiations over insurance payments allegedly pledged to employees that the district reversed on. The issue was eventually settled, but Peacock’s removal as negotiator–a role that included a stipend of around $7,500–was a consequence. (See: “Damaging Trust with Unions, Flagler School Board Rejects a Rebate to Employees that Its Own Teams Had Agreed To.”)

That issue and Mittlestadt’s contract are now all coming to a head concurrently. While the board has discussed the contract several times in the last few weeks, it’s done so purely from procedural perspectives, as if the decision will be based only on data, evaluations, and analysis. In fact, intense lobbying is taking place in the community, as even Woolbright disclosed when she addressed the board–as her decision to address the board itself indicated–and as Hunt noted: “I don’t know about the rest of my board members, but I’m getting a lot of communication about Superintendent Mittlestadt’s contract,” Hunt said.

That’s not how mere contract renewals usually go for top government executives, except when there’s an attempt afoot to push them out by influencing elected officials.




The three people who spoke on the issue to the board during the public comment segment on Tuesday were more along the lines of disappointed Democrats who’d voted for Hunt (she is a registered Democrat; the race was ostensibly non-partisan), and who were responding to a mass email from their party seeking voices to pressure Hunt in favor of the superintendent. If there were tensions during Tuesday’s meeting, they were between Hunt and Massaro–the board chair who had cheered Hunt’s election.

Hunt said she intended to share her thoughts on the subject in an open meeting, an indication that she clearly has strong thoughts already formulated. She pressed for hard dates. That’s how the April meeting discussion on the 4th was scheduled, as was the decision to vote at the evening meeting later that month. When Hunt attempted to accelerate the timeline by two weeks, the rest of the board resisted, though at one point even Mittlestadt was willing to accommodate a faster track. Mittlestadt has her own future to think of.

“We have a timeline,” Furry said. “If somebody has something to say, let’s go ahead and say it. But we do, we have to have that self appraisal, we have to have the meeting with the superintendent, and I think these are important things in a very important decision, whatever the decision is, but we have to do our due diligence.”