‘We don’t have any money’: Tallahassee Classical faces enrollment woes, principal ouster

Tallahassee Classical School’s board of directors addressed a number of concerns for parents and teachers, including the resignation of former headmaster Cara Wynn and the school’s future during a special meeting Friday.

Former headmaster Cara Wynn was asked to resign Monday after an emergency board meeting, marking the sixth headmaster to leave since the school’s opening four years ago. While it was not disclosed why she was forced to resign, board chair Tim Qualls said a “fresh team spirit and a new approach” was needed at the struggling school.

“We needed a shot of encouragement for our teachers, and I heard from a plethora of teachers that the working environment wasn’t a team spirit,” Qualls, a Tallahassee attorney, said at Friday’s meeting.

The school is now adjusting its leadership as it comes under the umbrella of Great Hearts Academies in August 2025. Great Hearts is a classical charter company with schools in Arizona, Louisiana and Texas.

For instance, Hannah Pitts, former dean of Tallahassee Classical’s grammar school, was approved by the board Friday to return in the same capacity to help with planning and preparing for the transition in oversight for the upcoming school year. Pitts’ contract expired in May and she was not renewed by Wynn as an administrative decision.

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