Jill Woolbright, a former member of the Flagler School Board, has filed to run for another term in office in the 2026 election. Woolbright represented District 1 on the School Board from 2020 to 2022, and is now seeking to represent the same district from 2026 to 2030. At 68 years old, Woolbright has been a Flagler resident since 1989. She worked as a teacher in the county school district from 1991 to 2019.
The first time Woolbright won election to the School Board was in 2020, when she won a special election to fill out the last two years of Andy Dance’s term. Dance resigned that year to successfully run for County Commission. Woolbright beat former Palm Coast City Council member Vincent Lyon with 59.32% of the vote, a margin of over four thousand.
In 2022, Woolbright attempted to win a full four-year term in office. She faced Sally Hunt in that election, ultimately losing narrowly with 48.68% of the vote. Less than 800 votes out of 29.5k decided the race. Hunt ultimately resigned less than halfway into her term, leading to the appointment of Derek Barrs to replace her. Barrs himself then resigned in 2025 after being appointed to President Donald Trump’s Department of Transportation.
During her tenure, Woolbright was an outspoken voice for conservative values on the School Board. The races and members are nonpartisan in nature, but political beliefs commonly become known within certain issues. She openly described herself as a conservative Christian, and attracted attention for her efforts to enact the removal of a controversial memoir from school libraries.
The book All Boys Aren’t Blue, was written by non-binary queer author George M. Johnson. Due to passages containing explicit sexual experiences, Woolbright pushed strongly for it to be taken out of libraries at all grade levels in Flagler County. She was met with opposition from student activists, ultimately creating a tense and charged debate over literary content that spread across the nation.
The issue reached a head when Woolbright called the Flagler County Sheriff’s Office on then-Superintendent Cathy Mittelstadt alleging criminal wrongdoing for the book’s continued presence in libraries. The FCSO and Sheriff Rick Staly did not pursue charges.
In 2022 Woolbright was endorsed by Gov. Ron DeSantis at the height of the governor’s advocacy for conservative policies in Florida’s public schools. Two other Flagler School Board candidates, Christy Chong and Will Furry, were also endorsed by DeSantis and won their races. Woolbright did not.
As of the weekend, one other candidate is filed for the District 1 seat on the Flagler School Board: Cathy Moon. Only incumbent Will Furry has filed in District 2, while District 4 has incumbent Christy Chong and challenger Ron Long.
Chris Gollon is a Flagler County resident since 2004, as well as a staple of the local independent music scene and avid observer of Central Florida politics, arts, and recreation.
