2 Flagler School Board Races Decided, 1 Headed to Runoff

Flagler County’s three School Board races appeared on the ballot Tuesday. Two were decided in the primary election, while the third will advance to a runoff in November with the top two candidates. First-time candidate Cathy Moon defeated former School Board member Jill Woolbright in District 1, dealing Woolbright her second loss in four years. Another first-time candidate, Rob Wood, defeated one-term incumbent Will Furry in the race for his District 2 seat. The District 4 race drew three candidates, meaning it was the only race with the potential for a November runoff. Since no candidate received more than 50% of the vote, that’s exactly what happened. Former School Board member Trevor Tucker and incumbent Christy Chong advanced, with challenger Ron Long falling short. District 1 Cathy Moon has won election to the Flagler School Board, defeating former member Jill Woolbright. With her victory Tuesday, Cathy Moon will serve on the Flagler School Board from 2026 to 2030. “I was hopeful but I was not confident that we would win,” Moon said. “Because I know the mathematical equation here. So I’m very excited that the Flagler voters have decided to ignore some of the tactics that have been used in the past successfully and they decided to send me to sit on the School Board. I’m excited to work with LaShakia Moore and the rest of the Board and to move this county forward so that we have the best possible schools for our kids.” Though all Florida School Board races are nonpartisan, the District 1 race became a de-facto political bout. Flagler County Democrats largely rallied behind Moon, as did a significant amount of Republicans. False images circulated putting Moon next to LGBTQ+ Pride flags and calling her ‘woke’. Woolbright was backed by a large portion of the county’s Republicans, having been endorsed by Gov. Ron DeSantis in 2022. “I can’t assume that [Woolbright] was behind some of the antics that occurred over the weekend, so I won’t say that she was.” Moon said. “Someone that wanted her to win was definitely behind it. But she and I got along fine.” Jill Woolbright was initially elected to the School Board in 2020 to serve the final two years on Andy Dance’s term after he left to run for County Commission. She defeated Vincent Lyon with with 59.32% of the vote. In 2022 when Woolbright sought a full four-year term, she lost to Sally Hunt with only 48.68%. Ever since the 2022 election, the District 1 seat has been a consistent source of uncertainty and strife. Hunt resigned from office in 2024 after months of attending meetings only by phone, leaving the seat vacant for a month. Gov. DeSantis’s appointed replacement, Derek Barrs, departed for a role in President Donald Trump’s Department of Transportation in 2025. The Flagler School Board has been down a seat ever since. Flagler School Board, District 1 Cathy Moon – 55.93% – 15,000 – WINNER Jill Woolbright – 44.07% – 11,818 District 2 Rob Wood won election to the Flagler School Board on Tuesday, unseating one-term incumbent Will Furry. Wood will serve as the District 2 School Board member for a four-year term in office spanning from 2026 to 2030. “I’m just incredibly humbled that our residents and electorate would entrust our kids and faculty and staff and administrators in my care,” Wood said after the results came in. “I’ve experienced this new community with a bunch of people who’ve supported me and pushed and helped and just surrounded me in ways I couldn’t have even imagined.” Wood, a local small business owner, was the only candidate who filed to challenge Furry, who works as a realtor by day. Though School Board races are nonpartisan, both candidates are registered Republicans. Though he eventually set off on an ultimately unsuccessful re-election campaign, Furry first planned on seeking a higher office. Last year the 51-year-old announced his intention to run for U.S. Congress, mounting a primary challenge against Republican incumbent Randy Fine. Furry dropped his congressional bid in January. In 2022 Furry won the general election with a 58.38% majority. His drop in performance from one election to the next may be partly due to Gov. Ron DeSantis’s decision not to endorse School Board candidates this time around. Furry was DeSantis’s pick four years ago at the height of state involvement in local education. Furry spent two years as Flagler School Board Chair, totaling half of his single term in office. He now serves as Vice Chair, a position he was given after a nine-hour meeting with a 103 votes in which he and colleague Lauren Ramirez were both vying for the position. “Congratulations to Rob Wood on his win,” Furry said. “I am grateful to have served on the School Board, including two terms as chair, and I am incredibly proud of the progress we made together from strengthening district leadership and financial stability to achieving continued academic gains and returning Flagler Schools to an A-rated district. I sincerely thank everyone who supported me along the way, and I will do everything I can to ensure Rob is prepared to take the seat when my term concludes in November.” Flagler School Board, District 2 Will Furry (i) – 40.95% – 10.866 Rob Wood – 59.05% – 15,688 – WINNER District 4 The District 4 race for the Flagler School Board will go to a runoff in November, with candidates Christy Chong and Trevor Tucker advancing. Their opponent, Ron Long, placed third in Tuesday’s primary election and has thus been eliminated. If one of the three candidates on the ballot Tuesday received over 50% of the vote, they would’ve won the election then and there. With that generally being an unlikelihood with three viable campaigns, a runoff in District 4 appeared likely from the outset. District 4 was the only School Board race with the potential to move on to November. Both District 1 and District 2 had only two candidates: Cathy Moon and Jill Woolbright, and Will Furry and Rob Wood respectively. The incumbent candidate, Christy Chong, is headed for a rematch against the former School Board member she defeated in 2022. Trevor Tucker served for three terms before being unseated by Chong four years ago. As of Tuesday, he feels confident he’ll reclaim his place on the Board. “If I didn’t think I cold get the seat back I would’ve never ran,” he said Tuesday. “I just want to say thank you to the voters in Flagler County that showed up, I’m honored to have their vote,” Chong said. “I look forward to the run off with Mr. Tucker again and encourage more people to come out and vote in the General Election. I’m proud of the work that’s been done in our schools the last few years and where we are today. I am incredibly grateful to our teachers, students, and staff for our A rating, and I’m glad I’ve had a chance to be a part of the leadership of Flagler Schools. I hope they will trust me to serve again for another four years.” Though school board races in Florida are nonpartisan, all three candidates are associated with conservative beliefs. Chong was even endorsed by Gov. Ron DeSantis in the 2022 election, and Long serves as the secretary of the Flagler County Republican Party. Tucker, a moderate conservative, generally refrains from partisan politics. Flagler School Board, District 4 Christy Chong (i) – 37.20% – 9,831 – ADVANCES TO RUNOFF Ron Long – 23.29% – 6,156 Trevor Tucker – 39.51% – 10,442 – ADVANCES TO RUNOFF