Jill Woolbright, the former Flagler County School Board member who lost her seat two years ago after she said she was engaged in “satanic warfare” against “evil spirits” at the school district, has filed to run again for the District 1 seat.
Woolbright filed on Wednesday, a Supervisor of Elections official said, though the filing posted on the supervisor’s website only this morning.
Cathy Lynn Moon, a retired executive, also filed for the District 1 seat on Wednesday. That filing was not in reaction to Woolbright. Moon said she was unaware that Woolbright was running.
“I’m back,” Woolbright said in a brief news clip that aired this morning on WNZF, which first reported her announcement.
Woolbright, a former teacher, was elected to the board in 2020 in a special election for the District 1 seat, which Andy Dance had resigned to run for (and win) a County Commission seat. That election was for just a two-year term. Woolbright, a hard-right Republican, amplified cultural issues such as pronouns, Pride flags and especially book bans, over teaching and learning issues, and pressed to arm school employees on campuses.
Working closely with then-board member Janet McDonald, she wanted criminal charges filed against then-Superintendent Cathy Mittelstadt and then-School Board attorney over books, a push Sheriff Rick Staly rejected.
Woolbright, 68, ran again in 2022 for what would have been a full four-year term. She won Gov. Ron DeSantis’s endorsement, and in an appearance at a local church, said “we have not had a conservative, God-fearing majority on our board, and we don’t have it in the district office either.” She said “we need conservative Christians, and the lord has put in this race three conservative Christians. He’s heard my prayers.”
The other two candidates she was referring to were Christy Chong and Will Furry, who won and who are now running for reelection. Woolbright, perhaps anticipating her loss, said it was a “privilege and an honor to just–I don’t even know if I call it suffering–but to suffer like Christ suffered, right?” She said when she went to the district, she had “never in my life been in such a satanic warfare, spiritual warfare that I’ve felt for the past two years on the board, and especially during this election season.” She promised she would “bring prayers” to School Board meetings and said that despite difficulties “in the end we know who wins.”
Sally Hunt beat her with 51 percent of the vote. Hunt’s brief tenure was turbulent. She resigned less than two years into her term, though not before successfully orchestrating the firing of Mittelstadt and Kristy Gavin, the school board attorney–and hiring LaShakia Moore, the current superintendent, who is widely credited for both insulating the district from board politics and keeping the district functioning. The Hunt seat was briefly filled by Derek Barrs, who had himself lost an election to the board, but has again been vacant since Barrs took a job in the Trump administration. (It would not be surprising if the governor were to appoint Woolbright, giving her a leg up, and that her announcement is part of an orchestrated strategy. DeSantis likes his appointees to be electoral challengers.)
Despite fumbles and culture-war distractions, the board has maintained a level of seriousness with the election two years ago of Janie Ruddy and Lauren Ramirez. Woolbright’s appointment would decisively shift the balance toward the culture warriors.
Furry dragged the board back into dysfunction and spectacle last November when he and Chong filibustered for nine hours to prevent Ramirez from being vice chair. Furry wanted the title for himself. He was just ending a two-year tenure as board chair. Chong refused to extend Ramirez the same courtesy a previous board had extended her, when she was named vice chair with only a year on the board.
(Saying God told him to do it, Furry attempted a run for a congressional seat, drew no support, and retreated to a reelection run for the school board seat.)
“The biggest goal is to get student outcomes to rise, and we want to continue to be safe. I would be in favor of bringing in the Guardian program,” Woolbright said in the WNZF clip, referring to the provision in Florida law that allows for the arming of certain civilians, including teachers, on school campuses, though the district’s relationship with the Flagler County Sheriff’s Office has been strong and the schools haven’t had significant safety issues.
“Vouchers and all that doesn’t (sic) concern me,” the former teacher said, “because I know that we can show the community what we do for children in Flagler County, and therefore they will choose us over Anything else.” The district has been losing enrollment to vouchers, the state program that awards $8,000 to $35,000 to individual students per year to attend the private school of their choice, or to homeschool. The district has not gained enrollment in almost two decades despite a surge in the county’s population.
Moon’s candidacy would not have attracted immediate attention had Woolbright not also filed. Moon, 67, retired with her husband to Palm Coast in 2017 after a career in the U.S. Postal Service, where she started as a letter carrier and rose through the ranks to the agency’s Washington, D.C. headquarters, overseeing a budget of $260 million. Her last years there she was tasked with finding efficiencies, and says she “drove $400 million out of the organization.”
She and her husband have four children but just one granddaughter. The children are in four different states. The granddaughter is in Jacksonville. The couple scouted various places in Florida, including St. Augustine and Ponte Vedra. “When we got to Palm Coast, we’re like, this is the place, this is where we belong,” Moon said this morning.
“I believe in public schools. I graduated from public schools, as did my children,” Moon said. “I believe in school choice. But I believe our best choice should be public schools.” Moon said she decided to run because she believes in the district in spite of certain challenges.
“I’m concerned about the financial challenges that come from the voucher funding and believe I can use some of my skill set from working with the Postal Service for ways to look to cut costs without hurting students,” Moon said. She also spent two years at the Commerce Department’s National Technical Information Service, linking federal agencies with the private sector.
“We can find solutions. There are ways to make this work. I’m not here for culture issues,” Moon said.
chris conklin says
Please no. Tell me this is a bad dream.
Justbob says
Well that’s not good.
The dude says
Like a bad rash… these people never go away…
Kendall says
I was thinking more like herpes.
Mothersworry says
Wonderful! Who ordered up this idiot?? Maybe don’t sign he nomination papers.
DMFinFlorida says
With all the drama going on worldwide right now, I really needed a good laugh. This did the trick! I can’t repeat the unladylike response I elicited to my husband when he read me this headline! Suffice it to say, my sailor uncle would be proud. (Psst, Jill, seriously?!)
Wooly mammoth joke says
Right there. She’s not doing this for children, she just said she wants the board and the district to be a bunch of nut balls.
Tired of it says
The sad thing is that people have forgotten the problems she caused, the controversies, her narrow minded views…And, we all know that if she runs as a Republican, they will vote the party line.
Flagler County Republican Executive Committee member says
Woolbright must have a very short and selective memory.
She lost the last school board election because even Republicans voted against her.
After losing the school board election, she decided to run for chair of the Flagler County Republican Executive Committee. I was there in attendance for that vote, and she only garnered a handful (5) of votes.
After that, she supposedly sold her house in Palm Coast and meandered off to Tennessee.
After hearing the news on WNZF on Wednesday afternoon of her school board candidacy via a political ad, “I’m BACK!!!!”, I checked to see if she’s a current homeowner in Flagler County. Unless she’s purchased very recently, the name Woolbright does not show up on the Flagler County Property Appraiser’s website. So is she going to be campaigning from Tennessee?
You’d think she’d have moved on in life by this time. We just can’t get rid of these people who feel they are God’s gift to politics despite the fact that no one wants them.
To Jill Woolbright directly: Jill, no one in Flagler County wants you to run for school board for the THIRD TIME. Just move on for God’s sake.
If Tennessee is so great, why doesn’t she run for school board in Tennessee, though maybe no one wants her there either.
I think Flagler County residents have had enough of her type of toxicity.
Mindy Robertson Moore says
Woolbright has been married 4 times. The second and fourth time to the same man. He cheated on her again and she divorced him for the second time.
That’s why she moved back.
Just overflowing with christian values. Can’t make this stuff up.
Laurel says
Okay, Flagler County residents, are y’all starting to see a pattern…yet?
My thoughts on the toxic woman says
I work in Flagler County schools. The kids in high school now in 2026 can’t read, don’t even know their multiplication tables and have very poor motor skills when it comes to writing by hand. In fact, their handwriting looks like the handwriting of a 5 year old, and it’s barely decipherable.
Just about any tradesman will have to use multiplication, addition, subtraction and division in daily life.
Apparently Jill Woolbright was an elementary school teacher for 29 years here in Flagler County. Elementary school is when kids are supposed to learn how to read, write by hand AND learn their multiplication tables. What the hell was Jill Woolbright doing in Flagler Schools for 29 years if the kids I’m now dealing with in 9th and 10th grade don’t know their multiplication tables, can’t add or subtract, can’t read and can barely write their names legibly?
It seems Jill Woolbright has been a failure all around, not only in schools but on the school board, in running for chair of the Flagler County Republican Executive Committee, moving to Tennessee and then coming back to Palm Coast.
I’m hoping DeSantis isn’t going to appoint her to Derek Barnes’ empty district 1 seat. But then again, seeing what’s been going on in the schools in Flagler County, I now see how destructive DeSantis has been in many respects.
Brad W says
No!!!
Deborah Coffey says
Maybe Ms. Woolbright should be concerned about her own lack of fear of God. The hate she spews is quite overwhelming.
Lil bird says
Hopefully she “will” fare the same as “will” did recently who also thought they were “Will-ed” by … play on words intended. Eye roll. Sigh.
P Spagnolia says
Just what we need! She did nothing positive during her term on the school board but create chaos! I am a strong believer in the separation of Church and State. We don’t need a religious zealot pushing her warped religious ideology in our school system.
God told her to run.. says
Talking tongues may get you elected as another Pastor J minion enters an election.
Republicans unite, don’t vote for this bull crap artists.
tulip says
Many many new people have moved here since woolbright left and, therefore, do not know anything about her, and could easily be pursuaded by ads. I hope a lot of the real truth about her keeps getting posted on social media, flagler live and elsewhere. People who just vote their party line are closed minded and they are a worry also. The same goes for Furry.
P Spagnolia says
Don’t forget Chong! She’s no prize either.