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Jill Woolbright, Flagler County School Board Candidate: The Live Interview

July 20, 2026 | FlaglerLive | 5 Comments

Jill Woolbright. (© FlaglerLive)
Jill Woolbright. (© FlaglerLive)

Jill Woolbright is one of two candidates for Flagler County School Board, District 1, running against Cathy Moon. Woolbright, a former School Board member defeated in 2022, declined to participate, as she did in 2022. (See: “School Board’s Jill Woolbright Says She’s in ‘Satanic Warfare’ Against ‘Evil Spirits’ at School District,” “School Board’s Massaro and Conklin Denounce Woolbright ‘s ‘Disgusting and Despicable’ Zealotry,” “Jill Woolbright Wants 4 Books Banned Over Anti-Racism, LGBTQ, Police Violence and Rape Themes,” and “For Second Time in 3 Weeks, Flagler School Board Members Reject Declaration Against Hate.”)

It is a non-partisan race: all registered voters regardless of party affiliation or non-party status may vote in the Aug. 18 primary, which will decide the winner, who will be sworn-in in November.

Three seats are up on the School Board in this election cycle. District 1 is an open seat, and has been an open seat since Derek Barrs, appointed to fill out the erm Sally Hunt did not complete, left for a job in the Trump administration last fall.

In District 2, Rob Wood is challenging first-term incumbent Will Furry, who had originally declared he was running for a congressional seat. He abandoned that effort after his campaign struggled, and announced he would run again for the School Board.

In District 4, former School Board member Trevor Tucker and Ron Long are challenging first-term incumbent Christy Chong. If any of the three candidates garners more than a 50 percent majority in the Aug. 18 primary, that candidate will be the winner. If none of the candidates clear the 50-percent threshold, the top two vote-getters will contest the seat in the Nov. 3 general election.

Furry, Chong, like Woolbright, have declined to answer the Live Interview’s questions. They alone, among the 19 candidates running in the three major local elections in the primary, have declined.

Flagler County School Board members serve four years. They’re paid $44,152 a year, an amount that will likely go up by a few thousand dollars by next year.

The Live Interview format changed this year. Since 2010, FlaglerLive had submitted identical questions to all candidates, enabling them to answer in writing. There typically were a round or two of follow-up questions, also in writing. Artificial intelligence has made that approach obsolete now that candidates can run the questions through AI and spit out prefab answers. To get around that, candidates were invited to a video interview. The video and the transcript are provided below.

The candidates were provided the same basic question within half an hour or less of the scheduled interview, but obviously not the follow-ups, which all differed. The questions to county commissioners are here.

Following the interview and before publication, the interview transcript went through two rounds of editing at this end, once by AI (yes, the irony is inescapable) for spell checks, copy editing and to smooth out verbal tics or repetitive words, and once by me for the same purpose. The candidates were then provided with the interview transcript and the video to review–not to make substantial changes, but to verify transcription accuracy, and, if they so chose, to add a postscript: if they felt they may have misspoken, or not clarified a point, or preferred to revise an answer, they were given that chance in the postscript, without changing the original text in the transcript. The postscript window is remaining open for subsequent additions, until the election.

The interviews can be quite long–not a surprise for a site pathologically incapable of brevity, but the county is awash in candidat quickies. We offer a little more depth, seeking to draw a profile rather than check off boxes: an election is not a speed date but a four-year commitment. The Live Interview’s aim is to elicit as much candor and transparency as possible, and to learn about the candidate beyond the basics in what amounts to extended conversations about the person, the character and temperament behind the candidate, the candidate’s seriousness, and the issues.

The rest is in the voters’ hands.

–Pierre Tristam

The 2026 Live Interviews
Flagler County Commission
Greg Feldman (Dis. 2, R)
Theresa Pontieri (Dist. 2, R)
Anna Jones (Dist. 4, R)
Drew Moss (Dist. 4, R)
Leann Pennington (Dist. 4, R)
Flagler County School Board
Cathy Moon (Dist. 1)
Jill Woolbright (Dist. 1)
Will Furry (Dist. 2)
Rob Wood (Dist. 2)
Christy Chong (Dist 4)
Ron Long (Dist. 4)
Trevor Tucker (Dist. 4)
Palm Coast City Council
Tony Amaral Jr. (Dist. 2)
Jeani Duarte (Dist 2.)
Jimmy Hengy (Dist. 2)
Dylana Dee Galery (Dist. 4)
John Kvederis (Dist. 4)
Ramon Marrero (Dist. 4)
Darlene Sheley (Dist. 4)
The candidates' interviews will be live-linked the day their interview publishes.

The Interview Themes in Summary: Quick Links

  • Basics
  • Preparation and Character
  • Vision
  • Evaluating the current board
  • The YMCA
  • Arming school staff
  • IB and Cambridge AICE
  • Enrollment’s flatline, vouchers
  • A rating vs. national standards
  • DEI
  • Funding loss from U.S. Department of Education
  • Prayer in schools
  • Rap sheet
  • Postscript

 

The Video: 

The Basics: 

Jill Woolbright declined to answer.

See how Cathy Moon answered

Preparation and Character

Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Vision
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Evaluating the current board
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

The YMCA
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Arming school staffers
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

IB and Cambridge AICE
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Enrollment flatline
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

A rating v. national standards
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

DEI
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Funding loss from U.S. Department of Education
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Prayer in schools
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Rap Sheet
Jill Woolbright declined to answer.

See how Cathy Moon answered

 

Postscript

Support FlaglerLive
The political climate—nationally and right here in Flagler County—is at war with fearless reporting. Your support is FlaglerLive's best armor. After 16 years, you know FlaglerLive won’t be intimidated. We dig. We don’t sanitize to pander or please. We report reality, no matter who it upsets. Even you. Imagine Flagler County without that kind of local coverage. Stand with us, and help us hold the line. There’s no paywall—but it’s not free. become a champion of enlightening journalism. Any amount helps. FlaglerLive is a 501(c)(3) non-profit news organization, and donations are tax deductible.
You may donate openly or anonymously.
We like Zeffy (no fees), but if you prefer to use PayPal, click here.
If you prefer the Ben Franklin way, we're at: P.O. Box 354263, Palm Coast, FL 32135.
 

Reader Interactions

Comments

  1. Justbob says

    July 20, 2026 at 10:56 am

    Declined to answer? Ok, we decline to vote for her.

    17
    Reply
  2. DP says

    July 20, 2026 at 11:02 am

    This right here goes to show you, she’s not fit to be on the school board a second time, by refusing to participate in this process. Along with her, Chong, & Furry, these 3 have caused alot of undue heartache, discord, and discontent. With all 3 of them refusing to participate, just goes to show all of us, of how things will go if they get elected. WHY, WHAT DO THEY HAVE TO HIDE???? Let’s do the right thing, and protect the kids, and the school board integrity, by not allowing these 3 another chance. Good riddance to all 3.

    20
    Reply
  3. Samuel L. Bronkowitz says

    July 20, 2026 at 11:27 am

    This particular demon needs to be cast out and banished back to the hell it came from.

    14
    Reply
  4. Callmeishmael says

    July 20, 2026 at 12:09 pm

    Just what we need, a return of the wacko. The three candidates who declined to be interviewed think they can be elected by confining their platforms to their right-wing echo chambers.

    No thanks.

    16
    Reply
  5. Jim says

    July 20, 2026 at 4:03 pm

    She was a disaster the last time and clearly there is no possibility of improvement this time.
    She declined to answer because she has nothing positive to say and I don’t think she even knows or understands the issues. She’s just a sleazy, hateful never-was.
    But I will thank her for her “responses”. Makes it easy for anyone paying the slightest bit of attention to vote for Cathy Moon!!

    13
    Reply

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