Q&A: Miles & Bailey face off for an unexpired term on the Green Mountain district board
The Chester Telegraph | Feb 24, 2026 | Comments 4
From left, Randy Miles and Jesse Bailey
Two Chester residents are vying for one year of an unexpired three-year term that was held by Tuckerman Wunderle, who left the board for post-graduate study. Those candidates are Jesse Bailey and Randy Miles. Jerry Ucci was appointed to the open seat in 2025, but has decided to run for a full three-year term.
We asked all candidates for the school board the same questions, except for two who are running for two town elective offices — Jerry Ucci and Patricia Benelli. We also asked each to limit each reply to 250 words. All of the candidates agreed to participate and have their photos taken for this. But in this instance, one candidate later chose not to respond to the Telegraph’s questions. That is noted in the responses.
1. Give our readers a short biography of yourself. You can include your background, education, accomplishments, family life and goals.
JESSE BAILEY: I grew up in a small town in Pennsylvania. We used to joke it had more cows than people. After college, I moved to Virginia, where I lived for the next ten years. During that time, I met my wife. Our first trip together was to Vermont, so it’s always meant something special to our relationship. Then, less than a year after getting married, we made the move to Chester. Since then, this has been my home, and I want the best for it. Whatever ways I can give back, I’m willing.
RANDY MILES: Declined to answer.
2. What prompted you to run for election to the GMUSD Board of Directors? And what talents/abilities would you bring to the office that are unique?
RANDY MILES: Declined to answer.
JESSE BAILEY: I got tired of just complaining about the things I thought could be done differently or done better. That gets us nowhere. So I’m trying to do my part. As for what I can bring to the table, I think my most important contributions are my sincerity and my determination. I won’t play political games with education and I won’t be pressured into supporting policies I think are bad for the students.
3. Should the compensation of the District’s administration (superintendent, principals etc.) and their continued employment be contingent on a metric of student success and well-being? If so, what should that metric be?
JESSE BAILEY: I think administrators’ base pay should be a strict multiplicative of the average teacher’s pay. Recent evidence suggests high administration salaries correspond to low student performance. Moreover, teachers are directly responsible for most of the heavy lifting as far as actual education goes. Tying the two together would mean we can’t cut teachers’ pay while increasing administration salaries.
I do think there should be one bonus metric, however, and that’s student well-being. If a certain percentage of students report high well-being levels while at school, then annual bonuses should be allotted to both teachers and administrators. I think this would serve to incentivize both teachers and administrators to report, correct, and prevent bullying.
RANDY MILES: Declined to answer.
4. It appears that school consolidation in some form is once again in our future. What should the district do today to be best positioned for various contingencies? Are there issues that the board is wrestling with today that may not make a difference once consolidation takes place?
RANDY MILES: Declined to answer.
JESSE BAILEY: I think the board should be prepared to pre-emptively consolidate on our own terms with a favorable board structure. That way, if the state decides to allow preemptive consolidations, we’ll be ideally positioned. I also think the board should continue pursuing PCB remediation and facilities improvement because–aside from those being the right things to do for the students and their health–those would be the only things giving Green Mountain High School a shot at remaining open after consolidation.
5. Bullying has been a consistent problem within the school system over the years. And some have been with racist overtones. What can board members do make sure that the school reduce or eliminate such occurrences?
JESSE BAILEY: Again, I think bonuses tied to student well-being would be a strong incentive for teachers and administrators to be increasingly watchful of this behavior. Beyond that, the board should consider harsher penalties for bullying. The bottom line is people bully because they think they can get away with it. If you create stronger incentives for teachers to report that behavior and stronger disincentives for students to engage in it, you’ll have a reduction in instances.
RANDY MILES: Declined to answer.
6. What actions will you take to keep politics out of the Board of Directors?
RANDY MILES: Declined to answer.
JESSE BAILEY: Politicizing education almost always comes at the cost of the students, which we often overlook because we’re focused on the ideologies, not the real world implications. I’ll make it a point to shine a spotlight on that cost every time.
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Hi Randy,
On Feb. 16, you wrote to me saying that you had received the questions and would be working on answering.
Then on Feb. 18, in a comment on a letter to the editor you said that would not be answering the questions, writing: “The chester Telegraph need to take a good look at there reporting and what is fair or none bias.Therefore when the Telegraph posts candidates questions asked by them. My response will be not answered because of how unfair I see there reporting.” You also indicated you would be at an event at the Fullerton Inn and would answer questions then.
I was quite surprised by your decision since two years ago, you answered our questions for a school board candidates Q&A.
Then on Saturday, Feb. 21, you sent in one sentence – the same sentence – as a reply to each question, a reply that never even attempted to answer any of the questions.
As an example: If you are asked “Where do you live?” and you reply “My dog’s name is Blue,” you have not answered the question. If you are then asked “How old are you?” and you reply “My dog’s name is Blue,” you have not answered the question.
You refused to answer each question but instead suggested that people meet you at the Fullerton this coming Saturday. By publishing that non-answer, I would be allowing a terrible precedent for future candidate Q&As.
I responded: “Alternatives to answering the questions have never been part of the process and was never offered by The Chester Telegraph. Every other candidate has taken their time to answer every single question, which we and our readers appreciate greatly.
“I will be publishing a simple ‘Refused to answer’ under each of the questions with your name and photograph, which appears to be an appropriate description of your decision.
“You of course can still buy an ad or send in a press release or letter to the editor.”
I have yet to receive a letter to the editor or a press release about your event.
By not answering the questions, you disrespected our readers and your fellow candidates, all of whom took the time to respond.
If I may ask please, before some of you who do not know me very well judge me, you need to know this. For those of you who do know me, you understand me and how involved I have been in Chester over many years now. In short I have been involved with all town boards over the years going to meetings and speaking on issues. I have been to most GM school board meetings and spoke on public comment for a few years now. I am a Troop 206 Boy Scout leader, and have been for many years now. I also am working and raising money for our Chester Andover Teen Center just to name a few things I am involved in. So now to the question at hand? Why did the Chester Telegraph list (Declined to answer) for my 1-6 questions here? That is simply not true! I did submit answers to questions 1-6 but the paper chose to put in something differant , something I asked them not to do 3 times. So I will try and get this to all of you one more time through this paper? To the editor of the Chester Telegraph Please release my response for questions 1-6 I provided you on Saturday Feb. 21 at 1:44 pm. Also please submit this response to the artical listed here. With out changes please. I have a screen shot of this response and if you chose not to I will release to the public for them to view and decide for themselves. Sincerely, Randy Miles Canidate for GM School Board
Good questions. I appreciate the articulate answers given by Jesse. Having thoughtful, compassionate and intelligent people on the school board is important for our students. It is also so good to hear from someone who wants to serve our community in this capacity. It is not an easy job. I appreciate his willingness to do so. Thank you Jesse for your time and service.
It’s pretty clear that only one candidate is taking this important position seriously. Would you trust your children’s education with someone who regularly refuses to answer simple questions?