Debra Freeman, the executive director of the local Boys & Girls Club, who now has clear sailing toward a third term on the Waynesboro School Board, seems to have an issue with me coming around asking questions about the future of the city public school system, because of the timing.
“I get frustrated that we’re, and this isn’t towards you, this is in general, I get frustrated when we focus on topics during election season that have been a focus of topics for us prior to election season,” Freeman told me during a recent interview, which I’d asked for because she’s the only School Board incumbent on the Nov. 3 ballot, and because I’ve been giving the School Board and the central office h-e-double-hockeystocks for the better part of the last three months over … I mean, pretty much everything.
I say that Freeman now has clear sailing toward her third term on the School Board because her opponent in the Ward C race, Kelvin Washington, formally dropped out of the race last week, amid … a bunch of stuff.
ICYMI
- Waynesboro School Board race off the rails with legally dubious video accusation
- Digging into the dirt on that dirty Waynesboro School Board politics story
- Waynesboro: Kelvin Washington drops out of Ward C School Board race
Washington’s name is still on the ballot, but he indicated in the statement announcing his withdrawal from the race that he would decline to be seated should he somehow still be elected, after all that went down within his campaign last week.
While anything is possible there, Freeman looks to be on an easy track to starting a third term on the School Board in January.

But it’s clear that what Washington was making the centerpiece of his campaign – the need for a new direction in the central office, with Jeffrey Cassell, who has been the superintendent since 2013, set to retire at the end of the year, which is giving us the opportunity to start over, from scratch – was resonating with some folks.
Certainly with me; as we dove here at AFP into reporting on the School Board elections and the Cassell succession drama back in the summer, we stumbled into finding out just how poorly our schools are doing, from a data measurement standpoint.
Four of our six schools are rated as “off track” by the Virginia Department of Education, and the other two rate as “needs intensive support” – which is the lowest rating on the VDOE grade scale.
But the real problem here, to Freeman, isn’t that we’re behind – it’s that I’m only asking the questions now, on the eve of an election, and as the School Board rushes through a search to get a new superintendent on the job at the end of the year, when it could take into the summer if it wanted to.
From the archives
- Coverage of the search for a new school superintendent in Waynesboro: click here.
“I get frustrated when people want to start talking about where we’re at instructionally and in our testing and in our benchmarks and our accountability framework now, when we’ve been talking about it, sometimes I feel like, OK, this conversation has been ongoing for us,” Freeman said.
“We’ve invested intentionally, like, all of the reading and instructional and math and special aides and the extended school year program, and we continue trying to tick away to give our kids what they need to address these gaps and to help them achieve, and I feel like, I love that there’s a community conversation about it now since summer, I just wish there was a community conversation last summer and the summer before, because we’ve been working at this since before the pandemic and since the pandemic, and so, I hope that’s not offensive, but that’s just how I feel about it.”
So, the rest of us, who are Johnny Come Latelys to the our failing schools need our immediate attention discussion, our input on what to do next is … sought?
I’m not sure there, and I’m being nice saying it that way.
Because it sounds to me that the thinking from Freeman, anyway, is, people who want to have a voice need to put in a few years of sweat equity first.
The School Board did go through the motions of seeking public input on the superintendent search, but Freeman acknowledged that “we didn’t get a lot, or enough, feedback” – and offered an idea as to why that may be.
Spoiler alert: her assessment as to why there wasn’t much feedback is surprisingly spot on.
“I know people feel like their voices aren’t heard, and maybe that’s why we didn’t get as many surveys and things as I would have hoped to, or much from public comment, and really the only public comment we heard was, You’re rushing, and that’s what I heard. To me, I’ll take the hit,” Freeman said.
We’re about to get to the meat of the matter now, with who we’re going to end up hiring to run our school system, post-Cassell.
It feels rushed to me, and it feels to me that the process is being rushed because the School Board already knows who it’s going to hire – and that the hire is going to come from among the inner circle already in the central office that has not been able to prevent our schools from receiving consistently failing grades.
First things first: Freeman said it feels to us outsiders that the School Board is rushing its search process because those on the outside “don’t know all the other pieces.”
“Walking through a budget season, and joint meetings with City Council, and walking through the hiring process, recruitment, contracts, and all that stuff, it starts in January through April. There’s a lot of behind the scenes,” Freeman said.
At this stage, I interjected to make the point that the School Board, in looking at its annual schedule and saying, we need to have a new superintendent on the job ready to hit the ground running on Jan. 1 for the reasons stated above, related to budget and personnel, seems to be signaling that it is predisposed to going with an internal candidate.
Freeman’s roundabout answer didn’t disabuse me of that notion.
“A lot of the budget work’s been done by Jan. 1,” Freeman said. “We come back from Christmas break waiting, you know, to see if the General Assembly folks are on the same page with their two budgets, and then you’re waiting for the governor’s budget, like, our process is working between three different budgets. So, we’re doing our local stuff, but then there’s formulas that VDOE has to send us. There’s a lot of work that goes into December and January, the budget tools and all the things from them and their forecasters and things. There’s a lot of behind the scenes work that’s still going on into January, ahead of our first presentation, our first real look, in February.”
A new person coming in from another locality in Virginia, or from out of state, would come to work on Jan. 1 with Cassell’s staff already having done the heavy lifting toward seeing all of those things getting taken care of so that things could stay on schedule.
This, on top of the personal parts of making a move to take a new job in the middle of a school year – arranging for temporary or permanent housing, figuring out the situation with a spouse or kids in terms of their job or schooling needs.
Moving the hire back to the end of the fiscal year gives Cassell’s staff one the responsibility to see things through on budget and personnel decisions that they’re going to be setting into motion for a new person coming in mid-year anyway, and also allows the new person to use the first few months of the new term to get up to speed before the work begins on the 2027-2028 budget and personnel year next fall.
This is where I was reminded that, I’m not on the School Board, which, fair.
“I’m sure people will disagree that part of this was a business decision, an organizational stability and leadership decision, but that’s what it is,” Freeman said.
To the criticisms from the outside that I’ve been giving voice to, that the School Board needs to prioritize starting fresh with a candidate from outside the current leadership circle, Freeman acknowledged that “we have folks within our division who are eligible, and I am sure are interested, I mean, there’s folks we could have appointed to the role,” but later, she said, stressing that she was speaking for herself, “it doesn’t have to be an inside person; it has to be the right person.”
“For me, I’m looking for someone that can really help with our student achievement gaps. Someone who can help lead a community that’s diverse. We have challenging needs as a community, not only in our student population, but in our community resources that serve our families and students, and we have, you know, you’ve seen the statistics of our languages and our diversity,” Freeman said.
“I’m looking for specific strengths in what I feel like our next superintendent needs, whether that’s an internal candidate, external candidate. Everybody should have a fair shot at this, I think. But also, I think we should be listening and hearing what the current employees are saying and what the community is saying, and what skills do we need, and that should be what paints the picture.”