Several readers, including two who identified themselves to us as teachers at Waynesboro High School, asked us to look into the placement of Kristi Williams, the former president and CEO of the now-shuttered local United Way, and reported former romantic interest of the superintendent, into a position as a special education teacher at the high school for the current school year.
This one, gotta admit, is an uncomfortable matter to have to report on, because it goes into the area of the personal, which I try to avoid getting into.
Once again, I’m the bad guy here, I guess.
First, to what we know: the WHS website lists a Kristi Williams as a special education teacher on the staff.

I’ve reached out, twice, to Jeffrey Cassell, the superintendent of Waynesboro Public Schools, to Ryan Barber, the assistant superintendent, and to Teresa Floyd, the administrative assistant to Cassell in the central office, about this Kristi Williams.
The first reachout was to try to confirm that she either is, or isn’t, the Kristi Williams who is the former president and CEO of the United Way.
I left out the part about the reported romantic link to Cassell in that first email, though you could say it was implied.
That first email was sent to the three people above on Thursday, Sept. 10.
No response.
In the interim, I was able to verify that the Kristi Williams on the WHS website and the Kristi Williams who was the president and CEO at the United Way are one and the same.
My second email to the group, more direct and to the point, was sent on Monday, Sept. 14.
I know that there’s a lot going on right now, but it would take two minutes for somebody to respond.
My information is that this is the same Kristi Williams, who not only was the president and CEO at the United Way from 2019-2024, but was also the subject of rumors that she was in a romantic relationship with Jeffrey Cassell in 2022.
I’m planning to write about this, because it feels like the public has a right to judge for itself if the school system hired someone with previous romantic ties to the superintendent to a teacher position following that person being let go from a previous job under the cloud of an embezzlement investigation.
If anybody wants to comment, feel free – and if you don’t, here’s your chance to give me information that can at least soften the telling, by pointing me to a past history that I’m not aware of with Kristi having a degree in special education, or anything else relevant.
If we need a deadline, let’s go with 5 p.m. today (Monday, Sept. 14).
I’m writing this at 2 p.m. Tuesday, so, that 5 p.m. Monday deadline has long since come and gone.
This whole thing is the hush-hush-est story that I’ve reported on in a while.
This is the not fun part of the job, because, obviously, it’s a small town, and I know all of these people.
Not as personal friends, but.

And no, this is not a good look for anybody involved here.
Nothing has come of the embezzlement investigation that was initiated by the Augusta County Sheriff’s Office in 2024, after board members at the now-shuttered United Way of Staunton, Augusta County and Waynesboro alleged that Williams had issued more than $20,000 in direct deposits to her personal bank account in 2023 and 2024, and took out loans using the names of employees and used the agency’s prior address on the loans, ahead of the move by the United Way Board to cease operations in November 2024.
ICYMI
I can’t say for certain that the matter is 100 percent closed, because the Sheriff’s Office hasn’t said one way or the other, but it does seem like it’s in the past now, which, if that’s the case, good news.
The other matter at play here is very much on the personal side, but we’ve reported on it before – involving Cassell and Williams and a legal matter involving the latter’s estranged husband, from 2022.
Neil Williams claimed in an affidavit that Cassell “stalked our household” and engaged in an affair with his wife.
The two men ended up engaged in a confrontation over whatever was going on there in the parking lot at a United Way Stuff the Bus event in front of the Wal-Mart in Waynesboro, in which Neil Williams alleged that Cassell “threw his shoulder” into Williams’ face and busted his lip, resulting in a misdemeanor assault and battery charge for Cassell.
It gets weirder: Cassell, in a petition for a protective order against Neil Williams, detailed a series of events that he framed as a pattern of harassment, including Williams following him to the school system central office to make accusations and threats, leaving Penthouse magazines on his porch and his vehicle, and filing a lengthy complaint against Cassell with the School Board.
The charge against Cassell was eventually dropped, but it’s not like you can just unknow something like that because the charge is dropped.
ICYMI
Neither can you unknow the part to this story about the embezzlement investigation, and the fact that the local United Way closed its doors as the investigation was beginning to become public knowledge.
What this all looks like: the school system gave the superintendent’s former romantic interest a lifeline.
And in case you’re wondering, I found an online resume for Williams, through her LinkedIn profile, and there’s nothing there indicating a prior background or program of study in education.
Nothing about this looks right, or feels right.
I really can see why so many folks on the inside with Waynesboro Public Schools – the teachers and staff who have been reaching out to me for the past two months, since Cassell announced that he will step down as superintendent on Dec. 31, and the Waynesboro School Board announced an expedited process for naming a replacement – think it’s time to clean house in the central office and start from scratch.
Contact the Waynesboro School Board
- Debra Freeman: [email protected]
- Amber Lipscomb: [email protected]
- Erika Smith: [email protected]
- Nigel Stewart: [email protected]
- Diana Williams: [email protected]