SOUTHBURY/MIDDLEBURY — The spring sports season came and went at the Region 15 School District without the administrator who had overseen it for nearly a decade.
Ron Plasky, the Director of Athletics, Health, and Physical Education for Region 15, was gone, and no formal announcement explained his absence.
Now, records obtained through a Freedom of Information Act request show that he has been on leave since March under a negotiated separation agreement, ultimately leading to his resignation.
A permanent no-rehire clause woven into the agreement means he cannot return, and a mutual non-disparagement provision means limits are placed on what can be said publicly.
The Record received those documents on June 3, 2026. The Region 15 Athletic Director job posting appeared publicly the following day.
The Paper Trail
In a brief email dated Tuesday, March 24, 2026, Plasky notified the district’s Human Resources Coordinator that he planned to be “out on personal leave through the April 2026 school vacation period.”
Three weeks later, on April 16, Plasky’s absence was formally designated under the Family and Medical Leave Act (FMLA). The correspondence from HR Coordinator Becky Fairbairn cites documentation received from his medical provider, indicating a health condition rendering him “unable to perform the essential functions” of his job. The FMLA designation became effective on the first school day following April break, on Monday, April 20.
The Record is not reporting on the nature of Plasky’s health condition.
The findings of the records request include a nine-page agreement outlining the stipulations of Plasky’s departure with the school district and the Pomperaug Administrators Association (PAA).
The document – officially a Separation Agreement and Full Release of All Claims – was signed by Plasky on May 4, 2026, and countersigned by Superintendent Joshua Smith on May 5, 2026.
What the Agreement Entails
The agreement states that Plasky’s leave went into effect on Monday, March 23, utilizing personal leave until April 19.
Upon the FMLA designation going into effect the following day, the agreement means that Plasky will be paid by utilizing “all of his accrued, unused paid sick leave” up to October 2, which is the approximate time he is due a lump sum of an additional $18,000 in severance pay.
He is to notify the district within five business days if he is hired elsewhere and will be provided extended health insurance coverage until then, or through the end of the year.
The agreement further states that Plasky “will not seek any further employment with the Board in any capacity at any time.”
A standard 21-day window was provided to Plasky to consider signing off on the agreement; however, documents do not specify the date when it was offered prior to his May 4 signature.
The broad range of potential legal claims that Plasky has agreed not to pursue includes the Americans with Disabilities Act, provisions covering hostile work environments, and the Age Discrimination in Employment Act.
If you can’t say anything nice…
The agreement also states that Plasky acknowledges that he and any member of his family “shall not make any disparaging or defamatory statements” about the school district and its business. The same restriction applies to Superintendent Smith and HR Coordinator Fairbairn, and Dr. Paul Jones, representing the PAA, who are each named specifically in the agreement.
The document also states that all parties agree that “all aspects of this Agreement shall be kept confidential by all parties to the extent permitted by law”, effectively serving as a confidentiality provision while acknowledging that disclosures required under Connecticut’s Freedom of Information laws could occur.
The agreement also affords Plasky a reference letter from the district, “noting Mr. Plasky’s positive contributions in Pomperaug Regional School District 15.”
The agreement explicitly states that it does not constitute an admission of wrongdoing by either party.
Where Things Stand
Attempts to reach Plasky via his district email are met with an automated “out of office” reply email reading, “I am currently out on personal leave and will not be checking email.”
In his absence, he directs inquiries to Acting Athletic Director Danielle McCauley.
McCauley was present at the beginning of an April 6 Board of Education meeting, attending it in her capacity as Acting Athletic Director to recognize the achievements of the district’s winter sports season.
At the conclusion of that meeting, the Record posed the direct question regarding Plasky’s status to the Superintendent. Smith said he was on personal leave, but offered no timeline, as it would have been too early for an agreement to be presented to all parties.
The matter was not addressed at any subsequent Board of Education meeting.
Following the public job posting, an updated request for comment was sent to the Superintendent, but no response had been received at the time of publication.
6/6 Update: In a comment received after publication, Superintendent Smith clarified that the district does not typically make broader announcements when a staff member is out on leave. With the position posted, he says, general protocols for hiring an administrator will be followed, which include screenings, interviews, and a final interview based on the recommendation of the superintendent to the Board of Education.
“We hope to have the process completed before the start of the school year,” Smith stated in an e-mail.
By Evan Triantafilidis
The Southbury Record 