Former Windsor high principal settles lawsuit over 2020 ouster


Valley News Staff Writer

Published: 01-19-2023 1:35 AM

WINDSOR — Windsor-area school authorities have agreed to pay former Windsor School Principal Tiffany Riley a total of $650,000 to settle a wrongful termination lawsuit she brought against her former employer. Riley alleged that she was improperly fired from her job in 2020 after social media posts about the Black Lives Matter movement.

The terms of the settlement — made public in the settlement agreement — also include a positive job recommendation for Riley from the Mt. Ascutney School Board that praises her for having “worked diligently with staff to change the school’s culture” and commending her “collaborative leadership style.”

Riley reached an out-of-court settlement with the Mt. Ascutney School Board and Windsor Southeast Supervisory Union last October, although terms of the settlement were withheld at the time pending finalization. A copy of the final settlement agreement was provided to the Valley News on Tuesday by the Burlington attorney representing the defendants in the case.

Under terms of the agreement, Riley is to receive $425,000: $191,250 in wages for the 20 months remaining on her 24-month contract at the time of her termination plus $233,750 to compensate for alleged violations of free speech and procedural due process. The settlement also covers $225,000 in Riley’s legal expenses.

“Tiffany Riley and the School District are pleased that they have resolved their legal dispute. The Parties regret that miscommunications and misunderstandings distracted from their shared focus on educating students. The Parties thank one another for their work on behalf of the Windsor School and wish each other well going forward,” the plaintiff and defendants said in a joint public statement.

The settlement agreement was negotiated by the Vermont School Board Insurance Trust, which provides risk and liability insurance services to Vermont schools and is responsible for fulfilling the “payment portion” of the settlement.

Riley, who now lives in Maine, did not immediately respond to a request for comment on Tuesday.

Amy McMullen, chairwoman of the Windsor Southeast Supervisory Union, and Elizabeth Burrows, chairwoman of the Mt. Ascutney School Board, also did not immediately respond to requests for comment.

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The settlement between Riley and the supervisory union and district boards concludes, at least as a legal matter, school officials’ actions after Riley made a comment on Facebook in 2020 that was seen as critical of the Black Lives Matter movement. The comment came at a time when incidents of police violence against Black citizens were spurring protests around the country and Windsor school officials were silent on a call to have a BLM flag displayed at graduation.

“I firmly believe Black Lives Matter, but I DO NOT agree with coercive measures taken to get his point across; some of which are falsified in an attempt to prove a point,” and “while I want to get behind BLM, I do not think people should be made to feel they have to choose black race over human race,” Riley wrote on her personal Facebook page.

The comment quickly spread across social media, provoking immediate pushback in Windsor and was described as “insanely tone-deaf” by one group of recent Windsor graduates.

Two days after Riley posted the comment, the School Board voted to place her on paid leave from her $113,000-per-year job, issuing a statement at the same time that “the ignorance, prejudice and lack of judgment in (Riley’s) statements are utterly contrary to the values we espouse.”

Burrows at the time made additional comments to the media, confirming Riley had been put on paid leave immediately and the board did “not intend to hire her back … we wanted to make sure we acted as quickly as we possibly could.”

That claim came back to undercut the defense’s case later.

Within weeks, Riley sued the School Board in Windsor Superior Court, alleging the board rushed to fire her “without seeking any input or explanation” from Riley while defaming her and violating her free speech and due process rights.

Moreover, Riley alleged, the board’s statements and actions damaged her by making Riley unemployable in the region.

The School Board contended that Riley had merely been placed on leave until her eventual termination hearing, which was required by law, after which the board voted to officially terminate Riley in October 2020.

The lawsuit moved to federal court in Vermont, where a U.S. District Court judge ruled that — contrary to the School Board’s claim that it had deliberated on the matter — Riley effectively had been fired at the outset before the required hearing, buttressing her claim of unjust termination.

In a draft of the letter of recommendation included as part of the settlement agreement — addressed “to whom it may concern” — the board praises Riley’s performance and record, noting that shortly after she was hired as interim principal in 2014 “she became a clear choice for the permanent role as principal. The letter cites Riley’s 2017 performance review that proclaims she “has the right stuff for increased leadership capacity.”

The letter then details Riley’s accomplishment as an administrator and ends by noting that “the Mt. Ascutney School Board and Ms. Riley have resolved the well-publicized litigation stemming from events leading to her employment termination. We thank Ms. Riley for her work at Windsor School and we wish her well.”

Contact John Lippman at