Former Windsor School principal settles lawsuit over firing

  • Tiffany Riley

Valley News Staff Writer
Published: 10/18/2022 10:29:38 PM
Modified: 10/18/2022 10:29:35 PM

Tiffany Riley, the former Windsor School principal who sued the school supervisory union and School Board, contending she was improperly fired from her job after posting comments about the Black Lives Matter movement on social media, has reached an out-of-court settlement with her former employer, according to a document filed in federal court last week.

The notice to the court followed by one day members of the Mount Ascutney School Board unanimously approving a settlement agreement negotiated by the Vermont School Board Insurance Trust, which is responsible for fulfilling the “payment portion” of the settlement, minutes from the Oct. 10 executive session of the school board show.

The board and Riley “have decided that it was in the best interest of all parties to resolve the case without further litigation,” the board said in the minutes of the executive session. “We are glad to have this matter behind us.”

Terms of the settlement have not been made public.

Riley and the Windsor Southeast Supervisory Union, along with other defendants, jointly notified the U.S. District Court in Burlington on Oct. 11 that “the parties have executed a settlement agreement resolving the claims and disputes” alleged in Riley’s 2020 wrongful termination lawsuit against the supervisory union, the Mount Ascutney School Board and members of the school board.

The filing further said the parties “anticipate that all the terms of the settlement agreement will be complete on or around Jan. 2, 2023” and asked the judge to freeze all deadlines in the case until Jan. 15, “at which time this case will be dismissed.”

Amy McMullen, chair of the supervisory union and vice chair of he Mount Ascutney School Board, declined to comment and referred questions to Elizabeth Burrows, chair of the School Board. Burrows pointed to Oct. 11 minutes of the board’s executive decision but declined further comment, referring questions to School Board attorney Sean Toohey.

Toohey, responding via email, said “per agreement of the parties, we are not making any comment until the settlement is finalized” in January and declined to answer when asked if the settlement agreement will be made public.

The settlement agreement does not come as a surprise, however: Last month both Riley and the defendants told the court that they had made “substantial progress” in their settlement talks and were seeking additional time to complete the documents necessary for approval by the School Board at a scheduled meeting.

A resolution between Riley, a Woodstock High School graduate and Vermont educator who became principal of the K-12 school in 2015 and the supervisory union and district board, would put to rest — at least as a legal matter — the defendant’s response to Riley’s Facebook post in June 2020.

Riley, 51, was put on paid leave after she wrote on a comment that was seen as critical of the Black Lives Matter movement at a time when high-profile incidents of police brutalizing Black people spurred protests around the country and local Windsor school officials did not respond to a call to have a BLM flag displayed at graduation.

In the Facebook post, Riley wrote, “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’s comment, which spread from her personal page and shared widely across social media, provoked an immediate uproar in the Windsor community and was described as “insanely tone-deaf” by a group of recent Windsor graduates.

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

School board chair Burrows made additional comments to the VTDigger, 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.”

Before the month was out, Riley sued the School Board in Windsor Superior Court in Woodstock, 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 argued 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. A U.S. District Court judge later ruled that Riley effectively had been fired the prior June, buttressing her claim of unjust termination because it occurred prior to the termination hearing.

The lawsuit was later moved to federal court in U.S. District Court in Vermont.

Messages for comment to Riley’s attorney, Bill Meub, were not returned on Tuesday.

Riley, who resided in Reading, Vt., subsequently opened an herbal beauty care products business, Backyard Herbals, and moved to Maine. The company’s most recent Facebook posting is dated Aug. 15 and Maine Secretary of State office shows that the business was dissolved effective Sept. 27 for failure to file an annual business report.

Contact John Lippman at

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