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Politics

The Teacher Trapped by Her Cancellation

Avery Collins
Last updated: October 28, 2026 5:46 pm
Avery Collins
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In the heart of Vermont lies the small town of Windsor—population: 3,559—otherwise known as the “birthplace” of the state. It was here that Vermonters adopted their first constitution in 1777. “The people have a right to freedom of speech,” it declares, “and of writing and publishing their sentiments.”

On June 10, 2020, in the febrile weeks after George Floyd was murdered, Tiffany Riley, the principal of Windsor School, availed herself of that right—then watched in horror as her life was torn to shreds. It began, as so many cancellations did that year, with a Facebook post. “I firmly believe Black Lives Matter,” she wrote, on her private page. “But I DO NOT agree with coercive measures taken to get this point across.”

“Just because I don’t walk around with a BLM sign should not mean I am a racist,” she went on. “While I understand the urgency to feel compelled to advocate for black lives, what about our fellow [Americans in] law enforcement?”

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The backlash was swift, and brutal. Within 48 hours, the superintendent of the school district had told her she was being put on paid administrative leave—“while we negotiate an exit strategy”—and the school board had sent an email to all parents and staff at Windsor School decrying the “ignorance, prejudice, and lack of judgment” in Riley’s post. Some parents disagreed with the board, but Riley didn’t know this at the time. In Windsor, she felt like a pariah.

From there, her story morphed from a small town scandal into what Riley calls a nationwide “firestorm.” National outlets like the New York Post covered it, while a national free speech advocacy group rallied to defend Riley’s right to keep her job. The media portrayed her as a villain, or as a hero, depending on which slice of the political spectrum they were catering to. “People’s reactions, regardless of the side, just felt so blown out of proportion,” she said.

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