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Ossining Superintendent Enjoys Last First Day Of School

OSSINING, N.Y. – Thousands of Ossining students filed into their classroom with bright smiles Wednesday morning for the first day of school, but perhaps no smile was brighter than that of Phyllis Glassman, the superintendent of schools who enjoyed her last first day with the district.

Glassman announced earlier this year that she would be retiring in January after more than five years with the Ossining School District. Many in the district say that Glassman is typically the first one to arrive in the morning and the last to leave, even on weekends. While she makes it a point to visit each of the district’s schools as often as she can, there was a hint of sadness when she visited each school Wednesday that the new students she met would be the last she would see come through the district under her leadership.

“I always love to go to the buildings and see the excitement on everyone’s faces,” Glassman said as she walked through Brookside Elementary School on Wednesday morning. “I try to know all 4,700 of our students and I want them to get to know me. The school year for me is always one of endless possibilities and I love it because it means rebirth and renewal for everyone in the district and I love being a part of that.”

The idea of not seeing Glassman in the buildings at the start of next year is a sad one for many in the district, including Angela White, the district’s assistant superintendent for business.

“I got sad thinking about it when she delivered her last back to school speech,” White said. “It’s a legacy she’s leaving behind. And it’s going to be difficult not seeing her walking up and down the halls after January. I think she has set a foundation that we’re going to keep for a long time.”

She may not be in the buildings next year, but Brookside Principal Ann Dealy said she will still be with the district in another way.

“It may be her last first day with us physically, but she’s done so much to help shape our district that I think the culture she created will live on for a long time,” Dealy said. “She’s a guru and I think she’s left us in a strategically sound position. She might not be in the buildings but so much of what she’s done will live on in everything we do and the students we teach.” 

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