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Ossining Superintendent To Retire In January

OSSINING, N.Y. – Superintendent of Schools Phyllis Glassman has announced plans to retire in mid-January, capping a career of more than 20 years with the Ossining School District.  

“This was a very, very challenging life decision for me,” Glassman said Tuesday. “I know this decision is going to come as a surprise for many and it was a very difficult one for me to make. I will always be a supporter and a cheerleader for Ossining and I will be taking Ossining pride with me wherever I go.”

When she steps down in January, Glassman will have served as Ossining School District superintendent for six years. She took over in 2007, replacing former superintendent Robert Roelle. Before that, Glassman served in a variety of roles in the district, including assistant superintendent of instruction and deputy superintendent.

Glassman said Tuesday it would be difficult to pinpoint one thing that led to her decision, but that she was very proud of the time she has served.

“There was not one single factor that led to this,” she said. “It was just looking back at a wonderful career and working with so many great people. There wasn’t any one thing that led to the decision. It was a collective series of decisions that got me here.”

Many in the community say Glassman is known for her planning skills, but when it comes to her life after retirement, Glassman says she is at a loss.

“I feel like I’ve planned extremely well for the district. However, I always leave myself last and I have not made plans for myself,” Glassman said, adding that she has no plans to leave Ossining. “I think I have a lot of soul-searching to do. I want to make sure I do an outstanding job from here until mid-January, and then I’ll look at my own plans.”

Bill Kress, president of the Ossining Board of Education, said Tuesday that Glassman's departure will be a “tremendous loss” for the district.

“The national average nowadays for a superintendent is around two or three years, and she’ll have been with us for six,” Kress said. “She’s extremely dedicated to this community. I know she did not make this decision easily. It was a very hard decision for her because she’s extremely dedicated to the students, staff and the whole community.”

Kress said the board has not discussed plans to hire a new superintendent, but added that it would be difficult to find a replacement who could match Glassman’s dedication. Kress later added that he expects the board to “discuss next steps” within the next three weeks. 

“You’d be hard-pressed to find someone with more dedication, or even another superintendent whose car is parked in front of the building on Saturday and Sunday on a regular basis,” Kress said. “She’s not only been here for way longer than an average tenure, but she’s worked harder during her tenure than I think any other superintendent. We are lucky to have had her and lucky to have her through January.”

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