A five-year service clause with no end date came back to bite the district years later

A New York school district owes a former employee 85% of his retiree health premiums, years after he quit, an appeals court has ruled.

The decision, handed down on August 5, 2026, is a plain reminder for HR: a benefit written into an employment contract can outlast the job when the contract sets no end date.

The employee worked for the Clarkstown Central School District from 2007 to 2014 as its Director of Instructional Technology and Information Services, a role on the superintendent's staff. His individual contract included paragraph 14, which promised: "After five years of full-time, continuous service to the District, serving on the superintendent's staff, you will receive 85% of a district contribution towards retiree health insurance."

He passed the five-year mark. In March 2014, he resigned and moved to another school district. He retired in April 2020 and applied for his benefits. When he asked Clarkstown to pay the promised 85%, the District refused.

The District's reasoning was simple: once he resigned, his contract ended, and every obligation inside it ended too.

The former employee sued for breach of contract in December 2022. Both sides asked the court to decide the case without a trial. In February 2025, a judge in Rockland County ruled for him on liability and denied the District's request to throw the case out. The District appealed.

The Appellate Division, Second...

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