UPDATED: Oysterponds to Rachlin: Not So Fast

Superintendent Stuart Rachlin's transition to the from might not be as smooth as he had expected. At a meeting on Tuesday night, the Oysterponds Board of Education voted to block Rachlin's $100,000 buyout if he remains the part-time superintendent in Wainscott.

On Wednesday morning as Rachlin was preparing to leave for his commute from Orient to Wainscott, he said he was "absolutely" surprised. "There was no heads up about this," he said. The board knew of his application to Wainscott and that he was a finalist for the position, which .

In a controversial move in November, and to start working part-time in January. He is working part-time at Oysterponds, on Tuesdays and Thursdays, until June.

Not so fast, says Thom Gray, Oysterponds school board member who said he personally felt "blindsided" by Rachlin's move. Gray contends that the posting for the Wainscott position was up in November, at the same time they were negotiating the buyout contract. In both Rachlin's original contract and the buyout contract, it stipulated he needed board approval for outside work.

The board might not have noticed the discrepancy, said Gray, if it was not for a review of the contract by the district's attorney a day before the school board meeting. Because of the late notice, the resolution was not put on the agenda prior to the meeting.

"When we were negotiating his buyout, we considered the personal financial hardship he would encounter with an early retirement," said Gray. "He did not negotiate his buyout contract in good faith. He is a highly visible public figure in a small community. He did not act prudently."

Gray said the board did not want to prohibit Rachlin from making a living, but Gray described his buyout as "richer" than it ought to be given the circumstances. The board narrowly passed the buyout in a 4-3 vote. Adding that Rachlin was "one of the highest paid public officials on the North Fork," Gray said Rachlin's recent actions confirms that the early retirement was the right move.

Rachlin's first day in Wainscott School is Wednesday, though his official start date was Monday, which was a holiday. He has planned on working in Wainscott on Mondays and Wednesdays or Wednesdays and Fridays, depending on what's going on at the school.

"I've been in touch with all the attorneys and I'm waiting to hear back on how they opine regarding this," he said referring to his personal attorney and to the Wainscott School attorney. He added that because a legal matter might come to bear -- something he said he hopes doesn't happen -- he would reserve further comment.

A Wainscott School District Board of Education meeting is scheduled for Wednesday night. It will be his first as the superintendent. "I plan on going out there and barring any reason for me not to participate, I plan on being there," he said.

Nancy McCaffrey, the Wainscott school board president, said she didn't have enough information to comment. "I have to hear what Dr. Rachlin has to say about it."

David Eagan, an East Hampton lawyer and member of the school board, said, "It was represented to us that he has the ability to work for us and wasn't under any contractual restrictions."

Gray said it's up to the attorneys to work it out at this point and that it's a "sad commentary" on the costs of education for small districts such as Oysterponds and Wainscott. He's hoping that the two sides can work something out and he feels Rachlin should have to compensate the school district.

"None of this is meant to be punitive. It's meant to be fair," Gray said.

This article will be updated as more information becomes available.