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Meeting Prompts Cheshire Treasurer to Retire

By Sabrina Damms
iBerkshires Staff
03:49PM / Wednesday, March 12, 2025
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CHESHIRE, Mass. — The town has a temporary town treasurer after longtime Treasurer/Collector Rebecca Herzog abruptly retired last week. 
 
Ben Gelb, part-time treasurer for Rowe, was appointed on Friday during a special meeting of the Board of Selectmen
 
Herzog's departure after 28 years was in response to an executive session scheduled last Tuesday  "to consider the discipline or dismissal of a public employee and/or to hear complaints or charges brought against a public employee."
 
The board had three issues with her office: failure to payout accrued time and benefits for a laid-off employee, concerns over bonding documents for the new fire truck and for not responding in a timely manner to requests from the board and the town administrator. 
 
Herzog blamed vacation and sick time accrual mistakes on the town's software system and said she'd been following the schedule for the bonding process and didn't see anything unusual.
 
She proffered her retirement letter to the Selectmen after requesting an open session. 
 
"I am retiring effective tonight. I'm done. You know, what a shame that this is the way my career ends over a mistake," she said, adding she had assumed she was being fired. "It was just to humiliate me."
 
Board members said that was not the intent of the session but rather to speak with her about problems that have surfaced in her office. 
 
Herzog was notified of the layoff of an employee on Nov. 22, 2024; however, the vacation payout did not take place until a month ago, board members said. This resulted in a demand letter being sent to the town with a claim of violations of state wage law. 
 
"This pending litigation may result in treble damages as well as litigation costs and legal fees," the hearing letter says. 
 
Herzog said the term "laid off" threw her at first, and she assumed "somebody would be called back at some time."
 
"I never gave it a second thought. It was not done intentionally. It was a mistake," Herzog said. 
 
The board also raised concerns surrounding ongoing problems with employee accruals and vacation time. One board member claimed the issue has been going on for over a year. 
 
The biggest issue with accruals is that "you want them to accrue on July 1, which is fine for personal and sick, but for vacation, we're doing it based on hire date," Herzog said. "I noticed that everybody that I fixed on July 1 as soon as their hire date came around. The system changed it." 
 
Selectwoman Michelle Francesconi said it seemed like a lot of manhours are being put into a software that is not working for the town.
 
"In the grand scheme of things, the town of Cheshire does not have that many benefited employees. When you compare it to other other there's a much larger organizations, much larger cities and towns that also deal with municipal payroll and and so I feel like there has to be something out there, a company that can provide a product that could allow this to function more smoothly," she said. 
 
Herzog said her office attempted to solve the issue numerous times with the system's customer service team but was unsuccessful. 
 
She expressed her frustration with the lack of direct communication between her and the individuals who say their time is off and claimed there has been a hostile work environment directed at her. 
 
A couple of board members said the reason they had Town Administrator Jennifer Morse address the issue with her was that staff members felt uncomfortable continuing a conversation that had not reached a resolution.
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