Few Facts, Fewer Answers as Fairfield First Selectman Fails to Properly Reimburse for Health Insurance

First Selectman Brenda Kupchick and John Mitola, chair of the Compensation Recommendation Committee


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FAIRFIELD – A new report suggests that First Selectman Brenda Kupchick has failed to properly reimburse the town for her share of health insurance coverage, but no one in town government – even the authors of the report – can say how the shortfall turned up, who is at fault, or how much exactly the town is owed.

“And are we talking thousands? Are we talking many, many thousands?” Selectwoman Nancy Lefkowitz asked after the presentation by the town’s Compensation Recommendation Committee. 

No answer.

“Does that mean that the first selectperson was paying 18 percent cost sharing?” asked Selectman Thomas Flynn.

No clear answer.

“Was the first selectperson cost sharing at all?” Lefkowitz asked.

No answer.

Neither Kupchick, nor the town officials who raised the issue, offered much explanation for the shortfall, and Kupchick herself raised doubts about whether the town would ever be able to fully explain the apparent shortfall.  

“Even if I wanted to try to get you the answer and get it for myself, there’s nobody there,” Kupchick said.

A few months after her election, Kupchick fired then-Human Resources Director Emmet Hibson for his alleged involvement in the mismanagement of the fill pile, resulting in the spread of contaminated materials around Fairfield. 

Kupchick said on Monday that no one currently employed by the town’s Department of Human Resources worked under Hibson, and her compensation package had been set prior to her election in 2019.

Three months before Kupchick, a Republican, was elected, the town’s Compensation Recommendation Committee recommended that starting in 2019 with the next administration, the first selectman would be responsible for 21 percent of the cost of their insurance premium, escalating 1 percent each year to a total of 24 percent in 2023. 

“For reasons that [are] unknown to us, that never happened,” John Mitola said. Then and now Mitola chaired the Compensation Recommendation Committee.

Mitola said the committee discovered the discrepancy while working on the compensation package for the next administration. 

Even acknowledging the “extraordinary circumstances” following the fill pile scandal, Flynn questioned how such shortfalls had gone so long unnoticed. 

“The fact that it lasted four years is a little difficult to swallow, quite honestly. But it is what it is,” Flynn said.


In an emailed response to CT Examiner shortly after publication on Tuesday, Mitola explained that the committee discovered the discrepancy after requesting past salaries and insurance contributions from the town’s Finance Department.

Mitola said Kupchick paid 18 percent of her insurance contribution instead of the prior committee recommendation, meaning there was a discrepancy of 3 percent in 2020, 4 percent in 2021, 5 percent in 2022 and 6 percent in 2023.

“It was not in our charge to find out why the recommendation of 4 years ago was not followed,” Mitola wrote. “However, we thought it was important to point this out to the BOS and that is what I did last night.”

On a Tuesday phone call, also shortly after publication, Kupchick told CT Examiner that she was unaware of the discrepancy until the committee members brought it to her attention.

She said the Finance Department would calculate the exact amount owed.

“I want to pay what I’m supposed to pay,” she said. “But when we didn’t know about it, it’s kind of a shock.”

Asked how the shortfall went unnoticed, Kupchick pointed to loose policies and mistakes made under the previous administration. She said she was unsure of how the town should rectify the situation moving forward. 

“If you have an employee in a company and your HR department doesn’t take out the appropriate amount for their health care or whatever it is, do we then say to the employee, “You gotta pay $15,000 because someone else made a mistake?’” she asked.

Human Resources Director Cathleen Simpson said she would search for documentation of Kupchick’s insurance contribution upon request from CT Examiner.