Town charters are to municipalities what the state constitution is to state government, and the federal constitution is to Congress. These documents provide a framework for how government is supposed to work and establish limits on what’s allowable.

But just as questions of interpreting the federal constitution have led to high-profile and high-emotion court cases about how certain phrases should be interpreted, so too can the wording of town charters lead to uncertainty about what exactly certain clauses direct local government officials to act.

That’s the situation certain members of Weston’s town government find themselves in—and not for the first time in recent years.

At issue are several interdepartmental year-end transfer requests and language in the town charter suggesting the town’s Board of Finance (BOF) should approve expenditures over $5,000 prior to the transfers occurring.

But while several BOF members have raised concerns about whether the proper process is being followed and potential liability that might arise from diverging from the charter, finding answers hasn’t been easy. While town attorney Ira Bloom has issued a legal memorandum on the issue, concerned BOF members say it doesn’t answer their questions. And they’ve been unable to have a direct or public conversation with the town attorney.

The issue first arose at an October 10, 2024 meeting of the BOF, where the board was scheduled to vote to approve line item transfers for town departments from fiscal year 2024.

Included in the transfers were approximately $400,000 of expenditures over $5,000 that hadn’t been brought to the BOF for approval at the time they were initially made. Year-end account transfer requests essentially transfer departmental surplus balances to deficit balances after the close of the fiscal year to balance their budgets.

The $5,000 sum is important because of language in Weston’s town charter.

Section 9.9 of Weston’s charter gives the Board of Selectmen (BOS) the power to make appropriations not already approved in the annual town budget if they are under $5,000.

It also gives the BOS the ability to make larger supplemental appropriations with the approval of the BOF.

The charter further states that a town office, board or commission can apply for an appropriation above what’s laid out in the charter, but “only in the amount, and on terms, approved by the Board of Selectmen, the Board of Finance and a Town Meeting.”

Section 9.10 of Weston’s charter also lays out rules for expenditures and accounting by town offices, boards, and commissions.

It stipulates that any division of the town “that desires to transfer funds within its appropriations from funds set apart for one specific purpose to another must first obtain the approval of the First Selectman, the Board of Selectmen and the Board of Finance.”

In the final three months of the fiscal year, Section 9.10(c) also authorizes the first selectman, with the approval of the BOS and the BOF, to transfer surplus funds between departments with their consent “for purposes for which the receiving entity or entities were authorized to expend appropriated funds” during the fiscal year.

Section 9.10(d) states that “every payment made in violation of the Charter shall be deemed illegal and every Official authorizing or making such payment or taking part therein and every person receiving such payment or any part thereof shall be jointly and severally liable to the Town for the full amount so paid or received.” The charter also states that any employee who authorizes or makes an expenditure in violations of those rules is subject to removal and “such other sanctions as may be prescribed by law.”

BOF member Theresa Brasco flagged several of those sections during the October 10, 2024, meeting. The last section in particular raised concerns about whether the board might be liable for voting to approve transfers that could be considered illegal under the charter’s requirements.

Brasco also stated that she had reviewed expenditures made during the year by various town departments, particularly at the hiring of new employees, and found expenditures that were never brought to the board.

BOF chair Michael Imber interjected, noting that Brasco’s questions were getting into legal interpretation of the charter and he didn’t feel qualified to answer them. He also asked how the answer would impact a vote on the transfer between funds.

“If we approve this transfer does that imply that we are approving it under the charter?” Brasco asked. “Because if it does, I’m not comfortable approving the transfer.”

Imber noted it was a practice that had been going on for years, but added he wasn’t necessarily saying it had been done correctly.

Rone Baldwin, another BOF member, said that the issue came down to the authority of the BOS and town departmental employees to exceed their budgets without a special appropriation. He said he was “confused” about how it was supposed to work.

The BOF ultimately decided to table the vote until their November meeting and get an interpretation of the charter’s language from the town council.

Between meetings, Brasco drafted a list of questions she wanted the town attorney to answer.

By the next meeting, held on November 14, 2024, Imber said he had received a “brief email” from town attorney Ira Bloom “indicating he was comfortable” with the transfers and the “pattern of behavior” the town had engaged in with approving year-end transfers without prior BOF or BOS approval for many years.

But, according to Brasco, none of her questions were answered. She stated during the meeting that the question submitted was about whether the line item transfers were permissible, but her questions were about the transfers that occurred prior to the line item transfers.

BOF vice-chair Jeff Farr added he believed the charter was “very clear that any movement of money within departments or between departments during the fiscal year” meant the board needed to be involved.

But Imber stated that he wasn’t sure he agreed with Farr’s interpretation of the charter, and he thought that the town had discretion over which transfers required approval, that the practice had been “open” for many years, and that an issue had never arisen before.

Imber also added that he was “getting the sense” that the issue required an opinion from the town counsel. He asked Brasco what information she was looking for.

Brasco said she wanted to know why her questions weren’t answered and asked if they’d been forwarded to the town attorney. Imber said he had forwarded them to town administrator Karl Kilduff, who had forwarded them to the town attorney.

As the conversation about whether to seek an opinion from the town attorney continued, Brasco said she thought it would be wise for the board to ask for an opinion as a group and “not have an intermediary in the middle.”

A question of funds for the lawyers’ opinion, estimated to cost between $5,000 and $10,000, also arose.

Baldwin added that while he had questions and wanted to talk to the town lawyers, he “was never thinking of a legal question” because last time the board had a legal question, “attorneys came back with answers that were unresponsive.” He said it was better to have a session with counsel and have them prepare based on questions submitted by the BOF ahead of time.

Baldwin added that he had been on the board for seven years and “there’s stuff that just happens and sometimes we have to kind of look at them.” He further said he assumed the town had a procurement policy but recently found out they didn’t.

Baldwin also said the BOF not questioning transfers had led to a situation “where people think it’s just automatic” and they don’t have to worry about transfers being approved.

Baldwin referenced recent financial issues the town had faced, referencing money that was freed up by a Municipal Employee Retirement System (MERS) contribution to the town, which led to additional headcount in town staff being added and increasing run rates.

Baldwin said the town was suddenly seeing large increases going into the budget for the next fiscal year because of increased headcount and union negotiations.

He added that Section 9.10(d) of the charter should mean the BOS and first selectman should worry about getting approval and engage the BOF early in the process so there’s no problem. Baldwin further stated that “effectively the check and balance system doesn’t exist anymore.”

Farr added that, from his perspective, oversight for changes in department transfers creates an “element of accountability” for department heads that make them responsible for managing their budgets. The current process of the BOF approving the end-of-year transfers, he suggested, allowed department heads to not worry about getting additional money because by the time the BOF approves the transfers at the end of the year, it’s too late to do anything about it.

Darling noted that the finance department gets reports every other week when they do vendor checks and will ask questions of departments if there are deficit situations, so there is some oversight.

Imber suggested reforwarding Brasco’s questions to Kilduff and first selectwoman Samantha Nestor with a message indicating the BOF needed to have a conversation with counsel. He suggested having an executive session if they needed to use attorney-client privilege, but Brasco objected, stating an explanation of the procedure would benefit all boards and taxpayers.

As Farr noted during the BOF’s November meeting, there has previously been tension between BOF members and town attorneys over charter interpretation questions.

In May 2024, an interpretation of the portion of the charter was the center of a controversy surrounding a tie vote at the all-town budget meeting (ATBM). At the meeting, Weston residents approved a roughly $300,000 reduction to the town’s operating budget and more than a $1 million reduction to the Capital Improvement Budget. An adjourned election followed the ATBM, and while voters approved a roughly $59.3 million Board of Education budget and $16 million Board of Selectmen Budget, the vote on the Capital Improvement Budget ended in a tie.

Under section 9.6 of Weston’s charter, the town budget must be approved by a majority of voters. Under section 9.7, which outlines procedures for what happens if the budget is rejected, if one or more components of the budget are not approved, they are returned to the BOF for reconsideration and are then to be resubmitted for another vote.

Weston followed this process following the tie vote on the Capital Improvement Budget.

But residents weren’t happy, arguing a tie was not the same thing as a rejection of the budget, and pointed to another section of the charter that lays out a process for breaking tie votes. Under section 7.5, a tie at a regular or special town election, primary election, or referendum conducted under the charter’s provisions, the town is to hold an adjourned election to determine the results.

Bamonte authored a legal memo explaining why section 9.7 of the charter governed the process following the tie.

“Although Charter Section 7.5 applies more generally to the resolution of a tie vote at a Town Meeting referendum and calls for a simple “re-vote” at a later date, that section does not apply to the more specific process for approval of the Annual Town Budget.” Bamonte wrote, adding that the more specific process laid out in section 7.4 took precedence over section 7.5’s “more general provision.”

At a May 9, 2024, BOF meeting, Bamonte elaborated more on his conclusion, stating that the charter doesn’t recognize ties on the portions of the budget that go to a ballot and that following section 9.7 wasn’t an unusual process in towns around the state. Bamonte added that this was the approach Connecticut courts take to similar issues.

But that explanation didn’t satisfy Brasco, who asked during the meeting and against the objections of Imber, whether Bamonte’s opinion was valid under the town charter.

Ultimately, the BOF voted 4-3 in favor of a proposal put forward by Imber, which restored roughly $450,000 of the cuts proposed in the budget that went to the town ATBM and kept approximately $795,000.

When the BOF next met on November 26, 2024, in a special meeting to vote on the year-end transfer requests, Imber said he had met with the town attorney the previous week. Imber said the town attorney “understood the nature of specific questions” and that the answer was a balance of legal and practical considerations, as well as past town practices and audit guidelines. Imber said the town attorney had also said there was no violation of the charter in the year-end transfer practices.

Brasco stated that she had reviewed the two previous meetings, and it was “clear she wasn’t asking about the transfers.” She was asking about multiple transfers in departments and how those are handled in the charter.

She asked if attorneys addressed the approval process for “any movement between line items within a department or between departments in excess of $5000.”

Imber said the attorney had received the questions she sent, and he didn’t think that question was among them. He also added that the point was the end-of-year transfers weren’t special appropriations above and beyond what had already been approved by the ATBM, they were money being moved internally and that the town counsel had said that practice was “consistent with all these factors that come into play.”

Brasco and Imber also went back and forth over whether the end of year transfers were supplemental appropriations under the guidelines laid out in Section 9 of the charter.

Brasco maintained that the larger issue was the BOF’s responsibilities over reviewing transfers within or between departments over the course of the year, which she said the town attorney’s response did not address.

Imber said that supplemental appropriations meant appropriations beyond what was approved through the ATBM, up to $50,000 and that anything over that amount required BOF approval, but transfers were not supplemental and involved moving money between departments within the existing budget boundaries.

A motion to approve the year-end transfers was passed during the meeting, by a vote of four to two.

The issue was again briefly raised at a January 9, 2025, BOF special meeting. Imber said that the town attorney would provide an opinion by their next regular meeting in February.

But several BOF members raised concerns about whether their questions would be addressed and dissatisfaction with their inability to meet directly with the attorney.

Farr stated that he wanted to be clear that the question the attorneys were answering was more about transfers occurring during the fiscal year than those done at the end of the year to rectify the accounts.

Baldwin stated that board members had asked to have a discussion with the attorney and they had “jumped from not being able to have a discussion to having to get a formal legal opinion.” Baldwin called this “quite a leap” and said he worried specific questions wouldn’t be answered.

Inside Investigator obtained a copy of Brasco’s questions and an email exchange about them between various town officials through the Freedom of Information Act (FOIA).

On October 11, 2024, Imber followed up on the questions via email.

In an email sent to Brasco and copying Nestor, Imber said he had spoken with the first selectwoman, who was “willing to engage Town Counsel to interpret Town Charter Sections 9.9 and 9.10 that you quoted during the discussion that was the basis for your objection to the transfer.” Imber asked Brasco to provide a list of questions to avoid “misinterpretation.”

Brasco provided the questions via email, and Nestor forwarded them to Karl Kilduff, the town administrator, and Rick Darling, the finance director and assistant town administrator. Kilduff then forwarded the questions to Bloom and Nicholas Bamonte. Both Bloom and Bamonte work for Berchem Moses PC and serve as town attorneys.

Brasco’s questions largely focused on how sections 9.9 and 9.10 of the charter applied to the BOF’s approval of the end of the year transfers.

Brasco asked:

• Whether language in section 9.9 of the charter meant the BOF was responsible for reviewing and approving transfers within departments that were approved in the annual town budget and was responsible for reviewing increases in departmental appropriations from those approved in the annual town budget prior to the transfers being made
• Whether in the last three months of the year, the charter’s requirement that the BOS and BOF give prior approval for the appropriations of transfers of surplus funds was limited to the funding purpose for which the receiving entity was authorized to spend money during the fiscal year
• Whether a decision by the BOF to approve year-end line item transfers as presented on the agenda for their October 10, 2024, meeting would give “implied or tacit approval to flawed compliance” with provisions in sections 9.9 and 9.10 of the charter if the transfers were not in compliance with the requirements of those sections
• Whether an elected or town official was responsible for “assuring approval review and authority compliance with provisions 9.9 and 9.10 of the Charter.”

On the last question, Brasco also wanted to know who was responsible for establishing processes to ensure the charter was being complied with.

Bloom and Bamonte issued a legal memo to the BOF addressing the issues surrounding the year-end transfers and ostensibly in response to Brasco’s questions on February 4. It found no conflict between the portions of the charter Brasco had highlighted and the year-end transfers.

“In consultation with Town officials and the Finance Director, we have been advised that most, if not all, transfers take place at the end of the fiscal year when the budget is reconciled at such time that the Finance Director has final confirmation of the accounts with surpluses and with deficits.” the memo stated.

“Throughout the fiscal year, the Finance Director will apprise the BOF of both realized and anticipated budget deficits throughout the fiscal year, including within the last three months. The surplus transfers to balance those deficits are brought before the BOF for formal approval at a public meeting before the close of the fiscal year. Legally, this practice, which has been occurring for at least the past twenty-two years, is entirely consistent with Section 9.10(d) of the Charter and is similarly utilized in other towns.” the memo continued.

Further, the memo stated that while the charter allows for surplus transfers in the last three months of a fiscal year, that language was “not a binding prerequisite that the BOF can only approve such transfers within the last three months.”

“In contrast to the preceding Section 9.10(c) regarding transfers that may be needed during the fiscal year, which expressly requires that BOF approval “must first” be obtained, this Section 9.10(d) authorizes the First Selectman to make surplus transfers “with” the approval of the BOF. Transfers are only allowed to fund purposes “for which the receiving entity or entities were authorized to expend appropriated funds during the Fiscal Year.”

According to the memo, BOF approval of increases to total departmental budgets is only required by the charter in certain instances.

“For mid-fiscal year increases of up to $5,000 to departmental budgets above what was approved by the ATBM, BOF approval is not required. The Charter calls this an “additional appropriation” only requiring Board of Selectmen approval.” The memo stated.

According to the memo, the charter requires BOF approval for mid-fiscal year increases over $5,000 or after a $50,000 cap is reached. Bloom and Bamonte determined that this is a “supplemental appropriation” under the charter and requires BOS approval “with” BOF approval under Section 9.9(b).

They further noted that the charter states a supplemental appropriation can be made for a specific purpose, “meaning, it can increase an existing line item within a departmental budget already approved by the ATBM or fund a new line item altogether.”

At a February 19, 2025, special meeting of the BOF, Imber opened discussion by summarizing the legal memo and noting that auditors who review the town’s financial transactions every year expect to see the transfers from surplus account line items to deficit line items to balance the books. He stated that Darling and Kilduff would confirm other towns in the state follow similar procedures and that the BOF’s approval of the year-end transfers was important to finalizing the town’s financials to submit to auditors to complete yearly reviews.

Imber also said that the town attorneys had answered in emails and in the opinion that the town’s transfer process was legal and consistent with the charter and said he hoped the opinion answered questions BOF members had raised.

Farr said he thought the “nature of the response” was dealing with accounting, while the charter spoke more to the board’s responsibilities prior to a transfer occurring that the BOF needed to understand or participate in approving it so it wasn’t a “rubber stamp fate accompli”. He added he thought the board needed to look closely at that and see if a process change was needed.

Baldwin said that just because the board had been doing something for 22 years didn’t make it right. He also said he understood the legal opinion on section 9.10(d) but wanted to echo Farr’s comments. He also said that he didn’t think the fact that the board receives quarterly updates on projections for departmental finances was the same as participating in a process where the board is aware there will be transfers between departments.

“It’s not fair to ask somebody to approve something when you haven’t been clear at the point when it can impact the course of action and you’re only asking for the approval later.” Baldwin said.

He further said he didn’t think the board was in compliance with section 9.10(c), which he understood to be about transfers within departments, and required prior approval from the BOF.

Baldwin asked if this reading of the charter language was correct. Darling said that he does not make transfers within departments until the BOF gives approval in the fall. Baldwin asked if that practice was consistent with the charter language, but Imber said he didn’t think it was fair to ask Darling to try to square the practice and the charter language because Darling had explained to the town attorneys what practices were going on and “they seemed comfortable with it.”

“In all my years on the Board of Finance there has never been a single vote with respect to a transfer of funds within a department during the year, so I’m at a loss when I read the language in the charter, when I read the legal opinion which is making a big distinction between 9.10(c) and 9.10(d), where (d) does not require the approval at any time as opposed to 9.10(c), which requires approval before the transfer is made during the fiscal year. It would be nice to have counsel to be able to explain this to us because, frankly, I’m confused by it.” Baldwin said.

Imber responded that the town attorneys were “unable to participate” in that evening’s meeting, but that if “a few of us that wouldn’t constitute a quorum” wanted to meet with them at town hall, “they’d be willing to do that.”

Brasco noted that at a BOS meeting that had occurred the previous week, Nestor stated the BOF has heard from the town attorney multiple times to answer questions about the charter. But Brasco said the memo was the first communication the BOF had received from the town attorney.

“Any further communications with the town attorney should be with the full Board of Finance so that we can ask questions and the full public can benefit from it as a public meeting.” Brasco said.

She also questioned why Bloom could “readily be available” to answer charter questions in Wilton, where he is also the town attorney, but “cannot be available for four months to come despite multiple requests by multiple board members to address questions on this.”

Brasco further said she thought she needed to review the “genesis” of the board’s questions about the year-end transfers.

Additionally, Brasco drew attention to the nature of a number of transfers, highlighting interdepartmental line item transfers from seven departments totaling $231,000 and increasing appropriations over what was budgeted by 62 percent. Brasco said she believed those transfers were covered by section 9.10(c) of the charter, but none came to the BOF for approval.

She also pointed to $291,000 in transfers from fiscal year 2023-2024 that were related to town employee salaries, totaling 53 percent of the total transfers, and stated that was what led her to review the charter.

Brasco expressed her dissatisfaction with the memo, finding it only fully answered her question about whether BOS and BOF approval for transfers required in the final three months of the year was limited to surplus funds. She said it only partially answered her question about Section 9.9 of the charter and that her other two questions were not addressed at all.

“I’m not happy with this opinion.” Brasco said, adding she didn’t feel it addressed the actions the BOF was required to take.

Imber replied that while the memo was the first time the town attorneys had communicated directly with the BOF, the town attorneys had previously emailed other town employees, including Darling and Kilduff, to address the board’s questions and a copy of the email had been in previous meeting minutes.

He added that he believed the memo answered the board’s questions and effectively closed discussion of the issue.

“A far as I’m concerned right now the opinion answers the questions for me and I’m not interested in continuing to beat this process.” Imber said.

Farr stated that he thought it was “far past time” for the BOF to have a conversation with the town attorneys.

“This has been going on for too long. I don’t understand why there’s a reluctance for us to have a discussion when as we observe in a neighboring town there’s never a problem with having a discussion and in our charter we’re certainly within our rights to request the discussion and we’ve raised questions that we don’t have an answer to yet. Unfortunately, this is a special meeting so I can’t ask for a vote or a motion but we need to do something going forward to fix this.” Farr said.

Imber did not respond and moved on to the meeting’s next agenda item.

But the matter was not quite closed.

On May 1, 2025, Brasco and Farr authored a letter addressed to both the BOS and the BOF, again asking for the opportunity to meet with the town attorneys.

“While we appreciate the invitation to meet with the Town of Weston legal counsel in a private non-quorum meeting on Tuesday, May 6th, we must decline the invitation.” the letter read.

“We are writing to formally reiterate our multiple requests for a public meeting with the Town Attorney to discuss important concerns about potentially impermissible transfers by the First Selectwoman of over $450K within and between town departments without the necessary Board of Finance approvals. As you know, we have been asking for over six months for the Town Attorney to attend a Board of Finance meeting to discuss these serious concerns. The Board of Finance Chairman and the First Selectwoman have refused our repeated requests and only offered a private “off the record” meeting with the Town Attorney and a legal opinion that was non-responsive to our questions.” it further stated, also calling Imber’s and Nestor’s “refusal” to “permit an open and transparent discussion” of the questions “extremely concerning.”

Nestor’s frustration with the BOF’s questions about the transfers was apparent during a February BOS meeting, where she dismissed the saga as political.

Brasco and Farr also raised concerns that “the pattern of town charter non-compliance” had extended to the 2025 ATBM, where voters were not able to reduce specific budget line items as was standard at past meetings. When questions about the change in procedure were directed at Bamonte during the meeting, according to the letter, he told them to “sit down” and said it wasn’t the time for questions.

Several months later, Farr told Inside Investigator that the letter still hasn’t been answered. With the matter no longer open for consideration before the BOF, members with outstanding questions are out of options, save for bringing a lawsuit against the town, which is extremely unlikely.

But questions about access to the town attorneys remain.

According to Russell Blair of the Freedom of Information Commission, town attorneys offering a private, non-quorum private meeting does not violate the Freedom of Information Act because it would not meet the law’s definition of a meeting. Blair also said that it would have been possible for the board to hold an executive session to discuss the memo had it been protected by attorney-client privilege. But as the BOF posted the memo in its meeting minutes and discussed its contents in a public meeting, that situation doesn’t apply.

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