WINDSOR — When Ryan Palmer took over as Windsor County sheriff at the beginning of 2023, he did so with a pledge of developing the department into a regional law enforcement agency that could provide policing services to towns too small to have their own police force.
Now, months after Palmer was arrested and charged with multiple felonies, including felony solicitation and stalking, the future of the law enforcement empire Palmer built is in doubt, even as the sheriff’s deputies left behind to run the department compete to try to preserve it.
There are questions about past and future contracts the department has to provide policing services to communities.
And a recent audit of the Windsor County Sheriff Department’s finances could not be completed due to “difficulties encountered in performing the audit,” according to a letter from an accounting firm.
Unclear status of contracts
According to Vermont state law, “an agreement or contract for services between a sheriff’s department and a governmental or nongovernmental entity shall be in writing if the total cost of the contract or agreement exceeds $2,000 or the duration of the services provided exceeds ten working days.”
State law also says that “the sheriff shall submit to the assistant judges for filing with the county clerk a report of all written contracts.”
According to Windsor County Clerk Pepper Tepperman, for the fiscal year that ended June 30, 2025, Windsor County only has records of three signed contracts with the Vermont towns of Reading, Barnard and Strafford.
Bob Allen, the Seletboard chairman in Reading, said he had at least a half dozen conversations with Palmer concerning the town’s contract for the fiscal year that started July 1, 2025 with the Windsor County Sheriff’s Department.
One took place at a picnic table at the Tunbridge Fair in September, he said.
“I’ll get it for you next week,” Allen recalled Palmer telling him at the fair.
“I never got it,” Allen said in an interview this month. That was despite the town still being invoiced for law enforcement services for “eight months.”
It is not clear if the town will continue to work with the sheriff’s department moving forward.
“Where we’re at right now,” Allen said, “is seeing how the (Windsor County Sheriff’s Department) survives this mess with the sheriff.”
Since taking over, Palmer, 39, had expanded the number of towns with which the department had policing contracts from nine to 15 by 2025, including four in Orange County. Today, the Windsor County Sheriff’s Department provides patrols to 13 towns across Windsor and Orange counties.
One of those is in Cavendish, one of the few contracts on file with the county. The 2025 contract with Cavendish stipulates an annual fee of $31,200 paid in monthly installments of $2,600 for the period of July 1, 2025 through June 30, 2026.
But it had only one signature on it: Palmer’s.
“It was voted on to accept the Sheriff’s department (contract) last year, but to actually have that signed contract, I didn’t,” Town Manager Richard Chambers said.
Chambers said the sheriff’s department was invoicing the town for patrol services as written in the contract without a copy of the contract itself which began on July 1, 2025. He added that he only received the contract “just recently,” but didn’t specify when.
Despite Palmer’s arrest, Chambers said the town plans to renew its contract with the department later this year and double hours of patrols, from eight hours per week to 16.
While Palmer has not been charged with any financial crimes, the investigation into him started after complaints of money being misused within the sheriff’s department. That investigation remains ongoing, according to Vermont State Police.
The man left to clean up the contract situation is Chief Deputy Claude Weyant, who has taken over managing the department in Palmer’s absence. (Palmer, whose term expires next January, has not resigned but he has stepped away from day-to-day operations.)
“We’ve got to get our contracts set up so I’m going around to all these different towns,” Weyant said. “I’ve been trying to make everything right the best I can.”
Leadership limbo
Weyant, 70, has worked at the Windsor County Sheriff’s Department since 2001, moving up the ranks and retiring as captain around when Palmer won the seat from former Sheriff Michael Chamberlain in 2022. Retirement after more than 40 years in law enforcement across multiple states and sheriffs departments was short-lived, he said.
“Sheriff Palmer kept me on,” Weyant said, explaining that he continued handling the scheduling for the department along with civil process duties.
In 2024, Weyant was elected high bailiff.
In late January, after a months-long investigation by State Police into the department, Palmer was arrested on multiple felony counts of sexual misconduct.
The high bailiff stepped in.
“One of (Palmer’s) last emails before he left, he shared with all the deputies and of course myself, he said that he was stepping aside and that I would be Chief Deputy in charge of the sheriff’s department,” he said.
Now Weyant is running as a Democrat in the Aug. 11 primary to replace Palmer for four more years.
Weyant has campaigned in the past. In 1994, he ran as a Democrat for a sheriff seat in Wood County, Wisconsin, where he was living on a dairy farm at the time. In 2002, Weyant was back living in Vermont and ran for sheriff again, this time for the Windham County seat.
But Weyant is not alone in wanting to take over.
When Palmer handed the reins of the department to Weyant in late January he also assigned Lt. Richard King, 63, to assist Weyant in daily management of the department.
Now King, who has over 30 years in law enforcement, is also running for Windsor County sheriff, as a Republican.
“I’ve been a Republican my entire life and I want to continue to do the work that Claude and I are working (on) right now to help the sheriff’s department dig out of the hole and move forward,” King said in a phone interview.
Under his leadership, Windsor County residents can expect to see more “transparency” and “accountability” from the department, King said.
Palmer hired King in May 2023 following his retirement after 20 years with the Ludlow Police Department, where Palmer worked under him for five years.
By the time Palmer was hired in Ludlow in October 2017, his law enforcement career in the Upper Valley already was plagued by internal investigations, suspensions, resignations and termination during his employment with the Claremont, Canaan and Windsor police departments.
“We didn’t run into those incidents in the background,” King said about Palmer joining Ludlow in 2017. “I wished I had, you know, hindsight being 20/20.”
King said he hasn’t heard from Palmer since his Jan. 28 arraignment in Rutland Superior Court, where he pleaded not guilty to two felony counts of obstruction of justice, two felony counts of aggravated stalking with a deadly weapon, a felony count of lewd and lascivious conduct and two misdemeanor counts of soliciting prostitution.
Palmer’s next court date is a status conference on Wednesday, April 1 at 8:45 a.m. in Rutland Superior Court.
“The bottom line is Ryan made some severely bad choices and he needs to deal with them and it’s had no effect on the day-to-day operations of the sheriff’s department,” King said.
Joshua Lake, a 30-year-old Chester, Vt., resident and patrolman with the Bellows Falls Police Department, is also running for Windsor County Sheriff, as a Democrat.
Though he has just over two years of experience as a police officer, Lake said he grew up in law enforcement — his father, grandfather and two uncles were police officers.
If elected sheriff, he hopes to bring more community-focused policing to Windsor County through increased social work partnerships and open forums with contracted towns. He also intends to restore transparency, he said, by releasing body camera footage after arrests and making public the department’s finances.
Financial questions remain
Palmer essentially disappeared after he was arrested and released on conditions in late January, Weyant said. He heard from Palmer for the first time just a week ago.
It was a phone call, Weyant said, regarding the $1.24 million U.S. Department of Justice technology grant awarded to the Windsor County Sheriff’s Department in 2024 for a project to upgrade radio communications.
“Now, the sheriff set that up … I don’t even have the password to it,” Weyant said. “I don’t know what was spent for what.”
In response to a public records request to the sheriff’s department regarding the 2024 federal grant of $1.24 million, Palmer responded with copies of invoices dated April 2025 to Williston, Vt.-based Burlington Communications for about $693,000, and Nashua, N.H.-based Beltronics for $324,000 dated January 2025.
Regarding the remaining $223,000 of the 2024 grant money, Palmer wrote in a Tuesday email to the Valley News that, “Beltronics has a roughly $55,000 invoice due … The remaining funds will cover any further costs Burlington Communications will incur in putting up the repeater sites on towers across the county.”
“I expect the project to finish in late summer or early fall 2026,” he added.
Palmer did not respond to an interview request concerning his arrest.
The recent felony sex and stalking charges against Palmer stemmed from tips received during a Vermont State Police investigation into the sheriff’s departments finances, which began in fall 2025.
On the investigation into the department’s books, Adam Silverman, a spokesman for the Vermont State Police, said in an email on Wednesday, “we don’t have any additional information to share about this investigation at this time.”
Vermont law requires that sheriff departments be audited by an outside accounting firm once every two years.
Under Palmer’s leadership, the Windsor County Sheriff’s Department has undergone two audits, the Valley News reported in September 2025.
The first was a transition audit that primarily looked at money handled by Chamberlain, the former sheriff, from July 1, 2022 to Jan. 31, 2023.
The second audit concerned finances from Feb. 1 through June 30, 2023, which revealed that the amount of money included in the Windsor Sheriff’s Department bank account decreased from just over $1 million to about $550,000. The value of vehicles and equipment increased from about $70,000 to over $450,000.
However, the report of the most recent biennial audit, from the period of July 1, 2024 through June 30, 2025, could not be completed due to “difficulties encountered in performing the audit,” according to a letter to Palmer dated March 24 provided by the Vermont State Auditor’s office this past week.
The letter to Palmer from the Andover, Mass., branch of Clifton Larson Allen, the company tasked to perform the audit, states “we have discussed these matters with you, on numerous occasions, but, in spite of our requests, the items have not been resolved.”
“Material weaknesses” also hindered the report’s completion, which were defined in the letter as “a deficiency or a combination of deficiencies, in internal control, such that there is a reasonable possibility that a material misstatement of the entity’s financial statements will not be prevented, or detected and corrected, on a timely basis.”
The difficulties encountered in performing the audit exhibited a theme of figures which were “unsupported” or “not traceable to documentation,” including over half a million dollars across balances of accounts receivable, capital asset inventory, payroll and non-payroll.
Additionally, according to the letter, “the department has neither designed nor implemented an approval process for payroll and non-payroll disbursements whereby the Sheriff reviews and approves all transactions in accordance with the Vermont Sheriff’s Association Uniform Accounting Manual.”
Weyant said he doesn’t have any insight into past accounting issues.
“I was working in courthouses twice a week. I don’t have much information on the past financials,” Weyant said. “I guess there’s things that happened possibly in the past, I guess we have to deal with them if and when they come. But right now, I’m just centered on building the sheriff’s department back up. I’m focusing on the future.”