
Oakridge City Hall
By ELLIE GRAHAM/for The Herald — The Oakridge city council is confronting a contentious item relating to vacation pay buybacks for city employees. In June of 2024 the city council requested a deep dive into analyzing vacation and sick time. This covered buyouts, usage, accruals and carryovers. and to explore options to recoup any overpayments.
The results of the investigation entered the public domain at the Dec. 19, city council meeting which involved a tense response across the board from councilors.
The issue of enforcement of the employee handbook–a lengthy manual that governs city employees–came to light along with accusations of mismanagement directed at the City Administrator, James Cleavenger. At the heart of the matter is Cleavenger’s sale of $38,000 worth of vacation and sick leave entitlement – a move that is said to have exceeded city policy limits and undermined the employee handbook.
The portion of the city’s handbook which governs vacation time and accruals is a 70-page document which was not signed by councilors and employees as intended, posing the question of if the document was distributed – there is no record of this.
Mayor Brian Cutchen addressed the issue during the recent meeting, emphasizing the need to enforce employee handbook stipulations. He said the controversy came to light after a city counselor submitted an information request to the finance department in mid-2024. This request revealed significant vacation buybacks by several employees, including Cleavenger, who sold back unused vacation time accrued during his previous role as a police officer.
“It’s the administrator’s responsibility to make sure that those (employee handbook) policies are enforced,” Cutchen said.
City policy states vacation pay can be carried over within a two-year period, anything not claimed is lost. This wasn’t the case here though.
Mayor Cutchen recalls asking for some further information from the finance director to ascertain what the city administrator’s accrual was since he came on board in July of 2022. He wanted to determine if he had enough vacation in order to sell back that much, and did he accrue vacation pay at the right rate.
The rate at which it is accrued is based on a number of factors including an employee’s years of service.
Typically, requests for buyouts require the City’s Finance Director’s sign-off, with hours exceeding 40 falling into the City Administrator’s responsibility and approval from the mayor if he is making a request of this nature for himself.
The City Attorney was brought into the fold to provide oversight into the language employed in the handbook. The updated version of the handbook, adopted in 2021 states, “non-represented employees may request a vacation buyout for up to 40 hours per year.”
In a letter addressed to the mayor, the City Attorney determined that the 40 hours of buyback has not always been followed. It also says enforceability of the handbook is not warranted as there is no record of city employees receiving or signing the handbook. It is also unclear whether city staff were aware of the limitations to buyback pay outlined in the document.
Cutchen did echo that the city has a history of not enforcing some of the policies contained in the handbook, but this is something he is looking to change.
Cleavenger’s employment contract – which the Herald has had sight of– does stipulate that his hours accrued as a police officer were eligible to transfer to his CA role. He cashed out the vacation pay in December 2022.
Mayor Cutchen said that the administrator, by policy, is meant to seek approval from the mayor to authorize the pay, which was not fulfilled.
“In hindsight, I should have cashed out all my vacation hours before transitioning to city administrator,” Cleavenger said. “Council was aware I’d eventually cash out this time, but the handbook’s specific requirements were unclear to me.”
The city’s employee handbook, last revised in 2021, was never distributed for signatures, complicating the enforcement of its policies. Since the situation emerged, the mayor and council are taking steps to revise and distribute the handbook.
“The policy that the city will buy vacation back is kind of an incentive to make the position more appetizing,” said Cutchen. It is not required by Oregon statute or anyone else that the organization buy back vacation from employees though.
Cutchen said, “We passed a motion in December to ensure every employee signs the handbook once the revisions are complete, so policies are enforceable moving forward.”
Missteps and accountability
Cleavenger’s vacation buybacks, spread across 2022 and 2023, with a record of $38,000 being cashed out – a pretax amount that left him with $24,000 after taxes. He acknowledged the need for repayment if his buybacks violated policy.
“I totally understand the mayor’s concerns, and we’re definitely looking into the issue of did I have too many hours carried over? And if that’s the case, I will absolutely pay it back,” Cleavenger said.
He went on to say he was confused as to why the former finance director put both of his cashouts in the next fiscal year.
Mayor Cutchen acknowledged the wider challenges but placed some responsibility on Cleavenger. “Delegation is necessary, but oversight is key, especially with financial matters,” Cutchen said. “That’s an expensive mistake to make because, by contract, he has to know all the ordinances and resolutions of the city and enforce them.”
The dispute has also revealed inefficiencies in the city’s payroll system, with some buybacks allegedly recorded in the wrong fiscal year. It is unknown why this was done.
The Herald has made attempts to discuss this matter with the former and current city finance directors but has not yet received a response.
A forward look
Union employees, whose policies are governed by collective bargaining agreements, which the city administrator negotiates, add another layer of complexity as the agreement ultimately overrides the employee handbook.
Cleavenger said the importance of union collaboration is key when reexamining the handbook and making revisions. “I’d rather work with unions upfront than impose changes that lead to grievances,” he said, in relation to not signing the handbook before it has been updated with sufficient time to comprehensively review it.
Jacqueline Taylor, recorder for the employees’ union since 2007, said that she had not discussed James’s case with the union and had no additional insights to add to the case.
The council’s next steps include revising the employee handbook with union input and reviewing vacation accrual data for all employees to ensure compliance. Cutchen is striving to ensure transparency and fairness is executed. He said it isn’t just about one person but about establishing policies that serve both the city and its employees.
As the council prepares for February’s work session, the controversy serves as a reminder of the importance of clear policies and accountable leadership.
The mayor encourages employees to take the leave they accrue if possible. “Vacation leave exists for the health of employees,” Cutchen said. “That’s why it’s there.”

ELLIE GRAHAM
Ellie Graham is a master's student in Journalism and Law & Conflict Studies at the University of Oregon. She also reports for the East Oregonian and Ethos Magazine. She hails from Liverpool, England but calls the Pacific Northwest home too. Ellie is an avid trail runner and snowboarder. Her pittie mixes keep her busy and up in the mountains.