After years of financial mismanagement allegations, Cleveland County Sheriff Chris Amason resigned from office after pleading no contest to one count of felony embezzlement today in exchange for Attorney General Gentner Drummond’s office dismissing three other counts the same day they were revealed publicly.
Amason’s same-day charging, deferred-sentence plea deal and court-system walkthrough marks the third time Drummond’s office has employed the unusual tactic when prosecuting public officials. Drummond previously revealed charges on the same day he accepted plea deals from a pair of Oklahoma House members in August and January.
A multi-county grand jury charged Amason with four counts of embezzlement in an indictment also filed Monday. Under the terms of a plea deal with Drummond’s office, Amason pleaded no contest to one charge: embezzling between $2,500 and $15,000 “by issuing check payments from his campaign account to himself and others.” Two of the other three charges also alleged the embezzlement of campaign funds, while the fourth was for allegedly embezzling money from Cleveland County for the purpose of paying for his wife to “attend government conferences.”
A press release from Drummond’s office — which said the attorney general was “officially walled off” from Amason’s case owing to their history of mutual endorsements — said the plea deal requires Amason to resign, surrender his CLEET card for five years and pay $10,000 in restitution. Amason received a five-year deferred sentence.
“Public officials are entrusted with taxpayer dollars and must be held to the highest standard,” Drummond said in a statement. “Sheriff Amason took an oath to enforce the law. He has neglected his duty and is no longer fit to serve the residents of Cleveland County.”
Amason, 54, did not respond to a phone call and text message seeking comment Monday.
Drummond ‘walled off’ from Amason case
Monday’s abbreviated prosecution comes after Drummond and Amason have been political allies for years, even as Amason faced accusations of financial malfeasance.
In 2024, Amason highlighted the attorney general’s endorsement of his reelection campaign on his website and in a mail piece featuring a quote of Drummond calling Amason “a leader you can trust.”
“Sheriff Chris Amason is a dedicated public servant doing an outstanding job as Cleveland County’s chief law enforcement officer,” Drummond said on the mail piece. “Chris is an honest, intelligent and principled leader who has never wavered in his commitment to serving and protecting. He also has been a forceful advocate against those who attempt to defund public safety or attack the integrity of the men and women in law enforcement.”
In January 2025, Amason stood behind Drummond during the Osage County announcement of his 2026 gubernatorial bid, praising him in a Facebook post about the event.
“Yesterday, I had the privilege of standing alongside Gentner Drummond as he officially announced his candidacy for governor of the great state of Oklahoma. As a sheriff, I’ve seen firsthand the importance of strong, principled leadership to tackle the challenges facing our communities,” Amason wrote. “Gentner’s vision, integrity, and dedication to the people of Oklahoma make him the leader we need to move our state forward. I’m proud to support him in this journey and encourage others to join me in backing his campaign for a brighter future. Let’s work together to make Oklahoma stronger than ever!”
Amason also appeared in Drummond’s “Work For You” campaign television ad, walking with other law enforcement officers while Drummond’s voice proclaimed himself as “a tough-on-crime attorney general.”
Asked why Drummond’s office did not recuse itself from Amason’s prosecution given their mutual political endorsements, Drummond’s communications director, Shauna Peters, said the attorney general himself played no role in the case.
“Attorney General Drummond was officially walled off from the Amason case,” Peters said. “He was not involved in the investigation or proceedings, nor was he included in any internal discussions on the matter.”
Drummond has emphasized investigating corruption in public office during his tenure as attorney general, and Amason’s plea deal reflects the third time he has arranged plea deals with elected officials before charges are made public. As in the cases of former Rep. Ty Burns (R-Morrison) and former Rep. Ajay Pittman (D-OKC), his office announced its plea deal with Amason the same day Amason was officially charged.
Court documents reflect that Burns and Amason were both represented by Rep. Chris Kannady (R-OKC), an attorney who has become a close political ally of Drummond’s.
Amason had served as Cleveland County’s sheriff since 2020, and he was often at odds with the Cleveland County Board of Commissioners for his office’s budgetary practices. The drama culminated in Amason accusing the commissioners of intentionally sabotaging him a little over one year after the commissioners bailed out his office. State Auditor and Inspector Cindy Byrd released an audit of the Cleveland County Sheriff’s Office in April 2025, which found the agency overspent its budget in Fiscal Year 2024 and had “poor budgetary practices.” The audit reviewed the office’s finances beginning in 2020.
In the plea agreement filed with the court Monday, an assistant attorney general referenced a similar time period while describing the “proof” that prosecutors would have presented at trial.
“State would call witnesses to show that between May 26, 2020, and June 10, 2024, the defendant in Cleveland County appropriated campaign funds for personal use by issuing checks to himself and others in violation of ethical rules,” the document states.
Amason: ‘I leave with sincere appreciation’
On Monday, Amason submitted a letter to Cleveland County Clerk Pam Howlett formalizing his resignation with no mention of his criminal charges.
“Effective immediately, I hereby tender my resignation as the elected sheriff of Cleveland County. After 33 years of law enforcement service, the time has come for me to retire and begin the next chapter of my life,” he wrote. “It has been one of the greatest honors and privileges of my life to serve the citizens of Cleveland County. I am sincerely thankful for the opportunity to serve this community and to work alongside the exceptional men and women of the Cleveland County Sheriffs Office. I leave with sincere appreciation for their dedication, professionalism and commitment to public service.”
A former Cleveland County Sheriff’s Office employee had previously accused Amason of financial mismanagement. Teri Allison, previously the CCSO’s chief financial officer, reached a $55,000 sex-based discrimination settlement in 2024 with the agency after she alleged she was unfairly fired in favor of a less-experienced male employee.
Further, Allison alleged she was terminated after submitting a report that accused Amason of misconduct. Her report included allegations Amason had obtained equipment for the office without filing purchase orders. She also alleged he and his wife had used CCSO funds for travel expenses — a claim reflected in one of the three counts the state dismissed in the terms of Amason’s plea deal.
Amason denied Allison’s allegations, according to The Norman Transcript’s Mindy Ragan Wood. County commissioners approved the settlement, but District 1 Commissioner Rod Cleveland stated neither the county nor any official accepted liability by doing so.
Allison and Landon Russell, a former Cleveland County Jail employee arrested in 2023 on a drug charge, were listed on the grand jury’s indictment as witnesses for the state.
Amason becomes the second Oklahoma sheriff indicted by a grand jury in the past year, following Coal County Sheriff Jason Smith, whose trial for removal from office has been pushed to November. Unlike Amason’s prosecution, Drummond’s office assigned Smith’s prosecution to the Pittsburg County District Attorney’s Office.
The Cleveland County commissioners jointly released a statement Monday afternoon and suggested they are still investigating how the process to replace Amason should commence:
Cleveland County Commissioners Rod Cleveland, Jacob McHughes and Rusty Grissom have been given a copy of the resignation letter from Cleveland County Sheriff Chris Amason on Monday, April 27. The Commissioners have also seen the indictment from the multi-county grand jury filed today, which included multiple embezzlement claims.
The commissioners extend their gratitude to the multi-county grand jury and Attorney General’s Office for their work on bringing these allegations to light.
During this time, the commissioners’ top priority is protecting Cleveland County residents and ensuring essential services at the Cleveland County Sheriff’s Office remain uninterrupted. The commissioners’ plan to individually seek guidance on next steps until they are able to speak together in a public meeting in the coming days. As next steps are determined, they will be announced to ensure continued public safety, transparency and accountability.
Commissioners Cleveland, McHughes and Grissom are strong believers in justice. As elected officials, the commissioners believe they have a duty to be responsible stewards of every taxpayer dollar, and to follow the law – and believe the sheriff is no different.
First Florida Credit Union filed a civil case against Amason in December 2024 for civil relief worth greater than $10,000 for indebtedness, but the claim was dismissed with prejudice in April 2025.
