January 1913- August 1913
E.R. Clewien September 1913-December 1914
Seth Lewis 1917-1921
C.B. Musselwhite 1922-1923
C.A. Cook 1923-1924
H.M. Freas 1911-1912, 1915-1917, 1921-1922, 1924-1929
B.P. McDonald 1929-1931
R.A. Shultz 1931-1933
Sheriff Dick Conner was a well-known figure in Osage, Oklahoma. He served as the sheriff of Osage County for several years and was highly respected in the community. Sheriff Conner was known for his dedication to upholding the law and ensuring the safety of residents in his jurisdiction.
During his time as sheriff, Sheriff Conner worked tirelessly to combat crime and maintain peace in Osage. He was known for his proactive approach to law enforcement, constantly staying vigilant and taking swift action when needed. His efforts earned him a reputation for being tough on crime, making him a highly effective sheriff.
Sheriff Conner was also known for his strong commitment to community outreach. He believed in fostering positive relationships between law enforcement and the community, regularly organizing events and initiatives to bridge the gap between the two. His approach helped build trust and cooperation between residents and the sheriff’s office.
Beyond his law enforcement role, Sheriff Conner was actively involved in various community projects and organizations. He was a strong advocate for public safety, always promoting initiatives that aimed to improve the well-being of Osage residents.
Sheriff Dick Conner’s dedication to his duty and the well-being of his community made him a beloved figure in Osage, Oklahoma. His legacy as a committed and respected sheriff continues to inspire and influence the law enforcement community to this day.
Charles Cass 1943-1955
Jerome “Dick” Streetman 1955-1965
George Wayman 1965-10/1989
George was born near Burbank, OK in 1923. He was destined to become a legendary lawman. He left school in his senior year to join the Army during World War 2. During his service, he received four battalion stars, a bronze star, an arrowhead and a good conduct ribbon. He came home to become a rancher and was called back to duty during the Korean Conflict in 1950 and returned home the next year with more commendations. In 1955, he was hired as a deputy sheriff and that quickly became his passion. He was promoted to undersheriff then appointed to sheriff of Osage County in 1965.
He was elected to the office the next year and ran eight more times, only drawing one opponent in all those years. During his final campaign in 1988, he was endorsed by 28 county attorneys, assistant attorneys and district attorneys. He’s the only sheriff born in Osage County, was the youngest one ever elected and served twice as long as any other sheriff. He worked hard to create an organization respected throughout the state with his simple philosophy that his office would treat others as they would like to be treated, with integrity, honesty, and respect. He didn’t just say it, he lived it.
He helped organize the Oklahoma Sheriffs Association in 1970 and they worked hard with other groups to channel their strength in numbers to work with the legislature to get a much needed retirement system put into place.
He had served on numerous committees and organizations, including being appointed by three governors to serve on the Oklahoma Crime Commission.
When he retired from law enforcement he became mayor of Fairfax for seven years and was very active in his church.
Wyman stated that being Sheriff never seemed like a job. It was just an honor and pleasure to serve the people of Osage County.” He was a man who believes in and exhibits the values of honor, family, country, and service to his very core