Founded in Joseph in 1884 by S. A. Heckethorn, the newspaper preceded the establishment of the county itself.[2][3] A few years after Enterprise was selected as the county seat, the paper relocated there.[2][4] Though the newspaper was named after Chief Joseph, it was not particularly friendly to Native American issues, and opposed a Joseph's request to resettle Wallowa Valley in 1900.[5]
George Cheney became the owner, editor, and publisher in 1911, on the wave of an economic boom experienced in Enterprise upon the completion of a railroad and sawmill, as well as a booming agricultural business. Cheney built a new building, designed to meet the needs of the paper, which it occupied beginning in 1916.[2] Cheney sold the newspaper in 1941, and the building in 1943, to Gwen Coffin. Coffin, who brought a more controversial approach to the paper, owned it until 1972.[2]
In March 2000, the East Oregonian Publishing Co. acquired the newspaper from the Swart family.[6]
In a 2006 article about Joseph, the New York Times cited the Chieftain's coverage of a new grocery store.[7]
In June 2024, EO Media Group announced the Wallowa County Chieftain will cease print publication and go online-only. All print subscribers will instead receive the East Oregonian, published weekly and including news from Wallowa County Chieftain's website.[9][10] In December 2024, the paper's editor was laid off, leaving only one reporter to cover Wallowa and Union counties.[11]