The Democrat-Journal's roots stem from the Stilwell Times, established February 8, 1898 by John W. Patton, a Mississippian by birth.
By 1901, the name had been changed to the Stilwell Standard. The Standard consolidated with the Adair County Sentinel in December 1910.
The Standard-Sentinel absorbed the Adair County Republican in June of 1915.
East Oklahoma Publishing, based in Sallisaw, bought the Standard-Sentinel in 1928 and changed the name of the paper to the Adair County Democrat.
In September of 1938, J.H. Clark sold the Adair County Democrat to J.S. Atchley, with the name of the paper being changed to the Adair County Democrat-Gleaner.
In May of 1943, the Gleaner changed its name to The Democrat, while the other paper in town became The Stilwell Journal.
J.C. and Roxie Hopkins purchased both papers on January 3, 1946 and consolidated them into the Stilwell Democrat-Journal.
Clark Coble purchased the DJ on November 2, 1950.
Due to health reasons, Coble sold the paper to Wade and Mabel Zumwalt on May 2, 1957.
Sam Love purchased a minority interest in the Democrat-Journal in July of 1966 and became a full partner four years later. He purchased full interest on July 1, 1975 and would remain as editor and publisher until until his sudden death in January 1995.
Indian Nations Communications, co-owned by Francis Stipe and Jim Monroe, purchased the Democrat-Journal on April 18, 1995.
Community Newspaper Holdings Inc. purchased the paper in January 2001.