History and demographics of Harlan County have presented both challenges and opportunities for the editorial staff of the newspaper as the coal-mining region it serves has been the site of labor disputes and a series of "boom and bust" cycles; a declining population since its highest level of 75,275 in the 1940 census down to 33,202 in the 2000 census with an estimate that the 2009 population has declined to 30,783, a 7.3% decline while the rest of Kentucky has an estimated growth of 5.6%; significant welfare rolls with an estimated 29.3% of residents living below the poverty level; and clearly divided socioeconomic classes.
It was locally owned until 1970, when it was sold to Worrell Newspapers of Charlottesville, Virginia.
[3] The New York Times Company acquired the Enterprise and seven other dailies from Worrell Newspapers in 1982.
[5] In 1998, the Enterprise was part of a 45-paper sale by Hollinger to Community Newspaper Holdings.
[8] Civitas Media sold the Enterprise and the Middlesboro Daily News to Boone Newspapers in 2017.