Four newspapers served Winston, MO, during the years between 1880 to World War I. These included the Winston New Era, the Winston Independent, the Winston Star, and the Winston Sentinel.
The first newspaper dedicated to the community of Winston, MO, was the Winston New Era established in December, 1880, by E.A. Martin. It lasted but 9 months. In 1883 Harvey L. Cross founded the Winston Independent, which gave way to the Winston Star in 1888. James H. Wise took possession in July, 1901, renaming the newspaper as the Winston Sentinel with H.L. Johnson as editor. The newspaper underwent several more ownership changes before and after World War I.
A 1914 penny postcard of the Winston Sentinel carries this message penned by Virgil H. Black: “This is a pretty good picture of my new building. The front is made of pressed brick. The side of concrete blocks. It is 40 feet long and 25 feet wide, divided into two rooms each being 12×40. The post office is in the west room and the Sentinel in the east room.” (courtesy Jim Mogg, Hamilton)