The Chieftain was established in 1868 by Dr. Michael Beshoar, the first doctor in Trinidad, Colorado.

Wilbur Fisk Stone and George A. Hinsdale were the first two editors.

[3] In June 2023, Gannett announced that its printing plant in Pueblo would be shut down permanently in August.

The remaining journalists at the paper kept their jobs, but they do not have an office.

[4] In June 2024, the newspaper announced it will switch from carrier to postal delivery.