It was named the Gresham Outlook from 1911 to 1991 and was published by H. L. St. Clair, who incorporated the business as the Outlook Publishing Company in 1917. The paper was renamed simply The Outlook in 1991.
The paper was purchased in 1960 by Lee Irwin and Walt Taylor, and Irwin was its publisher from 1960 to 1982. He was followed by Robert Caldwell for a relatively short period, with Steven J. Clark being named publisher effective April 4, 1983. Robert B. Pamplin, Jr. purchased the paper in 2000.