It was founded in 1911,[2][3] and is owned by the Pamplin Media Group.

The newspaper was named the Gresham Outlook from 1911 to 1991 and was published by H. L. St. Clair,[4] who incorporated the business as the Outlook Publishing Company in 1917.

[7] He was followed by Robert Caldwell for a relatively short period, with Steven J. Clark being named publisher effective April 4, 1983.

[8] Irwin and Taylor sold the Gresham Outlook in 1977 to the Democrat-Herald Publishing Co., which published the Albany Democrat-Herald.

[11] Disney sold its Oregon newspapers to Lee Enterprises in 1997,[12] and three years later Lee sold The Outlook to Robert B. Pamplin, Jr. in 2000.