Caldwell became editorial page editor of the Oregonian in 1995, in which capacity he also directed the newspaper's daily commentary pages and Sunday Opinion section. Previously, he was the Oregonian 's metropolitan editor for eight years and was the paper's first public editor, serving in that ombudsman post from 1993 to 1995.

Before joining the paper in 1983, he was a reporter, editor, and publisher at several newspapers in the Northwest. A native of Northeast Oregon and a graduate of the University of Oregon School of Journalism, he was active in professional organizations, having been president the Oregon Newspaper Publishers Association, the Oregon Newspaper Foundation, and the Western Oregon chapter of the Society of Professional Journalists. He also served as a member of the Oregon Press-Bar-Bench-Broadcasters Committee. In 1993, he served as editor-in-residence for two new daily newspapers in Romania, Cotidianul in Bucharest and Monitorul de Iasi in Iasi, consulting for other publications in the Balkans as well.

Listen to Caldwell describe his role as editorial page editor.