[5] After leaving Pacific University, Hilliard started the Portland Challenger, a weekly publication targeted at the local black population.
When he was named city editor it was considered national news, warranting an article in Time Magazine.
In 1980 he served as one of four panelists in the nationally televised debates between President Jimmy Carter and Ronald Reagan.
[1] In 1987, Hilliard was named editor of The Oregonian, with "full control over the newspaper's news and editorial departments.
[1] Hilliard served as president of the American Society of Newspaper Editors (ASNE) in 1993–94,[4] the first African-American to be elected to that position.