Jackson grew up in the Birmingham housing project. He earned a bachelor of science in political science and journalism at Baker University in Baldwin, Kansas in 1975 and returned to Birmingham as a reporter for the Birmingham Post-Herald that year. In 1980 he left to report for the United Press International wire service and was promoted to state news editor for UPI in 1983. In 1985 he moved to Philadelphia as an assistant national editor for the Inquirer, but returned to Birmingham a year later to join the News staff as an assistant city editor.
Jackson joined the paper's editorial board in 1987. He, Ron Casey and Joey Kennedy were jointly awarded a 1991 Pulitzer Prize for Editorial Writing for their series, "What They Won’t Tell You About Your Taxes," which analyzed inequities in Alabama's tax system and proposed reforms.
Jackson served as president of the Birmingham Association of Black Journalists from 1990 to 1992. In 1993-94 he taught at the University of Alabama as a Freedom Forum Professor of Journalism. The following year he moved to Baltimore, Maryland as an editorial writer for the Baltimore Sun, and served as a journalist in residence at Loyola College of Maryland for two years beginning in 1997. He re-joined the staff of the Philadelphia Inquirer in 1999 and was promoted to deputy editorial page editor in 2004 and editorial page editor in 2007.
Jackson and his wife Denice have two children; Annette and Dennis.
- Brennen, Elizabeth A. & Elizabeth C. Clarage (1999) Who's who of Pulitzer Prize Winners. Greenwood Publishing Group ISBN 1573561118