He quickly became a legal reporter for the AP, covering the high-profile Susan Smith trial in Union, South Carolina for the news cooperative, earning him the Associated Press Managing Editors John L. Dougherty Excellence Award.

He later became the statehouse reporter, covering the South Carolina government including Governors Carroll Campbell, David Beasley and Jim Hodges.

[6] He transferred to the Albany, New York bureau in 1999, where he covered education, state government, Governor George Pataki and Hillary Clinton's first U.S. Senate run.

[7] Holland left the Associated Press in September 2019 to take a position as Distinguished Visiting Scholar in Residence at the John W. Kluge Center at the Library of Congress.

Holland left the AP in 2005 to write his first book, Black Men Built The Capitol: Discovering African American History In and Around Washington, D.C., which was published in 2007.