Edward Tyler Rollins Jr., former owner, board chairman and publisher of The Herald-Sun, died November 5, 2006, just shy of two years after selling to Paxton Media Group.

[13] Upon assumption of operations, on January 3, 2005 Paxton's executives fired 81 of the newspaper's approximately 350 employees, including president and publisher David Hughey and longtime executive editor, vice-president Bill Hawkins, photographer Ross Taylor, editorial cartoonist John Cole and longtime columnist Jim Wise.

He explained that fired employees were escorted from the building immediately due to security concerns and on the advice of the company's lawyers.

The acquisition made The Herald-Sun a sister paper to the other major daily newspaper in the Triangle, The News & Observer of Raleigh.

"[26] The Herald-Sun also came under fire for having "not written a single editorial critical of the way in which Mike Nifong proceeded" at the time the North Carolina Attorney General declared the defendants "innocent.

Despite the basic offerings, the site won a Newspaper Association of America Digital Edge Award for its online guide to local and national candidates during the 1996 elections.

[13] Apart from an automated feed of AP wire stories, the site was no longer updated during the day, even during the course of major local and national events.

The redesign also introduced compulsory, free, registration for users wishing to read any article, including the AP-wire feed stories.

Between January 1 and March 31, 2008, the paper was estimated to reach less than 20 percent of households in Durham and Orange counties, its primary subscriber base.

By comparison, The Herald Sun's primary market competitor, the Raleigh News and Observer lost less than one percent of its daily subscribers in the same period.