According to the 1999 Editor & Publisher International Yearbook, the paid circulation of the Herald-Leader is the second largest in the Commonwealth of Kentucky.

[3] It had also been a finalist in six other Pulitzer awards in the 22-year period up until its sale in 2006, a record that was unsurpassed by any mid-sized newspaper in the United States during the same time frame.

Despite the common ownership, the two papers had different editorial stances; the Herald was moderately liberal while the Leader was conservative.

On July 11, 2001, the paper reduced four positions due to declining advertising revenue and higher newsprint costs.

[7] Long-time columnists Don Edwards and Dick Burdette took voluntary early retirements but are still published occasionally as contributing writers.

On June 27, 2006, the McClatchy Company purchased Knight Ridder for approximately $4 billion in cash and stock.

[9] It was a 158,990 square feet (14,771 m2) structure that featured 14 Goss Metro offset presses that had the capacity to produce 600,000 newspapers in a typical week.

In June 2016, it was announced that the Herald-Leader would cease its printing operations in Lexington, contracting them out to Gannett from the Louisville facilities for the Courier Journal.