A slaveholder, Prentice initially supported Unionist candidate John Bell in the 1860 U.S. presidential election, and after the American Civil War, he urged Kentucky to remain neutral.

Both of his sons joined the Confederate States Army, one dying in 1862, and Prentice's editorials lampooned Kentucky's military governor, Union General Stephen G. Burbridge.

Prentice's biting editorials and the savage wit of his replies to detractors helped make the Journal the most widely circulated newspaper in western America in the next four decades.

In Louisville, this culminated in the Bloody Monday riot of August 6, 1855, in which 22 people were killed as mobs tried to prevent Irish and German citizens from voting on election day.

Both Prentice's sons joined the Confederate army, and the elder, William, died September 21, 1862 (shortly after the Battle of Antietam and as Union troops massed in Louisville to attack General Braxton Bragg's forces).

[9][additional citation(s) needed] His son Clarence rose to the rank of Major in Dortch's 2nd battalion, Kentucky Cavalry.

[citation needed] In 1864 Prentice created the famous "Sue Mundy" guerrilla character to mock Union General Stephen G. Burbridge, military commander of Kentucky.

[10] After the war Prentice opposed many of the policies of Reconstruction, as did the city's other major editor, Walter N. Haldeman of the Louisville Courier, which Union forces had seized and shut in September 1861 because of Haldeman's Confederate sympathies (he moved to Nashville, Tennessee, and then Madison, Georgia, and returned to Louisville a hero after the war's end).

[12][13] His successor editor at the Louisville Courier-Journal delivered and printed a eulogy, and a Philadelphia publisher republished the 1859 essay collection in 1870 with a new preface.

A compromise reached at one point involved the city placing a new plaque for the statue, describing Prentice's "tarnished legacy.