Starr writes that in the days prior to the Civil War, like many others in New York, the "Pfaffians were exposed increasingly to the clamour of a world beyond their ken. Something like a revolution was afoot in the realm of journalism, a revolution that would lift these light-hearted pranksters from their subterranean retreat and whirl them in its vortex. Soon O'Brien, Aldrich, Thomson, Williams, and Stedman, together with others in Clapp's happy coterie--Charles G. Halpine (who stammered to fame at Pfaff's, speaking inadvertantly of 'H-H-Harriet Beseecher Bestowe'), William Conant Church, William Swinton, E.H. House, Charles Henry Webb, a couple of artists, Frank H. Bellew and Thomas Nast: in all more than half of the identifiable clientele at the Cave--would take the field along with hundreds of other youths of like mind to participate in the greatest undertaking in the history of journalism" (9).
Starr describes him as one of the "withering realists" of the time (259).
Webb traveled with the Times and the large group of journalists that witnessed the first Battle of Bull Run (43).
Of Webb's skill, Starr writes: "Charles Henry Webb of the Times far outshone him [Smalley]. Despite a talent for mischief Webb brought with him from Pfaff's, he was a competant reporter, among the first in the North to comprehend the genius of Thomas J. Jackson." Starr prints an excerpt from Webb's report on Jackson and the battle of Cross Keys (121).
Webb, "later a close friend of Mark Twain, imparted a light touch to the correspondence of the New York Times. Webb delighted in unexpected twists in the midst of perfectly sensible recitals, ending one dispatch: 'I hope to date my next letter from Richmond,' a sentiment so trite as to be painful, adding, '-not from the tobacco factories, however'" (260-261).
Starr also notes that Webb nearly drowned while crossing a stream that was too high for the troops to cross in the spring of 1862. Starr also writes that "Unlike many of his fellows, Webb retained his perspective in writing of the enemy. 'Of the horrors and atrocities that are related as having been practiced by the Confederate troops,' he wrote, 'I must confess I do not believe one. These men are our countrymen...Are we to believe that the lapse of a year has transformed them to fiends?' This was the resolute fair-mindedness that prompted him to given Stonewall Jackson his fair due" (261).