This, of course, was in the future, and initially the level of cooperation between the two commanders was superb, especially in Bragg’s willingness to loan two divisions of veteran infantry to Smith, and thereby greatly bolstering Smith’s offensive capacity. In devising their strategy, at first there was some disagreement over the ultimate campaign goal, Bragg favoring a focus on recovering Middle Tennessee and cutting off Buell’s overextended forces. In contrast, Smith favored a drive into the heart of Kentucky to recruit troops, acquire provisions, and possibly seize the state for the Confederacy. Smith’s thinking was influenced in no small part by recent intelligence received from the adventurous Col. John Hunt Morgan. Earlier that month Morgan had led a successful cavalry raid throughout central Kentucky wreaking havoc. He reported that not only was the area weakly defended by Home Guards, but that upon the approach of a significant Confederate force the population would rise up in support, and 25,000-30,000 men would immediately enlist in the Southern forces.2

While events were to prove that Bragg and Smith never reached a mutual understanding on the ultimate campaign goals, they both were in agreement that Smith’s initial move should be to eliminate the threat and impediment posed by the Union forces under Brig. Gen. George Morgan at Cumberland Gap. Nestled in the rugged Appalachians at the border of Tennessee, Virginia, and Kentucky, the gap was a critical gateway necessary to any force conducting a long-term operation into those states. The defenses at the gap were garrisoned by more than 8,000 men and were near impregnable to a frontal assault. Obtaining Bragg’s concurrence, Smith ordered his small army to advance on August 13 up to and around the Union stronghold at Cumberland Gap (see Map, Pg. 10).

Leading the main advance were the small battle-tested divisions of Brig. Gens. Patrick R. Cleburne and Thomas J. Churchill. They swung to the west of Cumberland Gap and crossed into Kentucky and the Union rear via the rugged but unguarded Rogers Gap. This was a nearly impassable notch on the crest of the Cumberland Mountains that rose about 1,000 feet above the surrounding hills and was nothing more than a horse track.3 They were joined by another division under Brig. Gen. Henry Heth moving through Big Creek Gap. To fix the attention of Union forces at Cumberland Gap, the large (9,000 men), but less experienced division under Brig. Gen. Carter L. Stevenson moved to the southern approach of the pass. Ahead of the main force was a small brigade of cavalry under Col. John S. Scott (left), tasked with the dual mission of screening Kirby Smith’s infantry and operating in the Union rear to disrupt their slender supply channel.

Scott, a prominent Louisiana planter who had opposed secession, carried out his mission with zeal and speed.4 His brigade consisted of the 1st Louisiana Cavalry, 1st Georgia Cavalry, 4th Tennessee Cavalry, and a small Kentucky company known as the Buckner Guards, his entire command totaling about 1,000 men.5 On August 17, Scott’s vanguard surprised and captured a Union supply train of about 150 wagons near London, Kentucky. In addition to depriving the Union garrison at Cumberland Gap of these supplies, they were a godsend to the Confederate forces descending into the barren and rugged mountain region of southeastern Kentucky.6 From all accounts the advance was a logistical nightmare with most troops subsisting on little more than hardtack and green corn for considerable periods. Kirby Smith wrote to Bragg describing the difficult situation, stating that “the roads from between here and East Tennessee were much worse than I supposed,” and that the country “had been almost completely drained of all kinds of supplies.” Nor was any help or support forthcoming from the sparsely populated area. It was overwhelmingly Unionist in sentiment and the Confederate advance was constantly plagued by bushwhackers who infested the area. In a nutshell, this was why Smith realized that a conventional siege of Cumberland Gap would fail, and why a rapid move to the abundant Bluegrass region was critical to the campaign’s success.

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