About three miles due north from El Pozo, and between three and four miles in a northeasterly direction from Santiago, there was a small village called Caney,[4] which, on account of its geographical position, was regarded as a place of considerable strategic importance. It was connected by roads or practicable trails with Santiago on the west, Guantanamo on the east, and El Pozo on the south; and an enemy holding it would not only outflank us on that side as soon as we should pass the Pozo farm-house, but, by means of a rapid cross-march in our rear, might cut or seriously imperil our only line of communication with our base of supplies at Siboney. The fact was well known, furthermore, that there was a strong division of Spanish regulars (about six thousand men) at Guantanamo; and if this division should undertake to reinforce the garrison at Santiago, Caney would be directly on its line of march. In view of these considerations, General Shafter, after a survey of the country from the summit of the hill at El Pozo, determined to seize Caney, and, having thus cut off reinforcements from Guantanamo and protected himself from a flanking movement on the right, advance directly upon the city. The plan was good enough, as far as it went; but General Shafter had made no reconnaissance on the Siboney-Santiago road beyond El Pozo, and was wholly ignorant not only of the strength of the enemy's position there, but of the nature of the country to be traversed. It is true that he had superficially looked over the ground, once, from the top of the Pozo hill; but he could get, in that way, very little accurate knowledge of the topography of the region, and still less of the Spaniards' defensive strength.
Our only possible line of advance, in the center, was the Siboney-Santiago road, which ran, through a dense jungle, down the valley of the Aguadores River, crossed a small stream flowing into that river from the north, then crossed the San Juan River, another tributary of the Aguadores, and finally emerged from the forest directly in front of the San Juan heights. The enemy, of course, knew exactly where this road lay, and where it came out of the woods into the open country; and they had so disposed their batteries and rifle-pits that they could not only concentrate their fire upon the lower stretches and the mouth of the road, but sweep with a hail-storm of projectiles the whole margin of the forest where we should have to deploy and form our attacking line. General Shafter had not ascertained these facts by means of a reconnaissance, nor had he, apparently, considered such a state of affairs as a contingency to be guarded against; but Mr. Richard Harding Davis asserts that General Chaffee, commander of a brigade in General Lawton's division, anticipated precisely this situation, and predicted, five days before the battle, that if our men marched down this trail into the open country they would be "piled up so high that they would block the road." He thought that it would be much better to keep away from the road altogether; cut trails parallel with the entire front of the forest and hidden by it, with innumerable little trails leading into the open; and then march the whole army out upon the hills through these trails at the same moment. Whether this suggestion was ever made to the commanding general or not, I do not know; but if it was, it failed to commend itself to his judgment. I refer now--perhaps prematurely--to a state of affairs in our immediate front which was not fully disclosed until much later; but I do so because knowledge of it is absolutely essential to a clear understanding of the way in which the battle of San Juan was fought.