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When Lawton's division swung off to the right to engage the enemy at El Caney, with the results described in the preceeding chapter, the divisions of Wheeler and Kent were ordered to proceed directly along the Santiago road toward San Juan. Within a mile from El Pozo, the point where they had bivouacked for the night of the 30th, the troops arrived at the Aguadores River, which crosses the road here within less than a mile from San Juan Heights. Wheeler's division headed the column, although that general was not commanding. He had been relieved on the afternoon of the 30th and did not resume command until about 4 o'clock on July 1,[19] long after the heights had been carried, although he was on the field shortly after 1 o'clock of that day.

The Dismounted Cavalry Division on the morning of July 1 presented 2,663 fighting men, including officers. The First Brigade, commanded by Colonel Carrol, had 50 officers and 1,054 men, in regiments as follows: Third Cavalry, 22 officers, 420 men; Sixth Cavalry, 16 officers, 427 men; Ninth Cavalry, 12 officers, 207 men, the Ninth having hardly one-half the strength of either of the other regiments of the brigade. The Second Brigade, commanded by General Wood, contained 1,559 persons, distributed as follows: Brigade sta ff, 9 officers, 14 men; First Cavalry, 21 officers, 501 men: Tenth Cavalry, 22 officers, 507 men; First Volunteer Cavalry (Rough Riders), 25 officers, 517 men.

Before the troops left El Poso, Grimes' battery had been put in position and had fired a few shots at a blockhouse on San Juan Hill, distance 2,600 yards. Using black powder, which created a cloud of smoke with every shot, the battery was readily located by the foe, and the shrapnel from their guns was soon bursting among our forces. The second shot from the Spaniards wounded four of the Rough Riders and two or three of the regulars, while a third killed and wounded several Cubans. As a matter of course there was a rapid movements of the troops from that immediate vicinity. The firing soon ceased, and the troops took up that general advance movement already noted.

It is no easy task to follow the movements of the Cavalry Division from the time it left El Poso that July morning until it finally entrenched itself for the night on San Juan Hills. As heretofore we will take the official reports first, and from them make up the itinerary and the movements of the battle that followed, as far as they will enable us to do so. General Sumner says the division proceeded toward Santiago, and when about three-fourths of a mile from El Poso was halted in a narrow road to await orders and remained there for nearly an hour, subject to the effects of heavy artillery fire from the enemy's battery. Major Wessells, of the Third Cavalry, says, while following the road toward Santiago that morn, "much delay ensued from some reason unknown to the undersigned," and that the First Brigade of the division arrived at San Juan ford about 10 o'clock. This creek was about five hundred yards farther toward Santiago than Aguadores River, and ran about parallel with San Ju an Heights, from which it was about three-fourths of a mile distant.

The orders for which General Sumner had waited nearly an hour under fire had come and were "verbal instructions to move to the San Juan Creek and hold it." Reaching this creek his advance guard was met by the Spaniards who fired one volley and retreated to a position on a hill on Sumner's right front, about 1,200 yards distant. Crossing this creek with sufficient strength to hold it, Sumner was now ordered to move by the right flank and connect with Lawton's left. While his troops were in this massed condition prior to deploying to the right through a thick jungle, the balloon that was in use for purposes of reconnoitering, came up the road and exposed itself to the full view of the Spaniards upon the heights. They needed no further invitation to direct toward our forces their artillery, for which the balloon became a flying target. Many officers and men were wounded here by exploding shells and small arms' fire of the enemy (Sumner). Under this fire, however, the troops were deployed as ordered.

Colonel Wood, who had charge of the Second Brigade, of which the Rough Riders were the leading regiment, says this "regiment was directed to change direction to the right, and by moving up the creek to effect a junction with General Lawton's division, which was engaged at Caney, about one and a-half miles toward the right, but was supposed to be working toward our right flank. After proceeding in this direction about half a mile the effort to connect with General Lawton was given up." This movement to the right took place between ten and eleven o'clock, at which time Lawton's forces had made no impression upon El Caney, and he was far from making any movement which might be described as working toward the right flank of the Cavalry Divisio n. Lawton was not found by that half-hour's search to the right; and it was evident that something must be done by these troops in front, and done quickly. The whole division was under fire, and the battle on the Spanish side was in actual progress. True our men were hidden away in the jungle that bordered the creek, but their position was known to the Spaniards, and leaves and boughs are no cover from shot and shell. They were receiving the fire of the enemy and making no reply whatever, save by the few ineffective shots from the far away battery on El Poso Hill.

Directly in front of the cavalry division was a little hill occupied by a Spanish force. This hill is called in General Wood's report East Hill, but in the literature of the battle it is usually mentioned as Kettle Hill. The fire in part was coming from here. Colonel Wood gives another report of the morning's experience in which he says: "The brigade moved down the road toward Santiago in rear of the First Brigade, with instructions to deploy to the right after crossing the San Juan, and continue to extend to the right, reaching out toward General Lawton's left and holding ourselves in rear of the First Brigade as a support. On reaching the stream the First Volunteer Cavalry, which was in the lead, crossed the stream with comparatively slight loss and deployed to the right in good order, but at this time a captive balloon was led down the road in which the troops were massed, and finally anchored at the crossing of the stream. The approach and anchoring of this balloon served to indicate the line of approach of the troops and to locate the ford, and the result was a terrific converging of artillery and rifle fire on the ford, which resulted in severe loss of men. Under this fire the First United States Cavalry and the Ten th United States Cavalry crossed the stream and deployed to the right where they were placed in position in rear of the First Brigade. Two regiments of the Second Brigade, to wit., the First and the Tenth Regular Cavalry, were located in the rear of the First Brigade. The First Regular Cavalry had begun its day's work as support of Grimes' battery, but had later come forward and taken its place in the brigade time enough to join in the action that followed.

"After completing the deployment," says Sumner, "the command was so much committed to battle that it became necessary either to advance or else retreat under fire." The troops were already in battle, but were not fighting, and could not do so in their present position, simply because they could not see the enemy. "Lieutenant Miley, representing General Shafter, authorized an advance, which was ordered, Carroll's brigade taking the advance, reinforced on the right by Roosevelt's regiment, and supported by the First and Tenth Cavalry." (Sumner.) Colonel Wood says: "After remaining in this position for about an hour (meaning the position held by his brigade previous to the coming of the order to advance) the order to advance was given, and the brigade advanced in good order as possible, but more or less broken up by the masses of brush and heavy grass and cactus; passing through the line of the First Brigade, mingling with them and charging the hill in conjunction with these troops, as well as some few infantry who had extended to the right." It must be remembered that the First Brigade consisted wholly of regulars, the Third, Sixth and Ninth Cavalry, while the Second Brigade had that remarkable regiment, the Rough Riders. This fact may account for their breaking through the lines of the First Brigade. Major Wes sells, who commanded the Third Cavalry in that fight, and was himself wounded at the close of the first charge, says his regiment became entangled with other regiments, but, nevertheless, was to the crest as soon as any. Of the advance of the whole division, General Sumner says: "The advance was made under heavy infantry fire, through open flat ground, cut up by wire fences, to the creek, distant about 600 yards. The advance was made in good order, the enemy's fire being returned only under favorable opportunities. In crossing the flat one officer and several men were killed and several officers and men wounded. Both sides of the creek were heavily wooded for about 200 yards. The creek was swollen, and the crossing through this space and the creek was made with great difficulty.

"After passing through the thick woods the ground was entirely open and fenced by wire. From this line it was necessary to storm the hill, upon the top of which is a house, loop-holed for defense. The slope of the hill is very difficult, but the assault was made with great gallantry and with much loss to the enemy. In this assault Colonel Hamilton, Lieutenants Smith and Shipp were killed; Colonel Carroll, Lieutenants Thayer and Myer were wounded. A number of casualties occurred among the enlisted men." The heights were carried by the whole division.