In the light of early dawn on July 1, the men ate a meal. Rumors flew about the day’s events. The bugles then sounded attention, and the soldiers lined up in double columns on the dusty road. At the head of each regiment the commander stood next to the regimental and national colors, which were cased in oilcloth covers. Bugles sounded again, and the troops moved forward. As regiment after regiment marched down the road to Santiago, McClernand and Miley of Shafter’s staff rode through the troops with their orderlies to coordinate the battle from the front. Shafter was in his tent, too ill to actively participate, and McClernand set up on El Pozo Hill, where he could communicate with Shafter by wire telephone and mounted orderlies.

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With blanket rolls slung over their shoulders and haversacks by their sides, the men trudged forward along the narrow road. At about 6 a.m., Grimes’ battery raced past the soldiers and up El Pozo Hill, where the artillerymen positioned the howitzers with their barrels aimed toward Santiago. Miley then rode to Shafter’s headquarters to report on the troops’ progress.

Around 7 o’clock, the sound of distant thunder to the north signaled that Capron’s battery had opened the battle for El Caney. By then, Wikoff’s brigade had joined the march. The remaining cavalry regiments pressed forward to join Sumner’s men at El Pozo. Infantry regiments crowded up against the cavalry, with as many as three regiments abreast. Journalists rode up and down the columns. Most of the correspondents, foreign military observers and senior officers enjoyed the view from El Pozo.

After he heard firing on El Caney for an hour, McClernand turned and gave Grimes permission to open his own cannonade, and clouds of white smoke billowed from the howitzers. Colonel Wood looked down on his brigade and commented to Lt. Col. Theodore Roosevelt that he wished the troopers were out of the line of fire. Moments later, a whistling sound split the air, followed by an explosion and then another as two quick-firing Spanish Krupp guns answered Grimes’ fire. A third round struck the little house on El Pozo, spraying shrapnel that killed two and wounded several other spectators. Before the next volley, men above and below the hill scrambled for cover, leaving Grimes’ battery alone to do its work. It continued to pour rounds into the enemy for nearly three quarters of an hour, but the smoke obscured Grimes’ view of the Spanish artillery.

Miley soon returned to El Pozo. The sound of the guns had stirred ‘Fighting Joe’ Wheeler to join the troops there. The former Confederate cavalry leader became the senior officer at the front and worked closely with McClernand. McClernand instructed Wood and Sumner to form their brigades and advance. Sumner asked, ‘What do I do then?’ ‘You are to await orders,’ replied McClernand.

McClernand then pointed to the blockhouse on San Juan Hill and told Kent that it was his objective. Kent was directed to follow closely behind the cavalry and deploy to the left, with his right anchored on the Santiago Road. Kent then passed on the same instructions to Hawkins. Neither had reconnoitered the area.

Miley rode to the front with his mounted orderlies to provide communications with McClernand. Passing Kent, he told him to give right of way so the cavalry could get into position first. At 9 o’clock, the cavalry column advanced down the jungle trail. Carroll’s brigade led, followed by Wood’s brigade and then Hawkins’. When the lead cavalry brigade reached the San Juan River, the men waded through the knee-deep water regiment by regiment and then peeled off to the right.

Kent and Hawkins, joined by Miley, rode to the river crossing to reconnoiter. Hawkins believed his brigade could ascend the hill, storm the blockhouse and then turn the Spanish flank. Kent had his doubts. Miley agreed with Hawkins, however, and with the authority delegated to him by Shafter, he directed Hawkins to take the hill. Riding back, Hawkins squeezed past the cavalrymen who were bottled up at the crossing, completing their slow deployment into a line. About that time, a dynamite gun and a battery of Hotchkiss guns arrived. Roosevelt claimed the dynamite gun, and Hawkins took command of the others.

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