With the men advancing down the road well within range of enemy guns, Shafter ordered Grimes’ battery to again open fire. At 10 o’clock, his howitzers belched fire and smoke, but to everyone’s surprise, the Spaniards did not answer. By that time, Captain Robert Lee Howze of Carroll’s staff rode up to report that his brigade had crossed the Aguadores. Meanwhile, Sumner had ordered Wood’s brigade forward. The heat rose as the tropic sun climbed high in the sky. Concealed in the trees along the road, snipers dressed in quilted canvas tunics filled with sand and covered with palm leaves formed the forward skirmish line of the Spanish defense force.

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Behind Wood’s brigade, four soldiers towed a balloon. On his own initiative, Derby ascended just above the trees in the partially filled balloon along with Major Joseph Edwin Maxfield of the Signal Corps, who commanded the balloon company. If the Spaniards had any doubt as to the Americans’ location, the sight of the rising balloon removed it. Mauser rounds and artillery shells began to cut through the air, snapping leaves and branches before finding their targets–the American soldiers below. The riddled balloon returned to earth, but not before Derby obtained one bit of useful information.

As Kent’s infantrymen pushed past the deflating balloon, Derby informed their commander of another trail several hundred yards up from the Aguadores to the left of the main trail. Since the cavalrymen still blocked the main road, Kent’s infantrymen could bypass them and more directly reach their assault positions on the left. The 6th and 16th Infantry regiments of Hawkins’ brigade had already passed the turnoff, so Kent turned the next regiment in line.

The 71st New York Volunteer infantrymen did not possess the same seasoned discipline and training as the Regulars. Demoralized by the incoming fire, they advanced down the new trail only a short distance before they froze. Kent and his aides rode up and reprimanded the men, but they would not budge. The officers then ordered the volunteers to make way for others, and Kent sent back for Wikoff to push his brigade through.

First Lieutenant Wendall L. Simpson ran back, waving his hat for Wikoff to hurry his men forward. Wikoff was leading his brigade down the trail and into the opening when at 12:30 p.m. he fell wounded. As some of his men carried him back in an abandoned chair they had found, he waved to the rest and cried, ‘Get on up, boys, they need you–hurry!’ Then he died.

Simpson turned to the first commander in line, Lt. Col. William S. Worth, and instructed the new brigade commander to hurry his 13th Infantry across the ford. Five minutes after Wikoff had fallen, a Spanish round hit Worth in the chest. His sword dropped from his hand, but he remained mounted, retrieved his sword with his left hand and waved it to his men. In spite of his determination, loss of blood forced him to the rear. Five minutes after Lt. Col. Emerson H. Liscum of the 24th (Colored) assumed command of the brigade, he, too, fell wounded. At last, Simpson reported to Lt. Col. Ezra P. Ewers, commander of the 9th Infantry, who brought the remainder of the brigade forward while another staff officer rode back to bring up Pearson’s brigade.

Meanwhile, shouts and insults rang out as the Regulars squeezed by the cowering New Yorkers. Little by little, the jeers goaded the volunteers to join in the advance. After Hawkins drew his 6th and 16th into line to the left of the Siboney Road, he looked for but could not find his reserve. He did not know that Kent had diverted it. With the exception of two companies, the 71st had ceased to exist as a unit. The American plan was beginning to unravel.

In the valley of the San Juan River, north of the road to Santiago, Sumner’s cavalry division had lined up for the impending assault. Carroll’s brigade formed the first line. His 9th (Colored) held the right, the 6th was in the center and the 3rd was on the left. Behind the 9th waited Roosevelt’s Rough Riders. To his left and a little forward rested the 1st, with the 10th (Colored) behind it in reserve. To the immediate front of the cavalry division rose the hill, topped by a few buildings, that would be their objective. Capturing ‘Kettle Hill,’ named by the Americans after a large iron kettle they found on it, would provide a foothold to the San Juan Hill complex.

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