Next came the historic battle of San Juan. When news of the battle reached General Shafter he was told that the Americans had been cut to pieces. It was also said that the regiment had passed the advanced outpost without orders. Shafter exploded.
“I will send that damned cowboy regiment,” he said, “so far to the rear that it will not get another chance.”
Later, however, came the news that the cowboys had been victorious, so Shafter wrote a flattering letter to Roosevelt, in command, congratulating him on the success of his attack.
There followed a period of inaction. Then the Rough Riders received orders to proceed against Santiago.
The regiment struck camp and marched to the front behind the 1st and 10th Cavalry. Every man carried three days’ rations.
Roosevelt’s command joined General Wood at El Paso Hill and camped for the night.
The next morning it was announced that the main fighting against Santiago was to be done by Lawton’s infantry division, which was ordered to take El Caney, while the Rough Riders were ordered simply to make a diversion with artillery.
When the firing began shrapnel shells exploded over Roosevelt’s head. One of the shrapnel bullets struck his wrist. The same shell wounded four men of his regiment. He at once led his men from their exposed position into the underbrush.
General Wood then ordered Roosevelt to follow behind the 1st Brigade, and the Rough Riders began a march toward the ford of the San Juan River. They reached the ford and crossed it. In front of them was a rise of ground, afterward called Kettle Hill. Roosevelt found the 1st Brigade engaged in a hot battle, so he halted his men and sent back word for orders.
On top of Kettle Hill were large haciendas, or ranch buildings. The Spaniards, from their stations on the hills, poured a heavy fire on the American troops, who were hidden in sheltered lanes and along the edge of the San Juan River, or in patches of jungle grass. Roosevelt, lying with his troops under this severe fire, sent messenger after messenger to General Sumner or General Wood to secure permission to advance. He had about determined to go ahead when Lieutenant-Colonel Dorst rode up with the command to “move forward and support the regulars in the assault on the hills in front.” The impatient Roosevelt leaped upon his horse. He had intended to go into action on foot, but he saw that he would be unable to run up and down the line and superintend matters if he were on foot. His men went eagerly to the attack. The Colonel started in the rear of his men, as was the custom for a Colonel, but his ardor soon bore him to the head of the regiment.