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San Juan Hill and another hill were separated by a small valley and pond with the river near the foot of both. Together, this geography formed San Juan Heights. The battle of San Juan Heights began with an artillery barrage on the Spanish position. When the Spanish returned fire, the Rough Riders had to move promptly to avoid shells as they were occupying the same space as the friendly artillery. Colonel Roosevelt and his men made their way to the foot of what was dubbed Kettle Hill for the old sugar refinement cauldrons which lay along it. There they took cover along the riverbank and tall grass to avoid sniper and artillery fire, but they were left vulnerable and pinned down. The Spanish rifles were able to discharge eight rounds in the twenty seconds it took for the United States rifles to reload. Luckily, rounds they fired were 7mm Mauser bullets, which moved at a high velocity and inflicted small, clean wounds. Although some of the men were hit, few were mortally wounded or killed.:70–80

Theodore Roosevelt, deeply dissatisfied with General Shafter's lack of reconnaissance and failure to issue specific orders, became uneasy with the idea of his men being left sitting in the line of fire. He sent messengers to seek out one of the generals and coax orders from them to advance from their position. Finally, the Rough Riders received orders to assist the regulars in their assault on the hill's front. Roosevelt, riding on horseback, got his men onto their feet and into position to begin making their way up the hill. He later claimed that he wished to fight on foot as he did at Las Guasimas, but that would have made it too difficult to move up and down the hill to supervise his men effectively. He also recognized that he could see his men better from the elevated horseback, and they could see him better as well.:75 Roosevelt chided his own men to not leave him alone in a charge up the hill, and drawing his sidearm promised nearby black soldiers separated from their own units that he would fire at them if they turned back, warning them he kept his promises. His Rough Riders chanted (likely in jest): "Oh he always does, he always does!" The soldiers, laughing, fell in with the volunteers to prepare for the assault.:49

As the troops of the various units began slowly creeping up the hill, firing their rifles at the opposition as they climbed, Roosevelt went to the captain of the platoons in back and had a word with him. He stated that it was his opinion that they could not effectively take the hill due to an insufficient ability to effectively return fire, and that the solution was to charge it full-on. The captain reiterated his colonel's orders to hold position. Roosevelt, recognizing the absence of the other Colonel, declared himself the ranking officer and ordered a charge up Kettle Hill. The captain stood hesitant, and Colonel Roosevelt rode off on his horse, Texas, leading his own men uphill while waving his hat in the air and cheering. The Rough Riders followed him with enthusiasm and obedience without hesitation. By then, the other men from the different units on the hill became stirred by this event and began bolting up the hill alongside their countrymen. The 'charge' was actually a series of short rushes by mixed groups of regulars and Rough Riders. Within twenty minutes Kettle Hill was taken, though casualties were heavy. The rest of San Juan Heights was taken within the following hou

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