Precisely BECAUSE it was a spontaneous moment, the charge to drive the Spanish from San Juan and Kettle Hills lacked any semblance of military order. What it lacked in order, it more than made up for in valor. The inter-mixing of the 13 regular and 2 volunteer regiments that assaulted the two-in-one hillside would lead to centuries of debate among historians about "who did what", and how much credit Colonel Roosevelt and his Rough Riders really deserved for their role in events. While historians continue the debate even today, the record of valor and co-operation that would result in victory is unchallenged.
Colonel Roosevelt had planned to dismount at the foot of the hill and lead his Rough Riders to victory on foot. As the sea of young soldiers rose and attacked however, he quickly found he could cover more ground more quickly on horseback, leading and encouraging his men forward. As he spurred Texas among the ranks of his charging Rough Riders, he soon found himself well into the lead, ahead of the attacking forces. Armed only with a pistol, appropriately salvaged from the wreckage of the USS Maine, his courageous leadership...bordering on carelessness in the face of enemy fire...inspired those who followed and generated a snap-shot view that would become a historic image of the war in Cuba.
Forty yards from the top of the hill, Colonel Roosevelt still far to the front of his regiment, reached the last line of enemy barbed wire. He dismounted, turning Texas over to his orderly who had managed to keep up with his colonel's reckless charge, to continue his advance on foot.
Behind him swarmed hundreds of American soldiers, the mixed assortment of volunteer cowboys, lawmen and outlaws that comprised the Rough Riders, the regular Army professionals of the 1st, 3d, and 6th US Cavalry, and the Buffalo Soldiers of the 9th and 10th Cavalry.
Color Sergeant J. E. Andrews of the 3rd Cavalry surged forward with the colors of his regiment when enemy fire struck him in the stomach. He called to his lieutenant to take the colors, but tumbled down the hill still clutching the flag, before a replacement could reach him. Sergeant George Berry of the 10th Cavalry was moving forward with the standard of his own regiment when he saw Andrews fall. Quickly he grasped the colors of the 3d Cavalry together with the colors of his own 10th Cavalry, raised them bravely and shouted "Dress on the colors, boys, dress on the colors!" and he valiantly carried BOTH standards up the hill.
As the Americans neared the blockhouse at the top of the hill the Spanish defenders quickly escaped down the opposite slope, retreating for the safety of Santiago. Quickly the Rough Riders planted their standards, while Sergeant George Berry planted the colors of both the 3d and 10th Cavalry. He became the only soldier in US military history to carry TWO standards through battle and plant them victoriously on the enemy's works.
The taking of Kettle Hill did not conclude the hostilities, or the ever present rain of enemy fire. From positions between Santiago and the heights, the Spanish now shelled the blockhouse and outbuildings they had occupied less than an hour earlier. Quickly fanning out across the hilltop, several soldiers took shelter behind a large kettle, presumed to have been used for processing sugar. Thus it was that the hill just to the north of San Juan Hill gained a name, KETTLE HILL. In the hours after their incredible victory, the American soldiers began digging in their own fortifications and preparing for an anticipated counter-attack. Except for Colonel Roosevelt, all senior officers of the six cavalry regiments had been killed or wounded either in the charge or by the enemy fire directed on the hill after it was taken, leaving the Colonel in command of the survivors of all six regiments.
From their vantage point on Kettle Hill the Rough Riders had an excellent view of the charge that was still in progress by General Kent's infantry on San Juan Hill. "Obviously the proper thing to do was to help them," Roosevelt later said, "and I got the men together and started them volley-firing against the Spaniards in the San Juan blockhouse and in the trenches around it."
Upward the infantry charged, the 9th, 13th and 24th Infantry leading the way and the 71st New York and 16th Infantry following from the river bottom below (as illustrated in the above painting by Charles Johnson Post). As the first elements neared the crest, Roosevelt ordered a halt to the firing lest the attacking American Infantry be subjected to danger from their neighboring units. The final stronghold was the yellow stucco home that had been converted into the blockhouse atop San Juan Hill. Inside 35 enemy soldiers remained barricaded as 19 Americans climbed onto the building's red, tile roof. Four dropped inside through a hole opened in the ceiling by an artillery round, all of them quickly overcome and killed by the Spanish defenders. The remaining 15 infantrymen jumped through the opening, engaging the enemy in hand-to-hand combat, subduing them and capturing their prize. It was 1:50 in the afternoon when Private Arthur Agnew of the 13th Infantry pulled down the Spanish flag.
But the fight was far from over as the retreating Spanish took up positions in their trenches across a ravine from the slope of the hill. Seeing this, and taking note of the heavy fire his own men were taking from those Spanish trenches, back on Kettle Hill Colonel Roosevelt ordered a charge and rushed in the lead towards the enemy position. Dodging enemy bullets, he leaped a barbed wire fence in his fearless assault, only to find that only five of his Rough Riders had followed him. One of them was killed, another wounded, and Roosevelt realized he could not continue to lead the remaining three men in the assault. Ordering them to cover, he raced back to the top of the hill, again leaping the fence, to angrily berate the bulk of his regiment for failing to follow his lead.
The failure of the assault was in no part a matter of cowardice by the Americans. In the confusion that reigned, only five men had heard the Colonel's order to attack. A short time later, leading the rest of his Rough Riders and elements of the other cavalry regiments, Roosevelt again jumped over the barbed wire fence to attack and drive the Spanish from their positions.
THE CROWDED HOUR from the time Lieuteant Ord led the opening charge until Private Agnew pulled down the Spanish flag that flew over San Juan Hill was an amazing example of finding victory in chaos. In the years to come men of the various regiments would debate who was first to reach the crests of each hill, which regiment was foremost in battle, and who was first to plant their flag. Unquestionably Colonel Theodore Roosevelt would emerge in the American media as the hero of San Juan Hill. But the simple facts of the disorganized but united charge of the intermingled regiments of General Shafter's soldiers prove one undisputable thing. The charge at San Juan Hill was a victory that belonged not to any single soldier or commander, not to any particular regiment, not the the regular army or the volunteers, but to the entire conflagration of brave young Americans.
In addition to Sergeant Major Baker, 13 soldiers would receive Medals of Honor (six from the 21st US Infantry, five from the 10th US Infantry, and one each from the 13th US Infantry and the US Volunteers). All but Baker and Captain Albert Mills of the US Volunteers were cited simply for "GALLANTLY ASSISTING IN THE RESCUE OF THE WOUNDED FROM IN FRONT OF THE LINES AND WHILE UNDER HEAVY FIRE FROM THE ENEMY." Captain Mills was conspicuous for his courageous leadership in the charge, even after being shot in the head and blinded.
In all the battle at San Juan and Kettle Hills cost the American forces 124 killed and 817 wounded.
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