The Battle of San Juan Hill (July 1, 1898) was the bloodiest and most famous battle of the Spanish-American War. The battle has become famous partly because it led directly to the major political rise of Theodore Roosevelt.
General William Rufus Shafter commanded about 15,000 troops in three divisions. Jacob F. Kent commanded the 1st Division, Henry W. Lawton commanded the 2nd Division, and Joseph Wheeler commanded the dismounted Cavalry Division but was suffering from fever and had to turn over command to General Samuel S. Sumner. Shafter's plans to attack Santiago de Cuba called for Lawton's division to move north and reduce the Spanish stronghold at El Caney, which was to take about 2 hours then join with the rest of the troops for the attack on the San Juan Heights. The remaining two divisions would move directly against San Juan Hill with Sumner in the center and Kent to the south. Shafter was too ill to personally direct the operations and instead set up his headquarters at El Pozo two miles (3 km) from San Juan Hill and communicated through mounted staff officers.
A company from the signal corps ascended in a hot air balloon to reconnoiter the hills. The balloon made for a good target for the Spaniards, and it was eventually filled with enough holes that it dropped back to the ground, but not before its officers discovered another path leading up the slope. Hawkins' brigade had already passed by the new found route and Kent ordered forward the brigade under Colonel Charles A. Wikoff. It was 12 p.m. by the time Wikoff began heading down the trail, and a half an hour later he emerged from the woods and was struck by a bullet. He died as his staff officers carried him to the rear. Next in command was Lt. Col. William S. Worth who assumed command but within five minutes fell wounded. Lt. Col. Emerson Liscom assumed command and within another five minutes received a disabling wound. Lt. Col. Ezra P. Ewers, fourth in command of the brigade, assumed command.
Kent and Sumner lined up for the attack and waited for Lawton's division to arrive from El Caney. Lawton did not arrive as scheduled, and no orders came from either Shafter or Wheeler and the troops waited at the base of the hill plagued by Spanish gunfire in areas dubbed "Hell's Pocket" and "Bloody Ford".
A myth arose in which the regulars stopped to fire at a depression in the hill; Roosevelt ordered them to charge but they refused because no orders to do so came from the brigade commanders. So Roosevelt led his volunteers past the regulars to charge up the hill.
In the meantime Hamilton Hawkins' brigade was faring no better than Roosevelt had in his original position. A brigade staff officer named Jules G. Ord initiated an unusual discussion with his commander by asking, "General, if you will order a charge, I will lead it." Hawkins made no response. Ord again asked "If you do not wish to order a charge, General, I should like to volunteer. We can't stay here, can we?"
"I would not ask any man to volunteer," Hawkins stated. "If you do not forbid it, I will start it," returned Ord. Hawkins again remained silent. Ord finally asked "I only ask you not to refuse permission." Hawkins responded "I will not ask for volunteers, I will not give permission and I will not refuse it," he said. "God bless you and good luck!"
With that response Ord rushed to the front of the brigade. With Ord in the lead the brigade moved out of the trenches and advanced up the slope. General Hawkins apparently was not opposed to the attack since once the men began he joined in directing the two lead regiments. 150 yards from the hill the troops charged, cutting their way through the barbed wire.
Seeing the spontaneous advances of Roosevelt and Ord, Wheeler gave the order for Kent to advance with his whole division while he returned to the Cavalry Division. Kent sent forward Ewers' brigade to join Hawkins' men already approaching the hill. Kent's men discovered that the Spanish had placed their trenches in faulty positions and were actually covered from their fire while the attackers climbed the hill. Ord, still in the lead, was among the first to reach the crest. The Spanish fled, but as Ord jumped into the trench he was killed instantly and Hawkins was wounded shortly after. After losing Kettle Hill, Linares's men still on San Juan Hill began to fire on the cavaliers' newly won position. While Kent's secured a blockhouse to the south after hand-to-hand fighting, Sumner also charged San Juan Hill. Roosevelt personally led the attack but paused after charging a few feet with only a handful of men following. He turned around and inquired why no one had followed. His men replied they had not heard the order and quickly joined the attack. Kent's remaining brigade under Colonel E. P. Pearson arrived after Hawkins and Ewers had already charged and moved further to the south and drove the Spanish off of a knoll on the Spanish right flank.
General Wood sent requests for Kent to send up infantry to strengthen his vulnerable position. General Wheeler reached the trenches and ordered breastworks constructed. Roosevelt's men did in fact repulse a minor counterattack on the northern flank. The Americans' position on San Juan Hill was exposed to artillery fire from within Santiago, and Shafter feared the vulnerability of the line and ordered the troops to withdraw. Wheeler assured Shafter that the position could be held; still Shafter ordered the withdrawal. Before the men could withdraw Wheeler called aside Kent and Sumner and reassured them that the line could be held, and during the night they worked at strengthening the lines while reinforcements arrived.
Lawton's division, which was supposed to join the fight early on July 1, did not arrive until noon on July 2, having encountering unexpectedly heavy resistance in the battle of El Caney. The Americans, along with the aid of Cuban insurgents, immediately began the investment of Santiago, which surrendered on July 17. The battle of San Juan Hill launched Theodore Roosevelt into national fame along with his regiment of "Rough Riders". Roosevelt returned to the United States a national hero and was elected governor of New York state later in the year, then became Vice President in the general election two years later. Roosevelt, along with 23 other participants were awarded the Medal of Honor. Political rivalries prevented Roosevelt from receiving his award during his lifetime, but in 2001 President Bill Clinton presented the award to Tweed Roosevelt.