Significant battle of the Spanish–American War
The Battle of San Juan Hill (), also known as the Battle for the San Juan Heights, was a major battle of the Spanish–American War fought between an American force under the command of William Rufus Shafter and Joseph Wheeler against a Spanish force led by Arsenio Linares y Pombo. The combined assaults on Kettle Hill and San Juan Hill that together form San Juan Heights proved to be one of the most significant battles of the war and, along with the Siege of Santiago, a decisive battle in deciding the fate of the United States Army campaign in Cuba. The American forces, outnumbering the Spanish defenders 16-to-one, charged upon the heights and dispersed the Spanish after suffering heavy casualties.
Tensions between Spain and the United States worsened over Spanish behavior during their efforts to quell the Cuban War of Independence, with many Americans being agitated by exaggerated reports of Spanish atrocities against the Cuban population. In January 1898, fearing the fate of American interests in Cuba due to the war, the cruiser USS "Maine" was dispatched to protect them. Less than a month later, the cruiser exploded while lying at anchor in Havana harbor, killing 267 sailors onboard and inflaming American opinion, with Spain being portrayed as the culprit in the American media without conclusive evidence. Two months later, war was declared.
The Americans, after already landing troops in the Battle of Guantánamo Bay, moved inland to seek a decisive encounter with the Spanish forces. Both sides drew blood at the Battle of Las Guasimas, with the Spanish moving to defend the strategically valuable San Juan Heights from the Americans. A week later, a significantly larger American force, including the famed 'Rough Riders', moved to clear the heights of the Spanish. After enduring artillery fire which inflicted heavy casualties, the Americans charged up the hill and dispersed the Spanish, suffering even more heavily in the process. The fight for the heights proved to be the bloodiest and most famous battle of the war.
The battle also proved to be the location of the "greatest victory" for the Rough Riders, as stated by the press and its new commander, Theodore Roosevelt. Roosevelt returned to New York and was promptly elected governor. He was posthumously awarded the Medal of Honor in 2001 for his actions in Cuba and became the only U.S. president to receive the award. 
The Americans won another engagement at El Caney the same day, with both battles highlighting the bravery and skill of the American/Cuban forces, as well as the Spanish defenders. Following the surrender of the Spanish army at Santiago, they agreed to depart Cuba, ending over four centuries of Spanish rule.
Background.
Spanish General Arsenio Linares ordered 760 Spanish Army regular troops to hold the San Juan heights against an American offensive on July 1, 1898. For unclear reasons, Linares failed to reinforce this position, choosing to hold nearly 10,000 Spanish reserves in the city of Santiago de Cuba.
Spanish hilltop entrenchments, while typically well-concealed, were not all correctly positioned for plunging fire, which made return fire at the advancing Americans more difficult. Most of the Spanish fortifications and trench lines were laid out along the geographic crest of the heights instead of the military crest. This meant that the fire from the Spanish troops would have difficulty hitting the advancing enemy when the attacking Americans reached the defilade at the foot of the heights. Once they began scaling the hill, however, the attackers would be in full view of the defenders, who could engage the Americans with both rifle and artillery fire.
Most Spanish troops were recently arrived conscripts, but their officers were skilled in fighting Cuban insurgents. The Spanish were well equipped with supporting artillery, and all Spanish soldiers were armed with 7 mm Mauser M1893 rifles, a modern repeating bolt-action weapon with a high rate of fire that was chambered in the high-velocity smokeless powder 7mm Mauser cartridge. This rifle was faster to reload than the American Krag. Spanish artillery units were armed mainly with modern rapid-fire breech-loading cannon, again using smokeless powder.
The American regular forces and troopers were armed with bolt-action Krag rifles chambered in the smokeless .30 Army caliber. However the soldiers of the 24th and 25th Colored Infantry (Buffalo Soldiers) still used the single shot Springfield Model 1873 (Trapdoor) which fired the .45-70 black powder cartridge. While the Rough Rider's troopers carried the Krag, each Rough Rider officer was equipped with a .30 Army caliber M1895 Winchester lever-action rifle, courtesy of Col. Roosevelt. However, U.S. 3.2-inch artillery pieces were of an outmoded design, with a slow rate of fire due to bag powder charges and lack of a recoil mechanism. They also used less powerful black powder charges, which limited the effective range of support fire for U.S. troops. The Americans also had a four-gun Gatling Gun Detachment commanded by Lt. John Henry Parker. Parker's men were equipped with four Colt Model 1895 Gatlings in .30 Army caliber. Although these guns were hand-cranked, they were nevertheless capable of 700 rpm or more in continuous fire, and were equipped with swivel mounts to allow greater field of fire coverage.
General William Rufus Shafter commanded Fifth Army Corps, of about 15,000 troops in three divisions. Jacob F. Kent commanded the corps' 1st Division (brigade and division numbers in this era were only unique within their parent formation), while Henry W. Lawton commanded the 2nd Division. 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, a task which was to take about two hours. Then they were to join with the rest of the troops for the attack on the San Juan Heights. The remaining two divisions would move directly against the San Juan heights, with Sumner in the center and Kent to the south. Shafter, too ill to personally direct the operations, set up his headquarters at El Pozo from the heights and communicated via mounted staff officers.
Order of battle.
U.S..
Fifth Army Corps – Major General William Rufus Shafter, Corps Executive Officer – Major General Joseph Wheeler (Cavalry Division)
The American assault line consisted of the following regiments: From the far left, attacking what later became known as San Juan Hill, was the 6th Infantry, the 9th Infantry, the 13th Infantry, the 16th Infantry, the 24th (Colored) Infantry, the 10th (Colored) Cavalry (the 10th was the only unit that assaulted both high points on the San Juan heights), with the 3rd Cavalry, 1st Volunteer Cavalry on the far right, attacking what later became known as Kettle Hill.
The Battle.
Initial troops cross the San Juan River and are pinned down.
A company from the Signal Corps ascended in a hot air balloon to reconnoiter the hills. The balloon made a good target for the Spaniards. Hawkins' brigade had already passed by the newfound route and Kent ordered forward the brigade under Colonel Charles A. Wikoff. Wikoff began heading down the trail at noon, and 30 minutes later he emerged from the woods and was struck by a Mauser bullet. He died as his staff officers carried him to the rear. Lt. Col. William S. Worth, next in rank, 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. Crossing the San Juan River, increasing numbers of troops waited at the base of San Juan Hill. Waiting for orders, they were plagued by constant Spanish Mauser gunfire firing down at them from San Juan Heights. The troops would call their precarious position, "Hell's Pocket" and "Bloody Ford".
The Attack on San Juan Hill.
As men waited at the base of the hill, General Hamilton Hawkins' 1st Infantry Brigade was preparing to assault San Juan Hill, the higher of the two hilltops forming San Juan Heights. The southernmost point was most recognizable for the Spanish blockhouse, a defensive fort that dominated the crest. The Cavalry Brigade then moved into position. Continuing to wait for orders from General Shafter, the Americans suffered casualties from rifle and artillery fire. As the volume of fire increased, officers began to agitate for action.
The 2nd and 10th Infantry regiments of the 2nd Brigade were ordered by the brigade commander, Col. E. P. Pearson, to advance towards the Spanish lines. Positioned on the far left of the American line, the two regiments moved forward in good order, advanced towards a small knoll on the Spanish right flank, and drove groups of Spanish skirmishers back towards their trenches. A former brigade staff officer, First Lieutenant Jules Garesche Ord (son of General E. O. C. Ord), officially of the 6th Infantry Regiment but temporarily assigned to D Company of the 10th due to sick and heat-disabled officers in the Fifth Corps, made a special request to General Hawkins. "General, if you will order a charge, I will lead it." 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!" Lt. Ord then asked the leaders to the right of the 10th Cavalry (members of the 3rd and 1st Volunteers) to "support the regulars" when they charged the heights. When Ord returned to his assigned unit, he advised his commander, Captain John Bigelow Jr. of D Troop, of his conversation with the general. Bigelow gave the honor to sound the advance to Lt. Ord. With a sword in one hand and a pistol in the other, Ord stood up and ordered the advance of his unit. The Buffalo Soldiers (members of the 10th Cavalry Regiment) moved out of the trenches and up the hill. Units to the right began moving forward in a ripple effect to support the regulars. To the left of the 10th, a cheer went out from members of the 24th all-black Infantry Regiment, and they too moved toward the top of the heights. They were accompanied by elements of the 6th Infantry Regiment, including E Company, led by Capt. L. W. V. Kennon, as well as units from the 9th and 13th Infantry Regiments. The 16th Infantry followed some distance behind the lead formations, while the 71st (New York Volunteer) infantry regiment, having failed to initially advance with the other regiments, remained at the rear. As the units began their advance up the hill, they became separated, with the battalions of some regiments placed between those of other regiments.
The Fifth Corps' newly formed Gatling Gun Detachment participated in the U.S. Army's first use of machine gun fire for mobile fire support in offensive combat. Because U.S. black-powder artillery pieces lacked the range to reach the Spanish positions, Lt. John Parker's Gatling battery of four .30 caliber 10-barrelled guns was originally conceived as providing covering fire for the artillery trains. The Gatling Gun Detachment was ordered to move forward in support of the U.S. assault, and Lt. Parker received orders from his colonel to detach one gun to General Shafter's aide, Lt. John D. Miley, then to take the remaining three guns forward "to the best point you can find". Parker set up his three Gatlings approximately from the San Juan Hill blockhouse and its surrounding trenches, occupied by Spanish regulars; away was another ridge-line, also with Spanish entrenchments. Being exposed, the Detachment soon came under attack and quickly lost five men to wounds and others to severe heat stroke. Ordinarily, four to six men were required to operate each Gatling gun. Nevertheless, the crews continued to fire at the Spanish. Lt. Parker's three rapid-fire Gatlings provided covering fire for U.S. forces assaulting both hills. Equipped with swivel mountings that enabled the gunners to rake Spanish positions, the three guns poured a continuous and demoralizing hail of bullets into the Spanish defensive lines. Witnessing the assault on San Juan Hill, more than one observer from the U.S. side noticed some of the Spanish defenders fleeing their