Battle of San Juan Hill The Battle of San Juan Hill ( July 1 , 1898 ) , also known as the battle for the San Juan Heights , was a decisive battle of the Spanish – American War . The San Juan heights was a north - south running elevation about two kilometers east of Santiago de Cuba . The names San Juan Hill and Kettle Hill were given to the location by the Americans . This fight for the heights was the bloodiest and most famous battle of the War . It was also the location of the greatest victory for the Rough Riders , as claimed by the press and its new commander , the future Vice - President and later President , Theodore Roosevelt , who was posthumously awarded the Medal of Honor in 2001 for his actions in Cuba . The American press at the time overlooked the fact that the Buffalo Soldiers of the 10th and 24th Infantry Regiments had actually done much of the heaviest fighting . 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 used high - velocity cartridges and smokeless powder . 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 rifle s chambered in the smokeless . 30 Army caliber . However , U . S . artillery pieces were of an outmoded design , with a slow rate of fire . 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 detachment of older style hand - cranked Gatling gun s in . 30 Army caliber with swivel mounts to allow greater coverage . General William Rufus Shafter commanded 5th Corps , of 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 , 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 . . V 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 . Battle . " Hell ' s Pocket " . 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 . The troops waited at the base of the hill , plagued by constant Spanish Mauser gunfire in areas dubbed " Hell ' s Pocket " and / or " Bloody Ford " . San Juan heights . San Juan Hill . In the meantime , Gen . 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 . In open view of the Spanish positions on the heights , the Americans suffered casualties from rifle and artillery fire while awaiting orders from General Shafter to take the hill . 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 5th 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 of the 10th 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 V 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 . Parker ' s " ad hoc " Gatling battery of four . 30 – 40 , 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 trenches to escape the intense fire . The Gatlings continued to fire until Lt . Parker observed Lt . Ferguson of the 13th Infantry waving a white handkerchief as a signal for the battery to cease firing to avoid causing friendly casualties . The American assault then broke into a charge about from the crest of the hill . Lt . Ord was among the first to reach the crest of San Juan heights . As the Spanish fled , Lt . Ord directed supporting fire into the remaining Spanish until he was mortally wounded by a shot to the throat . General Hawkins was wounded shortly after . At 13 : 50 , Private Arthur Agnew of the 13th Infantry pulled down the Spanish flag atop the San Juan blockhouse . General Wood sent requests for General Kent to send up infantry to strengthen his vulnerable position . When General Wheeler reached the trenches , he ordered breastwork s constructed . The Americans ' position on San Juan was exposed to artillery fire from within Santiago , and General Shafter feared the American position on Kettle Hill was vulnerable to counter - attack by Spanish forces . A Spanish counter - attack was launched late in the afternoon , but was easily beaten back with the aid of supporting Gatling fire from San Juan Hill . Though General Wheeler assured Shafter that the position could be held , Shafter nevertheless ordered a withdrawal . Before the men on Kettle Hill could withdraw , General Wheeler called aside Generals Kent and Sumner and reassured them that the line could be held . During the night , the Americans worked at strengthening the lines while awaiting reinforcements . Kettle Hill . The 1st Volunteers ( Rough Riders ) , along with the 3rd Cavalry regiment , began a near simultaneous assault with the regulars of the 10th Cavalry ( Buffalo Soldiers ) up Kettle Hill , supported by the fire of three Gatling guns commanded by Lt . John H . Parker . Trooper Jesse D . Langdon of the 1st Volunteer Infantry , who accompanied Col . Theodore Roosevelt and the Rough Riders in their assault on Kettle Hill , reported : During the battle , Parker ' s Gatling guns expended approximately 18 , 000 rounds in eight and a half minutes ( over 700 rounds per minute of continuous fire ) into the Spanish defensive lines atop the heights , killing many of the defenders and forcing others to flee the trench lines , while disrupting the aim of any still alive who continued to resist . Col . Egbert , commander of the 6th Infantry assaulting San Juan Hill , stated that his regiment was brought to a halt near the top of the hill to await the cease - fire order , as the Gatling fire striking the crest and trench line was so intense . Col . Theodore Roosevelt later gave much of the credit for the successful capture of the Spanish positions atop the heights to Parker ' s inventive use of his Gatling Gun Detachment : " I think Parker deserved rather more credit than any other one man in the entire campaign . . . he had the rare good judgment and foresight to see the possibilities of the machine - guns . He then , by his own exertions , got it to the front and proved that it could do invaluable work on the field of battle , as much in attack as in defense . " Roosevelt observed that the hammering sound of the guns raised the spirits of his men : " While thus firing , there suddenly smote on our ears a peculiar drumming sound . One or two of the men cried out , ' The Spanish machine guns ! ' but , after listening a moment , I leaped to my feet and called , ' It ’ s the Gatlings , men ! Our Gatlings ! ' Immediately the troopers began to cheer lustily , for the sound was most inspiring . " Under continuous fire , the advance slowed as troops dropped from heat exhaustion . Officers from the rest of Wood ' s brigade , along with Carroll ' s , bunched up under fire . When the regulars of the all - black Buffalo Soldiers punched toward the top of the hill , the units became intermingled . One of the 10th ' s officers who took part in the attack , Lt . John J . " Black Jack " Pershing , would later reach the highest rank ever held in the United States Army by a living officer — General of the Armies . Pershing later recalled that : When the American formations ( 10th , 3rd & 1st Volunteers ) reached the summit of Kettle Hill , they briefly fought hand to hand within the Spanish defensive works , at which point the Spanish retreated . Some reports name the first American soldier to reach the crest of Kettle Hill as Sgt . George Berry of the 10th Cavalry . However , Thomas H . Rynning is also credited with being the first American to reach the top of the hill , where he rallied his men with the Rough Riders ' flag . Another version states that Berry took his unit colors and that of the 3rd Cavalry to the top of Kettle Hill before the Rough Riders ' flag arrived . This is supported in the writings of Pershing , who fought with the 10th on Kettle Hill and who was present when Col . Roosevelt reached the top . Politics and racial discrimination led to many myths about the African - American involvement in the fighting in Cuba . General Linares ' s troops on San Juan heights fired on the newly - won American position on the crest of Kettle Hill . The Americans returned fire on the entrenched Spanish troops . Seeing the " spontaneous advance " of the 1st Infantry Brigade , led by the 10th Cavalry , General Wheeler ( having returned to the front ) gave the order for Col . Kent to advance with his whole division and ordered the 3rd Brigade into the attack . General Kent sent forward the 3rd Infantry Brigade , now effectively commanded by Lt . Col . Ezra P . Ewers , to join the advance , which had successfully reached the heights . Spanish counterattack . Witnessing the assault on San Juan Hill , Col . Roosevelt crossed the steep ravine from Kettle Hill to San Juan Hill to support the ongoing fighting . Calling for his men to follow , he ran forward , only to find just five of the Rough Riders following him ( most had not heard his command ) . Roosevelt returned , gathered a larger group of men . He led them down the western slope of Kettle Hill , past a small lagoon , and up the northern extension of San Juan Hill , but by then the fighting was over at the top of the heights . General Summer intercepted Roosevelt and ordered him to return to Kettle Hill immediately to prepare for the expected counterattack . When he returned , his men were exhausted and his horse was spent from the heat . After the Spanish positions atop San Juan Hill had been taken , two of Lt . Parker ' s Gatling guns were dragged by mules up the slope to the captured position on San Juan ridge , where both were hurriedly emplaced among a line of skirmishers . As the Americans were setting up the guns , the Spanish commenced a general counterattack on the heights . Though the attack on San Juan was quickly broken up , the men on Kettle Hill faced a more serious attack from some 600 Spanish regulars . Ignoring an order from Col . Leonard Wood to reposition one or two of his Gatling guns to the top of Kettle Hill to support the 1st Volunteer and 3rd Cavalry , Parker instead ordered the closest Gatling , manned by Sgt . Green , to fire obliquely against 600 enemy soldiers attacking Kettle Hill . From a range of , Sgt . Green ' s Gatling responded , killing all but 40 of the attackers . After the counterattack was driven off , Lt . Parker moved to Kettle Hill to view the American positions , where he was soon joined by Sgt . Weigle ' s Gatling and crew from San Juan , detached to the service of Lt . Miley . Miley ( who was primarily tasked with inspecting troop positions for General Shafter ) had restrained Weigle ' s crew from opening fire during the entirety of the fighting . Parker then ordered Sgt . Weigle and his crew to emplace their gun on Kettle Hill . This Gatling was used to eliminate Spanish sniper fire against the American defensive positions on Kettle Hill . Returning to the two Gatlings on San Juan Hill , Lt . Parker had the guns relocated near the road to avoid counter - battery fire . Despite this precaution , the guns were bombarded by a heavy Spanish gun . Parker located the enemy gun and trained the two Gatlings using a powerful set of field glasses . The two Gatlings then opened fire , silencing the Spanish gun at a range of roughly . July 4 , Parker ordered his three operational guns moved into the battle line around the city of Santiago . The wheels of the Gatling carriages were removed , and the Gatlings , along with two 7 mm Colt - Browning machine guns ( a gift from Col . Roosevelt ) were placed in breastworks where they could command various sectors of fire . The fourth Gatling was repaired and placed in reserve . However , it was soon moved to Fort Canosa , where it was used during the siege of Santiago to fire 6 , 000 – 7 , 000 rounds into the city to help force a surrender . Aftermath . The Americans suffered almost five times as many losses as the Spanish . The Spaniards fought to the knife , losing a third of their force in casualties but yielding very few prisoners . In view of the large number of U . S . casualties incurred from small - arms fire , the Army decided to update and modernize its small arms arsenal . The . 45 - 70 and M1892 ( Krag ) Springfield rifles were quickly retired from service in favor of new Mauser - pattern . 30 - 03 ( later . 30 - 06 Springfield ) M1903 Springfield rifles , while the remaining . 30 Army Gatling guns were replaced in 1909 by the M1909 Benet - Mercie machine gun . Lawton ' s division , which was supposed to join the fight early on July 1 , did not arrive until noon on July 2 , having encountered unexpectedly heavy resistance in the battle of El Caney . The Americans , aided by Cuban insurgents , immediately began the investment of Santiago , which surrendered on July 17 . Roosevelt and the Rough Riders achieved considerable fame with the victory . Other soldiers fared less well . Ord never received recognition in the popular press of the day for his actions . The Army turned down requests for a medal for his heroism from his commanding officer and his commanding general .