Battle of El Caney The Battle of El Caney was fought on 1 July 1898 , during the Spanish – American War in southeastern Cuba . Background . At El Caney , Cuba , 514 Spanish regular soldiers , together with approximately 100 armed Spanish loyalists under the command of General Joaquín Vara del Rey y Rubio were instructed to hold the northwest flank of Santiago against the American 2nd Division commanded by Brigadier General Henry Ware Lawton . Battle . Although the Spanish defenders had no machine guns , they were well - equipped with modern smokeless powder rifles and a battery of two modern breech - loading 80mm mountain howitzers ( " Cañón de 8 cm Plasencia Modelo 1874 " , designed by Colonel Plasencia of the Spanish Army ) that also utilized smokeless ammunition . The Spanish regular infantry was armed with fast - firing M1893 7mm Mauser rifles , while the loyalists were equipped with single - shot Remington Rolling Block rifle s in . 43 Spanish ( also using smokeless powder ) . Denied promised reinforcements from Santiago , Vara de Rey and his forces held over 6 , 000 Americans from their position for nearly twelve hours before retreating , preventing General Lawton ' s men from reinforcing the U . S . assault on San Juan Hill . Some of the American forces were hindered by their equipment ; in the case of the 2nd Massachusetts , the men were equipped with antiquated black - powder single - shot . 45 - 70 Springfield rifles . According to Frederick E . Pierce , a trooper of the 2nd Massachusetts , the Americans " . . . received such a shower of bullets that it seemed at one time as if the company must be wiped out of existence . " Because of this unequal contest , the 2nd Massachusetts was later taken out of the line and replaced with troops armed with more modern weapons . The American forces also lacked effective support fire , as the single Gatling Gun Detachment had been sent to support the troops assaulting San Juan heights . General Lawton ' s artillery support consisted of a single battery of four 3 . 2 - inch ( 80mm ) Model 1885 Field Guns - light breech - loading rifled cannon using black - powder ammunition . The relatively short range of the American gun battery - together with the signature cloud of black smoke generated with each volley - forced gun crews to endure a fusillade of Mauser rifle fire from the Spanish defenders . General Lawton ' s initial decision to continually shift the battery ' s fire to multiple targets resulted in minimal effect on the Spanish strongpoints . Continued assaults took a heavy toll of the attackers . During the fighting , General Vara del Rey was killed , but Spanish resistance continued . After an initial repulse , Lawton ordered his battery of four 3 . 2 - inch guns , commanded by Capt . Allyn Capron , to concentrate fire on the " El Viso " strongpoint in the Spanish defenses . Capron ' s guns successfully breached the strongpoint walls at a range of 1 , 000 yards . An attack was then launched by two U . S . infantry regiments , the 12th and the 25th , and after a bloody firefight , " El Viso " was captured . Private T . C . Butler , Company H , 25th Infantry , was the first man to enter the blockhouse at El Caney , and took possession of the Spanish colors . Once " El Viso " was taken , the U . S . battery reduced each Spanish strongpoint in turn . The fighting ended about 5 : 00pm with the withdrawal of the Spanish troops . Aftermath . Though eventually successful , the attack on the fortifications of El Caney had proved to be of little real value . The attack on two strongly defended points at both El Caney and San Juan diluted the strength of American forces , resulting in delays and additional casualties . The Americans lost 81 dead and 360 wounded , although other sources say that may have fallen to 1 , 500 soldiers , with Cuban rebel losses estimated at around 150 killed and wounded . The number of killed and wounded on the Spanish side is not known with certainty , as many of the defenders who survived the battle at El Caney were later killed , wounded , or captured in a fruitless attempt to recapture the Spanish trenchworks at Kettle Hill . One of the Spanish wounded was Colonel Salvador Diaz Ordóñez , who commanded the Spanish artillery and was the designer of the Ordóñez guns that the Spanish used as coastal artillery in Cuba . Approximately 400 - 600 of the retreating Spanish defenders at El Caney later participated in a hastily - organized counterattack against troopers of the U . S . 3rd Cavalry and the 1st Volunteer Infantry atop Kettle Hill . After closing to within 200 yards of Kettle Hill , they were taken under fire at a range of 600 yards by a single ten - barrel . 30 Gatling Gun atop San Juan Hill manned by Sgt . Green of the Gatling Gun Detachment . According to Spanish commanders captured after the battle , all but 40 of the 600 attacking Spanish troops were killed by the Gatling gun fire .