Siege of Santiago The Siege of Santiago also known as the Siege of Santiago de Cuba was the last major operation of the Spanish - American War on the island of Cuba . This action should not be confused with the naval battle of Santiago de Cuba . Santiago Campaign . The primary objective of the Americans on Cuba had been the capture of the city of Santiago de Cuba . U . S . forces had driven back the Spaniard ' s first line of defense at the Battle of Las Guasimas . General Arsenio Linares pulled his troops back to the main line of defense against Santiago along San Juan Heights . In the charge at the Battle of San Juan Hill U . S . forces captured the Spanish position . At the Battle of El Caney the same day , U . S . forces took the fortified Spanish position and were then able to extend the U . S . flank on San Juan Hill . The destruction of the Spanish fleet at the Battle of Santiago de Cuba allowed U . S forces to safely besiege the city . Siege . On July 3 , 1898 , the same day as the naval battle , Major General William " Pecos Bill " Shafter began the siege of Santiago . Shafter fortified his position on San Juan Heights . General Henry W . Lawton ' s division moved up from El Caney extending the U . S . right flank to the north . To the northwest , Cuban rebels under the command of Calixto Garcia extended the U . S . line to the bay . General Arsenio Linares had been severely wounded at the Battle of San Juan Hill and was replaced by General Jose Toral . Toral had a good defensive position and Shafter knew he would sustain severe casualties from a frontal assault . Instead , the Americans settled on a siege of the city . U . S . artillery sited on the heights pounded the city , while U . S . forces supported by Cuban rebels choked off all water and food supplies to the city . On July 4 , a . 30 Army Gatling from Lt . John Parker ' s Gatling Gun Detachment was moved to Fort Canosa in support of the siege . Over the next thirteen days , it was used to fire 6 , 000 to 7 , 000 rounds into the city of Santiago , causing many casualties . On July 3 , a relief column was able to fight its way through Garcia ' s rebels and into the city bringing Toral ' s force to a total of 13 , 500 . On July 4 , a cease fire was enacted to evacuate roughly 20 , 000 citizens from the city . On July 8 , Toral proposed to surrender Santiago if his troops could be evacuated to another city . Washington officials would not accept Toral ' s proposal . Shafter was now pressed for time . Disease had begun to take its toll on the U . S . forces , and the officials in Washington wanted results . Shafter and the U . S . Navy under William T . Sampson continued to bomb the city . Surrender . Everyone involved wanted a quick end to the campaign . Major General Nelson A . Miles , the commander - in - chief of the U . S . Army , arrived on Cuba and , on July 13 , Toral , Shafter and Miles met between lines to discuss surrender terms . In order to keep the Spanish happy and bring about a quick surrender , Shafter and Miles avoided the word " surrender " . Shafter relied on his friend Dr . George E . Goodfellow ’ s excellent knowledge of Spanish to help negotiate the final surrender after the Battle of San Juan Hill . Goodfellow attributed part of his success to a bottle of “ ol ’ barleycorn ” he kept handy in his medical kit which he properly prescribed to himself and Spanish General Jose Toral , lending a more convivial atmosphere to the conference . On July 17 , after both governments agreed to the terms , Toral surrendered about 11 , 500 soldiers within the district of Santiago plus an additional 12 , 000 soldiers stationed around Santiago . The Spanish also ceded Guantanamo City and San Luis . Aftermath . The siege effectively ended the major fighting on Cuba , but the war was not yet over . Yellow fever had spread through the U . S . Army before the surrender had taken place , and some 4 , 000 U . S . soldiers were ill . Many officers , notably Theodore Roosevelt , fought for the removal of the army from Cuba , which was recalled and sent to containment camps in coastal cities in the U . S to deal with the infected troops . Plans were made for a major assault on Havana , but the next major campaign of the war came on Puerto Rico , led by General Miles .