The road towards Santiago was now open. The going was difficult with a narrow path through the jungle. At the end of the trail the Spanish were dug in on the crest of San Juan Ridge and in the village of El Caney.
The American plan developed by General Shafter, called for an assault first on El Caney by 5400 Americans, then once it was captured the whole American army would then swarm up the San Juan Hills.
Unfortunately when the American forces advanced on El Caney before dawn on July 1 the actual assault did not develop as planned. Instead of taking an hour to overcome the Spanish defenses it took four assaults and all day. In the meantime the main part of the army had become ready to attack San Juan Hill.
They made their way out of the jungle and into a meadow where they were subjected to withering fire. The men immediately took cover. They seemed trapped until three American Gattling guns came forward and held down enemy fire.
Then almost spontaneously the American rose to their feet and began charging the hill. Teddy Roosevelt rode his horse leading the men to the top of the hill. The Hill was in American hands. The battle cost 205 American and 215 Spanish lives.
cr: History Central (Backlink)