Spanish General Arsenio Linares Pomba confronted the possibility of attacks from the west by the powerful U.S. fleet that blockaded the harbor and from the east by General William R. Shafter’s army. He chose to concentrate his defenses to the west and stationed only 500 soldiers atop San Juan Heights (including Kettle Hill) and another 520 on his northern flank at El Caney.

Spanish General Arsenio Linares Pomba confronted the possibility of attacks from the west by the powerful U.S. fleet that blockaded the harbor and from the east by General William R. Shafter’s army. He chose to concentrate his defenses to the west and stationed only 500 soldiers atop San Juan Heights (including Kettle Hill) and another 520 on his northern flank at El Caney.

Theodore Roosevelt (center) with his Rough Rider regiment at San Juan Hill. (U.S. Army War College)

The offensive came from the east. Shafter sent 5,000 men against El Caney, but instead of a quick victory, the U.S. soldiers struggled for nine hours before the stubborn Spanish fell back. Meanwhile, the main U.S. force advanced on San Juan Heights. While Spanish soldiers poured down deadly fire, a group of volunteers under Colonel Theodore Roosevelt launched their famous charge up Kettle Hill. Roosevelt’s Rough Riders were at the forefront of an 8,000-man offensive that eventually overwhelmed the outnumbered Spanish. Both sides endured heavy casualties. The United States lost 205 killed and 1,180 wounded. The Spanish suffered 215 killed and 376 wounded. The fall of Santiago prompted Admiral Pascual Cervera y Topete’s fleet to flee the harbor and face destruction by the U.S. Navy.