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The Spanish-American War ran its course in the spring and summer of 1898. Between April 25 and August 12, U.S. forces destroyed two Spanish fleets, seized the Philippines, captured Guam and Puerto Rico, and pursued a campaign in Cuba that set the island on the road to independence. The latter assault targeted Santiago de Cuba, on the southeastern end of the island, which harbored the Spanish cruiser squadron. By capturing the city, the Americans hoped to force out enemy ships into the guns of waiting U.S. warships.

On June 20, the 15,000-man V Corps landed at the villages of Daiquirí and Siboney. Spanish troops in Santiago Province numbered 36,000 at the time, but the Americans met no serious resistance until the 24th.

Maj. Gen. William Rufus Shafter, V Corps commander, was a Civil War combat veteran, but at age 62, he was incapacitated with gout. He established his headquarters near an overlook called El Pozo, 8 miles east of Santiago, from which he and his officers could observe the San Juan Heights and El Caney village.

Early on July 1, Brig. Gen. Jacob F. Kent’s 1st Infantry and Brig. Gen. Samuel S. Sumner’s dismounted Cavalry Division, about 8,000 men in all, trudged along the rutted road from Siboney toward the hills under small-arms fire from the 750 Spanish troops defending the heights. At midmorning, during a lull in the advance, a Signal Corps detachment towed an observation balloon over troops massed at a ford of the San Juan River. Under fire, the balloonists spotted a trail that could relieve congestion on the road.

With men dropping from Mauser bullets and heat exhaustion, and no orders forthcoming, some officers, including Colonel Theodore Roosevelt and his demi-regiment of 1st U.S. Volunteer Cavalry (the “Rough Riders”), grew impatient and crossed the shallow river to the base of Kettle Hill. At about half past noon, with Roosevelt leading on horseback, mingled units of U.S. regulars and volunteers swept up the hill and captured it. On the heels of that assault, Maj. Gen. Joseph Wheeler, who was ill with fever, rose from his sickbed, resumed command of the cavalry and ordered Kent to charge nearby San Juan Hill. Most of V Corps participated in the frontal attack.

At about 1:30 p.m., Lieutenant John H. Parker reached the front with four horse-drawn .30-caliber Gatling guns. The guns raked the hill for eight minutes with devastating effect: Spanish defenders poured from their rifle pits and fled west to a second defensive line as Kent’s infantrymen swarmed uphill on the left, followed by Wheeler’s cavalry.

The American units captured San Juan Hill within 20 minutes and all of San Juan Heights within an hour. More than 200 doughboys were killed and nearly 1,200 wounded in the day’s assaults. The Santiago campaign then stumbled along until July 17, when the Spanish forces surrendered.


  • Get a foothold fast. Foreign wars present immense logistical problems, such as transporting vast numbers of troops across water, even if only 90 miles of it from Florida to Cuba.
  • Learn the ground. U.S. Army planners were ill prepared for the difficult terrain, oppressive climate and disease-ridden jungles between the coastal landing sites and the San Juan Heights.
  • Be prepared. The Spanish-American War was the Army’s first real test since the Civil War, 33 years prior. A few battle-hardened men had served in the Union or Confederate armies or fought Indians on the frontier, but the San Juan Heights assault called for new tactics.
  • Choose a strong commander. Shafter, a courageous and once capable officer, was a poor choice to lead V Corps in Cuba. Obese, indecisive and suffering from gout, he lacked respect in the ranks.
  • Keep a low profile. The Spaniards used Mauser rifles with smokeless powder, while U.S. troops used Springfield breechloaders that emitted a cloud of smoke, wrote one newspaper correspondent, “somewhat the size of a cow.”
  • Learn what your enemy knows. Spanish soldiers in Cuba were accustomed to waging guerrilla warfare against the island’s anticolonial rebels.
  • Make local inquiries. Several thousand insurgents lived in the Santiago region, but the Americans mistrusted these ragtag bands, and vice-versa, so the Army failed to exploit their knowledge of the island and the Spanish military.


Originally published in the August 2008 issue of Military History. To subscribe, click here.