The most highly publicized land battle of the war took place in Cuba. This was the charge up San Juan Hill, outside Santiago, by Theodore Roosevelt’s Rough Riders.

Charge of the Rough Riders at San Juan Hill, a painting by Frederic Remington, depicts the celebrated unit, commanded by Theodore Roosevelt, in action in Cuba during the Spanish-American War of 1898. Roosevelt, on horseback, leads the troops. Remington had been sent to the island the previous year by publisher William Randolph Hearst to provide pictures of Spanish atrocities during the Cuban war for independence in the hope of boosting the New York Journal’s circulation.
An ardent expansionist, Roosevelt had long believed that a war would reinvigorate the nation’s unity and sense of manhood, which had suffered, he felt, during the 1890s. A few months shy of his fortieth birthday when war broke out, Roosevelt resigned his post as assistant secretary of the navy to raise a volunteer cavalry unit, which rushed to Cuba to participate in the fighting. Roosevelt envisioned his unit as a cross section of American society and enrolled athletes from Ivy League colleges, western cowboys, representatives of various immigrant groups, and even some American Indians. But with the army still segregated, he excluded blacks from his regiment. Ironically, when the Rough Riders reached the top of San Juan Hill, they found that black units had preceded them— a fact Roosevelt omitted in his reports of the battle, which were widely reproduced in the popular press. His heroic exploits made Roosevelt a national hero. He was elected governor of New York that fall and in 1900 became McKinley’s vice president.