National Portrait Gallery, Smithsonian Institution
In 1898, Theodore Roosevelt's political ambitions were greatly enhanced as a result of his participation in the Spanish-American War. Roosevelt had resigned his post as assistant secretary of the navy, from which he had argued the case for war against Spain, to organize the First U.S. Volunteer Cavalry Regiment, which served in Cuba. He returned a hero after leading his rugged regiment-the "Rough Riders"-to victory in the San Juan highlands above Santiago. Roosevelt received voluminous praise, as suggested by this cartoon from Judge magazine, in which he is shown riding upon an elephant, symbol of the Republican Party. His name was even being mentioned for the presidency. That fall, Roosevelt was elected governor of New York. Two years later, he was elected vice president for President William McKinley's second administration. When McKinley was assassinated in 1901, Roosevelt became, at age forty-two, the youngest president of the United States.