Roosevelt’s riders

12 min read

The future president of the United States led his Rough Riders into the history books during the Spanish-American War

In early 1898, Theodore Roosevelt was 39 years old. The scion of a wealthy and politically connected family, he had vigorously cultivated a public image – that of the adventurer, the Renaissance man and the personification of the uniquely American cowboy.

Born frail and asthmatic, the second child of businessman and philanthropist Theodore Roosevelt, Sr, and socialite Martha Stewart Bulloch Roosevelt, Teddy remembered as a six-year-old boy watching the funeral procession of President Abraham Lincoln as it coursed down Broadway in New York City in 1865. His education was the upper crust amalgamation of home school and Harvard, and he revelled in the opportunity to engage in the political discourse of the waning post-Civil War Gilded Age.

For Roosevelt, the future of America lay in its robust and vigorous men, assertive and forthright, brawny and boisterous. He had known personal tragedy, his wife and mother dying on the same day in February 1884, in his New York home. At the time Roosevelt was serving as a New York State assemblyman. In response to the tremendous loss, he had relocated to his sprawling ranch in the Dakota Territory.

Roosevelt’s energy there became ever more focused on the perceived virtues of manliness. The seeds of the cowboy persona grew to full flower, and he burnished his growing reputation as a naturalist and author of many well-received literary works, as well as his unbridled jingoistic national pride. Upon his return to political life, he published the four-volume series The Winning of the West, enhancing his status as a man’s man, a powerful embodiment of American masculinity.

Personally, Roosevelt grappled with the decision his father had made 30 years earlier not to serve in the US Army during the Civil War. The son’s sense of duty and affinity for martial pursuits – an affinity that some biographers have said bordered on bloodlust – were thematically persistent in his thought and political perspective. He became known as a trust-busting Progressive Republican, governor of New York, vice president of the United States, and upon the assassination of William McKinley in 1901 the 26th president of the United States. He was a renowned author, conservationist, explorer, big game hunter and a larger-than-life ‘bully’ persona with his likeness later carved into the face of Mount Rushmore.

Colonel Theodore Roosevelt and a group of Rough Riders stand atop San Juan Hill after the battle in July 1898

But prior to these immense achievements, Roosevelt made his name on the battlefields of the Spanish-American War (1898). When the people of Cuba rose up against the Spaniards, their lords and masters for nearly 400 years, the United States looked upon the revolt as one stoked by a year