Charging Up San Juan Hill

Here is a strange confession for someone who has been for most of the past forty years a historian of the early American republic: I have been fascinated by Theodore Roosevelt and his times since the age of fifteen. That year, as a tenth grader, I happened to find in my parents’ collection a book by Hermann Hagedorn, entitled The Roosevelt Family of Sagamore Hill. This book portrayed TR as a man of such energy, wide-ranging intelligence, and self-confidence that I could not resist him. Afterward, I quickly developed a teenage obsession with Roosevelt that did not abate until about halfway through college, where some of my favorite professors (in the early 1970s) let me know that an unquestioning admiration for such an imperialist president did not fit with the anti-Vietnam mood on campus. So, I learned my lesson and conformed. Later, after becoming a teacher myself, a keen interest in Roosevelt—a sense that somehow I could understand him—came back, though of course in a more balanced way than it had occurred years before. 

In addition to that, I had never entirely lost my childhood interest in wars and war heroes. As an adult, the issue became more one of why we choose the heroes that we do and how it is that war influences that choice. This question naturally led to some of the themes in my book Charging Up San Juan Hill: Theodore Roosevelt and the Making of Imperial America. I argue that as a story of American military history, that of TR, the Rough Riders, and the so-called Battle of “San Juan Hill” reflected broader dictates of culture and society as well as the more common considerations of weapons, strategy, leadership, and national interest. Further, the image of Roosevelt’s famous First Volunteer Cavalry Regiment—the Rough Riders—related much more closely to questions of nation- or empire-building than one might think. Certainly that image made the crucial difference in TR’s career. His successful military experience in Cuba confirmed Roosevelt as a popular force in American life before he became so much a political one. Without it, he would never have reached a position to become president and would most likely have gone down as just a minor figure in American history, one whose name few would recognize today.

Historians who have written full-length studies of the Rough Riders have focused much more on what they did than on what they meant, both to themselves and to other Americans. Few have analyzed the significance of their composition as a group, for example. Although billed as an “all-American” fighting force, they would pass no multicultural muster of today. The regiment reflected its time, along with prevailing social biases. It included no women and no African-Americans in those days of an all-male strictly segregated military. Nor did it contain many names reflecting the “new immigration” from eastern and southern Europe or Asia. Few Hispanic surnames appeared. The roster featured only a smattering of Catholics and Jews and included about 26 native-Americans. 

And yet, many commentators of the time thought the regiment to have been strange in design even for then. “In its ranks, serving as privates, are men of all social conditions and racial differences,” exaggerated the Springfield Republican. “On this account alone we are proud of ‘Teddy’s Terrors.’” All volunteers, they constituted a band of citizen soldiers but not just any citizens and, in some cases, hardly the most conventional. As critics initially judged them, the Rough Riders’ faults of composition seemed certain to outweigh their military potential. Some figured that about half the regiment consisted of people least likely to sacrifice for any cause: a bunch of rowdy, law-flouting, ungovernable far westerners on the one hand; on the other, a contingent of spoiled, soft, overprivileged sons of the wealthy eastern elite.

Though at first advanced as a criticism, this very fact constituted one of the most important points about them. The Rough Riders’ two commanders, Roosevelt and fellow Harvard graduate Leonard Wood, believed the unusual mix of troopers held great symbolic as well as military potential. They wanted the experiment to show that Americans all around still had greatness in them, whatever their political, social, and sectional differences. According to the regimental roster, the troopers represented 145 different occupations, professions, and trades. Only 160 of the eventual 1,252 enlistees described themselves as “cowboys,” along with another 58 who hailed as “ranchers” or “cattlemen.” Apart from those, the combination included 87 miners, 53 farmers, 44 clerks, 34 laborers, 32 attorneys, 31 railroad men, 26 students, 23 printers, 17 blacksmiths, 15 teachers, 15 polo players, 14 musicians, and 13 carpenters. In addition, 29 regular army men joined the regiment as volunteers.  For occupational range, the regiment featured a confectioner, two florists, a pair of nurserymen, three insurance agents, two singers, a hotelkeeper, a pharmacist, four watchmakers, and a sculptor. The vast majority of the men were, of course, young—in their 20s—and unmarried. Their wide variety of backgrounds strongly suggests that the Rough Riders never all that much resembled the wild bunch of “cowboy” soldiers that the newspapers—and later historians—found to make such engaging copy. As their story evolved, however, the scribes around the country started to find more interesting their real identities in contrast with their popular image. As one would say shortly after the fighting for San Juan Heights, it had been “childish” ever to imagine that every man was a “cowboy.”

The obvious takeaway from all this is that the past turns out always to have been more complicated than most of us would imagine, and so too were those people we regard as leading figures in the past. As a fifteen-year-old-boy, I found it easy to adopt Theodore Roosevelt as the personal hero that I wanted, and probably needed, in my life at that time—a great American that I might in some ways emulate while growing up. That is a concern of childhood, or in my case, adolescence, but one not so relevant in later life. For my part, the need for personal heroes lessened considerably as I got older. The more important story, the one that matters to me now, is how this man, TR, came to be regarded as such a hero to so many fellow Americans in his own time, and how the answer to that might today illuminate a little bit more of our convoluted history and political culture. A piece of that larger story is what I have tried to capture in Charging Up San Juan Hill.

John R. Van Atta teaches American history at the Brunswick School, in Greenwich, Connecticut. He is the author of Charging Up San Juan Hill: Theodore Roosevelt and the Making of Imperial America, Securing the West: Politics, Public Lands, and the Fate of the Old Republic, 1785–1850, and Wolf by the Ears: The Missouri Crisis, 1819–1821.