There were two sides to Theodore Roosevelt. One was the trust-busting progressive who reined in industrialist excess, won the Nobel Peace Prize for negotiating the end of the Russo-Japanese war, and set aside millions of acres of public land for wildlife conservation.

The other was the self-made “cowboy soldier,” a former asthmatic weakling who hardened his body and will by exposing himself to the harsh elements and lawless violence of the Western frontier. This Roosevelt, historians argue, helped seal the image of the cowboy soldier and physically embodied a new ideal of manliness—epitomized in a band of fighters he formed, called the “Rough Riders” who would see battle in the Spanish-American War. Mark Twain would come to describe Roosevelt as “clearly insane… and insanest upon war and its supreme glories.”

Sarah Watts, author of Rough Rider in the White House: Theodore Roosevelt and the Politics of Desire, says this second Roosevelt, the wild-eyed hunter, was actually the first to emerge, the product of being labeled a “wimp” (his father’s loving term) and a “Nancy boy” as a young New York assemblyman. Like other Eastern elites of the late 19th century, Roosevelt came to abhor both his own physical weakness and what he saw as the larger “degeneration” and “effeminization” of American civilization.

At the turn of the 20th century, industrialism and immigration had upset the old social orders, and the dominance of Northern white Protestant males was being threatened by radical unions, strikes and class conflicts, urban slums and the rise of the independent “New Woman.”

“The elites in the East began to be fearful that they couldn’t control this new society and all these elements,” says Watts.

So they looked to the West. In the 1880s, Buffalo Bill Cody brought his famous Wild West shows back East and the cult of the cowboy was born. For Roosevelt, the vigorous, unbridled life of the Western cowboy was the perfect antidote to the softness of comfortable city living that drained men of their “life juices.”

In 1883, Roosevelt eagerly traveled to North Dakota (complete with buckskin shirt) to hunt bison and ended up buying a cattle ranch. After the tragic deaths of both his wife and mother on Valentine’s Day, 1884, Roosevelt took refuge in his sprawling Western ranch. Over the next five years he became a prolific propagandist for the harsh beauty and lawless redemption of the wild West, authoring popular and colorful books like “Hunting Trips of a Ranchman” and a four-volume history of the early frontier.

In the 1890s, Roosevelt the politician/historian became buddies with Owen Wister and Frederic Remington, two of the most popular writers and artists of their day. Inspired by Roosevelt’s paeans to the cowboy, Wister and Remington collaborated on an 1885 essay in Harper’s Monthly called “The Evolution of the Cow-Puncher” that places the noble if barbarous cowboy in the same racial and cultural line as the Anglo-Saxons.

“In personal daring and in skill as to the horse,” the men wrote, “the knight and the cowboy are nothing but the same Saxon of different environments.”

This whitewashed image of the cowboy—far from the original Mexican vaquero —was the embodiment of a new masculinity that Watts describes as “the carrier of white civilization against the forces of social change at the turn of the last century.”

But Roosevelt’s greatest feat of masculine myth-making was yet to come. When the Spanish-American War broke out in 1898, Roosevelt immediately resigned his post as Assistant Secretary of the Navy and won approval to recruit a volunteer regiment that Roosevelt originally called the “cowboy cavalry” but quickly became known as the Rough Riders.

The Rough Riders were the physical manifestation of Roosevelt’s new masculine ideal, a mix of hardened frontier riflemen, skilled horseman and Texas Rangers, plus elite athletes from Eastern colleges, including championship quarterbacks and steeplechase riders.

Roosevelt and the Rough Riders fought heroically against the Spanish forces in Cuba, but apparently even acts of bravery and sacrifice—Roosevelt took a bullet riding back and forth in front of enemy fire to protect his troops—weren’t enough.

Through Roosevelt’s own breathless account of the battles of San Juan Hill and Kettle Hill, published that same year, and Remington’s painting The Charge of the Rough Riders (commissioned by Roosevelt), a highly fictionalized but enduring image of the cowboy soldier was permanently lodged in the American psyche.

“In Remington’s painting, it didn’t matter that Roosevelt wasn’t really on a horse. It didn’t matter that it was the wrong group of regular army troops. It didn’t matter that it was the wrong hill. It didn’t matter that he didn’t lead the charge,” says Watts. “Roosevelt wants the Rough Riders as an army regiment to be seen in the eyes of the public as the true inheritors of the cowboy tradition of white, aggressive, armed, nationalist manhood.”