Theodore Roosevelt in Cowboy-Land

As president of the United States, Theodore Roosevelt had a reputation for being a strong, brave, and rugged figure. T. R., as he was later known, is often credited with defining what it was to be a man at the turn of the century. In this view, masculinity was tough, adventurous, and uncompromising. But Roosevelt, born and raised in New York, did not learn the art of manliness among the East Coast’s high society or even in the tumultuous world of politics. He learned it, as many Americans did, on the western frontier. Lured by the promise of adventure after a personal tragedy, T. R. got his most important education from cowboys and ranchers, from lawmen and outlaws whom he encountered amidst the wilds. Afterward, he was able to utilize the symbols of the American West to his political advantage. Roosevelt would become the first cowboy president, influencing not just how the public viewed the presidency, but also the men who held the office.

Summary Overview

As president of the United States, Theodore Roosevelt had a reputation for being a strong, brave, and rugged figure. T. R., as he was later known, is often credited with defining what it was to be a man at the turn of the century. In this view, masculinity was tough, adventurous, and uncompromising. But Roosevelt, born and raised in New York, did not learn the art of manliness among the East Coast’s high society or even in the tumultuous world of politics. He learned it, as many Americans did, on the western frontier. Lured by the promise of adventure after a personal tragedy, T. R. got his most important education from cowboys and ranchers, from lawmen and outlaws whom he encountered amidst the wilds. Afterward, he was able to utilize the symbols of the American West to his political advantage. Roosevelt would become the first cowboy president, influencing not just how the public viewed the presidency, but also the men who held the office.

Defining Moment

After the death of his wife and mother on the same night in 1884, a young Theodore Roosevelt, heir to a wealthy and powerful New York family, fled west to the Badlands in Dakota Territory. As it did for so many countless other Americans in the mid- to late nineteenth century, the frontier, wild and untamed, held the promise of reinvention. Through hunting, killing, taming nature, facing danger, a man might truly become a man. It was there, amid the cowboys and Indians, that Roosevelt could escape his pain, and perhaps find new meaning. Equipping himself richly, with expensive clothes and western accessories, T. R. settled on a ranch on the banks of the Little Missouri. At first, the cowhands and ranchers he met and worked with had little respect for the New York dandy come to pretend he was a cowboy, but it wasn’t long before this changed.

Roosevelt threw himself into his new life with fierce determination, and soon, he earned the respect of the frontiersmen and settlers he met. In a famous episode, which he would retell often in later years, he knocked out cold a cattlehand who dared make fun of his glasses. Roosevelt came to embody the essence of what it was to be an American cowboy. Never giving up, facing nature under even the most brutal conditions, relying solely on himself, T. R. would be reborn or die trying. Roosevelt did everything one can do in the West. He rode, drove cattle, drank, gambled, even pursued and captured outlaws. At one point, he met and befriended the famous sheriff of Deadwood, South Dakota, Seth Bullock, with whom he would maintain a friendship his whole life. The West did for T. R. exactly what he wanted. Life on the range reinvigorated the once sickly youth. He grew stronger, more confident, and more determined.

Upon his return east, Roosevelt wrote of his experiences in a book titled, Ranch Life and the Hunting Trail. Published in 1888, the book was a great success. It stirred the imagination of an American public already fascinated by the frontier. It also enlarged Roosevelt’s stature, giving him the credentials of a strong and powerful man. Most importantly the book helped build, in the eyes of millions of Americans, the myth of the West—a magical place where men are men.

Author Biography

Theodore “T. R.” Roosevelt was born in New York City on October 27, 1858 to a noted upper class family. Suffering from poor health throughout his youth, T. R. sought strength in his father, a businessman and philanthropist, whom he idealized as a model of strength and courage. After his father’s death in 1878, Roosevelt threw himself into his studies, eventually publishing a highly influential book on naval warfare. After the death of his first wife, T. R. travelled out West, where he reinvented himself as a rugged frontiersman and naturalist. Upon his return to New York he quickly remarried and pursued a career in politics, becoming assistant secretary of the Navy in 1897, only to resign a year later to join the fight during the Spanish-American War. After leading a company of cavalrymen famously called the Rough Riders, T. R. was celebrated as a war hero and leveraged his fame to win the governorship of New York, becoming Vice President a short time later. After the assassination of McKinley, T. R. became the twenty-sixth president of the United States, overseeing the breaking of the trusts and the building of the Panama Canal. After a failed bid for a third term (though technically only his second) in 1912, under the Progressive ticket, T. R. spent the remainder of his life exploring, writing, and loudly denouncing the policies of both Republican and Democratic presidents. He died in 1919.

Historical Document


by Theodore Roosevelt



Cattle-ranching can only be carried on in its present form while the population is scanty; and so in stack-raising regions, pure and simple, there are usually few towns, and these are almost always at the shipping points for cattle. But, on the other hand, wealthy cattlemen, like miners who have done well, always spend their money freely; and accordingly towns like Denver, Cheyenne, and Helena, where these two classes are the most influential in the community, are far pleasanter places of residence than cities of five times their population in the exclusively agricultural States to the eastward.

A true “cow town” is worth seeing,—such a one as Miles City, for instance, especially at the time of the annual meeting of the great Montana Stock-raisers’ Association. Then the whole place is full to overflowing, the importance of the meeting and the fun of the attendant frolics, especially the horse-races, drawing from the surrounding ranch country many hundreds of men of every degree, from the rich stock owner worth his millions to the ordinary cowboy who works for forty dollars a month. It would be impossible to imagine a more typically American assemblage, for although there are always a certain number of foreigners, usually English, Irish, or German, yet they have become completely Americanized; and on the whole it would be difficult to gather a finer body of men, in spite of their numerous shortcomings. The ranch-owners differ more from each other than do the cowboys; and the former certainly compare very favorably with similar classes of capitalists in the East. Anything more foolish than the demagogic outcry against “cattle kings” it would be difficult to imagine. Indeed, there are very few businesses so absolutely legitimate as stock-raising and so beneficial to the nation at large; and a successful stock-grower must not only be shrewd, thrifty, patient, and enterprising, but he must also possess qualities of personal bravery, hardihood, and self-reliance to a degree not demanded in the least by any mercantile occupation in a community long settled. Stockmen are in the West the pioneers of civilisation, and their daring and adventurousness make the after settlement of the region possible. The whole country owes them a great debt.

The most successful ranchmen are those, usually South-westerners, who have been bred to the business and have grown up with it; but many Eastern men, including not a few college graduates, have also done excellently by devoting their whole time and energy to their work,—although Easterners who invest their money in cattle without knowing anything of the business, or who trust all to their subordinates, are naturally enough likely to incur heavy losses. Stockmen are learning more and more to act together; and certainly the meetings of their associations are conducted with a dignity and good sense that would do credit to any parliamentary body.

But the cowboys resemble one another much more and outsiders much less than is the case even with their employers, the ranchmen. A town in the cattle country, when for some cause it is thronged with men from the neighborhood, always presents a picturesque sight. On the wooden sidewalks of the broad, dusty streets the men who ply the various industries known only to frontier existence jostle one another as they saunter to and fro or lounge lazily in front of the straggling, cheap looking board houses. Hunters come in from the plains and the mountains, clad in buckskin shirts and fur caps, greasy and unkempt, but with resolute faces and sullen, watchful eyes, that are ever on the alert. The teamsters, surly and self-contained, wear slouch hats and great cowhide boots; while the stage-drivers, their faces seamed by the hardship and exposure of their long drives with every kind of team, through every kind of country, and in every kind of weather, proud of their really wonderful skill as reinsmen and conscious of their high standing in any frontier community, look down on and sneer at the “skin hunters” and the plodding drivers of the white-topped prairie schooners. Besides these there are trappers, and wolfers, whose business is to poison wolves, with shaggy, knock-kneed ponies to carry their small bales and bundles of furs—beaver, wolf, fox, and occasionally otter; and silent sheep-herders, with cast-down faces, never able to forget the absolute solitude and monotony of their dreary lives, nor to rid their minds of the thought of the woolly idiots they pass all their days in tending. Such are the men who have come to town, either on business or else to frequent the flaunting saloons and gaudy hells of all kinds in search of the coarse, vicious excitement that in the minds of many of them does duty as pleasure-the only form of pleasure they have ever had a chance to know. Indians too, wrapped in blankets, with stolid, emotionless faces, stalk silently round among the whites, or join in the gambling and horseracing. If the town is on the borders of the mountain country, there will also be sinewy lumbermen, rough-looking miners, and packers, whose business it is to guide the long mule and pony trains that go where wagons can not and whose work in packing needs special and peculiar skill; and mingled with and drawn from all these classes are desperadoes of every grade, from the gambler up through the horse-thief to the murderous professional bully, or, as he is locally called, “bad man”—now, however, a much less conspicuous object than formerly.

But everywhere among these plainsmen and mountain-men, and more important than any, are the cowboys,—the men who follow the calling that has brought such towns into being. Singly, or in twos or threes, they gallop their wiry little horses down the street, their lithe, supple figures erect or swaying slightly as they sit loosely in the saddle; while their stirrups are so long that their knees are hardly bent, the bridles not taut enough to keep the chains from clanking. They are smaller and less muscular than the wielders of ax and pick; but they are as hardy and self-reliant as any men who ever breathed—with bronzed, set faces, and keen eyes that look all the world straight in the face without flinching as they flash out from under the broad-brimmed hats. Peril and hardship, and years of long toil broken by weeks of brutal dissipation, draw haggard lines across their eager faces, but never dim their reckless eyes nor break their bearing of defiant self-confidence. They do not walk well, partly because they so rarely do any work out of the saddle, partly because their chaperajos or leather overalls hamper them when on the ground; but their appearance is striking for all that, and picturesque too, with their jingling spurs, the big revolvers stuck in their belts, and bright silk handkerchiefs knotted loosely round their necks over the open collars of the flannel shirts. When drunk on the villainous whisky of the frontier towns, they cut mad antics, riding their horses into the saloons, firing their pistols right and left, from boisterous light heartedness rather than from any viciousness, and indulging too often in deadly shooting affrays, brought on either by the accidental contact of the moment or on account of some long-standing grudge, or perhaps because of bad blood between two ranches or localities; but except while on such sprees they are quiet, rather self-contained men, perfectly frank and simple, and on their own ground treat a stranger with the most whole-souled hospitality, doing all in their power for him and scorning to take any reward in return. Although prompt to resent an injury, they are not at all apt to be rude to outsiders, treating them with what can almost be called a grave courtesy. They are much better fellows and pleasanter companions than small farmers or agricultural laborers; nor are the mechanics and workmen of a great city to be mentioned in the same breath.

The bulk of the cowboys themselves are South-westerners; but there are also many from the Eastern and the Northern States, who, if they begin young, do quite as well as the Southerners. The best hands are fairly bred to the work and follow it from their youth up. Nothing can be more foolish than for an Easterner to think he can become a cowboy in a few months’ time. Many a young fellow comes out hot with enthusiasm for life on the plains, only to learn that his clumsiness is greater than he could have believed possible; that the cowboy business is like any other and has to be learned by serving a painful apprenticeship; and that this apprenticeship implies the endurance of rough fares hard living, dirt, exposure of every kind, no little toil, and month after month of the dullest monotony. For cowboy work there is need of special traits and special training, and young Easterners should be sure of themselves before trying it: the struggle for existence is very keen in the far West, and it is no place for men who lack the ruder, coarser virtues and physical qualities, no matter how intellectual or how refined and delicate their sensibilities. Such are more likely to fail there than in older communities. Probably during the past few years more than half of the young Easterners who have come West with a little money to learn the cattle business have failed signally and lost what they had in the beginning. The West, especially the far West, needs men who have been bred on the farm or in the workshop far more than it does clerks or college graduates.

Some of the cowboys are Mexicans, who generally do the actual work well enough, but are not trustworthy; moreover, they are always regarded with extreme disfavor by the Texans in an outfit, among whom the intolerant caste spirit is very strong. Southern-born whites will never work under them, and look down upon all colored or half-caste races. One spring I had with my wagon a Pueblo Indian, an excellent rider and roper, but a drunken, worthless, lazy devil; and in the summer of 1886 there were with us a Sioux half-breed, a quiet, hard-working, faithful fellow, and a mulatto, who was one of the best cow-hands in the whole round-up.

Cowboys, like most Westerners, occasionally show remarkable versatility in their tastes and pursuits. One whom I know has abandoned his regular occupation for the past nine months, during which time he has been in succession a bartender, a school-teacher, and a probate judge! Another, whom I once employed for a short while, had passed through even more varied experiences, including those of a barber, a sailor, an apothecary, and a buffalo-hunter.

As a rule the cowboys are known to each other only by their first names, with, perhaps, as a prefix, the title of the brand for which they are working. Thus I remember once overhearing a casual remark to the effect that “Bar Y Harry” had married “the Seven Open A girl,” the latter being the daughter of a neighboring ranchman. Often they receive nicknames, as, for instance, Dutch Wannigan, Windy Jack, and Kid Williams, all of whom are on the list of my personal acquaintances.

No man traveling through or living in the country need fear molestation from the cowboys unless he himself accompanies them on their drinking-bouts, or in other ways plays the fool, for they are, with us at any rate, very good fellows, and the most determined and effective foes of real law-breakers, such as horse and cattle thieves, murderers, etc. Few of the outrages quoted in Eastern papers as their handiwork are such in reality, the average Easterner apparently considering every individual who wears a broad hat and carries a six-shooter a cowboy. These outrages are, as a rule, the work of the roughs and criminals who always gather on the outskirts of civilisation, and who infest every frontier town until the decent citizens become sufficiently numerous and determined to take the law into their own hands and drive them out. The old buffalo-hunters, who formed a distinct class, became powerful forces for evil once they had destroyed the vast herds of mighty beasts the pursuit of which had been their means of livelihood. They were absolutely shiftless and improvident; they had no settled habits; they were inured to peril and hardship, but entirely unaccustomed to steady work; and so they afforded just the materials from which to make the bolder and more desperate kinds of criminals. When the game was gone they hung round the settlements for some little time, and then many of them naturally took to horse-stealing, cattle-killing, and highway robbery, although others, of course, went into honest pursuits. They were men who died off rapidly, however; for it is curious to see how many of these plainsmen, in spite of their iron nerves and thews, have their constitutions completely undermined, as much by the terrible hardships they have endured as by the fits of prolonged and bestial revelry with which they have varied them.

The “bad men,” or professional fighters and man-killers, are of a different stamp, quite a number of them being, according to their light, perfectly honest. These are the men who do most of the killing in frontier communities; yet it is a noteworthy fact that the men who are killed generally deserve their fate. These men are, of course, used to brawling, and are not only sure shots, but, what is equally important, able to “draw” their weapons with marvelous quickness. They think nothing whatever of murder, and are the dread and terror of their associates; yet they are very chary of taking the life of a man of good standing, and will often weaken and back down at once if confronted fearlessly. With many of them their courage arises from confidence in their own powers and knowledge of the fear in which they are held; and men of this type often show the white feather when they get in a tight place. Others, however, will face any odds without flinching; and I have known of these men fighting, when mortally wounded, with a cool, ferocious despair that was terrible. As elsewhere, so here, very quiet men are often those who in an emergency show themselves best able to hold their own. These desperadoes always try to “get the drop” on a foe—that is, to take him at a disadvantage before he can use his own weapon. I have known more men killed in this way, when the affair was wholly one-sided, than I have known to be shot in fair fight; and I have known fully as many who were shot by accident. It is wonderful, in the event of a street fight, how few bullets seem to hit the men they are aimed at.

During the last two or three years the stockmen have united to put down all these dangerous characters, often by the most summary exercise of lynch law. Notorious bullies and murderers have been taken out and hung, while the bands of horse and cattle thieves have been regularly hunted down and destroyed in pitched fights by parties of armed cowboys; and as a consequence most of our territory is now perfectly law-abiding. One such fight occurred north of me early last spring. The horse-thieves were overtaken on the banks of the Missouri; two of their number were slain, and the others were driven on the ices which broke, and two more were drowned. A few months previously another gang, whose headquarters were near the Canadian line, were surprised in their hut; two or three were shot down by the cowboys as they tried to come out, while the rest barricaded themselves in and fought until the great log-hut was set on fire, when they broke forth in a body, and nearly all were killed at once, only one or two making their escape. A little over two years ago one committee of vigilantes in eastern Montana shot or hung nearly sixty—not, however, with the best judgment in all cases.


apothecary: a person who prepared and sold medicines and drugs

teamster: a driver of a team of animals

Document Analysis

Theodore Roosevelt paints for the reader a portrait of life on the frontier. Life on the prairie revolves around cattle-ranching. People of all shapes and sizes, from all corners of the United States can be found in the “cow towns” that dot the region. These are strong men, rugged men, and, Roosevelt says, “it would be difficult to gather a finer body of men, in spite of their numerous shortcomings.” Roosevelt writes time and time again about which men are suited for which professions, and he describes the various interdependencies at play. Mostly however, his account is full of romanticism. Hunters, mountain men, settlers, ranchers all together, lounging under wooden awnings or galloping through town—these are true Americans, the rough core of the nation. They are men doing manly things in pursuit of business and progress. And among them, the cowboy is king.

The cowboy in T. R.’s writing is the hero of the West. Not as big or as strong as some of the other frontiersmen, the cowboy is lean, quiet, stoic, and duty-bound. He wears a hat, a scarf, and boots. He is the sentinel of the West. The perfect expression of Americanism, the cowboy embodies all the traits that make the nation great—courage, restraint, civility, and knowhow. Only when he’s drunk does the cowboy let loose with “mad antics,” firing off his pistols in boisterous fun, but real men are allowed to let off steam. Real men are allowed to sometimes run wild. For Roosevelt, there is no comparison, the cowboy is everything a man should be, far greater than farmers, laborers, or factory workers. And more to the point, the ideal cowboy is white because, for the Victorian T. R., nothing else could do.

Roosevelt warns his readers that the best cowboys are from the nation’s Southwest. Easterners are not suited and not necessary for this type of work. Only in rare, exceptional cases—such as his own—can an Easterner hope to replicate a cowboy’s skill and silent grace, for a cowboy is skill incarnate, an artist as much as a cowhand. And yes, T. R. admits that there are bad elements on the frontier, but these are not cowboys. Yes, they may wear the same costumes, but horse thieves and outlaws are not of the same class. They are corrupted, foul, often former buffalo hunters made evil by the destruction of the bison. The cowboy, however, is pure and perfect and good. In the end, the forces of darkness will be eliminated. It’s happening even now.

Essential Themes

Roosevelt’s account of life on the frontier and specifically his descriptions of the cowboy, served both to romanticize the West, but also the image of a sort of perfect manliness. For T. R., a nineteenth-century Victorian, raised on notions of American exceptionalism and the superiority of the white race, cowboys were the embodiment of perfection—stoic, silent, courageous men. In this narrative, cowboys were the leaders of American progress. It’s no coincidence, then, that Roosevelt strongly linked himself to the image he so greatly admired. The cowboy was the perfect man, and through his experience, T.R. just happened to be a one. Although not a calculated political move to better position himself for a future in the public sphere, as T.R. was generally very self-centered, the link between himself and the frontier strongly resonated with voters across the nation. Roosevelt became the embodiment of the West, and in turn, the West helped shape Roosevelt. The notion of a white America, strong and resolute, standing firm against a sea of savagery would inform most of T.R.’s foreign policy and that of many presidents to follow. But perhaps more importantly, the image of the cowboy president, the rugged loner, the ultimate decision maker, forever transformed the office of the presidency itself. Before Roosevelt, the presidency was a relatively weak office, but after T.R.’s brand of frontier leadership, the office would grow increasingly more powerful. As the balance shifted towards the executive branch, the men elected to that position in the decades to follow were expected to have the same grace, the same stoic perfection as those men of the frontier, the lone warrior, never afraid to do what had to be done in order to guarantee success. This notion of the cowboy-in-chief is still very much alive in American politics, as is the cowboy as hero, evident in popular culture, and the cowboy as ultimate expression of masculinity. No matter how far removed we are from the period when Americans settled the West, some aspects of that history still paint our national character today.

Bibliography and Additional Reading

  • Bederman, Gail.Manliness and Civilization: A Cultural History of Gender and Race in the United States, 1880–1917. Chicago: U of Chicago P, 1995. Print.
  • Di Silvestro, Roger L.Theodore Roosevelt in the Badlands: A Young Politician’s Quest for Recovery in the American West. New York: Walker Publishing, 2011. Print.
  • Morris, Edmund.The Rise of Theodore Roosevelt. New York: Random House, 1979. Print.