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Roosevelt, saddled up here in 1910, had ventured west to Dakota Territory a quarter century earlier to write, raise cattle and grieve the loss of his mother and young wife. (Library of Congress)

‘Roosevelt met and conquered the challenges that had brought him to the Badlands, rebuilding his life and setting his political career on a vector that would lead to the White House’

The following article originally appeared in the October 2009 issue of Wild West. Western Writers of America has recognized the article with its 2010 Spur Award for Best Short Nonfiction.

On June 9, 1884, Theodore Roosevelt stepped from a train to the prairie earth of the Dakota Territory Badlands for the second time in nine months, disembarking at the station in Medora. Evening was settling over the town, which was barely a year old and comprised about 100 buildings overlooking the Little Missouri River to the west. Medora was home to some 300 permanent and transient residents, mostly young men—cowboys, ranchers, former buffalo hunters and the like. Town itself held little interest for Roosevelt. He had come to hunt the region’s big game, enter the cattle business and perhaps leave behind one of the most stressful, tragic periods of his life.

Though just 25 years old, Roosevelt had accomplished more than many men twice his age. Over the prior two years, he had become one of the leading lights of the New York Legislature, where he manned the vanguard of the reform Republicans—generally, young idealists who wanted to clean up the perennially corrupt state government. His dedication had earned him the respect of other legislators and made him a household name across the Empire State. “We hailed him as the dawn of a new era,” one Roosevelt contemporary later recalled. “‘Teddy,’ as we called him, was our ideal.”

Roosevelt had pursued other avocations as well. On December 3, 1881, at age 23, he had handed a publisher the finished manuscript of The Naval War of 1812, a book he had started writing while a student at Harvard. It appeared in bookstores five months later, the first of about 40 books he would write in his lifetime. Within two years it would sell three editions and become a textbook at several colleges. By 1886 it would be required reading on every vessel in the U.S. Navy.

But now it was late spring 1884, the Dakota Badlands were a mighty long way from the sea, and Roosevelt’s spirits were in desperate need of a boost. On his first visit to Dakota Territory the prior year, the bespectacled Easterner had hunted and gotten a taste of prairie ranching. Now he planned to immerse himself in Western life and make ranching his primary business. In so doing, he would acquire the “cowboy image” he later cultivated when running for mayor of New York in 1886, state governor in 1898 and president of the United States at the dawn of the 20th century.

Born on October 27, 1858, Theodore Roosevelt came from a high-society New York City family. The Roosevelts were “Knickerbockers,” wealthy descendants of the first Dutch families that settled Manhattan. But social status could not protect him from personal tragedy. On Valentine’s Day 1884, Roosevelt’s mother, Mittie, died of typhoid at age 48 as he stood at her bedside. Only 11 hours later, in the same house, his 22-year-old wife, Alice Hathaway Lee—golden-haired daughter of a rich Boston family—died in his arms from kidney failure scarcely a day after giving birth to their first child, a girl named after her.

Roosevelt relinquished the care of his infant daughter to his older sister, Anna, and tried to bury his sorrow under a crushing load of political work. He led opposition to the nomination of James G. Blaine, a former U.S. senator from Maine, as the Republican Party’s presidential candidate, a task that took him to the June 1884 convention in Chicago as head of the New York delegation. Reformers pilloried Blaine as the personification of political corruption, yet he won the nomination (he would later lose the election to Grover Cleveland). When Roosevelt subsequently endorsed Blaine, reformers turned on the young New Yorker, charging he had forsaken honest politics. Roosevelt believed his political life was finished. What was he to do now, a father with no mother for his child and no career?

But Roosevelt had a plan, about which in April he had written to a political ally: “For the next few months I shall probably be in Dakota, and I think I shall spend the next two or three years in making shooting trips, either in the far West or in the Northern Woods—and there will be plenty of work to do writing.” So it was that practically the moment the GOP convention ended, Roosevelt boarded a train bound for the Badlands (in present-day North Dakota). There, he hoped to launch a career as a writer, forget his sorrows and mend his broken health.

This last goal marked the culmination of what had been a lifelong effort. Roosevelt had been sickly as a child, weak, plagued by asthma and digestive problems and often picked on by more robust boys. When Teddy was not quite 12 years old, his father had encouraged him to build up his body, hiring a personal trainer to work with the boy. But even in college and immediately following, he had suffered bouts of asthma and incapacitating stomachaches, especially during times of stress. In the clean Western air of the Badlands, he hoped to transform himself.

The Dakota Badlands comprise a tortured landscape of open grassland and high buttes, crisscrossed by myriad feeder streams of the Little Missouri and further sculpted by water and wind into strange, almost eerie formations. Coal seams lace the area, often close to the surface, and when ignited by lightning or some other source of fire, they might burn for months, sending up columns of smoke and lending a hellish glow to night skies. The Badlands, Roosevelt wrote in one of his books, look the way the poems of Edgar Allen Poe sound.

Regardless, the region was a major tourist attraction in the early 1880s, one of the last places northern Plains bison still roamed, if in small, scattered groups; where hunters could find elk and bighorn sheep; and where mules and white-tailed deer still abounded. The Northern Pacific Railroad had completed a line through the Badlands in 1883, and that drew hunters and cattlemen.

That September, Roosevelt came to the Badlands to hunt bison. He liked the area enough to invest $14,000 in cattle and start a ranch south of the neighboring towns of Little Missouri and Medora, the latter having recently been established by the Marquis de Morès. Like Morès, Roosevelt and other adventurous Eastern bluebloods and European aristocrats were eager for a bit of sport and a chance to make a quick buck, as ranching was to the 1880s what tech stocks were to the 1990s.

Ranching in the Badlands was unlike any livestock operation in America today. The land was unfenced. Grass, like wind and rain, was free. A rancher simply built a house, hired a few cowhands and bought cattle, which he would brand before releasing them to feed at will on the Plains. In spring and fall, ranchers rounded up the cattle, separated them by brand, marked new calves and sold stock to the meat markets. The ranchers did not own the land on which they grazed livestock—it was federal or railroad land; they owned only the cattle and, arguably, the houses they built.

Roosevelt’s Maltese Cross Ranch (named for its brand and also known as the Chimney Butte Ranch) lay east of the Little Missouri, on a major trail used by cowboys, hunters and other travelers. Roosevelt found it too busy for his taste, however, and in June 1884 laid claim to a second ranch, 35 miles north of Medora, which he called the Elkhorn. He left the bulk of the everyday work to his managers and hands, devoting his own time mostly to hunting and writing. He also scheduled frequent trips home to see family and conduct business. His longest visit out West was less than four months, and he rarely stayed as long as two. In fact, his time spent in the Badlands between 1883 and 1887 only totaled around 360 days. Still, he would live much of the next four years in the iconic context of the American cowboy.

If ever a man seemed unlikely cowboy material, it was Theodore Roosevelt in 1884. He spoke with an Eastern “rah-thuh” accent; at 5-foot-8 and 135 pounds, he was anything but robust; he shaved his beard and brushed his teeth daily, slept with his head on an inflatable rubber pillow—even when on the hunt—and bathed in a rubber tub. All in all, he presented a rather poor candidate for acceptance into the Western fold. To make matters worse, he donned a fringed buckskin suit accoutered with a sterling silver hunting knife crafted for him at Tiffany’s. As one cowboy recalled on first meeting Roosevelt, the New Yorker was “a slim, anemic-looking young fellow dressed in the exaggerated style which newcomers on the frontier affected and which was considered indisputable evidence of the rank tenderfoot.”

Thus one of Roosevelt’s first tasks was to establish himself as a man among men—what’s more, men armed with guns and knives, generally with no local lawmen to keep them in line. He had already made progress on this front during his 1883 buffalo hunt, when he had insisted on riding horseback (rather than with his guide in a wagon) and had killed his first buffalo. He had pushed so hard—hunting in the rain, sleeping out on wet ground, suffering without complaint a tumble when his horse stepped in a badger hole—that his guide, an experienced range rider, had worried Roosevelt might wear him out. During the big 1885 spring roundup, locals noted that Roosevelt worked as hard as anyone who had ever sat a saddle. And then there were the fights.

The most dramatic of these, reported countless times, unfolded in Mingusville, Montana Territory. Roosevelt had just checked into the Nolan Hotel after a day of chasing down stray horses. On his way to the hotel bar for dinner, he heard one or two shots. He didn’t especially like the idea of going in, but there was nowhere else to go in tiny Mingusville.

Almost as soon as he stepped inside, Roosevelt ran up against a bully direct from central casting. The man had a six-shooter in each hand and had already drilled a few holes in the face of the barroom clock. Calling the spectacle-wearing Roosevelt “Four Eyes,” he ordered Teddy to buy drinks for everyone. Roosevelt tried to laugh off the cowboy’s order, but the man persisted, and Roosevelt said, “Well, if I’ve got to, I’ve got to,” and then delivered his fists—right, left, right—to the man’s jaw. The guns went off as the man fell, hitting his head on the bar before sprawling senseless on the floor. Roosevelt picked up the guns, while other patrons dumped the unconscious man in an outdoor shed. The next morning, Roosevelt was pleased to hear the bully had fled town on a train. As word of the incident spread, Badlands locals began to reassess the little Easterner.

Roosevelt solidified his reputation by directly confronting a local badman who reportedly had threatened to kill him. When Roosevelt arrived armed at the gunman’s house and suggested they have it out right then, the man said the whole thing was a misunderstanding, which Teddy took as an apology. Such direct interactions in a virtually lawless area drew admiration. “There were all kinds of things I was afraid of at first,” he wrote years later, “ranging from grizzly bears to ‘mean’ horses and gunfighters; but by acting as if I was not afraid, I gradually ceased to be afraid.”

Roosevelt boosted his manly reputation when in March 1886 three men stole a rowboat he kept for crossing the river at his Elkhorn Ranch. Roosevelt and two hired hands built another boat and pursued the thieves 150 miles downriver. They arrested the trio at the mouth of Cherry Creek and marched them overland to the Dickinson jail. Locals seemed to admire Roosevelt’s bravery but questioned his common sense. One rancher told him: “Roosevelt, no one but you would have followed those men with just a couple of cowhands. You are the only real damn fool in the county.”

Roosevelt’s first experience on the cattle range came during the spring 1885 roundup, which began on May 19 at Box Elder Creek. Some 60 cowboys spent five weeks scouring 200 miles of the Little Missouri Valley, about 100 miles on either side of the river, combing every ravine, creek and coulee for all the free-roaming cattle they could find, about 4,000 in number. They also herded along the 300 horses needed for the work.

Cowboys meeting Roosevelt for the first time at roundup took him for a weakling. “You could have spanned his waist with your two thumbs and fingers,” one rider recalled. Roosevelt didn’t help matters with his fussy gear: toothbrush, razor, bedroll and spectacles. No self-respecting cowboy wore eyeglasses. “When I went among strangers, I always had to spend 24 hours in living down the fact that I wore spectacles,” he wrote, “remaining as long as I could judiciously deaf to any side remarks about ‘four eyes,’ unless it became evident that my being quiet was misconstrued and that it was better to bring matters to a head at once.” At the roundup, he told one Texan who called him “Storm Windows” to “put up or shut up,” either fight or be friends. The Texan opted for friendship.

When the cowboys learned Roosevelt could ride 100 miles a day after a full night in the saddle and spend 40 hours on horseback while wearing out five horses, they came to respect him. Roosevelt explained years later, “As with all other forms of work, so on the roundup a man of ordinary power, who nevertheless does not shirk things merely because they are disagreeable or irksome, soon earns his place.”

After 32 days and a thousand miles on the trail, the other Badlands cowboys accepted Roosevelt as one of their own. One tough ranch foreman’s assessment: “That four-eyed maverick has sand in his craw a-plenty.” Roosevelt even received public acclaim in the Sioux Falls Daily Press, which wrote of him, “When he first went on the range, the cowboys took him for a dude, but soon they realized the stuff of which the youngster was built, and there is no man now who inspires such enthusiastic regard among them as he.”

Ranching also markedly improved Roosevelt’s physique. By autumn 1884, the underweight mite who had retreated west in the spring was a new man. “What a change!” wrote one Pittsburgh Dispatch reporter. “Last March he was a pale, slim young man, with a thin, piping voice and a general look of dyspepsia….He is now brown as a berry and has increased 30 pounds in weight. The voice…is now hearty and strong enough to drive oxen.”

For Roosevelt, the transformation was a personal triumph. Ranch life had finally brought him the health and strength that had long eluded him. Although he would still vent the occasional wheeze, mentions of asthma and digestive problems vanished from his journals during the Badlands years.

It was not ranching alone that strengthened Roosevelt. He spent much of his time out west hunting—heading up into the mountains of Wyoming and Montana territories for such big game as grizzly bears, elk and mountain goats. He also hunted deer and pronghorn around his Elkhorn Ranch. Those prairie treks and mountain excursions built his stamina.

In the Badlands, Roosevelt also pursued his literary career. In the mid 1880s, he wrote at least two books and several magazine articles on ranching and hunting, as well as a biography of Thomas Hart Benton, Missouri senator and leading advocate of frontier expansion. But Roosevelt still suffered emotionally from the loss of his wife. During one grizzly hunt, he told Frank Merrifield, a Maltese Cross Ranch manager and Roosevelt’s guide on this trip, that the grief he had experienced was “beyond any healing.” As Merrifield started to console him, Roosevelt cut him off: “Now, don’t talk to me about, ‘Time will make a difference.’ Time will never change me in that respect.”

Roosevelt had no intention to remarry. Certainly, in his era and among members of his social class, to do so within a few years of a spouse’s death would have been considered an ethical and moral lapse. But for Roosevelt there existed a living threat to his resolve—Edith Carow, a slim, sensually rounded woman with peach complexion, wide mouth and pale blue eyes. He had known Edith since childhood and, before he met Alice, may even have proposed to her—and been rebuffed. She was a friend and frequent houseguest of Roosevelt’s sister Anna, little Alice’s caretaker, with whom Roosevelt stayed during New York visits. On those trips, he carefully avoided Edith, keeping away from the house if she were there. But one day, sometime in early October 1885, he arrived to find Edith descending the hall stairs toward him. Their relationship progressed quickly, and on November 17 he again proposed. This time Edith accepted.

Roosevelt and Carow forged ahead with their intention to wed but kept it so secret even Anna remained oblivious. Most of the surviving letters Edith wrote to Teddy during this period bear the admonition, “Burn this!” In his diaries, he denotes joining her for some event or activity with only a scant “E.” By August 1886, they were planning a December wedding in London, to avoid the press. Roosevelt’s days as even an occasional rancher were nearing their end.

Events at the ranch were deciding matters for him. When the price for cattle dropped to $10 a head less than the cost of raising the animals and shipping them to market, Roosevelt’s Elkhorn Ranch managers advised him to get out of the business. With his investment draining, Roosevelt shuttered the ranch, turning over its stock to his Maltese Cross managers.

Then nature slammed the door on an already declining Badlands economy. By the time Roosevelt and Carow exchanged vows in London on December 2, 1886, a punishing blizzard had swept the territory—burying grass, denying fodder to increasingly desperate cattle, plunging temperatures into the minus 40s and stacking 100-foot snowdrifts along river bluffs. By spring three-quarters of the cattle that had wintered in the Badlands were dead. Carcasses hung from tree limbs, marooned by melted snowdrifts, and choked the Little Missouri as the spring thaw swept them away—“Death’s cattle roundup of the upper Little Missouri country,” one of Roosevelt’s neighbors called it.

When Roosevelt returned to the Badlands in April, he hoped to find enough living cattle to rebuild the herd. If he could hang on a few years, he might recover a significant portion of the $85,000 he had invested piecemeal over the past two years. But though he had been one of the luckier cattlemen—losing only about two-thirds of his herd—he wrote to one friend: “The losses are crippling. For the first time, I have been utterly unable to enjoy a visit to my ranch. I shall be glad to get home.” His adventure as a hands-on rancher was over.

Blizzards or not, the free-range period of Roosevelt’s life would have ended about this time anyway, and not only because of his marriage. During his tenure in the Badlands, he had remained a presence in Eastern politics. Although he held no office, his reputation was such that people were interested in whom he was supporting for president in 1884. Even after the election, he continued to attract interest, due to his role as a Progressive reform politician. His political life soon revived.

In fall 1886, the Republican Party named Roosevelt its candidate for New York mayor, labeling him the “Cowboy Candidate.” The three-way election pitted him against a Democrat and a left-wing reformer. The Democrat won, but Roosevelt barely paused to lick his wounds, leaving almost immediately for England and marriage. By spring 1887, he not only was physically fit and remarried but also had resumed care of his daughter and was reentering the world of the career politician. Roosevelt had met and conquered the challenges that had brought him to the Badlands, rebuilding his life and setting his political career on a vector that would lead to the White House.

The effects of his Western years would echo throughout his life. Witnessing firsthand the loss of game to uncontrolled hunting, as well as the destruction of grasslands by overgrazing, Roosevelt became an active conservationist. In 1887 he founded the Boone and Crockett Club, devoted to big-game conservation, and in early 1894 he testified in Congress for stronger wildlife protection in Yellowstone National Park, where poaching threatened to wipe out the nation’s few dozen remaining wild bison. Accordingly, that spring Congress enacted the first Yellowstone protection laws, imposing fines of up to $1,000 and jail sentences of up to two years for poachers caught in the park with dead game.

In May 1898, Roosevelt sold his remaining cattle and Elkhorn Ranch to one of his managers. By then, according to account ledgers, he had lost more than $20,000, excluding interest, in the Badlands. On the plus side, Roosevelt had gained physical and emotional health. He also had learned to deal face to face with “common men” and was no longer the foppish, class-conscious Knickerbocker who arrived in the Badlands in 1883. Roosevelt had made friends among the cowboys and begun to establish the broad support he would need in presidential politics. He solidified his cowboy image in Cuba in July 1898 as the mounted Spanish-American War hero who led the vaunted Rough Riders (volunteer cavalrymen mostly from Western states) on a bold charge up Kettle Hill. He capitalized on that image to become governor of New York, vice president under President William McKinley and president when McKinley was assassinated in 1901.

In his autobiography, Roosevelt wrote of the Badlands, “I owe more than I can ever express to the West, which of course means to the men and women I met in the West.” On several occasions he said that if not for his experience in Dakota Territory, where he learned to relate to working people, he would not have been elected president. In later years, Roosevelt asked a friend rhetorically to guess what one part of his life he would want to remember were fate ever “to have erased from my memory all other experiences”—his roles as state legislator, New York City police commissioner, federal Civil Service commissioner, assistant secretary of the Navy, New York governor and U.S. president. His answer: “I would take the memory of my life on the ranch, with its experiences close to Nature and among the men who lived nearest her.”

Author Roger Di Silvestro is a senior editor of National Wildlife magazine. His 10th book, about Roosevelt’s ranching years, is slated for publication in early 2011. Suggested for further reading: Theodore Roosevelt: The Formative Years, 1858–1886, by Carleton Putnam, and The Rise of Theodore Roosevelt, by Edmund Morris.

Read a review of Theodore Roosevelt’s History of the United States, His Own Words Selected and Arranged by Daniel Ruddy (Smithsonian Books, 2010).