Theodore Roosevelt

Theodore Roosevelt

Facts, information and articles about Theodore (Teddy) Roosevelt, the 26th U.S. President

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26th President of the United States

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Theodore Roosevelt summary: Theodore Roosevelt or Teddy, was the 26th president of the United States. Roosevelt was born in 1858 in New York. He was primarily schooled at home, followed by Harvard College and Columbia Law School. Roosevelt didn’t finish law school, opting instead to become a member of the New York State Assembly. He also served as a captain in the National Guard, a police commissioner for New York City, and an assistant secretary of the U.S. Navy. He later organized a cavalry made up of volunteers; this cavalry, known as the Rough Riders, gained notoriety in the Battle of San Juan Heights after charging San Juan Hill. He is well-known for is strong masculinity, his wide range of varied interests and for leading the Progressive Movement.

In 1898, Roosevelt became the governor of New York. In 1901, he became vice president under McKinley. McKinley was assassinated soon after his inauguration, and Roosevelt assumed the office of president, becoming the 26th president of the United States. Roosevelt is known for his anti-monopoly stance and his “square deal” reform of working conditions for Americans. He also built up the Navy during his presidency. In addition he formed a cavalry of men known as the Rough Riders. Roosevelt was awarded a Nobel Peace Prize for his efforts that led to an end in the Russo-Japanese War. He is also known for his environmental efforts. He left office in 1909, but ran again in 1912; he lost the election to Woodrow Wilson. Roosevelt died in 1919.


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Featured Article

Teddy Roosevelt’s Ride to Recovery

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, 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.”

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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.”

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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.

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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).

Featured Article

Theodore Roosevelt: Leading the Rough Riders During the Spanish-American War

President William McKinley, roused from a deep sleep by an aide at 2:00 a.m. on February 16, 1898, received terrible news. The battleship Maine had exploded in Havana harbor with heavy loss of life. McKinley, who had been gently ministering to the public’s war fever for more than a year, was stricken. ‘The Maine blown up,’ he mumbled over and over to himself. ‘The Maine blown up!’ He hated the thought of war to the core of his being. ‘I have been through one war,’ said the Civil War veteran. ‘I have seen the dead piled up, and I do not want to see another.’ This sentiment was shared by every member of his administration, save one.

As always, Assistant Secretary of the Navy Theodore Roosevelt was up early that morning, and working in his office in the Navy Department on Sixteenth Street. ‘I would give anything if President McKinley would order the fleet to Havana tomorrow,’ ‘T.R.’ wrote to a friend. ‘This Cuban business ought to stop. The Maine was sunk by an act of dirty treachery on the part of the Spaniards, I believe; though we shall never find out definitely, and officially it will go down as an accident.’

He was certainly correct about the latter. A naval board of inquiry concluded that the Maine had been destroyed by a submarine mine of unknown origin. Predictably, Spain issued a report stating that the cause of the explosion had been internal. Americans who did not work in the White House or on Wall Street thought little of such formal deliberations. They only cared that 260 American sailors were dead, and they wanted a reckoning.

That day of reckoning was at hand, for the rusted, antiquated Spanish empire had prolonged its existence for far too long. It was not the sinking of the Maine, not the rantings of the yellow press, nor the jingoistic dreams of American imperialists that brought on the war of 1898 — it was the incredible incompetence, myopic short-sightedness, and stunning brutality of the Spanish imperialists in Cuba that made conflict inevitable.

A string of cruel acts in Cuba had enraged Americans for more than a generation. In 1873, five years into a Cuban uprising, a Spanish warship captured the American steamer Virginius as it attempted to deliver guns, ammunition, and medical supplies to Cuban patriots. Four rebel leaders aboard the Virginius were subsequently shot, decapitated, and their heads displayed on pikes. Captain Joseph Fry and 48 of his crewmen were summarily executed by firing squad. Spain reluctantly released the survivors of the Virginius and paid a small indemnity, but the bloody incident was not forgotten in the United States.

In April 1895, the cry of ‘Cuba Libre!’ again resonated across the island. Spain responded to this latest revolt by sending General Valeriano Weyler y Nicolau to Cuba. Dubbed ‘Butcher Weyler’ by the New York press, his scorched-earth policy devastated eastern Cuba and led to the deaths of thousands of civilians in concentration camps. The Spanish seemed intent on breaking the Cuban people in a desperate bid to continue the pretense of their position as a world power. In America, President Grover Cleveland was stridently against intervention. He could take solace as he left office in March 1897 that his successor, William McKinley, held similar views. The business interests in the country adamantly opposed war, as did most of the leading men in Congress. When the Spanish government recalled Weyler and granted more autonomy to Cuba it seemed that the crisis might pass.

Yet nothing could silence the Cuban cry for freedom. By 1897, Cuban rebels were even appearing nightly in ‘Buffalo Bill’ Cody’s Wild West extravaganza as part of his ‘Congress of Rough Riders of the World.’ The press exploited every Spanish atrocity, real or imagined, to full effect. The American people fumed with indignation over Cuba, idealizing the insurgents as soulmates of the American revolutionaries of 1776. Their slow-burning anger needed just a spark to explode in rightful wrath. The Maine was that spark. Poet Richard Hovey gave them their call — ‘Ye who remembered the Alamo, Remember the Maine!’ — and as it became their byword, action became their creed.

War advocates had their man in the 39-year-old Roosevelt, who had worked hard for a year to improve the navy. Now, as the days passed, he became nearly frantic over the administration’s continuing inactivity. President McKinley, T.R. grumbled to a confidant, ‘has no more backbone than a chocolate eclair.’

Roosevelt, although liked and respected by both McKinley and Secretary of the Navy John Long, found himself increasingly isolated within the administration and the Republican Party. The president would no longer see him, while Long simply humored him. Roosevelt found solace in his correspondence and talks with influential expansionists such as Senator Henry Cabot Lodge, naval officers Alfred Thayer Mahan and George Dewey, and, most importantly, army Captain Leonard Wood.

Wood and Roosevelt had met the previous June, and their jingoistic sensibilities and mutual love of football and vigorous walks led to an instant and warm friendship. A New Englander, Wood was a Harvard graduate like Roosevelt, having received an M.D. in 1884. Bored with private practice, he had gone west, hiring on as a contract surgeon with the army in Arizona and winning high praise (and eventually the Congressional Medal of Honor) for his heroic service during the campaign against the Apache leader, Geronimo. Promoted to captain and assistant surgeon in the regular army in 1891, Wood was transferred to Washington, D.C., four years later.

In the nation’s capital, Captain Wood was appointed assistant attending surgeon, giving him medical responsibility and unlimited access to high-ranking military officers, the secretary of war, and the president. He became close to President William McKinley, who placed his faith in Wood’s skill and compassion in treating Mrs. McKinley, who suffered from epilepsy.

When Roosevelt came to Washington in the spring of 1897 as assistant secretary of the navy, he found himself somewhat in awe of Captain Wood. ‘It was a pleasure to deal with a man of high ideals,’ he wrote, ‘who scorned everything mean and base, and who also possessed those robust and hardy qualities of body and mind, for the lack of which no merely negative virtue can ever atone.’ They were, in every way, kindred spirits.

Mckinley made a last ditch effort for peace, demanding that Spain declare an armistice in Cuba as of April 1, 1898. The Spanish government hesitated, then finally agreed to end the fighting on the island and to submit the Maine question to arbitration. Only the question of Cuban independence reMained. By then, however, it was too late. On April 11, 1898, McKinley asked Congress to intervene on behalf of Cuba. On April 19, the Senate and House of Representatives passed a joint resolution calling for American armed intervention to secure Cuban independence, while disclaiming any designs on annexing the island. On April 23 Spain declared war on the United States, who reciprocated two days later.

McKinley called for 125,000 volunteers to augment the 28,000-man regular army. Young men from every section of the country rallied to his call. They were anxious to prove themselves equal to the task and worthy of their place as Americans. Among the first to volunteer was the man who had perhaps been the leading advocate for war — Theodore Roosevelt.

Everyone was astonished by this act. His wife, Edith, opposed it, as did best friend Henry Cabot Lodge. ‘Theodore Roosevelt,’ wrote diplomat John Hay, ‘has left the Navy where he had the chance of his life and has joined a cowboy regiment.’ Secretary of the Navy Long also fretted over this act of recklessness but foresaw that the great risk was not without potential reward. ‘He has lost his head to this folly of deserting the post where he is of the most service and running off to ride a horse and, probably, brush mosquitoes from his neck on the Florida sands,’ he confided to his diary, ‘and yet how absurd this will sound, if by some turn of fortune he should accomplish some great thing and strike a very high mark.’

President McKinley twice attempted to change Roosevelt’s mind, to no avail. ‘One of the commonest taunts directed at men like myself is that we are armchair and parlor jingoes who wish to see others do what we only advocate doing,’ declared Roosevelt. ‘I care very little for such a taunt, except as it affects my usefulness, but I cannot afford to disregard the fact that my power for good, whatever it may be, would be gone if I didn’t try to live up to the doctrines I have tried to preach.’

Included in McKinley’s call for volunteers had been an appeal for three regiments ‘to be composed exclusively of frontiersmen possessing special qualifications as horsemen and marksmen.’ Secretary of War Russell A. Alger offered command of the first such regiment to the administration’s only bonafide cowboy, Roosevelt, who had once operated a ranch in Dakota Territory. Roosevelt wisely declined because of his lack of military experience, suggesting that Leonard Wood be named colonel and that he go as second-in-command. Alger agreed.

The First U.S. Regiment of Volunteer Cavalry was to be recruited in the southwestern territories, with 340 men to be raised in New Mexico, 170 in Arizona, 80 in Oklahoma, and 170 from the Indian Territory. Within days of the sinking of the Maine, West Point graduate Alexander Brodie, a Prescott, Arizona, mining engineer, along with Phoenix journalist James McClintock and Prescott mayor William ‘Buckey’ O’Neill, had already begun recruiting volunteers.

The first to formally enlist was O’Neill, a frontier legend at age 38 and among the most popular men in Arizona Territory. Born in Ireland, he had come to Arizona in 1879. He was working as a journalist for the Tombstone Epitaph at the time of the O.K. Corral gunfight and soon had his own reputation for gunplay as the hard-riding sheriff of Yavapai County. His nickname came from his passion for faro, or ‘bucking the tiger’ in that frontier game. Dedicated to the cause of Arizona statehood, he was now prepared for the greatest wager of his life. ‘Who would not gamble,’ he wrote to a friend, ‘for a new star in the flag?’

Brodie secured an appointment as senior regimental major, with O’Neill and McClintock as company commanders. By May 4, 200 recruits were gathered in the Prescott plaza. Accompanied by Josephine, a rather ill-tempered young mountain lion given to the troops as a mascot by a local saloon owner, they boarded trains amidst much fanfare and set off for their San Antonio training station.

New Mexico Governor Miguel Otero wasted no time in recruiting troops and a remarkable corps of officers. Captain William Llewellyn of Las Cruces had been a federal lawman in Dakota Territory, famed for destroying Doc Middleton’s outlaw gang. Captain George Curry, the strapping former sheriff of Lincoln County, had known both Billy the Kid and Pat Garrett, while Captain Maximiliano Luna belonged to one of the most prominent Hispanic families in the territory. The New Mexico recruits reached San Antonio on May 10, joining the troops from Arizona and 83 men from Oklahoma raised by Captain Robert Huston of Guthrie. A week later, 170 more men arrived from the Indian Territory — including full or mixed-blood Cherokee, Choctaw, Chickasaw, Pawnee, and Creek Indians. Within days they were augmented by a remarkable contingent of about 50 well-to-do easterners. These Ivy League friends of Roosevelt included some of the best athletes and richest young men in America. The westerners initially viewed them with skepticism, and not a little contempt, but were soon won over.

‘These men are the best men I have ever seen together,’ Colonel Wood wrote to his wife, ‘and will make the finest kind of soldiers.’ Cowboys and polo players, teamsters and yachtsmen, lawyers and day laborers, lawmen and outlaws, miners and football players, Indians and Indian fighters formed a strange amalgam that forecast, in Roosevelt’s eyes, the new American century while harkening back to the old frontier. ‘Wherever they came from, and whatever their social position,’ he wrote, ‘[they] possessed in common the traits of hardihood and a thirst for adventure.’

Roosevelt did not arrive in San Antonio until May 15. He had remained in Washington to secure weapons, uniforms, and supplies for the regiment. The press had already dubbed the unit ‘Roosevelt’s Rough Riders’ — a name T.R. did not relish because of its obvious reference to Buffalo Bill’s Wild West show — and the men were anxious to see their namesake lieutenant colonel. Many were at first unimpressed with his somewhat comical appearance, but that quickly changed. Lieutenant Tom Hall sized him up immediately: ‘He is nervous, energetic, virile. He may wear out some day, but he will never rust out.’

Rumors abounded that Spanish Admiral Pascual Cervera’s Atlantic fleet was headed for either Puerto Rico or Cuba. On May 29, Commodore Winfield Scott Schley’s ‘Flying Squadron’ found Cervera moored in the harbor at Santiago de Cuba and set up a blockade. That same Sunday morning, the Rough Riders — 1,060 strong with 1,258 horses and mules — began boarding Southern Pacific Railroad cars for the journey to Tampa, Florida, their jump-off point for Cuba. ‘In all the world there is not a regiment I would so soon belong to,’ Roosevelt wrote to the president. ‘We earnestly hope we will be put in Cuba with the very first troops; the sooner the better.’

All was confusion in Tampa. Major General William Rufus Shafter, a Civil War veteran and former Indian fighter, was in command of the Fifth Army Corps. Weighing more than 300 pounds and afflicted with various ailments that did little to sweeten a notoriously foul temperament, Shafter was totally unfit to lead an expeditionary force into the tropics. In charge of his cavalry was the diminutive Alabama Major General Joseph ‘Fighting Joe’ Wheeler, famed Confederate cavalryman and current congressman. Ten regular and two volunteer cavalry regiments would be under his command. Despite his age and seeming frailty, Wheeler was as energetic and bold as Shafter was sloth-like and cautious. Brigadier Generals J. Ford Kent and Henry Lawton would command infantry divisions. In all, some 17,000 men were to embark for Cuba.

Shafter, under intense pressure from Washington to depart for Santiago, did not have the transports necessary to move his entire force. He therefore ordered Wood to dismount his cavalry and to select eight out of his 12 companies for the invasion. Roosevelt and Brodie were selected to command the two squadrons in Cuba.

On June 14, after even more high command bungling and mismanagement, the 578-man Rough Rider contingent finally departed from Tampa Bay aboard the Yucatan. ‘We are just like amateurs at war,’ correspondent Richard Harding Davis noted acidly.

Amateurs or not, they were off to change the course of history. Colonel Wood noted ‘that this is the first great expedition our country has ever sent overseas and marks the commencement of a new era in our relations with the world.’ For the men, however, there was little thought of world politics, just much card playing and even an occasional chorus of the Rough Rider’s adopted theme song — ‘There’ll Be a Hot Time in the Old Town Tonight.’

Roosevelt, who often shared the ship’s railing with Buckey O’Neill, was surprised to find that the two-gun Arizona lawman was also ‘a visionary, an articulate emotionalist.’ Under the starlit sky they contemplated the odds against them, with O’Neill expressing a soaring ambition tempered by a dark fatalism. ‘He had taken so many chances when death lay on the hazard,’ T.R. noted, ‘that he felt the odds now were against him.’ Some years before O’Neill had written a short story containing an eerily prescient passage: ‘Death was the black horse that came some day into every man’s camp, and no matter when that day came a brave man should be booted and spurred and ready to ride him out.’

The soldiers reached their destination near Santiago, Cuba, in five days and General Shafter, after conferring with Admiral William Sampson and Cuban rebel leader Calixto Garcia, decided to land his troops at Daiquir and then march inland to Siboney and finally Santiago. Daiquir was supposedly undefended, with a broad beach and even an old wooden pier built by an American iron company years before. On June 22 the troops began to land. They were fortunate to face no opposition, yet the landing was a fiasco. Since there was no transport for the horses and mules, they were lowered by sling into the water and released, or simply pushed off the ships into the sea to swim ashore. Mercifully, by afternoon the Rough Riders were all ashore, although the landings continued into the night.

Shafter promptly ordered General Lawton to occupy Siboney with his infantry division and Wheeler’s dismounted cavalry. Just after dusk on June 23, Wood and Roosevelt entered Siboney. They found Joe Wheeler, ‘a regular gamecock’ as T.R. characterized him, anxious to conduct an armed reconnaissance toward Santiago in hopes of finding the Spanish rearguard. Cuban rebels had spotted enemy troops entrenched a few miles to the north at Las Guasims.

Wheeler moved out at dawn on the 24th with more than 900 men, including all eight Rough Rider companies and 400 men from the regular First and Tenth regiments. The Cubans estimated the Spanish force ahead at 600, but it proved to be three times that number. Moving across unfamiliar terrain against a force of unknown size was dangerous work for seasoned regulars, much less untested volunteers. Wheeler led his regulars down the main road while the Rough Riders traversed a narrow trail to the left. The heat was oppressive in the thick and tangled jungle.

Some three miles from Siboney, a group of Rough Riders led by Captain Allyn Capron and Sergeant Hamilton Fish made contact with the still unseen enemy. As the bullets of the Spaniards’ Mauser rifles whined about them, Capron’s men fanned out, briskly returning fire with their .30 caliber Krag-Jorgensen carbines. Wood and Roosevelt had wisely procured these guns for the unit as replacements for the older, black powder Springfield rifles other volunteers had received. Now the Rough Rider commanders hurried their men forward, deploying them on both sides of the trail.

Cherokee Rough Rider Tom Isbell drew first blood for the Americans, dropping a Spanish sniper just as he received the first of seven wounds — which he somehow survived. Sergeant Fish and Private Ed Culver were also hit at almost the same time. Fish asked Culver, ‘You all right?’ then slumped over, dead. Captain Capron rushed forward to Fish’s body, killing two Spaniards as he advanced before being mortally wounded himself.

Wood calmly led his men forward, taking cover and firing and then advancing again. The Spanish, still well hidden in the jungle, began to melt away before the pressure. Caught up in the excitement of the moment, newspaper correspondent Edward Marshall joined in the combat. The deadly humming of the 7mm Mauser slugs filled the air, like ‘a nasty, malicious little noise,’ wrote Marshall. Within moments he was wounded by a bullet near his spine. Adjutant Tom Hall, witnessing this from afar, mistook Marshall for Wood, and fled to the rear where he reported the colonel dead and the Rough Riders routed. He was later allowed to quietly resign.

Major Brodie was hit in the arm and went down. Six-foot-six Color Sergeant Albert Wright was grazed three times. Captain James McClintock took a bullet in the leg and also fell. Still the Rough Riders advanced, with Roosevelt taking command of Brodie’s squadron as well as his own. O’Neill’s volunteers now joined up with a unit of regulars, and the Spanish began to pull back. With a whoop Captain Robert Huston’s troops opened fire on a group of panic-stricken, fleeing Spaniards. ‘Don’t shoot at retreating men,’ Wood angrily shouted. He ordered the men forward to occupy a deserted, ramshackle building. Black troopers of the Ninth Cavalry now moved up to reinforce the Rough Riders, but the battle was over.

Roosevelt walked the corpse-littered field with Buckey O’Neill. The Rough Riders had lost eight killed and 31 wounded. ‘Colonel,’ O’Neill asked, ‘isn’t it Whitman who said of the vultures that `they pluck the eyes of princes and tear the flesh of kings?’ ‘ Roosevelt, still a bit stunned by the scene, could not recall but later remembered it to be Ezekial: ‘Ye shall eat the flesh of the mighty and drink the blood of the princes of the earth.’

Generals Shafter and Lawton were angry with Wheeler for bringing on an engagement — or walking into an ambush, as many of the regular officers thought. Ambush or not, the Rough Riders had fought their way through, driving a superior force of entrenched infantry from a vital strategic point on the road to Santiago. For six days Shafter kept his men encamped along that road while more supplies and troops came ashore and the road up from the beach was improved.

Already men were dropping in great numbers with fevers, General Wheeler among them. Brigadier General Samuel Sumner took temporary command of the cavalry, with Wood taking over the second brigade. Roosevelt now became colonel of the Rough Riders. Shafter, himself ill, needed to act quickly before sickness further reduced his army. From El Pozo, a commanding hill about five miles east of Santiago, Shafter could easily see the Spanish entrenchments on the San Juan Heights, about a mile and a half away and rising some 125 feet above the valley. A blockhouse stood on the highest of these crests — San Juan Hill — while to its right lay another hill topped with ranch buildings and several old sugar cane cauldrons. It was promptly dubbed Kettle Hill. Between the two heights was a small valley and a pond. Roughly four miles to the north was the Spanish strongpoint of El Caney. Between El Pozo and the San Juan Heights flowed the San Juan River.

Shafter decided to attack on July 1. General Lawton’s Second Infantry Division would assault El Caney. Following Lawton’s success, a force of roughly 8,000 men was to charge the San Juan Heights. Shafter had apparently learned little since the Civil War, when it took a good soldier at least 20 seconds to load and fire his single-shot rifled musket. The entrenched Spaniards could fire eight shots from their 7mm Mausers in the same amount of time. If Major General Arsenio Linares y Pombo’s units had any automatic weapons, the American frontal assault would turn into a bloodbath.

Roosevelt, whose contempt for Shafter was growing by the minute, was astonished at the vagueness of the general’s orders. ‘No reconnaissance had been made,’ he grumbled, ‘and the exact position and strength of the Spaniards were not known.’ Astride his horse, Little Texas, Roosevelt led the Rough Riders forward late on the afternoon of June 30 onto the increasingly congested trail leading to El Pozo. The heat, as always, was intense so he had cast off his jacket in favor of a dark blue shirt, khaki pants, and a polka-dot bandanna around his neck. A similar bandanna floated from his crumpled campaign hat much like a knight’s plume. He carried a pistol retrieved from the Maine on his hip. Four hours later he halted to encamp for the long, sleepless night before the battle.

At 8 a.m. on Friday, July 1, 1898, Captain George Grimes’ battery opened fire on the San Juan Heights. For nearly an hour he dueled with the Spanish artillery. Enemy fire killed one Rough Rider, wounded four others, and brought down Wood’s horse. Shrapnel grazed Roosevelt’s wrist. Shafter finally ordered the cavalry to ford the San Juan River, moving to the right in hopes of meeting up with Lawton. Lawton, however, was having a hard time of it at El Caney, where 500 tenacious Spaniards were putting up a brave defense. Roosevelt got his men across the river and within an hour had them positioned along a sunken trail to the left of Kettle Hill. Spanish sniper fire was as intense as the suffocating heat, however, and the men were quickly pinned down. Volleys now came at regular intervals from the Spanish entrenchments just a few hundred yards away.

Quickly recognizing his position as untenable, Roosevelt turned to his orderly, Harvard man William Saunders, only to find him stretched in the grass, near death from heat prostration. He called to another private, ordering him back up the trail to ask the first general officer he found for permission to charge. As the trooper saluted, a bullet struck his throat and he fell dead into Roosevelt’s arms.

Not far away Buckey O’Neill was strolling along the line smoking a cigarette, ignoring the hail of bullets. His prone men kept begging him to get down, but he laughingly refused, declaring at one point that ‘the Spanish bullet isn’t made that will kill me.’ Moments later a bullet drove through his mouth and out the back of his head. Roosevelt was devastated, believing O’Neill’s death to be the ‘most serious loss that I or the regiment could have suffered.’

An officer suddenly galloped up, breathlessly ordering Roosevelt to support the regulars in their assault on the hills. Instantly mounting Little Texas, Roosevelt galloped up and down shouting orders to his officers and cheering on the men. They needed no encouragement. William Pollock, a Pawnee artist from Guthrie, gave out a chilling war whoop and soon all the men were shouting and rushing forward.

As they advanced into the tall grass, the adrenaline-charged troops came upon the position of the Ninth Cavalry. Captain Henry Barber was holding his men in position, for he had no orders to advance. ‘Then let my men through, sir!’ demanded Roosevelt. He led them on, and the black troopers of the Ninth now joined the charge, orders or not. Two Ninth cavalrymen tore down a wire fence in their path, and Roosevelt galloped forward, waving his hat and yelling ‘Charge!’

The whole line surged forward, as the men of the regular cavalry regiments — the First, Third, Sixth, and Tenth — rushed Kettle Hill alongside the Ninth Cavalry and the Rough Riders. Lieutenant John J. Pershing of the Tenth — whose service with black troops earned him the nickname ‘Blackjack’ — remembered that charge as a moment of unification: ‘White regiments, black regiments, Regulars and Rough Riders, representing the young manhood of the North and South, fought shoulder to shoulder, unmindful of race or color . . . mindful only of their common duty as Americans.’

Atop El Pozo an assortment of officers, foreign observers, and journalists watched in amazement. The foreigners were as one in condemning the folly of the charge. ‘It is gallant, but very foolish,’ said one officer. Melancholy New York World reporter Stephen Crane was lost in the glory of it all. ‘Yes, they were going up the hill, up the hill,’ Crane wrote. ‘It was the best moment of anybody’s life.’

It was certainly the best moment of Colonel Theodore Roosevelt’s life. He was the only man on horseback, but his life seemed charmed. ‘No one who saw Roosevelt take that ride expected him to finish it alive,’ wrote correspondent Richard Harding Davis. ‘He wore on his sombrero a blue polka-dot handkerchief, la Havelock, which, as he advanced, floated out straight behind his head, like a guidon.’ Like Crane, Davis was overcome by the sheer emotion of the charge. ‘Roosevelt, mounted high on horseback, and charging the rifle-pits at a gallop and quite alone, made you feel that you would like to cheer,’ he declared.

Forty yards from the summit, a wire fence stopped Little Texas. Roosevelt dismounted and with his new orderly, Arizona miner Henry Bardshar, jumped the fence and blazed away at the Spanish troops above them. Bardshar killed two Spaniards directly in front of them. Other Rough Riders crowded forward, firing their Krags and taking cover behind the huge sugar cauldrons near the summit. New Mexico troopers planted their guidons on the summit as the defenders fled.

From Kettle Hill Roosevelt could see General Jacob Kent’s First Infantry Division moving painfully up San Juan Hill. At the same time the Rough Riders came under both artillery and volley fire. Suddenly, they heard a drumming sound and a cry went up that the Spaniards had machine guns. Roosevelt, however, recognized the sound. ‘It’s the Gatlings, men, our Gatlings!’ he exclaimed. The troops cheered as Lieutenant John Parker’s battery of rapid-fire Gatling guns raked the Spanish trenches on San Juan Hill.

With the enemy pinned down, now was the time to act. Roosevelt impetuously rushed forward, leaping a wire fence and heading toward San Juan Hill to support the infantry. Suddenly he realized that he had only five men with him, and within moments two of them were hit. Leaving his surviving comrades behind, he angrily backtracked to the crest of Kettle Hill. ‘We didn’t hear you!’ the Rough Riders exclaimed sheepishly. ‘We didn’t see you go. Lead on. We’ll follow.’ And off they went.

They rapidly crossed the little valley, splashing through the pond and up the hill toward the Spanish trenches. Roosevelt and Bardshar were in the lead when two Spaniards jumped up and fired directly at them. Roosevelt returned the fire, killing one of them. The enemy was now in full retreat as Roosevelt’s men overran the trenches and pushed over the crest of San Juan Hill. Suddenly they found themselves overlooking the city of Santiago. As Roosevelt and his exhausted men stood there a staff officer came up, ordering a halt. The men were to entrench and hold the ridge at all costs. Roosevelt found he had but 339 men still fit for service.

Shafter, far to the rear, was characteristically unsure of the outcome. He had lost more than 220 men killed and 1,000 wounded since daybreak and now actually contemplated retreating from the exposed San Juan Heights. Little did he realize how fortunate he had been that General Linares had committed but 1,200 men to defend the Spanish positions. Roosevelt was simply disgusted with his commander. ‘Not since the campaign of Crassus against the Parthians has there been so criminally incompetent a general as Shafter,’ he wrote to his friend Lodge. ‘The battle simply fought itself.’

Two days after the battle, Admiral Cervera’s small squadron challenged the American fleet under Commodore Schley and Admiral William T. Sampson and was promptly wiped out. Santiago then surrendered to General Shafter on July 17. On August 12 the humiliated Spaniards agreed to an armistice that secured the freedom of Cuba and transferred Puerto Rico, Guam, and the Philippines to the United States. The Spanish-American War was over.

Soon after the battle of July 1, Theodore Roosevelt posed with his Rough Riders atop the crest of San Juan Hill. Volunteers and regulars — Hispanic Americans, Native Americans, African Americans, and Anglo Americans — stared grimly yet proudly at the camera. They did not yet know it, but on that bloody hillside they had not only helped liberate Cuba, they had moved to heal their own country’s sectional wounds and made their nation into a world power. Roosevelt had led them, as he soon would the whole nation, into the new century. San Juan Hill was a moment of momentous transition — for the world would never be the same again.


This article was written by Paul Andrew Hutton and originally published in American History Magazine. For more great articles, subscribe to American History magazine today!

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