News that Colonel Roosevelt was looking for men spread quickly, and he received 23,000 applications. The colonel, using no particular method, personally chose 780 men from the West and later added about 200 men from the East and South. Theodore said the 1st United States Volunteer Cavalry Regiment was “as typical an American regiment as ever marched or fought. We have a few from everywhere including a score of Indians and about as many men of Mexican origin from New Mexico; then there are some fifty Easterners—almost all graduates of Harvard, Yale, Princeton, etc.—and almost as many Southerners. Three fourths of our men have at one time or another been cowboys or else are small stockmen.”
Newspapermen, as always, were drawn to Theodore. The reporters tried various alliterative names for the regiment—Teddy’s Terrors, Roosevelt’s Rangers, Cavalry Cowpunchers, Teddy’s Texas Tarantulas, Teddy’s Righteous Rounders—before finding one they liked, Roosevelt’s Rough Riders.
Theodore, true to his reputation as a dude, ordered a tailor-made uniform from Brooks Brothers in New York, and he had the foresight to sew twelve pairs of glasses into the lining of his hat. His men wore a distinctive uniform of blue flannel shirts, brown trousers, slouch hats, leggings, boots, and blue bandannas knotted around the neck.
After training several weeks in San Antonio, Texas, the Rough Riders rode by train to Tampa, Florida, where they joined thousands of other soldiers squeezing onto a flotilla of ships bound for Cuba. The expedition was led by General William Rufus Shafter, a three-hundred-pound veteran of the Civil War. Theodore criticized General Shafter from the beginning. “The folly, the lack of preparation, are almost inconceivable,” he noted in his journal. There weren’t enough vessels, so over half of the Rough Riders and all of the regiment’s horses, except those for officers, had to be left behind. Nonetheless, the sixteen thousand soldiers and three thousand horses and mules that embarked on June 14, 1898, were, at that time, the largest American military expedition ever sent abroad.
Eight days later the Americans waded ashore in Cuba and fought their first battle. “Yesterday we struck the Spaniards and had a brisk fight for 2 ½ hours,” Theodore wrote to Corinne. “We lost a dozen men killed or mortally wounded, and sixty severely or slightly wounded. One man was killed as he stood beside a tree with me… . The last charge I led on the left using a rifle I took from a wounded man… . The fire was very hot at one or two points where the men around me went down like ninepins.” After the battle he picked up bullet casings as souvenirs for his children.
The “fight really was a capital thing for me,” Colonel Roosevelt felt, “for practically all the men had served under my actual command, and thenceforth felt enthusiastic belief that I would lead them alright.” The colonel, even though he had a horse, chose to march with his men on the rough road to the port city of Santiago, in southeastern Cuba. The Americans were attacking that city because six Spanish warships, the only ones in Cuba, huddled in a narrow harbor protected from the American navy by Santiago’s batteries.
Colonel Roosevelt, always looking for good publicity, made sure two of his favorite reporters were by his side: Richard Harding Davis of the New York Herald and Edward Marshall, who would be paralyzed by a bullet, of the New York Journal. Numerous other reporters, including Stephen Crane, the author of The Red Badge of Courage, also accompanied the invasion force.
Early on the morning of July 1, American soldiers and Cuban insurrectos began their assault on the village of El Caney, just outside Santiago, and on San Juan Heights, the fortified hills protecting the city. The tallest part of the Heights was San Juan Hill. There was a smaller hill nearby that the soldiers called Kettle Hill because of a sugar-refining kettle at the top. At the crests of both hills hundreds of Spanish soldiers, armed with Geman-made Mauser rifles, were entrenched behind barbed wire. Some ten thousand Spanish soldiers were in Santiago. Because several top officers were ill with malaria and dysentery, Colonel Wood was promoted to general and given another command. Theodore was officially in charge of the Rough Riders.
OVERLEAF: Colonel Roosevelt and his men in Cuba, 1897.
“It was a very lovely morning,” he later wrote, describing the day of the attack. The “sky of cloudless blue, while the level, shimmering rays from the just-risen sun brought into fine relief, the splendid palms which here and there towered about the lower growth. The lofty and beautiful mountains hemmed in the Santiago plain, making it an amphitheatre for the battle.”
The Spanish artillery began shelling the Americans at six thirty that morning. A piece of shrapnel hit Theodore’s wrist, causing a welt. Six hours later, with the temperature above 100 degrees, the Rough Riders received orders from General Shafter’s headquarters to advance on Kettle Hill.
“The instant I received my orders I sprang on my horse and then my ‘crowded hour’ began,” the colonel recalled. As the Rough Riders marched along Camino Real, the one road across San Juan Heights, they met the 10th Cavalry Buffalo Soldiers, an African American regiment, clustered on the road waiting for orders. Many of them joined the Rough Riders advancing on Kettle Hill as “Mauser bullets drove in sheets through the trees and the tall jungle grass.”
Richard Harding Davis described the assault on Kettle Hill. Colonel Roosevelt, “the most conspicuous figure in the charge … mounted high on horseback, and charging the rifle pits at a gallop and quite alone, made you feel that you would like to cheer.” Behind him hundreds of Rough Riders and Buffalo Soldiers “walked to greet death at every step, many of them, as they advanced, sinking suddenly … but the others waded on stubbornly, forming a thin blue line that kept creeping higher and higher up the hill… . It was a miracle of self-sacrifice, a triumph of bulldog courage …”
When he reached a row of barbed wire, Theodore jumped off his horse, scrambled over the wire, and ran up the last hundred feet. He and another soldier were the first Americans to reach the top. The Spanish troops had withdrawn to higher ground. As the rest of the Americans gathered on top of the hill catching their breath they came under heavy rifle from San Juan Hill. They fired back for several minutes before the colonel yelled for his men to join the troops some seven hundred yards away charging up San Juan Hill. The men swarmed up the hill and overran the enemy fortifications. Many of the Spanish soldiers chose to die in hand-to-hand combat rather than surrender.
After the battle, as the troops settled in for the night, one Rough Rider observed Colonel Roosevelt walking about San Juan Heights, “reveling in victory and gore.” He appeared to be as happy as when he killed his first buffalo in the badlands. “Look at all of those damned Spanish dead,” he said to one fellow New Yorker. TR later wrote that he enjoyed “the fragrant air of combat.” The colonel thought he might have killed one man. He recalled emptying his revolver at two fleeing Spanish soldiers and seeing one “double up … like a jackrabbit.” But he wasn’t sure if one of his bullets or someone else’s had killed the man.
There’s no accurate count of American casualties for that day, the biggest battle of the Spanish-American War. The numbers range between six hundred to a thousand. Nearly one-fourth of the four hundred Rough Riders were killed or wounded, a rate, Colonel Roosevelt bragged, higher than any other cavalry unit—it showed his men were in the middle of the action.
“For three days I have been at the extreme front of the firing line,” TR wrote home. “How I escaped I know not.” He did have several close calls. A rifle shot killed a messenger the colonel was talking to. And while he rode his mare, Texas, alongside a soldier, yelling at him to move faster, the man keeled over dead from a bullet. And early on the morning after the battle for San Juan Heights, an artillery shell hit near Colonel Roosevelt, killing several men but only showering him with dirt and gunpowder. “I really believe firmly now they can’t kill him,” marveled one Rough Rider.
On July 4 the six warships in Santiago’s harbor attempted to break through the U.S. Navy’s blockade, but they were quickly destroyed or captured. Then insurrectos and American soldiers lay siege
to the city until the Spanish surrendered on July 17. Five months later, on December 10, Spain signed a treaty agreeing to give up the Philippine Islands, Cuba, and Puerto Rico, ending four centuries of Spanish colonialism in the New World. But way before then people in the States were celebrating their newest war hero.
Accounts of Colonel Roosevelt leading his men up San Juan Heights appeared in numerous newspapers and magazines. Theodore was even nominated for the Medal of Honor, but never received it. No one knows exactly why. It might have been because he sent a letter to newspapers criticizing the secretary of war for not quickly bringing the troops home from the jungle, where some five thousand Americans died of typhoid, malaria, dysentery, and other diseases. Or it might have been because he called General Shafter “criminally incompetent.” While not receiving the medal was disappointing, years later Theodore would declare, “San Juan was the great day of my life.”
It was certainly a great day for his career. He wrote an account of the expedition that was serialized in a magazine and published in 1899 as a book titled The Rough Riders. Because Theodore wrote so much about himself in the book, one wag suggested the title should be Alone in Cuba. And being a war hero immediately boosted his political career. Even before leaving Cuba, the colonel was receiving telegrams urging him to run for senator or governor of New York. He returned home on August 15, and by September 27, he was the Republican candidate for governor.
As usual, Theodore ran an intense campaign. Escorted by several Rough Riders in uniform to remind the public the candidate was a war hero, he crisscrossed the state, making as many as twenty speeches a day. The Republicans were out of favor with New York voters because the current Republican governor had weakened state civil service laws and failed to clean up blatant corruption in state government. But on November 8, Theodore managed to win by a slim margin of 17,794 votes out of a total of 1,305,636.
As governor he soon angered political bosses and businessmen by supporting legislation requiring utility companies to pay state taxes. Theodore knew that coming out for the tax hurt his chances of running for a second term, because “no corporation would subscribe to a campaign fund if I was on the ticket.” But he held firm to his position.
Observers began to talk of Governor Roosevelt as a presidential candidate. William Allen White, editor of The Kansas City Star, wrote that the governor was “more than a presidential possibility in 1904, he is a presidential probability. He is the coming American of the twentieth century.”
But when Vice President Garret A. Hobart died on November 21, 1899, many Republicans supported Theodore for President McKinley’s vice presidential candidate when he ran for reelection in 1900. Senator Tom Platt, the reigning political boss in New York, especially wanted Theodore to be vice president. He feared that two more years of him as governor would wreck the Republican Party in New York. All of the “high monied interests,” TR explained to Senator Lodge, “that make campaign contributions of large size and feel that they should have favors in return are extremely anxious to get me out of the state.”
But Theodore didn’t want the new job. He told reporters he would “rather be in private life than be Vice President.” The Constitution gives the vice president few responsibilities, other than replacing the president in case he dies or is incapacitated, and presiding over the U. S. Senate and functioning as a tiebreaker in case of a tie vote. In the end, though, despite his feelings, Theodore agreed to do what was best for the Republican Party, and accepted the vice presidential spot. McKinley, running against Democrat William Jennings Bryan in his second presidential campaign, won by an 850,000-vote landslide in 1900.
After McKinley’s inauguration on March 4, 1901, exactly one hundred years after George Washington had been sworn in as the first president of the new republic, the senate met for only four days before adjourning until the following autumn. Theodore wasn’t sure what to do with all of his free time. “The vice president,” he wrote, “is really a fifth wheel to the coach. It is not a stepping stone to anything but oblivion.” That’s no doubt what the Old Guard had hoped for Theodore, but things didn’t turn out that way.
Roosevelt with prominent naturalist John Muir in Yosemite Valley, California, 1903.
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ON SEPTEMBER 5, 1901, while President McKinley was attending the Pan-American Exhibition in Buffalo, New York, a man named Leon Frank Czolgosz stepped out of the crowd and shot him at nearly point-blank range. The bullets tore through his stomach and colon and lodged in the muscles in his back. Nine days later McKinley died, making Vice President Theodore Roosevelt the twenty-sixth president of the United States.
“It is a dreadful thing to come into the Presidency this way,” TR wrote to Senator Lodge. “But it would be a far worse thing to be morbid about it. Here is the task, and I have got to do it to the best of my ability; and that is all there is about it.”
On President Roosevelt’s first evening in the White House, Edith and the children were still at Sagamore Hill, so he invited Bamie and Corinne to come to Washington for dinner. It was September 23, Thee’s birthday. He would have been seventy. “I feel that it is a good omen that I begin my duties in this house on this day,” Theodore told his sisters. “I feel as if my father’s hand were on my shoulder, and as if there were a special blessing over the life I am to lead here. What I would not give if only he could have lived to see me here in the White House.”
Whatever awkwardness the president felt after McKinley’s death quickly disappeared. “Now that I have gotten over the horror of the circumstances under which I came to the presidency,” TR wrote to one of his uncles, “I get real enjoyment out of the work.”
That was obvious to anyone who saw him. “His offices were crowded with people, mostly reformers, all day long, and the president did his work among them with little privacy and much rejoicing,” the journalist Lincoln Steffens wrote. “He strode triumphant around among us, talking and shaking hands, dictating and signing letters, and laughing.”
Theodore pledged “to continue absolutely unbroken the policies of President McKinley.” He began by insisting that the men in McKinley’s cabinet such as Secretary of War Elihu Root and Secretary of State John Hay keep their jobs. But, not surprisingly, the new president had his own ideas about what needed to be done.
High on Theodore’s to-do list was to get himself elected president in his own right in 1904. His biggest obstacle was an Old Guard Republican named Mark Hanna, a U.S. senator from Ohio. Hanna, sixty-three years old, was a rich industrialist who had managed McKinley’s ascent to the presidency. Soon after Theodore became president, Hanna reportedly exclaimed, “I told William McKinley that it was a mistake to nominate that wild man… . Now look, that damned cowboy is President of the United States!” And the senator later told Theodore straight out, “Theodore, do not think anything about a second term.” Many people assumed Hanna, who was popular with businessmen and labor leaders alike, wanted the nomination himself.
Like other presidents before him, Theodore knew that he had to build a network of loyal Republican supporters to help him win his party’s nomination in 1904. The president sent a dinner invitation to Booker T. Washington, an educator from Alabama and the nation’s most influential African American leader. Theodore wanted advice on which southerners he should appoint to federal jobs. Apparently the president wasn’t aware that no black person had ever been entertained in the White House. The October 16 dinner wasn’t publicized, but a newspaperman scanning the White House guest book saw the familiar name and reported the event.
“President dines a darkey,” shrieked a South Carolina newspaper. A Tennessee newspaper declared, “[t] he most damnable outrage ever perpetrated by any citizen of the United States.” White southerners were angry because eating with a black person violated the segregated South’s racial code.
“No one could possibly be as astonished as I am,” Theodore said about the reaction. While privately calling his critics vicious idiots, he praised Washington as �
�a good citizen and good American,” and insisted, “I shall have him to dine just as often as I please.” But Washington received no more White House dinner invitations.
Theodore wanted to reassure Congress and Wall Street that he wasn’t a reckless cowboy or hothead with his first major address to Congress. Unlike today, in Theodore’s time, the president didn’t give a State of the Union speech to a joint session of Congress. He sent his written address to the Capitol, where clerks read it aloud in each house.
The address, which is required by the Constitution, typically lays out the president’s legislative aspirations; it’s a kind of wish list. Unlike most presidents, Theodore wrote his own State of the Union after weeks of discussing the content with family, cabinet members, congressmen, and Wall Street friends. The president’s eighty-page address touched on his major goals: more government oversight of business, federal protection of natural resources, a stronger navy, a canal across Central America, and a bigger role for the United States in international affairs. Nothing in the address set off any alarms. On the contrary, it seemed reassuring, as an editorial in the New York Evening Post explained: The “‘Rough Rider’ and ‘the jingo,’ the impetuous youth of a year ago, has disappeared.” But time would tell.
While the president was busy reassuring the nation, newspaper reporters enjoyed writing about the tribe of Roosevelts in the White House. The staid mansion had never housed a president as young as Theodore, who had been only forty-two when McKinley was killed, or a family as large and rambunctious. They brought with them something TR called “the Oyster Bay atmosphere.”
Michael L. Cooper Page 6