Theodore Roosevelt: the Rough Rider who became president

Theodore Roosevelt packed several lives into one. A sickly boy who remade himself into a cowboy, soldier and statesman, he charged up a Cuban hill at the head of the Rough Riders, and three years later was president of the United States. He became the very image of American energy at the dawn of the twentieth century, and the war of 1898 was the hinge on which his whole career turned.²

A sickly boy from New York

Roosevelt was born in New York City on 27 October 1858 into a wealthy family. He was a frail and sickly boy who suffered from asthma, and he built himself up through exercise into a rugged young man and a lifelong believer in physical effort.³

He entered Harvard in 1876. His father died of cancer during his sophomore year. After graduating he married Alice Hathaway Lee and went into politics.⁴

Ranch, reform and the navy

In 1884 his mother and his young wife, Alice, died on the same day; Alice had just given birth to their daughter. Shattered, Roosevelt went west to the Dakota Badlands, where he worked as a rancher, rode with cowboys and lived the frontier life he would later write about.⁵

In 1886 he returned to New York and married his childhood friend Edith Kermit Carow. He then served as a US Civil Service Commissioner, as head of the New York City police board and as Assistant Secretary of the Navy. In every post he made a name for honesty and for upsetting party bosses who expected him to put politics before the law.⁶

On 15 February 1898 the battleship Maine blew up in Havana harbor, and many in Washington and the press blamed Spain. The United States declared war on 25 April.⁷

Raising the Rough Riders

Roosevelt resigned from the Navy Department to fight. He became lieutenant colonel of a new regiment of volunteer cavalry under Colonel Leonard Wood. Its official title was the 1st United States Volunteer Cavalry, but the public knew it as the "Rough Riders."⁸

The men gathered at San Antonio, Texas: cowboys and frontiersmen from the West alongside a contingent of eastern college men, a mixture that both Roosevelt and the war correspondent Richard Harding Davis wrote about. From Tampa, where the invasion army crowded onto transports, the cavalry sailed for Cuba without most of their horses and had to fight on foot.⁹

Las Guasimas

The army landed at Daiquiri, east of Santiago de Cuba, on 22 June 1898, and moved its landings to Siboney the next day. On 24 June Major General Joseph Wheeler pushed inland to Las Guasimas, a junction of two trails about three miles from the coast. The Rough Riders under Wood and Roosevelt took the left-hand trail while regulars of the 1st Cavalry and the African-American 10th Cavalry hacked their way along the other. The Spanish fell back, and the road toward Santiago was open.¹⁰

Davis, who marched with the regiment that day, described Wood at the head of the column and Roosevelt in the thick of the fight. A week later Roosevelt would lead the regiment into the biggest battle of the war.¹¹

The crowded hour

On the morning of 1 July 1898 the American army attacked the San Juan Heights, the ridge line guarding Santiago from the east, while another division fought all day for the fortified village of El Caney. The dismounted cavalry division, the Rough Riders among them, lay in tall grass along the San Juan River at the far right of the line, under rifle and shell fire from Spanish trenches on Kettle Hill and San Juan Hill.¹²

When the order to advance came, Roosevelt wrote, "I sprang on my horse and then my 'crowded hour' began." He went forward mounted, in plain view of his men and of the enemy. Davis watched him break out of the woods behind the line of the regular 9th Cavalry and urge the men forward, and called him, with the white-haired General Hamilton Hawkins, the most conspicuous figure in the charge.¹³

The Rough Riders went up Kettle Hill intermingled with regular cavalry, among them the African-American 9th and 10th, while the infantry stormed San Juan Hill nearby. From the crest the cavalry charged on against the next line of Spanish trenches.¹⁴

By nightfall the heights were in American hands. The cost was heavy, among white and Black regiments alike, and many of the officers who led from the front were killed or wounded.¹⁵

It was Roosevelt the newspapers celebrated, and he came home a national hero. But the fight had been won by many hands, and much of the hardest fighting was done by the regular army, including the Buffalo Soldiers of the 9th and 10th Cavalry.¹⁶ › Battle of San Juan Hill, 1898

Santiago and home

With the heights lost, the Spanish forces around Santiago agreed to surrender in mid-July. Disease then did more damage to the American army than the enemy had; the Rough Riders were brought home to a camp at Montauk Point on Long Island, where the army's units were gathered after Cuba.¹⁷

The whole war lasted 113 days. By the Treaty of Paris of 10 December 1898 Spain gave up Cuba and ceded Puerto Rico, Guam and the Philippines to the United States.¹⁸

Command style

Roosevelt had never commanded troops in war, and he served as second to an experienced colonel, Leonard Wood. What he brought was energy and a gift for leading by example: he went into action mounted and in plain view, and an eyewitness thought him the most conspicuous figure on the field.¹⁹

President

The war made Roosevelt. Elected governor of New York in 1898, he became William McKinley's running mate and was elected vice president in 1900. When McKinley was shot in Buffalo and died, Roosevelt was sworn in as the 26th president on 14 September 1901, at the age of 42. In 1904 he won the office in his own right.²⁰

At home he promised Americans a "Square Deal" of reform and government regulation of business. He was also the first president to make conservation a great national cause. Abroad he secured the rights to build the Panama Canal and worked to make the United States a world power.²¹

He also mediated the peace that ended the Russo-Japanese War in 1905, and for it received the 1906 Nobel Peace Prize.²² › Battle of Mukden, 1905

Later life and death

Roosevelt kept his promise not to seek another term in 1908, and William Howard Taft succeeded him. Disappointed with Taft, he ran again in 1912 as the candidate of the new Progressive Party, split the Republican vote, and lost to Woodrow Wilson.²³

When World War I came, he attacked Wilson's neutrality. After the United States entered the war in 1917, all four of his sons served. The youngest, Quentin, a pilot, was killed in July 1918, and his father never recovered from the blow. Theodore Roosevelt died at his home, Sagamore Hill in Oyster Bay, on 6 January 1919, at the age of 60, and was buried in Oyster Bay.²⁴

Legacy and memory

Depending on how it is counted, his administration set aside between about 200 and 230 million acres of forests, refuges and other public land.²⁵

The Medal of Honor he believed he had earned in Cuba was denied him in his lifetime. A campaign by the Theodore Roosevelt Association and members of Congress revived the case from 1996, and on 16 January 2001 President Bill Clinton presented the medal posthumously at the White House, honoring him for leading the charge on 1 July 1898.²⁶

Follow the campaign in our account of the Battle of San Juan Hill, meet another officer of that day, John J. Pershing of the 10th Cavalry, explore the industrial age, or see what else happened on 1 July.