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Teddy Roosevelt and The Rough Riders

A group of Rough Riders

Rough Riders

The Rough Riders are best remembered for their charge up San Juan Hill on July 1, 1898.

The most famous of all the units fighting in Cuba, the “Rough Riders” was the name given to the First U.S. Volunteer Cavalry under the leadership of Teddy Roosevelt. Roosevelt resigned his position as Assistant Secretary of the Navy in May 1898 to join the volunteer cavalry.

He organized the Rough Riders, the first voluntary cavalry in the Spanish-American War. The U.S. was fighting against Spain over Spain’s colonial policies with Cuba. Roosevelt recruited a diverse group of cowboys, miners, law enforcement officials, and Native Americans to join the Rough Riders. They participated in the capture of Kettle Hill, and then charged across a valley to assist in the seizure of San Juan Ridge, the highest point of which is San Juan Hill. 

The original plan for this unit called for filling it with men from the Indian Territory, New Mexico, Arizona, and Oklahoma. However, once Roosevelt joined the group, it quickly became the place for a mix of troops ranging from Ivy League athletes to glee-club singers to Texas Rangers and Indians.

Roosevelt and the commander of the unit Colonel Leonard Wood trained and supplied the men so well at their camp in San Antonio, Texas, that the Rough Riders was allowed into the action, unlike many other volunteer companies. They went to Tampa at the end of May and sailed for Santiago de Cuba on June 13. There they joined the Fifth Corps, another highly trained, well supplied, and enthusiastic group consisting of excellent soldiers from the regular army and volunteers.

The Rough Riders saw battle at Las Guásimas when General Samuel B. M. Young was ordered to attack at this village, three miles north of Siboney on the way to Santiago. Although it was not important to the outcome of the war, news of the action quickly made the papers.

A few days after the Rough Riders’ charge up San Juan Hill, the Spanish fleet fled Cuba. It was just a matter of weeks before the war had ended and the U.S. was victorious. 

They made headlines for their role in the Battle of San Juan Hill, which became the stuff of legend thanks to Roosevelt’s writing ability and reenactments filmed long after.

Teddy

Theodore Roosevelt

Born in New York City, Theodore Roosevelt spent the earlier part of his life battling asthma; once he conquered the disease, he passed the remainder of his days battling external foes, often conquering them as well. His greatest gift, among many, was his unerring ability to promote himself in the media. Despite his upper class upbringing and education at Harvard College, Roosevelt was always able to get along with men of any class and social background. He sought a political life in order to reform society and prevent what he perceived was the threat of revolution by the lower classes.

His fearless work as president of New York City’s Board of Police Commissioners caught the attention of political associates of William McKinley. After his election as President, McKinley appointed Roosevelt assistant secretary of the Navy in 1897. Much to Navy Secretary Long’s chagrin, Roosevelt would make policy himself particularly when the secretary was out lunching. One such case involved the appointment and supply of Admiral Dewey’s Asiatic Squadron with orders that they head for Manila harbor.

After resigning his post in May 1898, Roosevelt joined Colonel Leonard Wood’s First U.S. Volunteer Cavalry, soon to become known as the Rough Riders. After Wood’s promotion, Roosevelt took command of the group and on July 1 led the right wing of the attack on San Juan Hill on July 1. His uncanny flair for publicity coupled with his own writings of the affair made him the most celebrated participant of the Spanish-American War except for Admiral Dewey himself.

At the conclusion of the war, Roosevelt almost immediately was elected Governor of New York State. In order to get him out of New York, the head of the Republican machine there, Thomas C. Platt put him on the ticket as McKinley’s running mate for the second term. They were elected, but on September 14, 1901 McKinley was assassinated and Roosevelt became the 26th President of the United States. He was one of the most activist presidents in U.S. history and is usually rated in the top five of those who have held that office.

One of his greatest disappointments was President Woodrow Wilson’s refusal to allow him to fight in World War I. Library of Congress

In Honor of a President
When Theodore Roosevelt came to Dakota Territory to hunt bison in 1883, he was a skinny, young, spectacled dude from New York. He could not have imagined how his adventure in this remote and unfamiliar place would forever alter the course of the nation. The rugged landscape and strenuous life that TR experienced here would help shape a conservation policy that we still benefit from today.

Teddy, A Deeper Dive

With the assassination of President William McKinley, Theodore Roosevelt, not quite 43, became the 26th and youngest President in the Nation’s history (1901-1909). He brought new excitement and power to the office, vigorously leading Congress and the American public toward progressive reforms and a strong foreign policy.

Teddy Roosevelt in Puerto Rico
Historia de Puerto Rico LOC.gov


History of the Theodore Roosevelt equestrian statue to be removed

Those wiping out the history of the United States want the statute removed. At the time the Statute represented the pride of the Native American and African American with Teddy Roosevelt, but the meaning of the “inclusion” has been turned upside down.

The statute will not be destroyed but rather, it will be moved to the Theodore Roosevelt Museum.

The statute is controversial, as have become virtually all statutes in the United States. Some see Teddy as proud to be depicted with American icons, some see him as portraying superiority.


He took the view that the President as a “steward of the people” should take whatever action necessary for the public good unless expressly forbidden by law or the Constitution.” I did not usurp power,” he wrote, “but I did greatly broaden the use of executive power.”

Roosevelt’s youth differed sharply from that of the log cabin Presidents. He was born in New York City in 1858 into a wealthy family, but he too struggled–against ill health–and in his triumph became an advocate of the strenuous life.

In 1884 his first wife, Alice Lee Roosevelt, and his mother died on the same day. Roosevelt spent much of the next two years on his ranch in the Badlands of Dakota Territory. There he mastered his sorrow as he lived in the saddle, driving cattle, hunting big game–he even captured an outlaw. On a visit to London, he married Edith Carow in December 1886.

During the Spanish-American War, Roosevelt was lieutenant colonel of the Rough Rider Regiment, which he led on a charge at the battle of San Juan. He was one of the most conspicuous heroes of the war.

Boss Tom Platt, needing a hero to draw attention away from scandals in New York State, accepted Roosevelt as the Republican candidate for Governor in 1898. Roosevelt won and served with distinction.

Roosevelt emerged spectacularly as a “trust buster” by forcing the dissolution of a great railroad combination in the Northwest. Other antitrust suits under the Sherman Act followed.

Roosevelt steered the United States more actively into world politics. He liked to quote a favorite proverb, “Speak softly and carry a big stick. . . . ”

Aware of the strategic need for a shortcut between the Atlantic and Pacific, Roosevelt ensured the construction of the Panama Canal. His corollary to the Monroe Doctrine prevented the establishment of foreign bases in the Caribbean and arrogated the sole right of intervention in Latin America to the United States.

He won the Nobel Peace Prize for mediating the Russo-Japanese War, reached a Gentleman’s Agreement on immigration with Japan, and sent the Great White Fleet on a goodwill tour of the world.

Some of Theodore Roosevelt’s most effective achievements were in conservation. He added enormously to the national forests in the West, reserved lands for public use, and fostered great irrigation projects.

He crusaded endlessly on matters big and small, exciting audiences with his high-pitched voice, jutting jaw, and pounding fist. “The life of strenuous endeavor” was a must for those around him, as he romped with his five younger children and led ambassadors on hikes through Rock Creek Park in Washington, D.C.

Leaving the Presidency in 1909, Roosevelt went on an African safari, then jumped back into politics. In 1912 he ran for President on a Progressive ticket. To reporters he once remarked that he felt as fit as a bull moose, the name of his new party.

While campaigning in Milwaukee, he was shot in the chest by a fanatic. Roosevelt soon recovered, but his words at that time would have been applicable at the time of his death in 1919: “No man has had a happier life than I have led; a happier life in every way.”

The Presidential biographies on WhiteHouse.gov are from “The Presidents of the United States of America,” by Frank Freidel and Hugh Sidey. Copyright 2006 by the White House Historical Association.


During the Spanish-American War, Roosevelt was lieutenant colonel of the Rough Rider Regiment, which he led on a charge at the battle of San Juan. He was one of the most conspicuous heroes of the war.

The Presidential biographies on WhiteHouse.gov are from “The Presidents of the United States of America,” by Frank Freidel and Hugh Sidey. Copyright 2006 by the White House Historical Association.


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