Theodore Roosevelt was born to a society family of wealth and prestige in New York State. Almost from his birth, he began to rebel against the privilege to which he was born. Instead of pursuing the life of ease which was his station, he preferred to work with his hands as well as his mind. He had to overcome many obstacles, not the least of which was his poor eyesight. While he never let these obstacles stop him they taught him the humility it took to be a great leader who knew his limits. He loved the open range and spent many years in the cattle business in the Dakota Territory. His determination to know himself well and demand the best from his own ability gave him insight into how to produce and expect the same from those he lead. It made him a very well loved chief.
Roosevelt had a very heightened sense of the value of freedom. When Spain declared war on the United States because of its support for Cuban independence, he decided to take an active roll. He decided to take leave from his role as Assistant Secretary of the Navy to raise a cavalry regiment to help free Cuba. Roosevelt knew enough to call on others experience where he was deficient. He procured the help of President William McKinley’s very own personal physician to be the Colonel of the regiment. He asked to be a Lieutenant Colonel because he felt he needed more military experience. He recruited an experienced group of cowboys, hunters and miners who knew how to ride hard and were proficient with firearms. He took pride in the fact that they came from all different walks of life but as a regiment were one in purpose and without division. Because of these volunteers rough existence in their civilian lives they came to be known informally as the Rough Riders.
After a training in San Antonio, the First United States Volunteer Cavalry Regiment traveled to Tampa Bay to be transported to Cuba. On July 1, 1898 they drew up to Kettle Hill in Cuba, where they spent an agonizingly long time waiting to take action. During that time many of their number were hit with fire from the Spanish guerillas who seemed to be taking indiscriminate shots in their direction using smokeless gunpowder. Finally General Samuel Sumner appeared with the call to action. Roosevelt mounted his horse and then his “crowded hour began”. As the assault on the hill progressed, Roosevelt came upon a couple of companies that were lying in wait. Not seeing another commanding officer he took it upon himself to order the charge. At first the other companies hesitated but when they saw the Volunteers go through they all followed the charge and Kettle Hill was won.
At the top of Kettle Hill they faced withering rifle fire from the enemy but that was soon silenced by Gatling machine guns from their own artillery. In his exuberance, Roosevelt called for a final charge up San Juan Hill and jumped over a barbed wire fence and led the charge. After about a hundred yard sprint he looked around and noticed that only 5 of his men had joined him. One was fatally shot and another wounded as bullets flew all around them. Roosevelt realized that the rest of his men had not heard the command and went back to get them. They resumed the charge and made it as far as the grass covered crest where they lie down to take advantage of what sparse cover there was. That night they dug entrenchments for themselves and prepared to take San Juan Hill the next day. Just before dawn there was sporadic fire from the Spaniards but they could not dislodge the Americans. An hour later, the assault began. The Rough Riders along with the other army units distinguished themselves well against a very gallant foe but in the end the enemy could not stand up to their charge. After San Juan Hill, the city of Santiago was easily taken and the Rough Riders were destined for glory, while their beloved Colonel was headed for the White House.
The Rough Riders by Theodore Roosevelt, 1899, Collier Books
Theodore Roosevelt Cyclopedia http://www.theodoreroosevelt.org