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Theodore Roosevelt’s Medal of Honor

Roosevelt earned highest award in Cuba charge

A century after his July 1, 1898, charge up San Juan Hill in Cuba, the nation awarded the Medal of Honor to U.S. Army Col. Theodore “Teddy” Roosevelt. To some the award seemed overdue. To others, it was unearned. Roosevelt fought in his famous battle during the Spanish-American War, which lasted from 1898 to 1901.

Although he served two terms as president, wrote 40 books, and earned the Nobel Peace Prize, Roosevelt called San Juan Hill his finest moment. He left little doubt in the minds of others that he fully expected to receive recognition. “I am entitled to the Medal of Honor and I want it,” Roosevelt said.

“I am entitled to the Medal of Honor and I want it.”

Roosevelt served with the 1st U.S. Volunteer Cavalry Regiment, the Rough Riders – described by historian Virgil Carrington Jones as “a colorful regiment of cowboys, Indians, and Ivy League athletes” – for a mere four months. But, said Roosevelt, “There are no [other] four months … to which I look back with more pride.”

The battle, properly called the battle of the Santiago Heights, began when Spanish troops pinned down Roosevelt’s cavalry at the base of Kettle Hill, one of two peaks making up the San Juan Heights. With the advantage of high ground, the Spaniards were firing down at the cavalry and accompanying U.S. infantry soldiers. With men being killed and wounded around him – and grazed by a Spanish bullet – Roosevelt must have decided there was no choice about what to do next.

Lt. Col. Theodore Roosevelt

From left to right: Maj. George Dann, Maj. Brodie, Gen. Joseph “Fightin’ Joe” Wheeler, Chaplain Brown, Col. Leonard Wood, and then-Lt. Colonel Theodore Roosevelt, June 1898. This photo was taken at the American embarkation camp at Tampa, Fla., just before the voyage to Santiago de Cuba. U.S. Army photo

Roosevelt led his regiment of volunteers up Kettle Hill alongside Army regulars.

He acted “in total disregard for his personal safety,” reads the citation for the award. “Accompanied by only four or five men, [Roosevelt] led a desperate and gallant charge up San Juan Hill, encouraging his troops to continue the assault through withering enemy fire over open countryside. Facing the enemy’s heavy fire, he displayed extraordinary bravery throughout the charge, and was the first to reach the enemy trenches, where he quickly killed one of the enemy with his pistol, allowing his men to continue the assault. His leadership and valor turned the tide. “Gen. Joseph “Fightin’ Joe” Wheeler, commander of U.S. Volunteers, reportedly rose from his sickbed at the sound of battle to take overall command of the forces that included Roosevelt’s. Months later, undoubtedly after some prodding from the already-famous colonel, Wheeler recommended the award. Wheeler found a witness who said: “On two occasions during the battle, when I was an eyewitness to [Roosevelt’s] conduct, it was most conspicuous and clearly distinguished above other men.” The witness also wrote:

“At the base of the San Juan, or first hill, there was a strong wire fence or entanglement in which the line hesitated under grueling fire and where the losses were severe. [Roosevelt] jumped through the fence, and by his enthusiasm, his example and courage, succeeded in leading to the crest of the hill a line sufficiently strong to capture it.”

“At the base of the San Juan, or first hill, there was a strong wire fence or entanglement in which the line hesitated under grueling fire and where the losses were severe. [Roosevelt] jumped through the fence, and by his enthusiasm, his example and courage, succeeded in leading to the crest of the hill a line sufficiently strong to capture it.

“In this charge,” continued the witness, who is not named in Army records, “the cavalry division suffered its greatest loss, and the colonel’s life was placed in extreme jeopardy owing to the conspicuous position he took in leading the line and being the first to reach the crest of that hill while under heavy fire of the enemy at close range.”

The Charge of the Rough Riders

Frederic Remington’s “The Charge of the Rough Riders” depicting Col. Theodore Roosevelt on horseback at the head of his Rough Riders. Remington was present at the battle as a special correspondent for the New York World. Courtesy of the Frederic Remington Art Museum

Roosevelt’s supporters say he was denied the medal during his lifetime because he was critical of the Secretary of the Army. But some historians argue that Roosevelt, and those who admired him, exaggerated his role. No one disputes that Roosevelt is credited with charging the wrong hill: San Juan Hill was the next peak over from Kettle Hill, where he actually fought.

Roosevelt became vice president in 1901. He assumed the presidency later that year when President William McKinley was assassinated. At 43, he was the youngest president in the nation’s history. In 1906, he was awarded the Nobel Peace Prize for his role in negotiating a settlement of the Russo-Japanese War of 1904-05. He remained president until 1909.

Roosevelt is the only president ever to be awarded the Medal of Honor.

Roosevelt is the only president ever to be awarded the Medal of Honor. His son, Brig. Gen. Theodore Roosevelt, received the medal for being the first general ashore during the Normandy landings on D-Day in 1944. The only other father and son to receive Medals of Honor were Gen. Douglas MacArthur and his father Gen. Arthur MacArthur, who won the medals respectively in World War II and the Civil War.

Leaving the presidency in 1909, Roosevelt soon jumped back into politics. In 1912, he ran for president on the Progressive ticket. While campaigning in Milwaukee, he was shot in the chest by a fanatic. Roosevelt soon recovered but was never elected again. He died in 1919.

By

Robert F. Dorr is an author, U.S. Air Force veteran, and retired American diplomat who...

    li class="comment even thread-even depth-1" id="comment-38468">
    DomainEarth

    This is a great article, wonderful old photos, and a Remington portrait too. I didn’t know he was there as a correspondent.

    li class="comment byuser comment-author-steven-hoarn odd alt thread-odd thread-alt depth-1" id="comment-38487">
    Steven Hoarn

    Frederic Remington went to Cuba before the war started to cover the ongoing revolution for the Hearst papers. In a much reported, but never verified story he wrote to Hearst and asked to be recalled, to which Hearst responded, “You furnish the pictures, I’ll furnish the war.” When the USS Maine was sunk, he returned to cover Teddy Roosevelt’s Rough Riders and was present at the battle.