Theodore Roosevelt’s Assessment of His Legendary Rough Riders: “There were no better natural soldiers in the world that those hunters, cow punchers, and miners of the West”

In a remarkable letter just months after they were mustered out, he passes judgment on his men, their training, their Spanish counterparts, and (very surprisingly) offers a blistering criticism of U.S. military leadership during the war.

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On his new job as New York Governor and the future: "I am going to make a pretty decent Governor, and then accept with entire philosophy whatever comes afterwards."

The Rough Riders are one of the most famous fighting units in American history, and his leadership of them made Theodore Roosevelt’s career....

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Theodore Roosevelt’s Assessment of His Legendary Rough Riders: “There were no better natural soldiers in the world that those hunters, cow punchers, and miners of the West”

In a remarkable letter just months after they were mustered out, he passes judgment on his men, their training, their Spanish counterparts, and (very surprisingly) offers a blistering criticism of U.S. military leadership during the war.

On his new job as New York Governor and the future: "I am going to make a pretty decent Governor, and then accept with entire philosophy whatever comes afterwards."

The Rough Riders are one of the most famous fighting units in American history, and his leadership of them made Theodore Roosevelt’s career. In April of 1897 TR was appointed Assistant Secretary of the Navy as a reward for his tireless campaigning for the newly elected President, William McKinley. When the U.S.S. Maine blew up in Havana harbor, the Spanish were blamed and an outcry for war arose. From that moment, Roosevelt believed that trying to prevent the war would be impossible. He sprang into action to ready the Navy for hostilities, moving ammunition, readying ships for action, and moving to have Congress allow for enlisting unlimited sailors. TR also made it known to the President and others that if war came, he wanted to leave his post behind a desk in Washington and head for the front.

Congress declared war on April 25, 1898, and that same day Roosevelt was officially offered (and accepted) second in command of the Rough Riders; he would soon take over full command of the unit. He immediately set about assembling the regiment, sorting through 23,000 applications and accepting just a fraction. The unit was made up of an effective assemblage of Western cowboys, hunters and frontiersmen, Native Americans, and Eastern athletes and sons of prominent citizens. This composition reflected TR’s own interests. The unit was mustered into service between May 1 and May 21, 1898 in various locations in Texas, New Mexico and what was then termed “Indian Territory” (Arizona and Oklahoma). At the time of muster in, the unit consisted of 47 officers and 994 enlisted men. It was trained quickly in San Antonio, Texas, and on May 27 it was ordered to Port Tampa, Florida, to prepare for the invasion of Cuba. It left for the front in Cuba on June 13, and on June 22, 1898 finally disembarked at Daiquiri, Cuba, on the southeastern side of the island near the strategically important port city, Santiago. On the eve of battle, Colonel Wood was promoted in the field to Brigadier General and Roosevelt to Colonel. He was now in command of the Rough Riders.

In Cuba, the Rough Riders fought at Las Guasimas, and then at the famous Battle of San Juan Hill. They played a key role in the outcome of the Spanish-American War, not merely by taking San Juan Hill, but by serving as the catalyst with other American units at Santiago de Cuba. For his efforts TR would eventually be awarded the Medal of Honor, the citation for which details the performance of TR and his regiment. “On 1 July, 1898, near Santiago de Cuba…while leading a daring charge up San Juan Hill. Lt. Colonel Roosevelt, in total disregard for his personal safety, and accompanied by only four or five men, 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 in the Battle for San Juan Hill."

Having courageously led his men to victory, Roosevelt returned a hero. The Rough Riders were mustered out in September 1898, thus fading into history.

At that time, New York was the most populous state in the nation, and it had the most electoral votes. Business and industry were headquartered there, and the most influential press were concentrated there.  Its governor was in a position to exercise power, to regularly obtain visibility on a national scale, and for an ambitious man, to be considered as a serious presidential candidate. TR appreciated all this, and back in New York, he immediately announced his candidacy for governor. With the gubernatorial election just two months away, he planned his campaign with astuteness and cleverness. The election was held on November 8, 1898, and it was very close. Roosevelt, who had campaigned on a promise to run a "clean" administration, won by just 19,000 votes out of some 1.3 million cast. But he won and his career was launched.

Herbert de Haga Haig was a Royal Engineer and Quarter Master to Maj. Gen. Middleton during the Northwest Canadian Rebellion by Native Americans in 1885.  He was also a friend of Roosevelt and a fellow-hunter.

Typed letter signed, on his New York Governor's letterhead, Albany, March 30, 1899, to Major Herbert de H. Haig in Agra India, assessing the qualities that made the Rough Riders a success, criticizes the U.S. military leadership in the conflict in Cuba, opines on the caliber of the Spanish soldiers fighting against them, and offers his own intentions on governing in New York, and ends by saying he looks philosophically on the future.  "My dear Herbert, I envy you being in India. Heavens and earth!  I don't believe I shall ever shoot at game again.  I am by no means certain that I could hit it anyway, unless it stayed very still and was very close up.  I am delighted to learn that you have children. I now have six. I am sorry that Mrs. Haig does not like India.  

"I am having great fun now and I had even greater fun last summer.  I had a great regiment for a volunteer organization.  Indeed its fighting record would have done credit to any raw organization.  I have always believed that with proper leadership there were no better natural soldiers in the world that those hunters, cow punchers, and miners of the West, and that if one paid attention to the essentials instead of the non-essentials of discipline, it would be very easy to turn them into a body which could do excellent work in fighting.  

"The Spaniards were a queer lot.  They possessed no initiative, and yet they stood and fought with extraordinary courage when behind cover.  They did not like standing in the open much.  The country was extremely difficult and on our side the battle was not delivered with very much judgment, so we lost heavily.  The fever was what laid us up, however.

"New York politics are too kaleidoscopic for a man to have much chance to keep on in it, but I am having a good run for my money and I am going to make a pretty decent Governor, and then accept with entire philosophy whatever comes afterwards."

This is the broadest assessment we have seen from TR of the Rough Riders, and the conflict in which they played so crucial a part and which made his career. Moreover, this is the only letter of TR that we can recall seeing directly criticizing his military superiors during the Spanish-American War. Just over two years after writing this letter, TR was President of the United States.

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