Theodore Roosevelt Describes His Battle Experience in Cuba as a Rough Rider to His Uncle, Saying He “saw a great deal of fighting”

In an uncommon letter as Vice President, he makes clear the powerlessness of that office

This letter was deaccessioned to us directly by the Theodore Roosevelt Association. It was never before been offered for sale.

The “Rough Riders” – the First US Volunteer Cavalry – was raised for the Spanish-American War by Theodore Roosevelt, who resigned as Assistant Secretary of the Navy to take the field. The regiment was mustered-in in May 1898 and many of the volunteers had known Roosevelt from the Badlands of the Dakota Territory as well as his time as New York City Police Commissioner. The regiment departed Tampa, Florida on June 14, 1898, landing near Daiquirí, Cuba on June 22. Although officially a cavalry unit, the regiment fought on foot. They immediately began marching toward their objective, Santiago. Two days later, the unit participated in the Battle of Las Guasimas. Though outnumbered, the American contingent was nonetheless able to force a retreat of the Spanish troops to the city of Santiago. On June 30, Roosevelt was promoted to full colonel and given formal command of the Rough Riders. The next day, American forces began an assault on the city of Santiago. The Rough Riders charged up Kettle Hill that was slightly to the north of San Juan Hill, though history recalls this as a charge up San Juan Hill. Roosevelt was the only one who was mounted; the others were on foot during battle. Spanish forces eventually surrendered on July 17. All told, in Cuba, the Rough Riders suffered a casualty rate of about 76% lost in battle, wounded, or down with disease. A few days after the Rough Riders’ charge, the Spanish fleet fled Cuba. It was just a matter of weeks before the war had ended and the U.S. was victorious. The Rough Riders made headlines for their role in the battle back in the states, which became the stuff of legend thanks to Roosevelt’s writing ability and reenactments filmed long after. The unit became famous, and its commander was on the road to the White House.

After returning to New York from Cuba in 1898, the young hero Theodore Roosevelt was quickly mentioned as a potential Republican gubernatorial candidate. However, boss Senator Tom Platt held the Republican Party in New York state in his hand and would thus control who received that nomination. Roosevelt was known for his independence, and Platt did not wish him to hold the governorship or any party office. But the Republican Party in New York was in such a poor condition that the likelihood that it would carry the upcoming election was slight. So thinking he would derail Roosevelt’s career by setting him up to lose a race so much in the public eye, he agreed to let TR have the nod. Roosevelt proved to be an excellent candidate and actually won. Now he was a bull in Platt’s china shop. His activism and extraordinary independence as governor, and the very important reforms which, in spite of the machine, he drove through the legislature, greatly increased his recognition and popularity throughout the country.

Platt and the machine naturally wished to get rid of this man who could not be manipulated, as by 1900 he was troubling them and costing them a bundle. Platt knew that it would not be safe for him to try to dominate Roosevelt, so he turned his attention to getting him out of New York. The method that most readily came to mind was to talk him up for the vice-presidency of the United States, a post then open, as Vice President Garret Hobart had died in 1899, and President McKinley needed a new man for the ticket in 1900. Roosevelt, however, wished to continue as governor for at least another two years, to carry on the fight against corruption, and to save himself from being laid away in the vice presidency – the receiving-tomb of many ambitious politicians. Despite knowing of Roosevelt’s disinclination, at the Republican Convention in Philadelphia, Platt promoted TR’s nomination for vice president anyway. There was little resistance, as the choice was genuinely popular with delegates, who saw the addition of the young crusader as helping the ticket. After renominating McKinley they insisted on nominating Roosevelt. Swept off his feet, and seeing that the demand came genuinely from representatives from all over the country, TR accepted and was chosen by acclamation. The ticket was elected in November 1900, and inaugurated March 4, 1901.

Now TR was vice president, and as he here tells his uncle Cornelius just a month later, he has discovered how little power the office has. Cornelius requested he intervene in a matter, likely an appointment or promotion in the Ordnance Department, as Ordnance chief General Adelbert Buffington was involved. TR declines, but in doing so discusses his Rough Rider experience in Cuba, the primacy of military matters in his thinking, and his feeling of powerlessness as Vice President. It’s the kind of directness and honesty one would only expect to see expressed to a relative.

Typed letter signed on his Vice President’s letterhead, Oyster Bay, April 9, 1901, to his uncle, Cornelius Roosevelt. “I return you Dr. Tuttle’s letter. This is just one of the cases in which I take the liveliest interest and where I am absolutely powerless to act. Mind you it is not the case, it is simply one of the cases. Down at bottom I think I am more interested in military matters than in anything else, and in the brief but active campaign before Santiago, I not only saw a great deal of fighting of various kinds, but I went straight up from a squadron to a brigade commander. Under these circumstances you can easily imagine that I saw countless things which I would like to remedy in connection with the War Department, and some of these things I regard as of vital importance; but I am absolutely helpless.

“I have the utmost confidence in Secretary Root, and feel he is one of the best Secretaries we have ever had. Now there are points on which his views differ from mine, just as while I was Governor there were points upon which my views differed from his. Occasionally, but very, very rarely, where I have a personal familiarity with the subject and doubt if he knows all about it, I have called his attention to it; but in a case like this I have no personal knowledge of the matter and his attention has evidently been called to it already. With General [Nelson] Miles on one side and General Buffington on the other, both of them presumably experts, it would be utterly idle for me to say anything in the matter, when I know and can know nothing of it personally. I am very sorry.”

This important letter was deaccessioned to us directly by the Theodore Roosevelt Association. It was never before been offered for sale.