Sold – Roosevelt on What It Takes to Be a Cowboy

In 1881, at the age of 23, Roosevelt was elected to the New York State Assembly. He quickly established himself as the leader of a group of young independent-minded Republican legislators, who fought to clean up New York politics by opposing the power of the Republican state machine and the Tammany Hall Democrats of New York City. He gained a widespread reputation for honesty, integrity, and vigor.  This seemingly charmed career was sidetracked in February, 1884, when he suffered the deaths of both his wife and his mother. The blow was tremendous, and declining to run for reelection, he instead went west to forget his sorrows. He purchased a ranch in the Dakota Territory and spent the next two years leading the strenuous life, tending to a large herd of cattle, chasing outlaws, writing popular books about the West such as “Hunting Trips of a Ranchman”, and creating an image as the nation’s most famous cowboy. During these years, TR made trips back east and regaled reporters with tales of his exotic adventures. This ensured that his name remained in the papers in New York, as well as spreading to locales far and wide. He stayed enough in the public eye that upon one of his return trips in 1886, the party nominated him for mayor of New York City. Though he lost, the attention he gained nationally led to his being named Civil Service Commissioner by Pres. Benjamin Harrison in 1889. Then in 1897, Pres. William McKinley appointed him Assistant Secretary of the Navy, and he found himself in this office when the United States declared war on Spain in 1898. Always ready for action, TR promptly resigned his post to form a volunteer regiment of western cowboys and eastern adventurers that the press dubbed “Roosevelt’s Rough Riders.” The Spanish-American War did not last long, but it was long enough for the Rough Riders to take San Juan Hill and pass into folklore. Roosevelt returned to the United States as the most famous man in the nation.

Autograph Letter Signed, 4 pages, Washington, August 4, 1890, to noted psychiatrist Dr. Herbert B. Howard, future President of Harvard’s Massachusetts General Hospital, who asked him about life as a cowboy.  “…To do well on a cow ranch a man must have a good knowledge of plainscraft, know about cattle, be a good rider of vicious horses, be hardy and resolute. Every cowboy has these qualities; to be anything more needs of course steadiness, soberness, thrift and persevering capacity to disregard the hard, narrow monotony of much of the life. An eastern boy or man is rarely worth his keep for the first year or two. There are plenty of good cowhands, trained all their lives to the business, ready for any job. A boy’s being ‘wild’ may or may not be a disadvantage. If he loves adventure but is willing to persevere and work hard he might do well; but if he thinks the life is not one of toil and on the whole of monotony he had better not go out. The man who does not work steadily and hard in the west becomes a mere bar room loafer and goes to the wall as quickly as in the east…Send him out with barely enough money to keep him in coarse food and under shelter at night for the first few months, and let him begin by working at any job he can pick up, at any of the small ranch towns. As he picks up knowledge of the country and of himself he can work towards ranch life.”  This is by far the best Roosevelt letter we have seen concerning being a cowboy and leading the strenuous life, both of which were not merely key facets of his personality, but led to his brilliant career on the national stage. With the original mailing envelope.