American History

How Theodore Roosevelt Developed His Cowboy Reputation

Theodore Roosevelt is an American icon and one of our better-known presidents. This is the story of how he became that way, going from rich boy to cowboy.

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Theodore Roosevelt is one of our best-known presidents. From his charming folk sayings to the very real work he did on building this nation’s modern infrastructure in the early 20th century, Roosevelt is an icon in American history. His face is even one of the ones carved on Mount Rushmore in South Dakota. If there is one thing he is known for besides being a famous and excellent U.S. president, it is being a real American cowboy. People have associated Roosevelt with the rough, wild west ever since he was president. In fact, he is considered one of the last real cowboys in the United States. But why?

Roosevelt started out about the farthest one could get from being a cowboy. Born into a wealthy socialite New York family, Roosevelt was raised to be a member of high society and to do impressive things with a top-notch education, impeccable breeding, a high paying career, and to further the reputation of his family’s name. And, Roosevelt started out his life as an adult doing just those things. He went to the prestigious Harvard University, then later to Columbia Law School. became a lawyer. He was also known for his scholarly pursuits in other areas, publishing a book on the War of 1812 (called The Naval War of 1812 in 1882). This established him as a serious historian and also as an author with respect and a high degree of public popularity.

He spent much of his time in law school writing his book on the War of 1812, and eventually grew disillusioned with the pursuit of a legal career. He dropped out of laws school when he was encouraged by members of his local Republican Association, with which he had become involved, to run for public office. Roosevelt declared to his family and friends that he intended to be one of the governing class.

Roosevelt was soon elected to the New York State Assembly and went to Albany to represent his district there. It was during one of his three consecutive tenures as an Assemblyman that he married his first wife, fellow socialite Alice Hathaway Lee. Alice was a member of another rich and politically powerful family, and the match with Roosevelt made sense. It also helped that Alice was known for her sunny and loving personality and an incredible physical beauty that was the envy of any other woman who met her. Roosevelt was utterly smitten, and after asking her three times, the married in 1884 on his 22nd birthday.

They had a happy marriage, and his few surviving letters to her and diary entries mentioning her indicate he thought the world of her. Sadly, their union was not a lengthy one. Alice became pregnant and gave birth to a daughter, also named Alice, in 1884. Unfortunately, his wife Alice had undiagnosed kidney disease, and the pregnancy masked its symptoms. No one knew anything was wrong with her until after she gave birth. By then, it was too late to save her, and she died two days after giving birth to their daughter. To compound Roosevelt’s misery, his mother died of typhoid the same day he lost his wife.

Roosevelt decided to get away from it all for a while since he was so grief-stricken over losing Alice. He sent his infant daughter to his sister’s house for her to raise until he could bring himself to pick up his fatherly responsibilities. He stepped away from local politics, too, even though he was a rising star there, already having established a reputation as an excellent politician of integrity and incredible moral character.

During his time away, Roosevelt went to some land he owned in North Dakota. He learned to ride like a cowboy, to rope, lasso, and hunt from horseback. While on his ranch, he earned the respect of the local cowboys, though they did not think his skills matched theirs. He devoted himself to what he called “masculine” pursuits, throwing himself into physical activity. He also met Sheriff Seth Bullock of Deadwood, South Dakota, and the two became close friends for the rest of their lives.

Roosevelt wouldn’t allow Alice’s name to be spoken in his presence, and did not even include her name in his autobiography or his official biography. He even called his daughter Alice by a nickname. He didn’t retrieve her from his sister until she was three years old when he remarried.

It was Roosevelt’s reputation as a cowboy that made him a popular president. Yet, without the death of his first wife and arguably true love, he would not have become the man we know today. He might have continued to be active and popular in New York and even national politics, but it is unlikely he would have captured the public imagination enough to be selected McKinley’s vice-president or to be elected again on his own after taking office following McKinley’s assassination. We certainly wouldn’t be seeing his image on the mountain today. For Roosevelt, tragedy made him the American legend he became.



Will founded Ancestral Findings in 1995 and has been assisting researchers for over 25 years to reunite them with their ancestors.