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Thoughts on “The Rough Riders” by Theodore Roosevelt

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Overall Thoughts

I’ve read books about Teddy (and I knew that he was an avid writer), but I never actually read anything by him. The Rough Riders was my first experience reading the man’s writing and it kind of annoys me how many skills this guy had. I mean beyond him being the President of the United States and all that, he published over 25 historical books in his lifetime, studied law, was the police commissioner of New York, was the assistant secretary of the Navy, was the governor of New York, VP of the United States, doubled the quality and quantity of national parks in the United States, built his own cabin, hunted all the time, and much more. The kicker: he did all of this while having extreme asthma (which was considered nearly fatal at the time).

This book is a war book. It’s about the Spanish-American war and how Teddy resigned from being assistant secretary of the Navy (a very prestigious position) to pull together a group of volunteers (called the Rough Riders) and head out to assist the military for the war. This was in 1898. The US was short on fighters at the time so Teddy rallied together what was essentially a group of some of the most badass cowboys and Indians to help. The book highlights the difficulties of leading a group of knowmads who were great individual fighters to work together (in 2.5 weeks !)

Impactful quotes

“When I [Teddy] went down to the camp at San Antonio he was on kitchen duty, and was cooking and washing dishes for one of the New Mexican troops; and he was doing it so well that I had no further doubt as to how he would get on.”

I love this quote… how you do the small things is how you do everything. The little things matter. Do whatever task you are given well. If you can’t wash dishes and care, what makes you think people would trust you to go into battle?

“He [Allyn Capron] won at once not merely their [the troops] admiration, but that soldierly affection so readily given by the man in the ranks to the superior who cares for his men and leads them fearlessly in battle.”

In other words, good leaders get the respect and trust of their men by making sure they know they can expect their leader to jump into battle with them, not stand off to the side.

“Credit should go with the performance of duty, and not with what is very often the accident of glory”.

Pretty straightforward and impactful.

“I was still very much in the dark as to where the main body of the Spanish forces were, or exactly what lines the battle was following, and was very uncertain what I ought to do; but I knew it could not be wrong to go forward, and I thought I would find Wood and then see what he wished me to do.”

When you don’t know what else to do you can’t go wrong with moving forward. Keep it pushing.

“My time was still much occupied with looking after the health of my brigade, but the fact that we were going home, where I knew that their health would improve, lightened my mind, and I was able to thoroughly enjoy the beauty of the country, and even in the storms, which hitherto I had regarded purely as enemies.”

I liked this quote because the weather was one of the biggest enemies of The Rough Riders. And here Teddy is essentially saying since the circumstances have shifted (and they were going home soon) he could actually enjoy the beauty surrounding him. There is beauty everywhere, it just depends what perspective you’re looking at it from.

“Some of the boys are poor, and in one or two cases they seemed to me really needy, but they all said no [to the money Teddy was offering them]. More than once I saw the tears come to their eyes, at thought of your care for them, as I told them of your letter.”

“Pardon me for burdening you with these details, but I suppose I am like your boys, who say, ‘The Colonel was always as ready to listen to a private as to a major-general’.”

After the war, a lot of the men lots their jobs and were wounded. Simply put: they were broke. Teddy and some men decided to reach out and offer money to the soldiers. Not many would accept anything from them. This quote is from a response to a letter Teddy wrote a teacher who let 4 of her students join the Rough Riders (his letter was essentially offering money to them or her). I don’t think any comments are necessary here.



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