Lessons in Manliness: Theodore Roosevelt and the Spanish-American War

by Brett & Kate McKay on May 1, 2008 · 38 comments

in A Man's Life, Lessons In Manliness

Theodore Roosevelt

Theodore Roosevelt, who arguably accomplished more than any other American man, called his experience in the Spanish-American War, “the great day of my life.” It was during his charge up Kettle Hill that Theodore Roosevelt’s leadership and confidence finally crystallized. He passed the test and emerged as a leader capable of ascending to the presidency. His actions during the war impart crucial lessons on manly leadership:

1. Walk the Walk. Theodore Roosevelt was a sickly child who grew up reading of ancient battles and warriors and longing to be one. He built up his body and as he got older started writing his own books about military feats. Yet he still longed to see action firsthand, and when the opportunity finally arrived, he wasted no time in seizing it. As soon as the Spanish-American War broke out, Teddy pestered the Secretary of the Navy for a commission in the army. He then sold his cattle ranch and some of his possessions, and took out life insurance in preparation of receiving it. He was fully prepared to put his money where his mouth (and pen) was.

2. Know your limitations. Teddy was never short on confidence, but he didn’t let cocksureness slip into arrogance. When Roosevelt got his wish for an army commission and was offered command of the First United States Volunteer Calvary as Colonel, he turned it down citing his lack of tactical experience. He instead accepted a position as Lieutenant Colonel and recommend Leonard Wood to be Colonel. (TR would later become Colonel when Wood was promoted to brigadier general.)

3. Pick the best men for your team. If you wish to surround yourself with the best men, you must be the kind of leader men fall over each to serve under. 23,000 men applied to be part of the First Calvary; most of them addressed their letters to Roosevelt even though Wood was technically in charge. Of the 23,000 only 560 were chosen. Some of the rejected cried, so heartbroken were they on not being able to be part of Roosevelt’s Rough Riders. Composed of the West’s best frontiersmen, marksmen, and horsemen and the East’s great athletes and prominent sons, the Rough Riders were a unique and unstoppable group.

Theodore Roosevelt and the Rough Riders

4. Be one of the men. The ship which transported the troops to Cuba did not have room for many horses; Roosevelt was one of the few men in the regiment able to take his. When the Rough Riders arrived in Cuba, they began their march to Las Guasimas. The temperature was simmering, and the men trudged through the heat in thick uniforms and heavy bedrolls. Still, Roosevelt walked alongside the men, refusing to ride while they were marching.

5. Lead by example. Don’t ask others to do anything you are afraid of doing yourself. When it came time to take the San Juan Heights, TR’s regiment ran into heavy fire from the Spanish. As bodies piled up all around him, TR stayed on his horse as an example of courage. However, there was a delay before they could start scaling the hills, and the men, including TR, were forced to lay low and take cover. When the order finally came to take Kettle Hill, the men were reluctant to rise to their feet. TR mounted his horse and shouted, “Are you afraid to stand up, when I am on horseback?” He promptly took off, galloping across an open area and under a hail of bullets.

6. See it through. After securing Kettle Hill, TR noticed that the attacks on the neighboring San Juan Hill were faltering. He shouted for his men to charge, leaped over a barbed wire fence, and ran down the hill. When he glanced back, he saw that only 5 of his men had followed. 3 of these 5 were shot and TR was practically leading the charge single-handedly. He ran back under heavy fire, formed the remaining men (who claimed to have not heard the initial order) into a formidable assault line, and began the charge again.

Roosevelt’s personal bravery and leadership were critical elements in the success of the Battle of Las Guasimas. In 2001, Roosevelt was posthumously awarded the Medal of Honor for his actions.

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{ 37 comments… read them below or add one }

1 cory huff May 1, 2008 at 11:08 pm

Great tips, Brett. Especially in the light of my new promotion. I’m going to be leading a sales team at work, and I’m a little bit intimidated, but very excited. I especially like the part about knowing your limitations and finding the best men for your team. Thanks for all of your posts!

2 Jen May 2, 2008 at 2:51 am

Nicely written article, and applicable to so many “disciplines”.

3 Jim O'Donnell May 2, 2008 at 8:02 am

Courageous, strong, compassionate, strict, driven…the list could go on and on when describing our 26th president. We’ve been fortunate in this country to have had men like Theodore Roosevelt to emulate. One of my colleagues was just promoted to a new leadership position. I just sent him a link to this post. Well written! Well done! You’ve proven once again that if we want to learn how to live in the future, sometimes that best thing to do is look to the past.

4 Cameron May 2, 2008 at 10:44 am

It’s hard to believe that there were actually men like this. In this day, it’s really hard to find a leader that people overwhelmingly want to follow.

Is it that our challenges are different now? Or are the challenges the same, but they are approached and handled differently? Political affiliation aside, when was the last time we had a hero for a president. Someone that led and inspired by example. Someone that charged the hill single handedly. I’d even settle for a metaphorical “hill”. Seriously, what happened?

5 Rod Homor May 3, 2008 at 7:08 am

Another great article. (I feel like I am starting to repeat myself with these words in regards to your site…) LOL.


6 James May 3, 2008 at 7:20 am

Sadly, we need leaders like T.R. again.

7 Adam Dummar May 3, 2008 at 12:34 pm

Even my liberal history teacher back in high school admired TR. He was one of the few great men to make it to the presidency.

8 prelox May 3, 2008 at 4:44 pm

Nice tips on how great TR was. Wish more of our current leaders would lead by example rather hide behind control centers.

9 simone dubois May 3, 2008 at 6:52 pm

I viewed your site because I am a single parent, raising a 7 year old boy and I thought you might have good tips for me. I read about your site on a catholic blog. I am disappointed however to see the advertisement for Gay Military Dating in the middle of your page. How is this consistent with your theme of Maniliness?

10 Brett May 3, 2008 at 7:23 pm

@Simone-Thanks for coming by the site. I don’t have control over which ads show up on the blog. The ads come from Google, who randomly change them every day and every hour. If I find an ad offensive, I can block it, but only after it shows up on the site.

11 Ken Renard May 4, 2008 at 11:04 am

I am a big proponent of manhood, and manliness, and think feminism has been a disaster in so many ways, not the least of which is feminising men. I like the idea of your site, but I have to agree with Simone that the ads are offensive, and contradict your message. If that is how Google wants to advertise, I think you need to do the manly thing, and find another way to get your site hosted. I would rather pay for a site I could read with my son, than have a free site where he gets to see ads for pornography. (Note, the ad I saw was different from what Simone described, but equally offensive.) Thanks for listening.

12 kleinzeit May 4, 2008 at 12:16 pm

Can you not be gay and manly? You know, responsible, respectful, consistent, dress well. What’s this sites views on manly homosexuality?

13 Charlie May 5, 2008 at 4:28 am

Great article, Brett, but I have to quibble on one particular angle. I have enormous respect for TR but I have always been annoyed for his behavior in choosing to attend this conflict. At the time, he had a wife and child at home to support, and running off to join in a war so he could have a bit of adventure seems, to me, not just irresponsible but gravely disrespectful to the people at home who were counting on him.

TR was a badass to be sure, and politically admirable, but he was itching to go to war the way a Boy Scout itches to get to camp (“I should welcome almost any war, for I think this country needs one.”) I for one don’t appreciate or revere that attitude, especially when it could leave a child fatherless.

Just my opinion! Keep up the great content!

14 stevos May 5, 2008 at 6:59 am

Great post Brett! Speaking of bad advertisement, I’ve been using Firefox as my web-browsing tool and they have a advertisement blocking add-on, called Adblock-plus, so I never see any bad ads . Very useful for safe surfing on the web.

15 NoPeanutz May 5, 2008 at 10:25 am

1. Excellent post on TR. And I cannot read enough about the incredible life that he led. Not every man needs to be a TR, but his influence and leadership are so incredible that they still inspire men to improve themselves even 100 years after his demise.

2. I feel compelled to respond to the comments above about banning gay dating sites from the blog. In fact, if I held my peace, it would be dishonest, disrespectful, and disingenuous, and therefore decidedly unmanly. Therefore, I would like to point out that I see no conflict between being gay and being a man. In fact, it takes a man to be gay. And more often than not, it takes a man of great courage to be gay, and to pursue his own course to happiness, even in the face of constant hate, ostracism and humiliation. Too often, facing ones homosexuality has meant making the ultimate sacrifice for one’s conviction. My fellow men, I ask you: is there anything more manly?

Kleinzeit correctly points out that even gay men can be honest, faithful, reliable, punctual, resourceful, neat, courageous and frugal. No where on this blog, or any where else for that matter, have I come across any worthwhile and universal literature that states that a robust sexual appetite after women is a prereq to manliness.

If your son cannot read this site because of indecency present in the ads, so be it. But if homosexuality is the issue, keep reading and learning and hopefully you will arrive at the heart of the matter.

Also, many of the heroes of our sex throughout history have been exclusively gay or attracted to men. If the ancient Greeks had been so closed minded, we would not know who Socrates, Plato or Aristotle were. Our whole tradition of Western Philosophy and literature would be lost. We never could have defeated the Nazis without the genius of a certain British scientist and codebreaker who was also a homosexual. Incredible achievements in the modern visual and performing arts would never have come to be. So much of Academia that has enriched our lives and enabled us to rise so far above the apes has sprung from the brilliant minds of gay thinkers.

And if femininity is the issue, then that is an entirely different issue from homosexuality. Many heteros, as well as homos, are equally effeminate. Although the two are often found together, it would be a grave and disastrous error for us to confuse correlation with causation. The two are not by any means mutually exclusive.

16 Tom Stanton May 7, 2008 at 5:22 am

With honor and so many virtues fading this is a real encouragement. Oh that God would raise up real men to lead us again!
forever HIS tom

17 Jerry Watson May 7, 2008 at 7:37 am

I agree with your stated precepts. I am also a great admirer of Theodore Roosevelt for the most part. Some time back I read a book that Roosevelt himself wrote about the Spanish American War. For the most part, I don’t recall any of the details that you state in your article above in Roosevelt’s book. I know about not being able to take horses to Cuba, about the Battle of Kettle Hill and San Juan Hill but the accounts I have read, including Roosevelt’s own, indicate that Roosevelt’s part in those conflicts was somewhat passive. Maybe you could email me your source for those statements. Thanks for your time and assistance.

18 evan mathews May 7, 2008 at 1:28 pm

Teddy was a pretty good man. If you look at the rest of his life, he stood for justice, virtue, and compassion. He was not a guy who said “I got mine” and ignored the rest of country. He even left the Robber Barron Republican party and formed his own Bull Moose party.

19 Michael Mattis May 8, 2008 at 4:08 pm

On behalf of Dandyism.net, I declare this post to by Bully!

20 Night Writer May 9, 2008 at 10:19 am

Coincidentally I just watched the 1975 movie “The Wind and the Lion” starring Sean Connery and with Brian Keith as Teddy Roosevelt. The movie is based on a true story and TR is compelling in the movie with his flaws and virtues (illustrated by real-life events and words from his writings). It’s a good film if you’re interested in Roosevelt and, as a bonus, if you’d like a little deeper insight into why the Middle East is the way it is today (which is as its always been).

21 Ben Geist May 13, 2008 at 10:14 am

I would like to vote for this on Digg but I can’t figure out how.

22 Brett May 13, 2008 at 11:10 am

@Ken-I will be getting real ads soon. In the meantime, I will keep the google ads because I spend around 20 hours a week on the blog, and so getting a few dollars a day makes me feel better. I hope you understand.

@Charlie-Interesting point. I think part of TR just wanted an adventure. But I think part of him sought the opportunity to fight for his country in what he believed to be a worthy cause. True, he ran the risk of leaving his family fatherless, but everyone who joins the armed services, now and then, take that chance. Making that ultimate sacrifice is the height of manliness. If he was just looking for a fun adventure though, then yeah, I question that move.

@Jerry-Some of it I got from Edmund Morris biography of TR “The Rise of Theodore Roosevelt.” And some of it came from TR’s own account of his actions in the war. It’s clear from his account, that he was front and center in the whole thing. You can find it online at: http://www.spanamwar.com/Sanjuantr.htm

@Night Writer-I haven’t seen that film, but I should check it out. I think Martin Scorsese is making another TR film with Leonardo DiCaprio as TR. It’s hard to imagine someone as pretty as Leo being TR, but he’s a great actor, so perhaps he can pull it off.

@Ben-Don’t worry about it digging it. It was dugg when it was posted and then promptly buried by digg. We seem to be on digg’s autobury list (everything that gets dugg from here is buried by the site) and thus AoM and so we won’t be using digg in the foreseeable future.

23 Pete May 13, 2008 at 7:25 pm

No Peanutz-

I think gay men can be manly. And I’ve seen gay men who seem manly. But most of the gay men I’ve met and see in the media act like weird women. Real men don’t talk with a lisp, obsess about fashion, love Barbara Streisand and musicals, ect. I’ve never understood why being gay would necessitate those things and they seem like they’re more part of a learned culture than being innate. If gay men want to be more accepted by society maybe they should start acting like men, instead of sissies.

24 Maria Salvador October 20, 2008 at 9:27 am

I need to know what he feared in his life. i know he was kind of fearful but their must be something right.

25 Kelsey January 16, 2009 at 9:44 am

thats nice to know

26 Da 1 n only February 24, 2009 at 5:21 pm

thank you this just helped me with my essay

27 Patrick H June 2, 2009 at 5:23 pm

The entire notion of ‘manliness’ is outdated, sexist bullshit. The whole ‘ban gay dating sites’ thing only reinforces the notion that ‘manliness’ as well as ‘femaleness’ are based on old gender constructs that have about nothing to do with the biological nature of sex and gender.

28 JustineL July 14, 2009 at 7:23 am

Hey – Loved the article but found the whole “men being feminised” thing ridiculous. As Ken above stated “am a big proponent of manhood, and manliness, and think feminism has been a disaster in so many ways, not the least of which is feminising men.” The truth is feminism came to being to PROTECT women (and children) from those that believed “manliness” stemmed from oppression and “oppression” is not limited to the obvious financial crippling; it included taking the right of one’s body from them, it included the ability to keep females from working (esp when the man left) and the inability to be educated. That men are now “feminine” is a direct fault of their own – they no longer wanted to be men via responsible man behavior. They want the booty – not the baby but won’t protect themselves (and females share this blame). I am not saying that there weren’t some crazed feminists out there but I think that men do need to understand that women have been forced to be “manly” by the inability of man to belly up to the bar and MAN UP! Just look at the statistics of “who leaves whom” …last time I did a history check – there are whole chapters dedicated to the subjugation of woman and all the different assortment of ways to make her worthless except in the eyes of a man. I don’t recall men being condemned both by politics and religions nor do I recall reading anywhere how man was forced to be “weak” as that was more desirable. Being a man is not equal to bullying – being a man is being responsible, is being honorable and just – being a man is being strong without the muscles – it has nothing to do with objects- whether human or otherwise and it certainly has nothing to do with an image.
About the comments of gay men – honestly you can be gay without acting like a silly girl and I have to agree with some of the commentary on that – there is nothing more shaming to both sexes than to see a man act like a girl and to see a woman acting like a man.

29 Tim J July 14, 2009 at 9:45 am

Patrick H, your post makes no sense to me. It is both biological and cultural, and this site deals mostly with latter.
Manliness has become outdated by the current younger generations. Many are trying to reintroduce the positive attributes of the masculine cultural role in past generations to others that missed it or were never given the opportunity.
I prefer not to be “gender neutral.” That’s why I’m here. Perhaps you’re on the wrong site.

30 k2000k August 27, 2009 at 6:19 pm

As a younger individual (>25 years old) I’d just like to say that the concept of manliness is being rediscovered. Ask any young man about the social constructs of men being the same as women and they will either roll their eyes, or flat out tell you its hogwash. We still seek men to emulate, unfortunately popular culture by and large leaves us with individuals that are narcissistic individuals not really worth emulating. There is a reason that the Chuck Norris jokes were so ubiquitous among young men and teenagers, not only because its funny, but the theme of those jokes being that he is the manliest man alive. This website, and any other likes these that exist, serve the vital of purpose of illustrating to young individuals such as myself that it is
a) Ok to want to be manly and tough
b) How to be manly and tough and not fall under the feminist caveman stereotype.
c) That real men, more than being manly and tough, have integrity and value honor.
d) Provide a forum were ideas about what makes a man a real man can be exchanged.

I especially like the articles on how to dress well without either looking like a dandy, or on the other extreme a lumberjack. Not that there is anything wrong with lumberjacks, they are very manly.

So a Bully to you artofmanliness.com the cure to all things ‘bro’

31 PK January 7, 2010 at 1:10 am

This is one of those situations where the truth may in fact be less glorious than what we’re told. By accounts on the day the bulk of the fighting in taking the San Juan Heights was done by African American troops. The Rough Riders were there, but did not as depicted in press accounts at the time, lead the charge to take the Heights. Custom of the day was that all black troops were lead by white officers in the event that the white officer was killed, the next nearest white officer was presumed to be in charge. In this case, Roosevelt. There is no denying that Roosevelt was quite a forceful character, but the version of the story that has the Rough Riders leading the capture of the San Juan Heights is actually false. The African American soldiers, much like Matthew Henson, never received the glory that they deserved. Truly unfortunate.

32 PK January 7, 2010 at 1:20 am

I have to amend my previous post. I should have checked my facts first and failed to do so. I apologize. The amendments are these, 1) it is not clear that the officer for the Buffalo soldiers was killed. 2) they did recieve praise at the time of the battle and commendations. Nevertheless, the Rough Riders were not the heart of the attack on the San Juan Heights and TR was not at the head of the main assault, though he did join in the assault after taking Kettle Hill with the Rough Riders.

33 David January 29, 2010 at 12:11 am

I think it’s hilarious that so many people are arguing about this. On the internet. With other people that argue on the internet. Arguing on the internet is like running in the Special Olympics. Even if you win, you’re still a retard.

(And yes, to all of the far-too-sensitive folks out there, I realize how terribly improper that joke is, and no, I don’t really mean anything by it.)

34 Richard March 28, 2010 at 10:28 am

I think the reason people argue with bigots and other idiots on the Internet is because sunlight is the best disinfectant.

I think a real man accepts people for what they are, regardless of the colour of their skin, whether they choose to have sex with women men or to abstain, whether they believe in a beardy man in the sky who is watching you or not.

People should be judged by the contents of their character. I know gay men who are honourable, generous, and in all the important ways much more of a man than many of the straight men I know. What they choose to get up to in their bedrooms is their business.

If you think a text only ad for Gay Military Dating is somehow offensive and a danger to your son, then I feel sorry for you.

35 Jeff January 12, 2013 at 2:51 pm

Great article. Please check out my article– 18 Fascinating Things You Didn’t Know About Teddy Roosevelt: http://socyberty.com/history/18-fascinating-things-you-didnt-know-about-teddy-roosevelt/

36 Thorsten D August 2, 2013 at 1:08 am

@simone dubois

After Battle of Chaeronea Phllipp II of Macedon said zhis over the members of the Sacred Band of Thebes (Who fought and died (nearly`) to the last man.

Perish any man who suspects that these men either did or suffered anything unseemly.

—Plutarch, Pelopidas

I don´t think you can get much higher and deserved praise and recognition for your valour, Determination, sense of duty, loyalty, ability as a true soldier and warrior.

The Romans considered the Parthians with their make up effeminate.

And so Crassus decided to invade the Parthian Empire and came to this place called Carrhae ….

Don´t judge a person on his style, his or her taste in Style says absolutly nothing of his or her substance.

Excuse my bad english

37 Dr. Mike August 15, 2013 at 5:08 pm

Very cool – I did not know that TR was a MoH winner.
Betcha he is the only president who has on of those!

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