Lessons in Manliness from Winston Churchill

by Brett & Kate McKay on July 9, 2009 · 44 comments

in A Man's Life, Lessons In Manliness


Editor’s note: This is a guest post from Jonathan W. Thomas. Mr. Thomas runs the world’s largest Anglophile blog – Anglotopia – which has become a gathering place for Anglophiles all over the world. You can connect with him on Twitter as @jonathanwthomas.

As an ardent Anglophile, I have a lot of respect and admiration for Winston Churchill – Britain’s leader during the crucial World War II years. While he was not a perfect man by any stretch – he was a great man whose life has much to teach us about manliness.

Winston Churchill really epitomized what it meant to be a man in the early twentieth century. So, what were these manly traits and how can we apply them to our own lives? Let’s take a look.

Loyalty and Love


Churchill loved the British Empire, his monarch and his country. It was a love that he had his entire live. It was a love that inspired him to write great books and speeches, paint great pictures, and lead his country through its darkest days. Even though he was a ‘manly man,’ he was in touch with his feelings and felt love. He was also very loyal to his wife, Clementine. They were married until the day he died.

Standing up for what you believe

Throughout his parliamentary career, Churchill was often a political pariah. By the 1930′s, his career was considered over, and he was seen as the sad old man of the House of Commons, suffering from the ‘get off my lawn’ syndrome.  He was one of the few voices that warned of the rise of Hitler and a newly ascendant Germany. No one wanted to listen to the truth, but he persisted in speaking it anyway.



Churchill wasn’t one to give up easily. He was a man that was ALWAYS working. His family was not particularly rich, and so he had to rely on his own skills and knowledge to make a living. Churchill was a man that could sit down and write massive tomes of history from beginning to end – a testament to his inability to give up. When he was defeated in the 1945 election and was ejected by the very people he lead to victory, did he quit? Nope, he stayed on as the leader of the opposition and led his party to victory again in 1950, becoming Prime Minister once more.


Churchill was always up for an adventure and managed to travel the world many times, before such trips were commonplace. At a young age, he joined the military and saw action all over the British Empire. He relished his military adventures and spun his experiences into fabulous tales for the newspapers back home. It jump started his writing career – something that would keep him financially afloat the rest of his life.


Churchill was a product of the British Public School system, meaning he was very well read. You can bet that he had to memorize entire works of literature – a skill recently featured on the Art of Manliness. Even though he was not a particularly great student – in fact he failed the military academy exams multiple times, he would go on to write great books of history and masterful speeches. He had a wit that could shut anybody up and was known for his wonderfully crafted insults.



Many men dismiss arts and crafts as unmanly and useless. Churchill, however, was an avid painter, a hobby that helped him keep the Black Dog, what he called his depression, at bay. He was actually a pretty good artist, and his paintings are very sought after in the art world. Many would argue that his paintings are much nicer than anything put out by Hitler when he was an artist. Churchill loved painting so much he even wrote a book about it called “Painting as a Pastime.” There is nothing more manly than appreciating a nice work of art or piece of classical music. Winston would; so should you.

Supreme Confidence

Churchill thought very highly of himself. He believed he was destined for greatness. This belief guided his every action and decision in life. I’m not suggesting that everyone should believe they will lead their country to greatness. What can be taken from this is that you really need to have confidence in yourself and your abilities before anything else. You are the source of all your success, and if you don’t believe that you can achieve great things, then you won’t.

Belief in the Greater Good

As a wartime leader, Churchill had many tough decisions to make. From destroying the French Fleet at Oran to the bombing of Dresden, he made many controversial choices that historians debate to this day. Whether or not his decisions were right or wrong, he believed he was doing the right thing and making the best choice for Britain.

Belief in the Written Word

Churchill was above all things, a writer. And a damn good one at that. He believed in the written word as a tool for inspiration and leadership. He hand wrote his speeches, working to create just the right flow and structure to maximize the speech’s effect on the listener. He used his words to stir his people, to comfort them, and inspire them to believe in the cause they were fighting for. He also wrote countless volumes on history from “A History of English Speaking Peoples” to his own Six Volume Account of World War II.



Not only could Churchill write a masterful speech, he could deliver one with true power and feeling. He was a superior orator and gave some of the greatest speeches in history. His voice was full of confidence and steadfastness. In Britain’s darkest hours, families huddled around their radio, scared, anxious, and worried about what was happening. Churchill’s voice flooded into their homes, bringing with it the comfort of knowing that the country was in the best of hands.


Churchill was not a man who particularly enjoyed vacations; he always needed to be doing something. Whether that was painting, reading or writing, he constantly kept himself busy. His productivity was enhanced by the routine he set for himself. Even when he was Prime Minister, he stuck to it. He rose late,  worked in bed in the morning, took a bath and nap in the afternoons and worked into the night, often until 4 am. Score one for night owls.

Willingness to Fight

Winston never gave up. Whether is was mastering painting, battling his own political party or defending his country, Churchill was not a quitter. He’s an excellent example of a man whom when confronted – confronts right back and never surrenders. Now, this does not mean that all men should look for a fight – only that we should care about the fights that MATTER.

What are your thoughts on Winston Churchill and his manly virtues?

If you’d like to read more articles like this check out Jonathan’s Anglophile blog.

{ 42 comments… read them below or add one }

1 Matt SF July 10, 2009 at 1:01 am

One of my all time favorite speakers and quote-smith.

I like a man who grins when he fights. – Churchill.

2 Bob Iger July 10, 2009 at 4:50 am

Winston Churchill is -for me- the greatest oratory of all times, a master of words. Unlike Adolf Hitler, Churchill used his superior skills for the good of mankind. Whenever I need a manly boost, I read his quotes.

The fact that he led a small nation through the darkest of times and managed to lift everyone’s spirits just by his words only adds to his manliness.

I wouldn’t call myself a Winston fanboy but I surely admire the man for the actual deeds he left to mankind.

3 Cowboy Bob July 10, 2009 at 6:28 am

It’s great to see Sir Winston get some of the respect that he deserves. Especially after certain American politicians showed supreme disrespect to him and to Britain in recent years. http://tinyurl.com/djhsbc Some of us mark November 30 on our calendars.

But also, Mr. Thomas points out that Churchill had skills and qualities that seem to be forgotten or even ridiculed by modern men. Many of us would rather be stripping down an engine, playing football because it’s so darn manly, guzzling beer or doing other things that “prove” manliness. In fact, it’s gotten to the point that some guys feel they have to purchase Estrogen Offsets of some kind because they dared to read a good book or indulge in the arts. Anybody with a grain of sense can see that Winston Churchill was not only a “real” man, but had many qualities and skills that could be emulated.

In my mind, he was a bit of a cowboy because he would do what needed to be done. Sometimes it was considered reckless, often controversial, but he would take swift action because he believed it was the right thing to do, and do it NOW.

4 Will July 10, 2009 at 7:57 am

Great article. But I do want to know: what is “get off my lawn” syndrome?

5 Steve Treacle July 10, 2009 at 8:04 am

He was, of course, both a heavy drinker and a manic depressive. In many respects, he was a complete nutter but this, of course, was just what Gt Britain needed to deal with Hitler.

I am a great fan of his put-downs, for example:

Lady Astor: Sir, if you were my husband, I would shoot you.
SWC: Madam, if I were your husband, I would shoot myself.

Lady Astor: Sir, I do believe you are drunk.
SWC: Madam, I believe you are ugly. The difference is, in the morning, I shall be sober.

David Lloyd George: Mr Churchill, please may I borrow a penny to telephone a friend.
SWC: Sir, you may have tuppence, and phone both of them.

6 jonathanwthomas July 10, 2009 at 8:10 am

“Get off my Lawn” syndrome refers to that mean old man down the street who’s always yelling at those young whipper snappers to get off his lawn, simply because he’s an old cranky man.

7 thehuhman July 10, 2009 at 8:31 am

I enjoyed this brief refresher on the great man. Unfortunately, we forget.

8 Nonconformist July 10, 2009 at 8:44 am
9 Rod July 10, 2009 at 10:57 am

The Churchill family to this day quotes, “A change is as good as a rest.”
Churchill’s grandson is a not insignificant politician in his own right.

10 Eric Vincent July 10, 2009 at 11:36 am

Disappointed the article said little about where Churchill came from in terms of his own development. As a young man he was a wastrel, showing little character or potential for any real achievement. His exasperated mother confronting him with the statement (if I remember correctly) that he wasn’t worth the air he breathed shook him enough to reexamine his life and begin the process of personal development that gave us this magnificent lion of a man. In light of this, the arc of his life is even more impressive.

11 Uberhack July 10, 2009 at 1:26 pm

Wish you had included the famous portrait photo by Yousuf Karsh. Possibly one of the most iconic portraits of a notable figure ever.
The story goes the Karsh was having a terrible time getting a decent pose out of Mr. Churchill. Finally, Karch walked up to Churchill, snatched the ever-present cigar out of his hand and quickly snapped this photo:

12 Dan July 10, 2009 at 1:50 pm

Churchill’s insults were some of the most well-crafted gems of all time… On Clement Atlee–his successor to PM in 1945—he said “he is a modest man with much to be modest about” and “An empty taxi arrived at 10 Downing Street, and when the door opened, Attlee got out.”

13 jaytee July 10, 2009 at 5:24 pm

I’ve always admired Churchill. Unfortunately they have omitted my favorite photo of him.
There’s a great picture of him in a suit and top hat, with a big cigar, a smile and a
Thompson submachine gun.


14 Neil July 11, 2009 at 5:17 am


Churchill is (despite his many flaws) one of the greatest men of the modern world. His gift to the western world being the fact that it is still free. The UK was the catalyst for defeating the forces of evil and oppression in WWII (the only country to oppose all the axis powers from start to finish). It would of course be naive to try and ignore the decisive contribution and sacrifice of our friends in the USA (and unpalatable as it is, the oppressive regime of the USSR).

Listening to some of his speeches (e.g. the ones he gave in America to try and rally support) is an incredibly moving experience to this day.

15 Perspective July 11, 2009 at 12:06 pm

@ Nonconformist

Being a nonconformist for the sake of it isn’t as great as you might think. I’ll take Churchill, with all his faults, over Lew Rockwell or Pat Buchanan every day of the week.

Also, no one has yet mentioned my favorite Churchill comeback:

Lady Astor: If you were my husband, I would put poison in your tea.
Churchill: Madam, if I were your husband, I would drink it!

16 R. J. Vincent July 11, 2009 at 11:57 pm

Churchill is one of the all time great men. His writing, oratory and diplomatic skills are legendary. Yes, he had his flaws and suffered from depression but he overcame them and kept his depression at bay. As to his drinking, I remember reading a quote by him that went (if I have it right): “I have taken more from alcohol than it has taken from me”. I’ve heard recordings of his speech about the Battle of Britain and every time I hear it, I get chills up my spine. I also love his way with the well crafted insult. We all should be able to have such great put downs. I wish I could have met him.

17 Perry Clease July 12, 2009 at 12:55 am

He has always been one of my heroes, since I was 9 or 10 years old, and I am a “Yank.” When he was a teenage student he was a championship boxer, marksman, and horseman including cavalry riding and polo. He was well read and studied history. He was very brave, almost reckless, and saw military action on the India-Afghan border, the Sudan, and France during WWI. During the Boer he was a war correspondent for a newspaper and was on a troop train that got ambushed; he rallied the troops and led many to safety, going back for wounded he was captured. He escaped from the POW camp and made it back to British lines. He then rejoined the Army. Youngest person to be named Chancellor of the Exchequer/Treasury. One of the few foreigners to appear on a US Postage Stamp, and there was US Navy destroyer named after him.

He was intelligent and brave, not without his faults nor mistake free, but still one of the greatest men of modern times.

18 Nicky July 12, 2009 at 10:14 am

I agree that the man had flaws, and he had skills that men would do well to learn. Or at least respect. Some of the things he said should have been heeded, then and now.

“I am certainly not one of those who need to be prodded. In fact, if anything, I am the prod.”

“Man will occasionally stumble over the truth, but most of the time he will pick himself up and continue on.”

“An appeaser is one who feeds a crocodile, hoping it will eat him last.”

“You have enemies? Good. That means you’ve stood up for something, sometime in your life.”

“Socialism is a philosophy of failure, the creed of ignorance, and the gospel of envy, its inherent virtue is the equal sharing of misery.”

19 Mike M. July 12, 2009 at 8:43 pm

If you want a good Churchill read, try “The World Crisis.” Everybody knows about his activities in World War II…but he was First Lord of the Admiralty at the start of World War I.

And there is one of the greatest Churchill tales. He lost the Admiralty post in 1916 (IIRC) over the failure of the Dardanelles assault. Spent a decade in various other Cabinet posts in the ’20s, spent a decade out of power in the ’30s. But never trusted with ultimate responsibility…until the catastrophe of World War II. Churchill returned to the Admiralty, to the post he had lost over twenty years before.

And took a path that would make him the greatest of Britons.

20 Art Gonzalez July 13, 2009 at 12:51 pm

What a fantastic post! Along the lines of standing up for what you believe and believing in the greater good, the other day I was listening to a speech-podcast by Joel Osteen called “Uncommon Faith” which I highly recommend to everyone here.

Many blessings,

Art Gonzalez

21 Perry Clease July 13, 2009 at 2:07 pm

“If you want a good Churchill read, try “The World Crisis.”

I also recommend “The Last Lion”

“He lost the Admiralty post in 1916 (IIRC) over the failure of the Dardanelles assault”

I think that he resigned, but whatever happened he next rejoined his regiment and served in the trenches. I guess that it as kind of an atonement or something along those lines.

I think that forcing the Dardanelles was the right idea, but wrongly executed. Had it succeeded then maybe it would have broken the stalemate in France and maybe the Russian Revolution would not have happened.

22 Steve Anthony July 13, 2009 at 4:46 pm

My two sons refer to me as a Churchill “sack rider”. Guilty as charged.

23 Greg T July 13, 2009 at 6:26 pm

My favorite war of words was between Churchill and George Bernard Shaw. Shaw sent Churchill two tickets for the opening night of his new play, “for you and an friend, if you have one.” Churchill sent his regrets saying would like two for the second night “if there is one.”

24 Matt July 14, 2009 at 10:42 am

Interesting post and comments.

I’d recommend a radio show based on minutes of the wartime cabinet meetings that you can get here:

The show’s both interesting and entertaining. I was surprised by the extent to which Churchill’s government was very much a Cabinet government.

You get a sense of the difference then between a Prime Minister and a President, of Churchill striving to get a consensus, and sometimes not getting his own way. You could argue this makes for better decision making, at least, in a British context

25 FP July 16, 2009 at 10:47 pm

Small point of pedantry – Churchill actually lost the 1950 election. It was 1951 when he was re-elected as Prime Minister.

26 Raz Shafer July 17, 2009 at 2:50 am

Winston was without a doubt one of the manliest men of all time. I’ve studied him extensively and wrote my college senior thesis about him. Such a great role model in so many areas.
On a side note, he achieved that level of greatness with very little assistance or encouragement from his parents. They gave him a nanny when he was pretty young. His mother neglected him, not even willing to come see him at his boarding school when he sent letters begging her to come at the age of 6. His father had syphilis which went untreated and caused dementia which caused him to be always critical of Winston and never give approval of anything he did.

27 BlackTiger August 27, 2009 at 8:35 pm

I am proud that he was part-AMERICAN in blood, wholly British in temper, and doggedly Determined in Character. Flaws? Yes, but who doesn’t have a few? Frankly, there are too few like him on EITHER side of the Atlantic (or any other body of water).

BTW: a friend recommended Churchill’s techniques of presentation as illustrated in an excellent book on Public Speaking (as a Manly Art): James C. Humes’ “Speak Like Churchill, Stand Like Lincoln” (Three Rivers Press). After ONE night’s reading of my local library’s copy, I KNEW I should add it to my personal library – and I sincerely recommend it. Get. This. Book. Immediately. Now! (Amazon has them in stock at the time of this posting).

28 kultron September 13, 2009 at 6:47 pm

Ok guys, sending thousands of men to die in Turkey for the most absurd reasons makes a real man eh? The last one in a very long line of British butchers, who made thousands die (whether it be their own people or others) for their own pointless gains.

29 Liam September 25, 2009 at 10:44 am

“Success is the ability to go from one failure to another with no loss of enthusiasm” has long been a maxim of mine!

Truly one of the greatest Britons in history.

30 Robbo September 25, 2009 at 10:45 pm

“He rose late, worked in bed in the morning, took a bath and nap in the afternoons and worked into the night, often until 4 am”

This is how I prefer to operate too. I knew I was on to something!

31 Luke - AspiringGentleman September 30, 2009 at 1:01 am

Another lesson: smoke a single cigar enough and they might even name it after you.

32 Jayne Irwin June 29, 2010 at 11:23 am

The American people need to follow Winston Churchill’s example and never give up!
No matter what we must stand against anyone trying to take over our politics, our Government and especially our God, and Jesus Christ.


33 Lefty July 10, 2010 at 3:25 am

In the comments, I read repeatedly “he had his faults.”

Is there a man that doesn’t ?

34 Simon July 11, 2010 at 9:57 am

Did you know that the voice we hear in the famous speeches is a radio actor who was employed to read Churchill’s speeches on the air to the public?

The original speeches given in Parliament weren’t recorded.

Sorry to spoil that for anyone.

35 The Doctor July 12, 2010 at 7:52 am

Mention Churchill and the Churchill myths come out yet again.

Alcohol abuser? http://www.winstonchurchill.org/learn/myths/myths/he-was-an-alcohol-abuser
An actor read his speeches? http://www.winstonchurchill.org/learn/myths/myths/an-actor-read-his-speeches

36 The Doctor July 12, 2010 at 7:58 am

Amazing how many myths, disguised as fact, are still bandied about as soon as a complimentary article to the man is written. Check out: http://www.winstonchurchill.org , scroll down, and find “Leading Churchill Myths.”

As for the utter, venomous nonsense spewed forth by Kultron, it hardly merits mention save that even a cursory study of history would disprove your statements, as well as the label of “butcher.”

37 The Doctor July 12, 2010 at 7:59 am

My apologies for the double post. Something slagged on my end and I didn’t see the first post until I had put the second one.

38 The Doctor July 12, 2010 at 8:01 am

@ Lefty – I noticed that too, and find it endlessly interesting. It’s as though we have to make sure we point out good and bad, as though we’d be guilty of abject hero worship if we didn’t take the opportunity to point out bad things about people.

What’s wrong with simply admiring someone’s good points, while realizing that, as a human being, they MUST have had bad ones?

39 The Doctor July 12, 2010 at 8:19 am


Perspectives, yes. Easy to make some, what, 60-80 years AFTER the fact, in the security of your home with your word processor? Yes.

And while we’re on perspectives… http://www.winstonchurchill.org/learn/books-about/we-read-them-so-you-dont-have-to/the-fine-art-of-selective-quoting

40 The Doctor July 12, 2010 at 8:21 am
41 Meg August 17, 2010 at 12:16 am

I’ve always admired Churchill for the way he dealt w/ depression. I had no idea he was an artist as well!

42 Carlo Gambino January 13, 2013 at 4:58 am

Interesting article.I agree with most of the ideas you have put forward here,they make a lot of sense and are helpful.However, He this article seems to be very biased and is intent at boosting the ego of Winston admirers especially when comparing Winston’s to Hitler’s art! r

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