Winston Churchill: The Anti-Keynes

“We make a living by what we get, but we make a life by what we give.”—Winston Churchill

Winston Churchill
Winston Churchill: The Money Bulldog

If you have ever visited the small town of Woodstock, to the north of Oxford in England, then the chances are you will have seen Blenheim Palace and its grounds. Not all of them, unless you had a very long time to fill. This emblem of British wealth and might extends to around 2,000 acres, features colonnades, turrets, towers and ballrooms in its main building, while statues and follies grace its ground.

It is the home of Winston Churchill, indomitable British Bulldog; conqueror of the most wicked regime to ever threaten the world—Nazi Germany; Prime Minister; and fearless soldier and author. History’s greatest Englishman (in the view of the English, at least). Surely, with such a career, such a home, Winston Churchill epitomizes financial success?

Or not.

Was Winston Churchill an impeccable man who overcame stuttering in his childhood and defeated the Nazis? Or a bullish chancer, an outspoken bully who got lucky when it mattered but often failed at what he sought to achieve? The answer, probably, is a bit of both. It is just that defeating Hitler rather skews things in his favor. Naturally, therefore, less attention has been paid to his financial life than his political or military achievements. Considering the immense success that Winston Churchill had in his career as a soldier, writer, war leader and politician, was he effective when making financial decisions in his personal life? As the grandson of a duke, did he inherit fortunes? How did he live? Surrounded by manservants and housemaids? Brought up largely by a nanny (then again, he was a bit of a disappointment to his father, Randolph, himself a successful politician, but one who died young, probably from syphilis. Meanwhile, his mother was generally busy in her “social” life, one which was certainly extremely social.)

Churchill’s Formative Years

Young Winston Churchill was born into aristocracy; his father was the Duke of Marlborough. He was also a firebrand politician, womanizer and bully; his mother, Jennie Jerome, was an American socialite.

Winston was never a good student. A rebellious streak lived in him, something not tolerated in the realm of the British public school system. Following beatings and obstinance, he changed his boarding prep school (a type of school for the wealthy elite of British society, catering to children—boys in those days—up to the age of 13. It is highly ironic that the “public” schools were anything but public). At one boarding school, as was the custom on Parents’ Day, the students were marching in in academic order—Winston was last—to the full amusement to the other parents whom all knew his father, Lord Randolph. One of his tutors complained, that, though acknowledging Winston’s raw intellect, bitterly complained about his lack of discipline, his irregularity, his desire to learn only the things he wanted to learn. The tutor concluded that these would pose an insurmountable barrier to his future career—if he could find any. Clearly a fine judge of character.  

In particular, learning Latin or Greek was a menace to Winston—later he would be proud of his resistance to traditional schooling and the studies of the classic. “No one ever made me write a Latin verse, and I never learned Greek beyond the alphabet!” he said in his characteristic growl.

Churchill’s father was an Eton man. Unusual for a boy with an aristocratic background, the Berkshire hive of privilege turned him down, and he was forced to attend Harrow instead. This was, in those days, considered home to the rich, but less talented and without the promising future of an accomplished political career. It was a failure to which Randolph would often refer.

Although generally school was a chore, there was one subject in which he excelled. That was English. He also displayed a love for history—military history in particular. From Harrow, he was considered clever enough only to enter a military academy, rather than a University (another cause for criticism from his father) and joined the exclusive home to Officers in the making, Sandhurst.

So began a distinguished military career that would bring forward a different side of his character. It was during the early days of this military career that his nanny, whom he called Woomany, died. Once Winston had been sent off to school, Woomany had been dismissed from service. It is a sign of Winston’s softer side that he financed the remainder of her life and made sure that could visit her on her deathbed and arrange for her funeral.

Like many ambitious young men of his time, he wanted to see military action, and his wish would be granted. Wounded, captured and eyewitness to the consequences of modern warfare, Churchill developed additional character traits of fortitude and strength of mind that would serve him throughout his political life.

It would also bring out another trait that would follow him throughout his life—in good as well as bad times—Churchill the gambler. Churchill’s calculations and decision-making were decided mostly on gut instinct rather than evidence or common sense; even sometimes self-preservation. On one well-documented occasion, serving in Africa, he rode up and down in front of enemy guns, while the opposition shot at him. On another, he led a cavalry charge that should, by all standards, have resulted in the slaughter of himself and his men. The impetuosity of the act seemed to subdue the enemy into subservience, and the charge was successful.

But it was when stationed in India, that he found his true passion: reading. Being fed by his mother one book after another, Winston enjoyed reading certain types of books rather than seeking those works that were popular at his time. It is said that he simply focused on a few great novels he would read over and over again, even committing many to memory—a skill that would serve him well later in Parliament, and especially during his great speeches of the war years.  

Despite the apparent spontaneity of these, they were in fact carefully prepared and learned by rote. The book that most likely influenced him the most was Edward Gibbon’s The Rise and Fall of The Roman Empire. Gibbon’s powerful prose can be found echoed in Churchill’s own writings. It was during these formative years as a young cadet, full of dreams and hope and eager for military adventure, that he really developed his style of writing—the powerful English prose for which Churchill today is so famous. It would serve him well financially, as well as securing his place in literary history.

Churchill’s Work and Income


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