"I was no more consulted about leaving home than I had been about coming into the world."
Boarding school was the routine for boys of Winston's class, and he was packed off in 1881 at age seven. He hated every minute of it.
His first school, St. George's, was brutal - "Flogging with the birch... was a great feature in its curriculum." Of school Winston would write, "It appears that I was to go away from home for many weeks at a stretch in order to do lessons under masters... After all I was only seven, and I had been so happy in my nursery with all my toys. I had such wonderful toys: a real steam engine, a magic lantern, and a collection of soldiers already nearly a thousand strong. Now it was to be all lessons..." He lasted less than a year when he withdrew for health reason.
He entered his second school in 1882, Brighton, which was more benign and he finished his elementary education there. Winston enrolled at Harrow in 1888 with very poor entrance exam scores, effectively placing him at the bottom of his class. This was a humiliating position for a proud boy, and an irritation to his father.
Winston possessed a keen mind, but also a spirit not suited to school regiment. However, he excelled in subjects that appealed to him - English and History. He also showed athletic ability by winning the Public Schools' fencing championship. The school newspaper reported, "His success was chiefly due to his quick and dashing attack, which quite took his opponents by surprise."
Winston's school days were deeply frustrating. "...I had hardly ever been asked to learn anything which seemed of the slightest use or interest, or allowed to play any game which was amusing. In retrospect those years form not only the least agreeable, but also the only barren and unhappy period of my life."
"For years I thought my father, with his experience and flair, had discerned in me the qualities of military genius. But I was told later that he had only come to the conclusion that I was not clever enough to go to the Bar."
For young gentlemen of Winston's social class only certain professions were considered suitable. The university was the gatekeeper to all but the military, and Winston's poor performance at school closed the university's doors to him.
Winston's lack of attention to studies nearly ended his military career before it began. He took three attempts to pass the entrance exams for the Royal Military College, Sandhurst, scoring just enough points to be admitted to the Cavalry, but not the Infantry.
Lord Randolph had hoped for at least an infantry career for his son, and was deeply disappointed.
The Cavalry became a source of both joy and tension for Winston. Riding became a passion and he proved exceptionally good at it. However, since the British Officer had to pay for his own uniforms and horses, Cavalry service taxed his family's financial resources.
But, at Sandhurst Winston finally hit his stride, applying himself to subjects that interested him and earning good marks. Sandhurst's eighteen months of practical studies concluded Winston's formal education, and he graduated 20th out of 130.