this seemingly underperforming
boy. The punishment book from Harrow and letters from the headmaster
to Churchill’s mother, trying to recruit her help in getting her somewhat-
irregular son to attend classes, would seem to confirm this view, one
which – helped by Churchill himself – has since taken on the status of myth.
In fact, Churchill excelled at the subjects he enjoyed – English literature and
history – even if maths and classics puzzled and bored him. His astonishing
memory, his indefatigable energy and, above all, his unflagging belief in
the dictum that he gave in his speech to Harrow schoolboys in the Second
World War – “Never, never, never, never give in”– ensured that sooner or
later he would realise his full potential.
Lady Randolph Churchill and
young Winston, aged two, in
Ireland, 1876.
“My mother always seemed to me a fairy princess: a
radiant being possessed of limitless riches and power.”
“[A]s a child my nursemaid could never prevent me from taking
a walk in the park when I wanted to do so. And as a man, Adolf
Hitler certainly won’t.”
“A woman is as old as she
looks; a man is as old as
he feels; and a boy is as
old as he is treated.”
Winston in a sailor suit, 1881.
A young Churchill with his
younger brother, Jack, and a
friend, circa 1882.
“I shall believe I am to be
preserved for future things.”
A debonair Harrow schoolboy,
aged fourteen, 1889.
Opposite left: Though an
extraordinary wit, he never played
the clown on the world stage.
Sandhurst, May 1894.
Opposite right: Lady Randolph
Churchill, born Jeanette Jerome
in Brooklyn, New York, on 9
January 1854 and known as
Jennie. Pictured here with her
two sons, Winston (on the right),
aged thirteen, and Jack, seven.
After Lord Randolph’s death, she
married twice more. She died in
1921, aged sixty-seven.
“We are all worms. But I do
believe that I am a glow-worm.”
“My mother made the same brilliant impression upon
my childhood’s eye. She shone for me like an evening
Star. I loved her dearly – but at a distance.”
Left: Mrs Everest, or ‘Woomie’,
Winston’s beloved nanny and
confidante. ‘Woomie’ was short
for ‘Woomany’, which seemed
to combine ‘woman’ and
‘home’, which she represented
to him. On her death, Winston
said he had lost “my dearest
and most intimate friend
during the whole of the twenty
years I had lived”.
Opposite: Winston (second
row, second from left) leaning
on his elbow at the school
of the Misses Thompson, on
Brunswick Road, Brighton, in
November 1886.
“My nurse was my confidante. Mrs. Everest it was
who looked after me and tended all my wants. It was
to her I poured out my many troubles.”
“[T]his interlude of school makes a sombre grey patch
upon the chart of my journey. It was an unending
spell of worries that did not then seem petty, and
of toil uncheered by fruition; a time of discomfort,
restriction and purposeless monotony.”
“I am always ready to learn, although I do not always like
being taught.”
Churchill with a grin, circled,
peers at the camera from a
staircase in his last year at
the Headmaster’s House at
Harrow, 1892.
“[O]ne must never be
discouraged by defeats in
one’s youth, but continue
to learn throughout one’s
whole life.”
Winston in his Harrow uniform in
1891, ready to collect a prize.
SOLDIER
A
s the end of his school years approached, a poor academic record, domineering father and youthful enthusiasm for all things military combined to push Churchill into applying to join the army. However, this was not a straightforward process – he failed the entry exams for officer training twice and even contemplated
a career in the church. With the help of a tutor, he finally passed on the third attempt – but only with enough marks to go into the cavalry, not the more highly regarded infantry.
Joining the military was the natural course for a boy who played toy
soldiers throughout his life, both metaphorically and literally. Typical of
an approach