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c. 1920s

The real Christopher Robin and Winnie the Pooh

The difficult backstory of one of the world's most iconic children's characters

Winnie the Pooh author A.A. Milne's son, Christopher Robin, sitting at home with his teddy bear.

In 1933, when he was 13, Christopher Robin learned to box. It was a skill he urgently required in order to defend himself from the unending attacks from boys at his boarding school.

Those attacks were generated because his childhood, and in particular his childhood toys, had become public property. He—or rather the fictional Christopher Robin—had become internationally beloved through the stories and poems of his father, Alan Milne.

Even before the success inspired by his son, A.A. Milne was a playwright and author of some standing.

Even before the success inspired by his son, A.A. Milne was a playwright and author of some standing. Marrying Daphne de Selincourt in 1913, he fought in WWI, and was wounded in the battle of the Somme.

But it was after the War that Milne became far more than another professional writer. Christopher Robin was born in 1920 and, taking his son’s toys as inspiration, Milne wrote two books of children’s poetry, and two books of stories—Winnie the Pooh, and The House at Pooh. 

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Writing for children was an entirely new departure. But he needn’t have worried —the entire world loved them.

The entire world—except, that is, for Alan Milne, and Christopher Robin. Milne was deeply frustrated that his name as a mature writer was now utterly eclipsed by nursery stories. 

As for Christopher Robin, he would eventually cease talking to his parents altogether, resenting what he saw as the exploitation of his childhood by his parents.

Daphne, his mother, did not communicate with Christopher for the last 15 years of her life, and refused outright to see her son on her deathbed. Christopher lived in relative seclusion running a small bookshop with his wife, until his death in 1996, aged 75.

Winnie the Pooh, meanwhile, went onto become the most valuable fictional character of all time, generating in excess of $3 billion each year. The character even has a star on the Hollywood Walk of Fame.

And what of the the original toys — Winnie the Pooh, Pigley, Eeyore, Tigger and Kanga?

They still exist. 750,000 people see them every year, on display in the New York Public Library, behind bulletproof glass.

1920s
A.A. Milne entertains his son in the nursery, Hartfield, East Sussex.
PA Images / Getty Images
1925
A.A.Milne with his son at their home in England.
Getty Images
1920s
Christopher Robin, sitting at home with Pooh.
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1920s
Christopher Robin Milner feeds Winnie the Pooh a biscuit.
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1925
Christopher Robin playing in a toy canoe in his nursery.
Sasha / Getty Images
1926
Daphne Milne hugging her son, Christopher Robin.
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1948
Christopher Robin Milne, and his fiancée Lesley de Selincourt.
J. Wilds / Keystone / Getty Images
1950s
A.A. Milne as an older man
Keystone / Getty Images
1981
Christopher Robin Milne unveiling a statue of a bear, in honor of his father A A Milne and his creation Winnie the Pooh, at London Zoo.
Keystone / Hulton Archive / Getty Images
1950
The real Winnie the Pooh
George Skadding / The LIFE Picture Collection / Getty Images

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