Winnie the Pooh and his friends are some of the most beloved characters of children’s literature. Before the myriad of cartoons and animated movies, toys and theme park rides, there were children’s books with simple but moving line drawings that brought these adorable creatures to life.

These books are so influential that they completely overshadowed their creator, who has always be known by his initials and, to most people, not much else. In this article, we’ll dive in to the background of this mysterious and endeavour to separate fact from fiction.

Alan Alexander Milne was born on the 18th January, 1882 in Kilburn, London. His father ran a local independent school, Henley House, which he also attended. He won a Maths scholarship to Trinity College, Cambridge, where he graduated in 1903. There he edited and wrote for Granta, then a student magazine. This caught the attention of the editor of Punch, a popular British humour magazine. He became a contributor there. He began writing steadily. The first iteration of Pooh stories were published in 1924, in a collection called A Gallery of Children, and would continue to appear sporadically in other poems and periodicals. About this time, the British actor Leslie Howard described him thusly:  “...About 35–certainly under 40. Blond and very boyish in appearance. He is very shy and retiring–as shy as Barrie [J.M. Barrie], who is one of his best friends."

Milne, Christopher and Winnie

At 27, he married Dorothy de Sélincourt and they had their only child, Christopher Robin, in 1920. When Christopher was five years old, they would settle at Catchford Farm in Sussex. There, as their young son grew up, Milne began writing stories based on Christopher’s stuffed toys. The principle of which was “Winnie”, named after a black bear in London Zoo during the war, and whom Milne and Christopher enjoyed visiting. “Pooh” evidently came from the name of a swan he liked to feed at Decoy Cottage in Sussex. The others — Piglet, Eyesore, Kanga, Roo and Tigger — also made up Christopher’s menagerie of soft toys. Their home, The Hundred Acre Wood, was inspired by Ashdown Forest, which the family lived on the edge of. His illustrator, E.H. Shephard, would draw on this for inspiration. In fact, the illustrations depict the forest as virtually identical - thousands of visitors every year flock to Pooh Bridge. 

Winnie the Pooh was published in 1926, followed by The House at Pooh Corner two years later. E. H. Shephard’s illustrations are nearly inseparable from the books, creating the lasting vision of Pooh and his friends. Shephard actually used his son’s teddy bear “Growler” as his inspiration for his drawings of Pooh. 

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The success came as a surprise to Milne, and he wore it uneasily. Once he had published four Pooh books, he was unwilling to capitalise on their success, and also disappointed that the books eclipsed all his other writing. He was also distressed by the fame this brought to Christopher, especially as he became older. Sadly, this would have a lasting effect. Both Milne and Dorothy would later become estranged from Christopher, who felt he had been exploited during this childhood. Christopher received mountains of mail from young fans, of which he would reply to with the help of his nanny. He acted in pageants and radio plays, playing himself. 

So what happened after Milne stopped writing Pooh books? Christopher went to boarding school, where he was teased often for his fame. And he wasn’t even much like his fictional character. His family called him Billy Moon, not Christopher (“Moon” because he could not pronounce “Milne”). But Shepherd’s illustrations do depict his likeness perfectly. After university, moping and directionless, he grew increasingly bitter at his lot in life, for which he blamed his father. He felt perpetually trapped, unable to escape the confines of boyhood. He later married his first cousin, and they opened a bookshop together in Darmouth, where he would agree to sign books in exchange for a donation to Save The Children. In 1974, he wrote an autobiography, called The Enchanted Place. He and his wife Lesley would have one child, Clare. They continued to run the bookshop until 1983, and it finally closed in 2011.

Milne would die at the age of 69 and was buried at All Hallows-by-the-Tower in London. Shortly after his death, his wife would sell her rights to the American tv and movie producer Stephen Slesinger, whose own wife would licence the rights to Walt Disney. And as they created ever more Pooh books, tv shows and films, the stories have continued to grow in popularity. The Slesinger family would later take Disney to court in 1991 for breach of contract, claiming they had been short-changed by Disney and were owed damages of $2 billion. After 18 years of legal battles, the court ruled in favour of Disney.

While Pooh’s legacy has been rather oversaturated by Disney, the books retain their beauty, humour and gentle wisdom.

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