The Tragic True Origin Story of Winnie the Pooh

The Tragic True Origin Story of Winnie the Pooh

Shannon Quinn - June 25, 2018

Winnie the Pooh and his best friend Christopher Robin are two characters that are known and loved all over the world. They have appeared in books, poems, cartoons, and movies, and have been translated into dozens of languages. But few people in modern times know that Christopher Robin and Pooh were both very real, and the children’s stories are loosely based on reality.

However, the true story of what went into the making of Winnie the Pooh is much darker than most people could imagine. What started out as a story of childhood innocence turned into a media machine that was out of control. This is a story of a lonely little boy who became a child star and the adults whose careers could never quite match the expectations that Winnie the Pooh places on them.

The Tragic True Origin Story of Winnie the Pooh
A.A. Milne with Christopher and Winnie Credit: Wikimedia Commons.

Alan Alexander Milne, or A.A. Milne for short, was an editor and writer for London’s Punch magazine. He specialized in comedic political commentary. He was also an acclaimed playwright. Audiences loved his clever wit, and he made a name for himself in the industry. He married a socialite named Dorothy de Sélincourt, or “Daphne” for short. She was estranged from her extended family and focused instead on the joys of living among the London upper-class- going to parties, re-decorating her home, and so on. The Milnes enjoyed having a marriage where they acted like they were still single. They each spent time with their own friends, and they would go on dates to parties and to see the newest London plays. Milne would go to The Garrick Club in London to grab a drink and spend time with his buddies. All was well in the world until A.A. Milne was drafted into World War I.

When he returned, he was traumatized by what he saw in the war. When the war ended in 1918, he wanted to write about his thoughts and feelings against war in general, but no one was interested in reading about it. They wanted to move on from the sadness and loss, and the public wanted more comedy, so he continued to write his jokes and plays. In 1920, the Milnes gave birth to their son, Christopher Robin, but they decided to call him “Billy”, because they had disagreed on a name, and decided it was easier to just call him a nickname. As a young child, he did not know how to pronounce “Milne”, and instead said, “Moon”. So, they called him “Billy Moon”, instead of his real name, Christopher Robin. One of his first gifts was a teddy bear that Daphne named “Edward”, and the boy grew up with it as his companion.

The Tragic True Origin Story of Winnie the Pooh
Christopher Robin feeding honey to the real “Winnie” bear at the London Zoo. Credit: CBC.

Even after having Christopher, the Milnes wanted to go back to the lifestyle they enjoyed before, so they hired a nanny, Olive Rand, to raise their son. They also hired cooks and maids to do all of the housework for them, so there was very little they had to do as parents. In his autobiography, Christopher wrote that his parents never decided to have family outings when the three of them spent time together. If he spent time with his parents, it was always separate. It was during one of these outings to the London zoo with his mother when he first saw a real-live bear from Canada, named Winnipeg. After that day, Christopher decided to call his bear “Winnie”.

The Tragic True Origin Story of Winnie the Pooh
Christopher was just a toddler, playing with A.A. Milne, Winnie, and a stuffed penguin. Credit:

The Beginning of a Life-Changing Adventure

The family was living in London, so Christopher never got to experience what it was like to play outside in the country. A.A. Milne decided that it would do their entire family a lot of good if they bought a summer house in Sussex. The house they bought was 40 miles away from London, and it was just outside of Ashdown Forest. The place is also known as “The Five Hundred Acre Wood“, which obviously served as the inspiration for the fictional “Hundred Acre Wood”. Christopher Robin thrived in this place, and he went on adventures pretending to be a knight on a quest and brought along his stuffed animals as companions.

When the boy was 6 years old, A.A. Milne watched Christopher Robin say his prayers with his nanny before he went to bed. He thought this was adorable, and he wrote up a poem about their son as a gift to his wife. She thought it was beautiful, and insisted that they should publish it. Milne told his wife that if she could find a publisher to accept the poem, she could keep the money to go shopping. This motivated her to send it out to everyone, and she got back an acceptance letter from Vanity Fair magazine. Mothers all over the country had their hearts melted by the sweet poem of childhood innocence, and they wanted to hear more about this little “character” named Christopher Robin. When word got out that this was based on a real person, it made people even more curious.

This was years before anyone knew about the dangers of what child stardom can do to someone’s psyche, and Mr. and Mrs. Milne probably never even considered that the entire world knowing their son’s name and likeness could possibly be a bad thing. A. A. Milne asked one of his co-workers from Punch Magazine, E.H. Shepherd, to visit his summer home in Sussex, and sketch the area around the Five Hundred Acre Wood. The first book he published was a collection of poems, called Now We Were Six, and he went on to make Winnie the Pooh children’s books. This is when Shepherd and Milne both began to brainstorm the possibilities. They invented characters like Rabbit and Owl, who were real animals living in the forest, rather than Christopher Robin’s stuffed animals.

The design for the teddy bear in the books does not look like Christopher’s actual bear Winnie, because Shepherd modeled his own son’s teddy bear for inspiration at home. All of the illustrations were inspired by the real Christopher as he played in the woods. They decided to name the bear “the Pooh”, because of an inside joke of calling a swan “Pooh”.

The Tragic True Origin Story of Winnie the Pooh
Christopher Robin Milne and his teddy bear, Winnie. Credit: Wikimedia Commons.

Newspapers began to photograph Christopher Robin, and conduct interviews which put his real face in the public eye. People began to believe that they knew the real boy, even though all they really knew was the fictional stories. He really enjoyed going to public events. Unlike being lonely and isolated at home, he was surrounded by people who wanted to be his friends. In his autobiography, he wrote about how it was the most amazing childhood anyone could ever ask for. He felt special, and he agreed to just about anything- from starring in a play to recording a narration, to standing in front of large crowds. Since he was having so much fun, his parents could not see the potential harm.

It was only when Christopher’s aunt and uncle spoke up about their concerns that A.A. Milne began to realize that things needed to change. When he was around 8 or 9 years old, they pointed out that he was being robbed of having a normal childhood. Instead of playing outside or having a normal education, he was cooped up in a room replying to fan letters with his nanny. Once he realized it had gone way too far, A. A. Milne made the decision to stop publishing any more Winnie the Pooh stories, and Christopher Robin was sent to a boarding school when he was 10 years old. His father hoped that he could make some friends, play sports, and live out a normal childhood while he was in school. Unfortunately, he was so famous, everyone knew who he was, and they bullied him out of jealousy. No matter how hard he tried to be known as his own person, everyone just identified him as “Christopher Robin” from the books.

The Tragic True Origin Story of Winnie the Pooh
Christopher and Lesley loved each other very much. Credit: The Daily Mail.

Time to Grow Up

After ending the Winnie the Pooh series, people were not nearly as interested in anything else A.A. Milne had to write. He tried to go back to writing plays since they were once his bread and butter. Unfortunately, critics called his main character “Christopher Robin all grown up”, and everything was always compared to Winnie the Pooh. He wrote other books for adults, but none of them ever even got close to the fame of his children’s characters. This made him feel as though people truly knew and loved his son, rather than his writing.

The illustrator, E.H. Shepherd, also had a rough time with his career after the books came out. His real career was being a political cartoonist for Punch Magazine, and he never planned on working in children’s literature. He wanted his legacy to be about his witty humor in political commentary, not for something in a children’s book. Whenever anyone talked about Winnie the Pooh, he called him a “silly old bear“. Even after he died, all of his sketches were auctioned off. Everything that was involved in Christopher Robin or Winnie the Pooh was sold for huge amounts of money, but his political cartoons sold for much less.

When Christopher Robin grew up, he went to Cambridge University, and he served in World War II. When he began applying for a full-time job, every single interview ended up turning into a conversation about Winnie the Pooh. This sickened Christopher, and he just wanted to be a normal person who was judged for their own accomplishments, and not pre-judged based on a fictional version of his childhood self. He resented this so strongly, he refused to take any of the money that the books made.

At 27, Christopher Robin met a young woman named Lesley de Selincourt, who just so happened to be his first cousin. Since his mother was estranged from her family, he never met that side of the family before. So, meeting Lesley was like meeting a stranger, and they fell madly in love with one another. After they got married, his mother Daphne was very vocal about how unhappy she was about their relationship, and she could only talk about all of the reasons why she hated her family. This made Christopher Robin’s relationship with his mom even worse than it was before, and when his father died, he completely stopped talking to her.

Christopher and Lesley opened up a bookstore, and they lived happily on their modest income. Tragically, their first and only child, Clare, was born with cerebral palsy. She was wheelchair-bound for her entire life and unable to take care of herself. Even though he did not want any of the money for himself, Christopher had to accept money from the Winnie the Pooh estate to pay for his daughter’s medical expenses.

The Tragic True Origin Story of Winnie the Pooh
Christopher Robin’s original stuffed animal collection is on display in the New York Library. Credit: Wikimedia Commons.

Walt Disney first bought the rights to distribute the stories from the Milne estate in the 1960s, and they began to come out with the cartoons. The estate received royalties twice a year, and Christopher made sure all of that money went to pay for Clare’s medical treatment. In 2001, Disney officially purchased Winnie the Pooh for $350 million. The money was divided amongst the Royal Literary Society, and The Garrick Club in London, and Clare. Today, Disney makes $2 Billion from selling Winnie the Pooh merchandise every single year.

Today, thousands of people still visit Christopher Robin’s real stuffed animals at the New York Library and explore the Five Hundred Acre Wood, where a large plaque commemorates the memory of Winnie the Pooh.


Where did we find this stuff? Here are our sources:

The Enchanted Places: A Childhood Memoir. Christopher Milne. 1975.

The True Tale of Winnie the Pooh, an unlikely World War One Legacy. CBC. 2015.

Why The Real Christopher Robin Hated ‘Pooh’. Maria Carter. Country Living. 2017.

The Man Who Hated Pooh. Tim Benson. BBC. 2006.

AA Milne and the Curse of Pooh Bear. Amanda Ruggeri. BBC. 2016.

Why the Real Christopher Robin Hated ‘Pooh’? Country Living. MARIA CARTER. JUL 31, 2018

The Story of How Winnie the Pooh Was Inspired by A Real Bear. The Guardian. Lindsay Mattick. Tue 24 Nov 2015

These Are The 100-Year-Old Photographs Of The Bear Called Winnipeg That Inspired The Real Christopher Robin To Name His Childhood Teddy Winnie-The-Pooh. Daily Mail. RICHARD SPILLETT. 17 March 2014

AA Milne And the Curse of Pooh Bear. BBC Culture. Amanda Ruggeri. 28th January 2016