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The True Story Behind Winnie The Pooh: Struggles Of The Real Christopher Robin

True Story Behind Winnie The Pooh and Christopher RobinEver heard of Winnie The Pooh? I’m guessing you answered yes to that :). I think it would be hard to find a person out there who hasn’t heard of loveable yellow bear with the round stomach and massive addiction to honey.

The adventures of Winnie The Pooh and his friends Eeyore, Piglet, Tigger, and Christopher Robin in the Hundred Acre Wood are so popular that they’ve become a part of people’s childhood memories.

But what most people don’t know is that there’s actually a true story behind it all…


Picture of the real Winnie The Pooh and Christopher RobinTo find out the true story behind Winnie The Pooh we have to go all the way back to the year 1920 in England, on the day a boy named Christopher Robin came into the world.

From the day he was born Christopher Robin had problems with his parents. They had the perfect little dresses and dolls in mind for their expected little girl, and a the perfect name, Rosemary, picked out for her. But instead of a beautiful little little girl they got a boy instead.

As he grew older it seemed hard for his parents to let go of their disappointment. His mother would often want him to dress in girly clothes, with a girl’s haircut. And his father was the first to admit that he didn’t even like children in the first place, so it was especially hard for him to bond with his ‘surprise’ son. He was a successful writer, and preferred to spend time on stories and poems rather than deal with the awkwardness of being around his young son.

It’s not that Christopher Robin’s parents didn’t love him but… let’s just say that they liked to keep their distance most of the time. So growing up he ended up being taken care of by a kind woman named Nanny Olive and usually only got to see his parents a couple times each day for short periods.


Picture of the real bear Winnie The Pooh was named after.With his parents out of the picture for much of the time, Christopher Robin relied on two things to get by during his childhood: the doting attention of Nanny Olive, who he secretly considered to be his ‘real’ parent, and the adventures that his imagination would take him on.

He loved to to run around a place called Ashdown Forest (which is basically the Hundred Acre Wood, only 5 times bigger) and have adventures with his stuffed animal friends… Winnie, Eeyore, Tigger, Piglet, Kanga, and Roo. Winnie was his absolute favorite and had been named after a famous bear he’d seen at the zoo. The bear had been adopted by a soldier in World War I and had traveled to England all the way from Canada.

Winnie The Pooh and Christopher Robin Playing Pooh Sticks true storyEven when Christopher Robin wasn’t in Ashdown Forest he would imagine that he and his friends were back there having a blast jumping over streams, exploring new places, and of course, standing on a bridge playing Pooh Sticks.

Christopher Robin loved to create elaborate adventures for himself and his friends. It was a magical, happy, time whenever he would be with Winnie and the others. So magical in fact, that it even caught the attention of his normally distant father. Imagine how thrilled Christopher Robin felt when his father announced he’d be writing about the adventures with Winnie and the others!

So ironically, the man who felt awkward around children ended up writing a book of stories for children. And he was quite good at it too. In no time Winnie The Pooh, Piglet, Tigger, and all of Christopher Robin’s stuffed animal friends became famous around the world.

The Real Winnie The Pooh Eeyore Tigger Piglet Roo Kanga

And alongside them Christopher Robin became famous as well. The stories were so popular that he was named one of the most famous children ever, alongside the children of people like kings and queens. But there was a price for all this fame.


Illustration from Winnie The Pooh book.Christopher Robin had never felt happier. He now shared something very special with his father and was often the center of attention when he was around other people. News reporters would come to his house to try and find out more about the kid behind the Winnie The Pooh stories, and he got tons of fan mail from all corners of the earth.

He rode the wave of fame happily, but it all came crashing down the moment he started school. Like most kids around him he was sent to boarding school at 8 years old, but unlike the other kids from the moment he stepped foot into the school he was bullied relentlessly. There were many kids who were jealous of his fame and wanted to make sure he knew his place. Here was Christopher Robin, a gentle, soft-spoken kid who was used to having adventures with his stuffed animals under the protection of his beloved Nanny Olive. But all those things were gone now, and he was on his own at boarding school.

The face of the real Christopher Robin as a childThe Winnie The Pooh stories that had made him the center of attention at home transformed him into an easy target at school. He couldn’t walk down the hall or even simply sit in his room without someone mocking him with quotes from the books that had made him famous.

The bullies ramped things up more and it got to the point were he was being beaten up over the Winnie The Pooh stories. Year after year this happened and Christopher Robin couldn’t help but to shudder at anything to do with
Winnie The Pooh. Things looked different to him now, and he watched with growing resentment as his father gained fame and money for the stories while he had to keep dealing with bullies. What had once been something special shared between him and his father, now became a big rift.

Picture of cover of the original Winnie The Pooh book of stories.Eventually he got in shape and studied boxing so that he could learn to fend off the bullies, but the relationship with his father continued to deteriorate. Christopher Robin graduated from school. He joined the army and survived being in World War II. He started a family and his own business. Still, the cold reality of fame followed him at every turn.

It seemed to me almost that my father has got to where he was by climbing upon my infant shoulders.

That he had filched from me my good name and that had and had left me with empty fame of being his son.
–Christopher Robin Milne

He was hounded by reporters and fans who wanted to connect with the innocent young Christopher Robin of the Winnie The Pooh books, but instead they found a grown man who was simply weary of the whole thing. He even got angry letters from people who insisted that he force himself to be happy about being the real Christopher Robin. Try as he might though, Winnie The Pooh reminded him of how his father hadn’t spent much time with him as a child, yet was able to gain fame from his imaginary world. But would he really live out the rest of his life like this?


Book cover of true story Written By Christopher Robin MilneIt turns out that the thing Christopher Robin needed was the very thing that had caused him so much trouble in the first place. After spending so many years of suffering because of a book inspired by his young life, he decided to sit down at the typewriter and write his own book about it at age 54. Not a fiction book like his father had written, but one about what really happened in his childhood, and to tell things as Christopher Robin the real boy had experienced it.

On January 1, 1974 his book The Enchanted Places was published. The first day of the year was a fitting time for it to be released, as it started off a new lease on life for him when it came to all things Winnie The Pooh. Being able to get his own story out to the public helped him come to terms with the fame and the bad memories, and he was able to start enjoying Winnie The Pooh stories again.

The Real Christopher Robin Grown UpAfter a while he started to make public appearances at Winnie The Pooh related events, and people were thrilled to see him. He would never be able to forget all of his suffering, but talking about it through his book helped to bring back the magic and innocence of his childhood adventures, and let him start to enjoy the stories once more.

He even started to play Pooh Sticks again, just like when he was a boy.