Winnie the Pooh has been beloved for 100 years. But fame wasn’t so enchanting for the real Christopher Robin

Before they became a fixture in children’s literature, Christopher Robin Milne and Winnie were just a boy and a bear, romping around the London Zoo instead of the Hundred Acre Wood. 

In the 1920s, Winnie became a fixture there, friendly enough that her keepers allowed select children to feed and play with her. Her gentleness was likely the result of being hand-raised by an officer in the Royal Canadian Army Veterinary Corps during the First World War. 

The bond between the real-life bear and Christopher Robin led the family to rename his teddy from Edward Bear to Winnie, says Gyles Brandreth, author of Somewhere, A Boy and a Bear, a biography of Alan Alexander Milne published in 2025.

How Pooh earned the latter part of his name has inspired several theories — all well-worn stories that likely hold varying degrees of the truth. As Brandreth tells it, the name emerged during a holiday, around the time Milne had started writing about his son’s stuffed menagerie.

“They [father and son] come across a swan in a lake and the swan, when they tried to feed it, wouldn’t come along,” Brandreth told The Sunday Magazine. “They said, ‘Oh, forget the swan, oh pooh to the swans.’ So it was dismissing the swan — and so you put the Winnie and the Pooh together [and] that’s how the name was born.”

One hundred years after Milne’s first stories about Pooh Bear, Piglet and Tigger were published, the characters continue to enchant readers, ranking as the third best-selling franchise in the world.

Though its origins have a happy beginning in the friendship between then-Lt. Harry Colebourn and the cub he named for his adopted hometown of Winnipeg, the story becomes more melancholy as the Milne family struggled with extraordinary fame. 

A bear, a train and a boat ride

Colebourn bought Winnie from the hunter who had killed her mother, paying $20 in White River, Ont., on Aug. 24, 1914, while en route to training in Valcartier, Que. There, she became the beloved mascot of the Canadian Veterinary Corps, wandering camp hoping someone would feed her apples and condensed milk or posing for photos in the lap of a soldier.

She sailed with the troops to England on Oct. 3, where they continued training at Salisbury Plain.

“She was more or less allowed to roam free; there are reports that she slept, actually, under [Colebourn’s] own cot in the tent,” said Canadian War Museum historian Teresa Iacobelli. 

But obvious logistical issues in sending a bear to the front lines in France led to Winnie’s tenure at the zoo, the first of six bears from Canadian regiments to find a home there between 1914 and 1915. 

“They kind of put a stop to taking bears to England after [1915],” said Gord Crossley, director of the Fort Garry Museum in Winnipeg, home to Colebourn’s original regiment. “But in the early days, pretty much anything went.”

That sentiment also seems to have defined the early days at the London Zoo. Young Christopher Robin would apparently whisper to a particular zookeeper, who would then unlock a series of doors to allow the boy into Winnie’s cage, according to his father’s introduction to Winnie-the-Pooh when it was published on Oct. 14, 1926. 

“Out trots something brown and furry, and with a happy cry of, ‘Oh, Bear!’ Christopher Robin rushes into its arms,” he wrote. 

‘More famous than Harry Potter’

The way Milne captured the innocence and bliss that can only belong to childhood captivated readers. The book became an almost-overnight success, selling more than 150,000 copies in the U.S. alone by the end of 1926, less than three months after its publication. 

But Brandeth said the author grew to resent the way Winnie-the-Pooh overshadowed the rest of his life. Milne wanted to be known for his wider body of work — which included mysteries, poetry and West End plays — not just for his children’s stories.

Worse still was the intense scrutiny that followed Milne’s son, who became one of the most notable children in the world in the 1920s, alongside Shirley Temple and Princess Elizabeth. 

“Christopher Robin was more famous than Harry Potter in his day,” Brandreth said.

Though the boy enjoyed some of the early attention, as Christopher Robin grew up he became the target of bullies at school. Brandreth suggests that one of the reasons Christopher Robin chose to serve in the Second World War was to prove to himself he was more than a storybook character.

Father and son remained especially close from about Christopher Robin’s 10th birthday into his early 20s. But the two drifted apart when the latter came home from war.

Brandreth writes that Christopher Robin began to resent the role his father had cast him in, while war and falling in love for the first time had broadened his horizons. He came home wanting to be a writer, but felt any job he got would be attributed to nepotism.

“In pessimistic moments, when I was trudging London in search of an employer wanting to make use of such talents as I could offer, it seemed to me, almost, that my father had got to where he was by climbing upon my infant shoulders,” the younger Milne later wrote in his memoir, The Enchanted Places.

“That he had filched from me my good name and had left me with nothing but the empty fame of being his son.”

In the final years of the elder Milne’s life, the two men rarely saw one another, Brandreth said, though the falling out may have been compounded by Christopher Robin marrying his cousin, of whom his parents did not approve. 

“So it became a sad story in the end, but life is complicated,” Brandreth said.

‘I’ll always be with you’

Winnie’s story ended in 1934 when she died at 20, or a few months short of it. During her lifetime,  she received hundreds of thousands of visitors, her fame rising alongside Christopher Robin’s. 

When Colebourn returned from war, he visited her often, and her popularity was one of the reasons he changed his mind about bringing Winnie back to Canada. 

Though he never saw the bear again after 1920, as her literary counterpart says, they remain with one another in spirit. 

“If ever there is a tomorrow when we’re not together, there is something you must always remember,” Pooh Bear tells Piglet. “You are braver than you believe, stronger than you seem, and smarter than you think. But the most important thing is, even if we’re apart, I’ll always be with you.“