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The little boy and the bear

Daily Express

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September 29, 2025

The real-life Christopher Robin had a love-hate relationship with his father AA Milne's world-famous cuddly creation. In a new book, his friend Gyles Brandreth examines the long shadow cast by Winnie-the-Pooh

- By Fran Winston

The little boy and the bear

TRUE CHRISTORY: Gyles Brandreth, right, with real Winnie-the-Pooh

AUTHOR, broadcaster and genial raconteur Gyles Brandreth has been in a reflective mood of late, and specifically about childhood.

This has in part been prompted by the 77-year-old’s podcast Rosebud, launched in September 2023, on which his guests recall their first memories and experiences, and which he is “enjoying enormously”.

“I talk to famous people about their childhoods, and we’ve been very blessed with some completely remarkable conversations with hugely achieving and interesting people,” he tells the Express with a grin. “Everybody we've talked to, from Dame Judi Dench to Sir Keir Starmer — their childhood is everything to them. They’re formed by their childhood sometimes.”

But the theme also features prominently in his life right now, as he’s just published a biography of Winnie-the-Pooh author AA Milne and his beloved creation. Somewhere, A Boy And A Bear coincides with the 100th anniversary of the iconic character but it’s also been a labour of love for Gyles who enjoyed a warm friendship with the author’s son, Christopher Robin Milne.

Anyone familiar with the honey-loving bear of very little brain — and most are, thanks to Disney’s production line of films since acquiring the rights to it in 1961 — will recognise that name as the human protagonist of the stories.

As a child, Christopher Robin inspired the books that became his father’s legacy. However, as Gyles attests, he had a complicated relationship with the world of Pooh.

“By the time I got to know Christopher Milne in the 1980s — his father died in 1956 and his mother died more recently, but they were both dead by then — his whole attitude had mellowed because the thing he said to me was: ‘Don’t worry, we can talk about Pooh. We can talk about those books.’

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