Somewhere, a Boy and a Bear: A. A. Milne and the Creation of "Winnie-the-Pooh"

by Gyles Brandreth

For the 100th anniversary of the publication of "Winnie-the-Pooh," Gyles Brandreth chronicles the writing of this beloved classic and the life of its creator, A. A. Milne.

Somewhere, a Boy and a Bear tells the remarkable story of A A Milne, a playwright, a bestselling crime writer, poet, polemicist, humorist, and the man who created Winnie-the-Pooh.

Gyles Brandreth explores "Winnie-the-Pooh," a bear beloved by his genesis, his life across a hundred years, his special philosophy, and the reasons for his worldwide popularity. Brandreth’s book is also the intimate biography of three generations of the fascinating and troubled Milne family, which knew fame and fortune, despising both for a time, but a family that ultimately found a profound reason to be grateful for the riches Pooh brought them.

With an extraordinary cast list that includes Elizabeth II and Walt Disney, Somewhere, a Boy and a Bear moves from idyllic childhood games in the English countryside to New York in the 1930s and the love affairs, litigation, and heartrending family rifts that touched the life of one of Britain's most brilliant writers and his most famous creation.

Genres: Nonfiction, Biography, Audiobook, Biography Memoir, History, Writing

416 pages, Hardcover

Published December 2, 2025

About the author

Full name: Gyles Daubeney Brandreth.
A former Oxford Scholar, President of the Oxford Union and MP for the City of Chester, Gyles Brandreth’s career has ranged from being a Whip and Lord Commissioner of the Treasury in John Major’s government to starring in his own award-winning musical revue in London’s West End. A prolific broadcaster (in programmes ranging from Just a Minute to Have I Got News for You), an acclaimed interviewer (principally for the Sunday Telegraph), a novelist, children’s author and biographer, his best-selling diary, Breaking the Code, was described as ‘By far the best political diary of recent years, far more perceptive and revealing than Alan Clark’s’ (The Times) and ‘Searingly honest, wildly indiscreet, and incredibly funny’ (Daily Mail). He is the author of two acclaimed royal biographies: Philip Elizabeth: Portrait of a Marriage and Charles Camilla: Portrait of a Love Affair. In 2007/2008, John Murray in the UK and Simon & Schuster in the US began publishing The Oscar Wilde Murder Mysteries, his series of Victorian murder mysteries featuring Oscar Wilde as the detective.

As a performer, Gyles Brandreth has been seen most recently in ZIPP! ONE HUNDRED MUSICALS FOR LESS THAN THE PRICE OF ONE at the Duchess Theatre and on tour throughout the UK, and as Malvolio and the Sea Captain in TWELFTH NIGHT THE MUSICAL at the Edinburgh Festival Fringe.

Gyles Brandreth is one of Britain’s busiest after-dinner speakers and award ceremony hosts. He has won awards himself, and been nominated for awards, as a public speaker, novelist, children’s writer, broadcaster (Sony), political diarist (Channel Four), journalist (British Press Awards), theatre producer (Olivier), and businessman (British Tourist Authority Come to Britain Trophy).

He is married to writer and publisher Michèle Brown, with whom he co-curated the exhibition of twentieth century children’s authors at the National Portrait Gallery and founded the award-winning Teddy Bear Museum now based at the Polka Theatre in Wimbledon. He is a trustee of the British Forces Foundation, and a former chairman and now vice-president of the National Playing Fields Association.

Gyles Brandreth’s forebears include George R. Sims (the highest-paid journalist of his day, who wrote the ballad Christmas Day in the Workhouse) and Jeremiah Brandreth (the last man in England to be beheaded for treason). His great-great-grandfather, Benjamin Brandreth, promoted ‘Brandreth’s Pills’ (a medicine that cured everything!) and was a pioneer of modern advertising and a New York state senator. Today, Gyles Brandreth has family living in New York, Maryland, South Carolina and California. He has been London correspondent for “Up to the Minute” on CBS News and his books published in the United States include the New York Times best-seller, The Joy of Lex and, most recently, Philip Elizabeth: Portrait of a Royal Marriage.

Reviews

[theliterateleprechaun · Rating 4 out of 5]

Did you know that 2026 will be the 100th anniversary of A.A. Milne’s Winnie-the-Pooh story?

It was published on Oct. 14, 1926.

This in-depth look at the author, A.A. Milne, his son, Christopher Robin, and his teddy bear, Winnie-the-Pooh also focuses on the relationships between fathers and sons, the influence parents have on their offspring, and the magic and mystery of childhood.

Brandreth invites his readers into the investigation from page one with his unique, almost journalistic writing style. It doesn’t take long to segue from A.A. Milne’s parents to Christopher Robin’s birth, but it’s at this point that the investigation slows down and changes from a reporting style to a more conversational style.

I appreciated
✔️a peek behind the curtain look at what factors contributed to Milne’s childhood that enabled him to write such well-loved books
✔️finding out what the A.A. stood for
✔️discovering that the animals were real toys of Christopher’s and that the setting was a real location
✔️understanding how Winnipeg (Winnie) influenced the teddy bear’s name
✔️learning about the family struggles the Milnes had under such fame and pressure

I’ve added a trip to the New York Public Library on Fifth Street to my bucket list and promised myself to read Milne’s two stories in 2026 as a result of this book.

I was gifted this copy and was under no obligation to provide a review.

[✨Little Lit Lady✨ · Rating 4 out of 5]

The story of A.A. Milne and his family dynamics was a revelation. It is hard to read of such a beloved series like Winnie the Pooh and hear of the heartache it brought upon the man who created it. Hearing how the real Christopher Robbin felt of the story that made him the most famous literary boy and how it made him feel was surprising. The way he felt was so profound that it had consequences that the public would not know. I like the way the author incorporated passages of Winnie the Pooh in this memoir to demonstrate some of the possible realities of the Milne family. Did you guys know Winnie the Pooh and friends live in the New York City Public Library, i know I didn’t. Overall this story was captivating and sad at times but very important to be told. I want to give thanks to NetGalley for letting me listen to this audiobook in advance.

[Laura · Rating 4 out of 5]

This biography of A. A. Milne corrects many of the not-quite-true narratives that have been presented about the Winnie-the-Pooh story. First, there is so much more to the lives of AA Milne and Christopher Robin Milne than just the hundred acre wood. The author is speaking directly to the reader, giving you facts, plus placing them in the time period and the traditions and mores of the time. It is a story of family, and all the complications that are so prevalent in relationships. Interspersed with each chapter were direct quotes from the writings of Milne, allowing the reader an insight into the inspiration for his works. This was an engaging read.

[Ray Palen · Rating 4 out of 5]

4 1/2 Stars

It is a safe bet to say that Winnie-the-Pooh is one of the most recognizable and important characters in both fiction and popular culture. The global success of that fictional bear came solely from the inventive mind of A.A. Milne, who was inspired by the stuffed bear he gave his son Christopher on his first birthday.

SOMEWHERE, A BOY AND A BEAR is the story written by Gyles Brandreth, a man who was not only personal friends with Christopher Milne but also connected to Winnie-the-Pooh and A.A. Milne through a play he wrote as well as the teddy bear museum he founded at Newby Hall called The Bear House. This book not only chronicles the lives of the entire Milne family and the events surrounding the unexpected success of Winnie-the-Pooh but also provides information and tidbits that were little known or never before published, making for a remarkably insightful read.

Since Pooh and Christopher Robin are so famous, I am not going to repeat the chronological history contained within this book. Rather, I will focus on the items that are both surprising and mostly unknown which moved me and I am sure will connect with anyone seeking to get behind anything to do with the Milne family and the creation of the legendary Winnie-the-Pooh.

In the enormous Prologue, which spans thirty-five pages, Brandreth gives us a treat as he outlines the heart of the story to come through his personal recounting of his connection to the Milne’s and Pooh. There is a cast of characters list provided just prior to the start of the book which allows readers to have a better understanding of the man that was Alan Alexander Milne and all those who touched his life. Brandreth started this book on Christmas Eve, 2024, which was the ninety-ninth birthday of Winnie-the-Pooh, and that felt quite prophetic and right to him. The best way to describe what is to come is by using his own words: ‘This is a book abut a boy and a bear, but it is also a book about fathers and sons, about the effects of parents on their children, about the nature of childhood itself – about the magic and the mystery and the importance of childhood.’

We get to visit the New York Public Library where in early 2025 Brandreth visited to take in the exhibit which featured some of the original stuffed animals, all remarkably preserved, which made up the original Pooh gang. There is also a funny story about how the President and U.K. Prime Minister were in negotiations to bring the dolls back to London. The first chapter introduces us to A.A. Milne, who was born in 1882, and his two brother Kenneth and Barry. It is also mentioned that the boys thought their father, J.V. Milne, was a god.

It was surprising to learn that his brother Barry meant nothing to him while Kenneth meant everything. Kenneth’s death at a relatively early age inspired A.A. Milne to create the original Pooh story, using his late brother as the inspiration for his bear who was also physically inspired by the stuffed doll he presented his own son Christopher on his first birthday. Milne’s poem, Us Two,’ speaks directly to his relationship with his brother Kenneth. I was also surprised to learn that A.A. Milne was quite the renowned playwright prior to his Pooh days, with several plays seeing success on both Broadway and London’s West End.

Of course, it will become all about Pooh. A.A. Milne credits some of his love of creativity to his close family friend, H.G. Wells, who continued to inspire him throughout his career. There are some wonderful photos contained in this book including the 1924 first illustrations of Pooh. Ironically, the bear that was given to young Christopher was originally known as Edward Bear, only to be renamed Pooh because it just felt appropriate. It was also surprising to know that the sales of the original Pooh stories outsold The Great Gatsby. Brandreth played a part in telling the Milne story in his own play, Now We Are Sixty, which starred British actor Aled Jones --- most famous for his song from the British animated Christmas film The Snoman – who portrayed Chrisotpher Robin.

It was amazing to learn about the eventual resentment both A.A. Milne and Christopher Milne had towards the Pooh stories, and even toward each other. A.A. felt its success overshadowed all of his other great work and Christopher would take many years to be able to live with the fact that he would forever be Christopher Robin to the rest of the world. He even changed his name to Billy Moon briefly to avoid this recognition. It was not until after A.A. Milne passed and his wife Daphne sold the film and merchandising rights to everything involving Winnie-the-Pooh to Walt Disney that the popularity of the franchise really took off. Christopher learned to live with and love this and in the words from the Pooh stories: ‘The Hundred Acre Woods: it is always there too…It’s somewhere a little boy and his bear will always be playing. Always.’ This is work not to be missed by fans of Milne, Pooh, or anyone who enjoys seeing the creation of something legendary.

Reviewed by Ray Palen for Book Reporter

[Paul · Rating 4 out of 5]

Before I begin, I’d like to thank Macmillan Audio and NetGalley for providing an advance copy of this audiobook for review.

This Christmas Eve will be the 100th anniversary of the first publication of a Winnie the Pooh story, in a London newspaper; next October will mark a century since the publication of A.A. Milne’s book. The Silly Old Bear’s still much beloved by people all over the world, but you don’t hear much about the person who created him. Thank goodness that Gyles Brandreth decided to correct that!

“Somewhere, A Boy And A Bear” shares the story of Alan Alexander Milne and his family. The son of a missionary who founded his own private school for boys, Milne was a very bright young man who seemed destined for a career in mathematics until he got into writing light verses; although we primarily know him for the four books of children’s stories he wrote, he was a successful journalist and playwright before his son Christopher and a set of toy animals Alan bought for him at Harrod’s inspired one of the most famous characters in children’s literature.

Brandreth, who for years spoke with Christopher Milne about his father, his family, and their relationship with Pooh, has a lot of interesting things to share about the Milnes. Alan’s science teacher in his father’s school was H.G. Wells; he also received advice on his writing career from J.M. Barrie, author of “Peter Pan”. Alan was one of those folks who had talent for many things, but tended to move on from something once he felt he’d succeeded, which may help explain why he wrote so few books featuring Pooh and his friends. Both Alan and Christopher had a difficult relationship with Pooh; they appreciated the success of the stories, but both wound up feeling trapped - for Alan, because Pooh was so strongly associated with him to the exclusion of anything else, and for “Billy Moon” (Christopher’s nickname; the family seldom called him Christopher Robin), he felt he could never get away from the fictional child that bore a slight resemblance to him featured in his father’s books and poems.

Gyles’ book takes us all over the world to tell us the story of the Milnes and Pooh, from London to the country house with the nearby forest that inspired the Hundred Acre Wood, from Jamaica (where Milne’s father was born) to New York ( where Christopher’s toys are the Crown Jewels of the New York Public Library) to Texas, where Milne’s papers are kept and where the community holds a yearly event in tribute to Eeyore. And of course, we pay a visit to Walt Disney, whose animated films starring Pooh and his friends have helped keep the characters familiar to generations of children.

Gyles demonstrates that he’s passionate about Winnie the Pooh and his creator; he devotes some time in his book to addressing the myths about Pooh and the Milnes, as well as to people in Alan’s life who gave life and personality to the characters. Gyles has a tendency to ramble from time to time and to occasionally repeat himself, but I can practically guarantee that however much you know about Pooh, you’ll finish the book having learned something new about Milne and the Silly Old Bear. Highly recommended!

[Bookreporter.com Biography & Memoir · Rating 5 out of 5]

One of the most recognizable and important characters in both fiction and popular culture, Winnie-the-Pooh came solely from the inventive mind of English author A. A. Milne, who was inspired by the stuffed bear he gave his son, Christopher, on the boy’s first birthday.

Gyles Brandreth is friends with Christopher Milne and is connected to Winnie-the-Pooh and A. A. Milne through a play he wrote, as well as the teddy bear museum he founded at Newby Hall, The Bear House. SOMEWHERE, A BOY AND A BEAR not only chronicles the lives of the Milne family and the events surrounding the unexpected success of Winnie-the-Pooh, it also provides information and tidbits that were little known or never before published, making for a remarkably insightful read.

In the 35-page prologue, Brandreth outlines the heart of the story to come. A list of characters that appears just prior to the start of the book allows readers to have a better understanding of Alan Alexander Milne and all those who touched his life. The best way to describe what to expect is by using Brandreth’s own words: “This is a book about a boy and a bear, but it is also a book about fathers and sons, about the effects of parents on their children, about the nature of childhood itself --- about the magic and the mystery and the importance of childhood.”

We get to visit the New York Public Library, where, in early 2025, Brandreth took in an exhibit that featured some of the stuffed animals, all remarkably preserved, that made up the original Pooh gang. He recounts a funny story about how President Bill Clinton and Prime Minister Tony Blair were in negotiations to bring the dolls back to London.

Milne credits some of his love of creativity to his close family friend, H.G. Wells, who continued to inspire him throughout his career. There are some wonderful photos here, including the first illustrations of Pooh from 1924.

It is amazing to learn about the eventual resentment that both Milne and his son had toward the Pooh stories, and even toward each other. Milne felt that its success overshadowed all of his other great work, and it would take many years for Christopher to be able to live with the fact that he forever will be Christopher Robin to the rest of the world. It was not until after Milne passed away and his wife, Daphne, sold the film and merchandising rights to everything involving Winnie-the-Pooh to Walt Disney that the popularity of the franchise really took off. Christopher learned to live with this and actually love it.

Timed to coincide with the 100th anniversary of WINNIE-THE-POOH's publication, SOMEWHERE, A BOY AND A BEAR is not to be missed by fans of A. A. Milne and Winnie-the-Pooh, or anyone who enjoys seeing the creation of something legendary.

Reviewed by Ray Palen

[Tammy · Rating 4 out of 5]

📚Somewhere, a Boy and a Bear
✍🏻Gyles Brandreth
Blurb:
For the 100th anniversary of the publication of "Winnie-the-Pooh," Gyles Brandreth chronicles the writing of this beloved classic and the life of its creator, A. A. Milne.

Somewhere, a Boy and a Bear tells the remarkable story of A A Milne, a playwright, a bestselling crime writer, poet, polemicist, humorist, and the man who created Winnie-the-Pooh.

Gyles Brandreth explores "Winnie-the-Pooh," a bear beloved by millions: his genesis, his life across a hundred years, his special philosophy, and the reasons for his worldwide popularity. Brandreth’s book is also the intimate biography of three generations of the fascinating and troubled Milne family, which knew fame and fortune, despising both for a time, but a family that ultimately found a profound reason to be grateful for the riches Pooh brought them.

With an extraordinary cast list that includes Elizabeth II and Walt Disney, Somewhere, a Boy and a Bear moves from idyllic childhood games in the English countryside to New York in the 1930s and the love affairs, litigation, and heartrending family rifts that touched the life of one of Britain's most brilliant writers and his most famous creation.

My Thoughts:
I love this book, really enjoyed reading it. I loved reading Winnie the pooh to my children when they were young. Now I enjoy those same stories with my grandchildren. I recommend this to those that love Winnie the Pooh.
Thanks NetGalley, St.Martin's Press, Author Gyles Brandreth for the complimentary copy I am leaving my voluntary review.
#NetGalley
#St.Martin'sPress,
#GylesBrandreth
#Sonewhere, a Boy and a bear
⭐️⭐️⭐️⭐️

[Bargain Sleuth Book Reviews · Rating 5 out of 5]

Thanks to NetGalley and MacMillan Audio for the digital copy of this book; I am leaving this review voluntarily.

Fun fact: when I was a little girl, my dad nicknamed me Pooh Bear. I grew up when the Disney Winnie the Pooh reigned supreme; the only store that was licensed to carry merchandise was Sears. I did not discover the classic look of a boy and his bear until I was older, and my father had passed. One of my brothers gave me a stuffed Pooh Bear for comfort, a gift I still have to this day.

That’s the long way of saying I grew up with Winnie the Pooh and have always wanted to learn more of how A.A. Milne created the forever fantastical Hundred Acre Wood. Somewhere, a Boy and a Bear tells the story. I’m always fascinated to read or listen to stories of famous families and their relationship with fame. This nostalgic and insightful audiobook gives a fuller portrait to A.A. and Christopher Milne’s life and relationship.

I’m so glad that the “Silly Old Bear” is still delighting children young and old in the run-up to the books’ 100th anniversary in 2026. The stories of how the real Christopher Robin coped with celebrity and his mixed feelings about it are worth a listen. Let me tell you, the author, Gyles Brandreth, does a bang-up job narrating this audiobook. This was such a nice and cozy listen. Definitely recommend!

[Annie · Rating 3 out of 5]

Somewhere, a Boy and a Bear is a reflective, informative book that gave me a deeper understanding of the real child behind one of the most beloved literary characters of all time.

I appreciated how much I learned from this book, especially about Christopher Robin Milne’s complicated relationship with Winnie-the-Pooh and the unexpected weight of growing up immortalized in fiction. Hearing his story in his own voice added an emotional layer that made the experience feel intimate and thoughtful.

That said, while I found the subject matter genuinely interesting, the pacing felt slow at times, and the tone could be a bit dry. This made it harder for me to stay fully engaged throughout, especially as an audiobook. I think readers who love literary history or are deeply invested in Winnie-the-Pooh will connect with this more strongly than casual fans.

Overall, this was an educational and meaningful read, and it left me feeling more reflective about the legacy of Pooh, especially with the 100th anniversary approaching this Christmas Eve. While it wasn’t a personal favorite, I’m glad I listened and came away with a greater appreciation for the story behind the stories and I learned a lot!

Thank you to NetGalley and the Macmillan Audio for the advance listening copy.

[Megan Beech · Rating 5 out of 5]

This was a very interesting audiobook experience about AA Milne and how the whimsical and nostalgic stories of the many adventures of Winnie The Pooh and his friends changed the literary world by storm. I loved reading these stories growing up and of course was raised on the Disney adaptations. I also love it when the author narrates their books! It always makes the listening and reading experience more authentic and personable to me.

I highly recommend this book/audiobook to anyone who loves a good background history story on masters of literature!

I would love to thank the author, narrator, publisher and NetGalley for giving me the opportunity to listen to this audiobook in exchange for an honest review.

[Liv Scott-Smith · Rating 5 out of 5]

Brilliant. Fascinating that everyone was nostalgic for the mid-war years — Waugh, Auden, Milne… Happiness and nostalgia are not the same thing. And a reminder not to lose my parents like AA and CR did.

Painstakingly researched and just the right amount of personal from Brandreth. I would like to read some of Milne’s plays. Milne was well-connected - H.G. Wells, J.M. Barrie, and even P.G. Wodehouse, whom he criticised vehemently for his time in Germany in WW2 and who found Milne very odd. I wish I could meet AA’s wife Daphne and decide for myself what she was like.

[Joanne Sher · Rating 4 out of 5]

Three and a half stars. Not bad. I found a bit too much of the author integrated into the story over the subject, and a fair amount of repetition that felt unnecessary, but Brandreth did seem to give a good and full overview of the life of A. A. Milne and, to a lesser extent, his son, "the Christopher Robin." Lots of Britishisms (that appears to be the audience - some terms I was not familiar with). Intriguing story about an intriguing man - I learned a LOT I did not know about this gentleman who was much more than a children's author.

[Tilly · Rating 3 out of 5]

Interesting to hear what Milne got up to before Pooh and how he felt about it all. I didn’t know he was a successful playwright and author beforehand. Really goes to show you can be the toast of broadway and the west end but still no one will put your shows on after you die. I had long heard Christopher Robin hated it all and also his father but strangely in this book he’s more of a weirdly cold fish who just reaches adulthood and the feels he’s outgrown his parents and basically never speaks to them again. Which is either a really strange personality or this book fails to get to the reality of how he felt…

[Dan · Rating 4 out of 5]

If you wanted to know all about A.A. Milne (the man who created Winnie the Pooh), then this is the book for you. It touches on his grandparents, delves into his parents, his childhood, his life as a playwright and author and his relationships with others. By researching Milne’s papers and interviews from the past, the author gets most of the story. There is even more about Christopher Robin and his life and death. Overall, a fascinating read.

[Ashley Tovar · Rating 4 out of 5]

As someone whose childhood was filled with Winnie the Pooh this book was a must. The writing varied throughout, sometimes whimsical & sweet, sometimes a bit dry & slow but the deep nostalgia was a constant. There are definitely parts of this book that will stay with me.

Big thanks to Netgalley & the publisher for allowing me to enjoy this.

[Josephine Sorrell · Rating 3 out of 5]

This is a biography that explores the complexities of British author, A.A. Milne, his family relationships, his fame and fortune as well as life beyond the Pooh Bear and the One Hundred Acre Wood.
Milne and Winnie-the-Pooh had something very special in common, living gratefully.

Well written but for some reason I had a hard time focusing on the story.

[Margaret Wigmore · Rating 4 out of 5]

A sad book in many ways with all the breakdown in family relationships but an interesting read.

[Rachel Godfrey · Rating 4 out of 5]

If you’re a fan of the Hundred Acre Wood, Somewhere, a Boy and a Bear is an absolute must-read. As someone who grew up with a Pooh-themed bedroom (decked out in the original Shepard sketches, not the Disney versions!), this book was such a beautiful, nostalgic trip down memory lane.

It does a wonderful job of weaving together A.A. Milne’s life, the real Christopher Robin, and the birth of Pooh into one seamless story. It’s a really intimate look at Milne’s childhood and the complicated relationship he had with his son, and it manages to be both whimsical and a little bit heartbreaking at the same time. While I found a few of the stories and quotes to be a bit repetitive toward the end, the overall narrative was so compelling that it didn’t take away from the experience.

I also have to give a huge shout-out to the audiobook! The narrator’s voice was perfect and the production was top-tier—it really brought the whole history to life.

I’m giving this a solid 4 stars. It’s a sweet, cozy read that would make the perfect gift for a parent or grandparent who used to read you these stories when you were little.

Thank you NetGalley and the publisher for an advanced listener copy!

[Kacey/Kris · Rating 5 out of 5]

What a wonderful time to put this book out. Celebrating 100 years of this amazing long standing story. This book is fo all of A.A. Milne fans!