Ian Fleming's Love Letters at Sotheby's

Fleming Letters at Sotheby's

A uniquely substantial and significant series of letters exchanged between Ian Fleming and the great love of his life, Ann (“Darling Darling Baby”, “Dear Monkey”, “Darling Pig”), will be offered for sale at Sotheby’s in December 2019.

The correspondence chronicles two decades of their lives from the intensity of their early secret love affair to the embittered final years of their marriage. The collection encompasses intimate love letters, lively descriptions of travels around the world, gossip of rich and famous friends, their shared passion for the natural world, the writing of the James Bond novels and their phenomenal success, which dominated his final years.

Dr Gabriel Heaton, Sotheby’s Specialist in Books and Manuscripts said: “James Bond was very much a product of Ian and Ann’s relationship. It is no coincidence that Ian wrote his first Bond novel in the same year they married, both as an outlet for his libido and imagination, and also in an attempt to make money for a woman who was used to being unthinkingly rich.

These letters remain largely unpublished and, in their scope and scale, must surely be an unmatchable record of the life of the author as his fortunes changed: they begin during the war, when he was working in intelligence, cover his post-war forays into journalism, long periods spent in his beloved Jamaica, and his creation of James Bond – one of the most enduring fictional characters of the last seventy years. As well as recording a relationship with an extraordinary erotic charge, this correspondence charts the meteoric rise of Bond and paints a vivid picture of high society living in the post-war world.”

Comprising over 160 letters written by both Ian and Ann, written across 500 pages, this correspondence will be offered as part of Sotheby’s London online sale of English Literature, History, Rock and Pop, Children’s Books and Illustrations (3-10 December) with an estimate of £200,000- 300,000.


Ian and Ann (née Charteris) first met in 1934, when she was married to her first husband, Shane, 3rd Baron O’Neill, and Ian was working in a desultory fashion as a banker in the City of London, a job that allowed him to pursue his passions: love affairs, high living, travel, and golf. They became lovers, but Ann also maintained a relationship with Esmond, Viscount Rothermere (the newspaper magnate who became her second husband in 1945) and Ian enjoyed various girlfriends. The letters from the 1940s reveal the intensity of the early years and are full of references to the sadomasochism that was always part of their relationship.

“I long for you even if you whip me because I love being hurt by you and kissed afterwards.” (Ann to Ian)


Their relationship shifted on its axis in 1948 when Ann became pregnant with Ian’s child, a girl who was born a month premature and lived only 8 hours. The collection includes a number of sad, kind, and gentle letters from Ian on Gleneagles stationery, written to comfort his mistress after the spending the day golfing with her cuckolded husband. Ann and Ian were bound together in a new way and they begin to write about whether they could make a life together.

“...I have nothing to say to comfort you. After all this travail and pain it is bitter. I can only send you my arms and my love and all my prayers...”) – Ian

“...This afternoon I forced myself to ask Esmond where she had been buried, I have been haunted by the thought for days. They christened her after me and put her next to my mother in the family churchyard at the edge of the sea at Aberlady […] while I was lying in a haze of morphia and you were playing golf…” - Ann, Warwick House, Monday evening, postmarked 7 Sept 1948

“…I wish a fairy would arrive with a wand and make everything alright, give Esmond a perfect wife and put me in your bed with a raw cowhide whip in my hand so as I can keep you well behaved for forty years...” – Ann

“it is all over London that E is not going to tolerate us any longer” - Ann


Marriage followed in 1952, almost twenty years after their first meeting. In the same year their son Caspar was born (an event Ian celebrated with the purchase of his famous golden typewriter); Ian wrote his first Bond novel, Casino Royale, and, of course, he founded The Book Collector.

To a man like Fleming it was always unlikely that Ann, as a wife and mother of his child, would have quite the same erotic appeal as she had when married to someone else; as Ann later complains when responding to a comment by Ian: “you mention ‘bad old bachelor days’ - the only person you stopped sleeping with when they ceased was me!”.

For all that the letters describe lives of glamour and privilege, the increasing unhappiness of life after their marriage is a regular theme. Each had to put up with the other’s infidelities, and Ian’s dislike of Ann’s social whirl often left him isolated (“…There is no one else in my life. There is a whole cohort in yours...”).

“In the present twilight, we are hurting each other to an extent that makes life hardly bearable” - Ian, BOAC stationery, “Thursday in the plane”.

“I envy you your life of parties and ‘the mind’ and you envy I suppose my life of action and the fun I get from my books … I am hopeless and like a caged beast in drawing and dining rooms and there is nothing I can do about it” – Ian


The writing of an annual Bond book gave shape to Ian and Ann’s year, as Ian would spend the winter months at Goldeneye in Jamaica writing the latest adventure. When work is going well he occasionally admits to his thrill in creating these adventures, but on other occasions he is just exhausted by his creation.

“Meanwhile the book is galloping along. I have written a third of it in one week – a chapter a day. I expect I shall get stuck soon but to date it does well & interests me. The first half is about Russia & that has always interested me. They have decided to murder Bond. A beautiful spy called Titania Romanova is about to appear. Coo er!” (Goldeneye, Sunday)

Ian took more pleasure in Goldeneye than did Ann (especially after Ian began an affair with Blanche Blackwood, a neighbour) so the collection includes many letters from after their marriage written when Ian was in Jamaica and Ann in the UK.

Goldeneye became a place to visit for Ann’s remarkable circle of friends and admirers, from artist Lucian Freud to Hugh Gaitskell, the Leader of the Opposition (with whom she conducted a long-lasting affair). Noel Coward was a friend and neighbour in Jamaica, making the area a destination for some surprising guests.

“Truman Capote has come to stay. Can you imagine a more incongruous playmate for me. On the heels of a telegram he came hustling and twittering along with his tiny face crushed under a Russian Commissars uniform hat [...] he had just arrived from Moscow[.]” – Ian

Fleming always enjoyed taking names for his books from his life so we hear, for example, that Blanche Blackwood has given him a small boat which “is very good for the reef and I have christened OCTOPUSSY”.

In the later years, the correspondence shows how producers and screenwriters were quick to see the cinematic potential of James Bond, and Ian’s letters contain several references to negotiations over possible adaptations. An early proposal for a TV series is judged “interesting but no gold mine at this stage”, but he senses the potential on a later trip to Hollywood when “people really seem to be after my books [...] its as usual a question of crossing fingers & waiting for someone to pry them apart & force some dollars between them.” 


Of course, these letters provide a much broader insight into Ian Fleming’s life and world than just the trajectory of his relationship with Ann. There is much gossip about mutual friends and acquaintances, including the divorce of Laurence Olivier and Vivien Leigh.

International travel was a regular feature of Ian’s life after his marriage, whether it be for newspaper work, research for the latest novel, or to deal with the increasing demands of the snowballing Bond phenomenon. Travel still had a glamour in the 1950s, and Ian describes sailing to New York on the Queen Elizabeth in 1953, giving him time to correct proofs for “Live and Let Die” and wonder at a passing pod of whales.

The correspondence includes richly evocative letters in which he reports back to Ann from different parts of the world: Hong Kong, Chicago (“...Bang! Bang! Here I am among the ghosts of the gangsters high up in a suite looking miles across lake Michigan…”), Bombay and Tangier, from which he reports on the city’s gay subculture frequented by Francis Bacon (another friend of Ann’s). In New York he found himself, with very British condescension, “submerged beneath a deep gloomth [sic] at the fabulous limitations of these people and their total unpreparedness to rule the world which is now theirs”.



English Literature, History, Children’s Books and Illustrations


This sale will present extraordinary material across the major collecting categories. It will include a remarkable collection from the Library of the Earls of Haddington as well as Shakespeare’s second folio from the Library at Spetchley Park. 

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