The Most Valuable Literary Bond Items of all Time

If you are interested in investing in James Bond first editions and Fleming paraphnalia, you’ll need to have deeper pockets than Auric Goldfinger. Here are some of the most expensive items to have ever sold at auction.

Special thanks to Simon Patterson at Hyraxia Books for his invaluable help.

$102,000 Moonraker, signed from Fleming to Raymond Chandler; Sotheby’s, 2004

moonrakeFleming and Chandler became friends after first meeting at a dinner in London in May 1955. Their meeting came at a pivotal moment in Fleming’s literary career.

“Fleming treated him with the deference he reserved for very few. Chandler had arrived in England a month before (April) and was just emerging from a long spell of drinking that had followed the death of his beloved wife Cissie…the year before…Two more different characters than the creators of Philip Marlowe and James Bond it would be hard to find, but since that dinner at the Spenders’ they had met on several occasions and got on well together” (Pearson, The Life of Ian Fleming, pp. 231-32).

FIRST EDITION of the third James Bond novel. Inscribed by the author to Raymond Chandler on the front free endpaper: “To / Field Marshall Chandler / from / Private Ian Fleming / 1955.” Fleming’s admiring and deferential inscription did not divert Chandler from looking at Moonraker with a close or critical eye: at the end of Chapter 1, on page 18, he has written a big, underlined “all Padding”; on the first text page, he has penned in the margin “2 1/2 barrel,” referring to the “Colt Detective Special” named in the book; and page 15 contains a marginal word in his hand, either “Bods” or “Bond” (Chandler’s handwriting often borders on the illegible). On the rear inside flap Chandler has written in ink several memos and notes to himself – about 24 words in his hand.

£97,250 Diamonds Are Forever final typescript prepared by Fleming’s secretary Ulrica Knowles. Sotheby’s, 2012

diamondsThis final typescript prepared by Fleming’s secretary Ulrica Knowles, checked by the publisher’s reader and by the author, with autograph revisions to almost every page, mostly in blue ballpoint but some in pencil, these mostly having the effect of tightening the text through deletions or changes to single words, with more extensive changes of one or more full sentences to at least eight pages (pp. 23, 79, 111, 119, 120, 194, 221, 263 verso), with the hoodlum ‘Dolly’ Kidd here called ‘Boofy’ Gore throughout (this name being changed following the objection of Fleming’s former schoolfriend from whom the name was taken).

A rare typescript that reveals the working practices of Ian Fleming as he honed the fourth Bond book into its final shape. This copy of the text was prepared by Knowles from Fleming’s first typescript, typed by the author in Jamaica and then revised by hand (now at the Lilly Library). This typescript, once checked and revised by the author and the publisher, then formed the copytext for the first edition.  Among the changes made by Fleming to this text was his heightening of the drama of an auction of racing thoroughbreds (p.111): “…a pause, a bang of the hammer, a look of sincere reproach towards the ringside seats where the big money sat…” 

$71,700 First Edition Live and Let Die, Christies, 2002


“To Sir Winston Churchill / From whom I stole some / words! / from / The Author /1954”. Churchill’s own definition of the British Secret Service, from his 1932 collection of essays Thoughts and Adventures, is printed on the inner flap of the dust jacket:

In the higher ranges of Secret Service work the actual facts in many cases were in every respect equal to the most fantastic inventions of romance and melodrama. Tangle within tangle, plot and counter-plot, ruse and treachery, cross and double-cross, true agent, false agent, double agent, gold and steel, the bomb, the dagger and the firing party, were interwoven in many a texture so intricate as to be incredible and yet true.”

Fleming’s father Valentine was made Member of Parliament for South Oxfordshire in 1910. A fellow MP, Churchill regularly attended weekend shooting parties at the Fleming mansion in Hampstead Heath. In 1917, when Major Valentine Fleming was killed on the Western front, Churchill wrote the moving appreciation of him that ran on the front page of The Times.

$68,500 Goldfinger, Sotheby’s, London 2012; Presentation copy to Raymond Chandler

GFPublisher’s gilt-lettered black cloth, gilt and blind-stamped skull (gold coins in for eyes) to front cover in pictorial dust-jacket designed by Richard Chopping; head of spine panel lightly creased and tiny spot of abrasion just under the “F” in Fleming to front panel, a little faint scattered spotting to rear panel.

An outstanding presentation copy from Fleming to Chandler and a wonderful example of the friendship between two masters of the thriller, the creator of James Bond and the creator of Philip Marlowe. “To Ray / with much affection / from / Ian” Ian Fleming had long admired Chandler’s work before their first meeting over a dinner in London at Stephen Spender’s in May 1955. His wife’s death the year before was still a fresh wound for the visiting Chandler and he had resumed hard drinking in his mourning: “He was very nice to me and said that he liked my first book, Casino Royale, but he didn’t really want to talk about anything much except the loss of his wife …” While such honest grief might usually be terribly awkward, for Fleming, Chandler “expressed himself himself with a nakedness that embarassed me while endearing him to me.” (Hiney, Pg. 221).

Fleming treated Chandler with “deference he reserved for very few” and greatly respected his advice, so much so that the present work might very well not have been written without Chandler’s input regarding the character of Bond in general. Fleming and Chandler began their somewhat unlikely friendship at a crucial time in Fleming’s literary career.

£62,400 Author’s final revised typescript of Diamonds Are Forever, Bonhams, 2009

The typescript is peppered throughout with authorial tweaks, written in Fleming’s characteristic blue ballpoint. When Bond checks himself into the Hotel Astor it was originally “in front of an elderly woman”; now it is “before a hatchet-faced woman with a bosom like a sandbag”. Or, at page 88, “too many expense-account customers” becomes “too much expense-account aristocracy”.

Chapter 17 was originally called “Bond Forces the Race” but becomes “Thanks for the Ride”. Every now and then the nagging voice of the publisher’s reader can be heard, saying at one point, but surely the world’s diamond centre is Amsterdam? This script was typed by Fleming’s secretary Ulrica Knowles (see the other lots in the present sale). Her work is jokingly acknowledged (as was his custom) in his presentation copy of the book: “To Rica/ who wrote it”. The book had originally been typed by Fleming at Goldeneye early in 1955, both the top copy and carbon of the original version being now at the Lilly Library at the University of Indiana. The catalogue further notes that:

Original manuscripts and typescripts of Fleming’s major works are extremely rare on the market. Indeed apparently the only ones not in the Lilly Library in Indiana are the present version of Diamonds Are Forever and the typescripts of Chitty-Chitty-bang-Bang”.


$57,600 An archive of correspondence between Fleming, Richard Chopping, Swann Auction Galleries, 2010

Realized $57,600 against a presale estimate of $12,000-$18,000. Photos courtesy Swann Auction Galleries.  The archive of letters between Fleming, Richard Chopping, and others involved in the production of nine of the 007 covers between 1957 and 1966 — from From Russia, with Love, through Octopussy and The Living Daylights — touch on details about the jacket art, praise for Chopping’s work, payment information, copyright issues, and other related topics. Together, 62 Letters including: 12 Typed Letters Signed by Fleming to Chopping; 9 Letters from Chopping, mostly copies, including one carbon and one fair copy to Fleming; and 41 letters to Chopping by others, including one of the directors of Fleming’s publisher Jonathan Cape Limited, Fleming’s secretary, and others involved in the production of the books and Chopping’s dust jacket designs. Single 8vo sheets. Mostly London and Essex, 1950s-60s

M19360-296 001

$47,800 First Edition Casino Royale, Christie’s 2002; Presentation copy to John Hayward

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FIRST EDITION OF FLEMING’S FIRST JAMES BOND NOVEL. A FINE PRESENTATION COPY, WITH A WITTY INSCRIPTION TO ONE OF HIS CLOSEST FRIENDS, JOHN HAYWARD, on front free endpaper: To John / This prenatal 1st Edition / of the first of the / collected works of / Balzac.

Ian Fleming’s inspiration for Casino Royale was a baccarat battle Fleming played in Lisbon during the Second World War against several Portuguese men. According to one biographer, Fleming whispered at the table to his friend John Godfrey: Just suppose these fellows were German agents — what a coup it would be if we cleaned them out entirely! (John Pearson, The Life of Ian Fleming, London, 1966, p. 131). Hayward has made numerous pencil corrections to the text; he challenges Fleming’s word choices, points out holes in the plot, and, at the baccarat scene (page 80), amends Fleming’s calculations to scores.

John Hayward was one of Fleming’s closest friends. They were neighbors in Carlyle Mansions in the respectable Cheyne Walk area of London: Fleming had the flat above Hayward and his roommate, T.S. Eliot. (Hayward was the titular dedicatee of Eliot’s Four Quartets, 1943). Along with Percy Muir, Hayward was the editor of the Book Collector, a small but respected bibliographical journal owned by Lord Kemsley. In 1952, Fleming bought the journal, then called Book Handbook from Kemsley. He was pleased to call the magazine his, but left Hayward and Muir in charge of all editorial decisions. The journal remains the leading bibliographical journal for the book trade, and Hayward’s bibliography English Poetry: A Catalogue of First and Early Editions (Cambridge, 1947) is one of the most important publications on the subject.

$ 46,360 First Edition The Spy Who Loved Me, Bonhams, 2010; Inscribed to Robert F. Kennedy

The Spy Who Loved Me. London: Jonathan Cape, [1962]. Original black cloth stamped in blind and silver, dust jacket. Jacket damp-stained, mostly apparent on verso, light creases.
First edition, signed and inscribed by Fleming to Robert F. Kennedy on the front free endpaper.

Provenance: the estate of Paul “Red” Fay [1918-2009], a close family friend of the Kennedy’s and advisor to JFK.

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£44,750 20 Typed Letters signed to Geoffrey Boothroyd; Bloomsbury, 2004

Kemsley House & 4 Old Mitre Court, Fleet Street, 31st May 1956 – 3rd April 1962, concerning the choice of gun James Bond should be using,

“you have entirely convinced me and I propose, perhaps not in the next volume of James Bond’s memoirs, but in the subsequent one, to change his weapons in accordance with your instructions. Bond has always admitted to me that the .25 Beretta was not a stopping gun, and he places much more reliance on his accuracy with it than in any particular qualities of the gun itself. As you know, one gets used to a gun and it may take some time for him to settle down with the Smith and Wesson. But I think M. should advise him to make a change; as also in the case of the .357 Magnum. He also agrees to give a fair trial to the Berns Martin holster, but he is inclined to favour something a little more casual and less bulky. At the present moment Bond is particularly anxious for expertise on the weapons likely to be carried by Russian agents and I wonder if you have any information on this”, technical aspects,ianf-letters-montage

“I sympathise with you about not liking silencers, but the trouble is that there often occasions when they are essential to Bond’s work. But they are clumsy things and only partially effective, though our Secret Service developed some very good ones during the war, in which the bullet passed through rubber baffles. I have tried a Sten silenced with one of these and all one could hear was the click of the machinery”,the design for the dust-jacket of From Russia with Love by Richard Chopping,

“by the way, the jacket of my present book is going to be a trompe l’oeil, painted by the only English master in the art, called Chopping, who really paints things so that you can pick them straight off the canvas. The picture will consist of a revolver crossed with a rose and it should be a very handsome affair. I have looked in vain for a Beretta 25 which would obviously be to the point but, if I fail to find one, would you care to have your own Smith & Wesson made forever famous?”, the progress of the picture, “incidentally, Chopping is very happy with the way the picture is going, though the finer points of the gun have been causing him pictorial agony”, reporting on the progress he has made with the technical information Boothroyd has been supplied with, “James Bond is now re-equipped from top to toe and I know you will chuckle when you read the chapter in which the Armourer features. The book is called Doctor No”.

£38,240 Editorial working type script of Diamonds Are Forever with Annotations; Sotheby’s 2002

DAFFleming’s original typescript of the novel, both top copy and carbon copy, as written by him at Goldeneye, Jamaica, in early 1955, is now in the Lilly Library at the University of Indiana, and contains a number of manuscript changes.

The present typescript is a revised version which incorporates those manuscript changes, but which has then been worked over to an extraordinary extent by one or more publisher’s copy-editors, who have made literally hundreds of alterations to the typescript text, in addition to instructions for the printer. As such, this annotated typescript throws remarkable light on the evolution of the novel before it reached its final printed form.

ORIGINAL MANUSCRIPTS AND TYPESCRIPTS OF FLEMING’S MAJOR WORKS ARE EXTREMELY RARE ON THE MARKET. Indeed apparently the only ones not in the Lilly Library in Indiana are the present version of Diamonds Are Forever and the typescripts of Chitty-Chitty-Bang-Bang.

$28,680 Notebook containing AUTOGRAPH NOTES for You only Live Twice, Christie’s, 2002

These notes were probably made at about the time of Fleming’s trip to Japan in 1961. He returned to Japan this time with the express purpose of making a trip that he could funnel into a Bond story. He wrote his friend Richard Hughes in advance with a detailed itinerary listing all the things they would need to see for the novel:

” After a couple of days in Tokyo, I would like us to take the most luxurious modern train down south to the inland sea… I would also like to see pearl girls diving – my heroine will be a beautiful girl who has learned to speak English working on an underwater film in Hollywood–and hot baths, a live volcano for suicides, and any terrifying manifestation of the horrific Japan” (Pearson The Life of Ian Fleming, London, 1966).

While jaunting around the hottest spots of Japan with Hughes, Fleming kept this notebook. Along with hotel and restaurant addresses, phone numbers, and simple Japanese phrases, the notebook contains several long prose passages. Philosophical jottings on the people and culture of Japan, include the followning: How many of one’s own nationals want to live in another country & how many of that country want to live in yours. Moshimosh = hello! Only the good can be bad – only the believer can blaspheme – only the black can be white. Flower – known as the FL service – or to the subs as FLOPPO.

FLEMING MANUSCRIPT MATERIAL is QUITE SCARCE and very few items of any significance have appeared at auction. Another notebook for You only Live Twice, similar in format but shorter (39 pages), was sold at Sotheby’s London, 20 July 1989, lot 174. A 120-page typescript, being Fleming’s working notebook of ideas for various Bond novels, kept from July 1957-January 1964, was sold at Sotheby’s London, 15 December 1992, lot 296. Besides these, and a few scattered notes for From Russia with Love and his article Bang, Bang. Kiss, Kiss, no other significant Fleming manuscript material has come to auction in thirty years. The present notebook may well be only one of a few pieces of Fleming manuscript material outside the Lilly Libary’s Fleming collection (purchased from Fleming’s widow in 1970, along with Fleming’s book collection).

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Incidental Intelligence

Ian Fleming Rare Books And Memorabilia

Letters to the Armourer

Correspondence between Fleming and Chopping

View to a killing: why do collectors pay so much for James Bond first editions?

Collecting James Bond First Editions

007 Ways to Buy James Bond 1st Editions

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