Probably the most significant advance in our knowledge of Ian Fleming that Nicholas Shakespeare presents in his brilliant new biography, Ian Fleming: The Complete Man, concerns the James Bond creator’s war record. With the steady release of files relating to the top secret activities of intelligence and other covert organisations operating during the Second World War, including the Naval Intelligence Division in which Fleming served as personal assistant to the director, we’re now gaining a much fuller picture of Fleming’s role. Far from the desk-bound administrator who was at arm’s length from all the action, Ian Fleming was at the heart of secret operations, being cleared for intelligence work at the highest level, liaising between organisations, devising and planning audacious schemes, and, more frequently than has been thought, travelling to war-torn Europe to oversee the commando missions that he had organised. 

Of course, during the Second World War, Ian Fleming could say very little about his wartime work, and there was little understanding of it within his social circle. Among his friends, acquaintances, and lovers (well, one in particular – Ann O’Neill (later Fleming), he gained the epithet ‘chocolate sailor’, which evoked the image of a smart and handsome, but ineffectual officer. What, though, was the origin of the phrase? 

In the latest biography of Ian Fleming, Nicholas Shakespeare writes that the phrase derived from a Hershey’s advertisement of the 1930s, which depicted the cartoon image of a soldier, his helmet bearing the words ‘chocolate soldier’. 

In his 1995 biography of Ian Fleming, Andrew Lycett offers a very similar explanation, which only differs in the brand of confectionary. ‘Chocolate sailor’, he suggests, is an allusion to the figure depicted in advertisements of Black Magic chocolates in the 1930s.

John Pearson, in his 1966 biography records that Ian Fleming was known as the ‘chocolate sailor’, but does not provide an origin.

Nicholas Shakespeare and Andrew Lycett may well be right in suggesting that the phrase owes its origins to confectionary advertising, but I wonder whether there’s another, more literary explanation. One of the many revelations in Nicholas Shakespeare’s book is that the writer Cecil Robert based a character, Ian Crawley, on Ian Fleming in his 1930 novel, Spears Against Us. I duly picked up a copy and was interested to read the following words spoken by another character, Tante Schlamm, who is decribing a former husband:

Your poor uncle Leopold would have been the first to admit his vanity. He died of a surfeit of medals, and he could never get into a battle, the dear man. It really isn’t much use being an Austrian soldier. We never fight anybody. I suppose that’s why that English dramatist, Shaw, wrote a play about us and called it The Chocolate Soldier.

The dramatist Shaw is George Bernard Shaw (actually Irish), who wrote Arms and the Man in 1894, which was turned by Oscar Strauss into an operetta in 1908 called The Chocolate Soldier.

Later in the novel, as the First World War rages, another character, Jack Cheriton, says of the Austrians, ‘I always regarded the Austrians as chocolate soldiers… I used to watch them pirouetting outside the Bristol in Vienna.’

It seems to me that in the literary circles to which Ann O’Neill and her friends belonged, the operetta would be more familiar to them than chocolate advertisements. But it occurred to me that the epithet could have come indirectly from Strauss’s work, with those who first applied the phrase ‘chocolate sailor’ to Fleming quite possibly alluding to the above passages from Robert Cecil, who was known to them all. After all, in their eyes, wouldn’t the description offered by Tante Schlamm also fit Ian Fleming? In any case, it is evident that the phrase ‘chocolate soldier’ had currency long before the advertisements of Hershey’s and Black Magic.