During WWII, Ian Fleming worked as the personal assistant to the Director of Naval Intelligence (DNI). This placed him at the heart of intelligence operations, giving him a strategic overview and allowing him to serve as both an ideas man and fixer for the DNI. Although Fleming carried out some fieldwork at the beginning of the war, his role was largely administrative.
Many of the files relating to Fleming’s work were destroyed after the war, but the legacy of that work can be seen in his writing. These are my five favourite James Bond stories that were shaped by Ian Fleming’s wartime experience.
Casino Royale follows Bond’s mission to bankrupt the Soviet agent Le Chiffre in a high-stakes baccarat game. In 1941, Fleming carried out operations on the Iberian Peninsula. While in Lisbon, Fleming is said to have played an infamous game of chemin de fer with German intelligence officers and was “cleaned out.” Whether or not he actually played against German agents is disputed, but Fleming said the game in Lisbon inspired the plot of his first Bond novel.
Other accounts suggest that Fleming got the idea for the novel when he watched Duško Popov, a suave British double agent, play cards at a Lisbon casino. Popov has also been credited as an inspiration for Bond.
James Bond investigates the theft of two nuclear bombs in Thunderball. The novel features extensive underwater action, culminating in a fierce undersea battle.
Much of the imagery and detail in Thunderball was inspired by the elite Italian naval commandos of Decima Flottiglia MAS, who carried out a number of stunning raids during WWII.
Fleming became familiar with the unit through his intelligence work, and references to the Decima Flottiglia appear throughout Thunderball. Emilio Largo, the novel’s Italian villain, is widely believed to have been inspired by Prince Junio Valerio Borghese, one of the Decima Flottiglia’s commanders.
Some of the Italian unit’s most famous actions were carried out against merchant shipping at anchor in Gibraltar, operating from an abandoned freighter, the Olterra, in Spain. It had a trapdoor below the waterline through which their human torpedoes were launched. The same device was used in Largo’s yacht, Disco Volante.
In From Russia, with Love James Bond is lured to Istanbul with the promise of stealing a “Spektor” machine that would allow British intelligence to read the Soviet Union’s most sensitive signals.
Echoes of this can be seen in the need to capture a German four-rotor naval Enigma machine during WWII. This was a driving force behind Fleming’s creation of 30 Commando, a unit that carried out raids to ‘pinch’ key intelligence and technology. During Operation Torch, 30 Commando succeeded in capturing its first Enigma machine, configured for use by the Abwehr. This enabled Bletchley Park to crack German intelligence traffic.
30 Commando’s operations against the V-1s and V-2s after D-Day also influenced Moonraker, which features a plot by Hugo Drax to transform the V-2 rocket into an intercontinental ballistic missile capable of destroying London. 30 Commando even captured a German scientist named Dr Walter, and Fleming gave one of Drax’s scientists the same name.
Octopussy is a short story about a former British officer whose wartime crime catches up with him when James Bond investigates his past, forcing him to confront his guilt and fate.
Strong hints of the work carried out by 30 Commando can be seen throughout the narrative. The antagonist, Major Dexter Smythe, a former Royal Marine Commando, could well have been a member of 30 Commando. He worked for the enigmatically named Miscellaneous Objectives Bureau, collecting intelligence on the Germans, and eventually comes into possession of two bars of Hitler’s gold.
By weaving real‑world experiences into his fiction, Fleming ultimately created an enduring character who is not only compelling but also remarkably believable.
Hunter Class by Alan Bardos is published by Sharpe Books now
From Naval Intelligence with Love: Five Ian Fleming Stories Inspired by His Wartime Service

