Bond. James Bond. In the 007 Case Files, join me as I read all of the James Bond books, encompassing Ian Fleming and beyond. For Your Eyes Only: there’s spoilers ahead.
Raymond Benson’s stint as a Bond continuation author can be neatly divided into three parts. First, there are the standalone novels like Zero Minus Ten and The Facts of Death. Then there’s his trio of novelisations based on screenplays, beginning with the Pierce Brosnan-led Tomorrow Never Dies. However, the centrepiece of his tenure is arguably The Union Trilogy (1999-2001), a triptych of novels that sees 007 face off against a terrorist organisation known as—you guessed it—the Union.
The Union is a compelling villainous organisation, taking us back to the very core of what makes Bond fun. Benson had previous played with similar ideas using The Decada, a mathematics based cult at odds with MI6. Yet The Union very much fills a void left by SPECTRE. Recalling classic Fleming, the shadowy head is known only as Le Gérant, and operates more like a criminal syndicate than a cartoonish supervillain collective, bringing a grounded menace to the story.
The Union Trilogy kicks off with High Time to Kill, a novel that sets itself apart from its predecessors with a high-stakes mountaineering climax and a plot steeped in betrayal. It’s a solid, back-to-basics Bond adventure, complete with professional rivalries, sweeping backdrops, treachery, and seductive intrigue. What makes this entry particularly striking is its refreshing simplicity—once the story takes off, it becomes a literal race to the top of a mountain.
The opening novel’s straightforward structure works brilliantly, almost like a murder mystery, though with a twist: the reader knows the identity of the villain well before Bond does. This tone of heightened stakes and physical challenges permeates the trilogy, pushing Bond to his limits in ways that Benson—and arguably even John Gardner—had not explored before.
The middle chapter of the Union Trilogy, DoubleShot, is arguably one of Benson’s finest Bond outings. Opening with the unsettling implication that Bond has gone rogue, Benson immediately puts readers on edge, offering a clever twist on a classic formula. While his outlook occasionally veers into prurience—particularly in the depictions of Dr. Feare and the Taunt twins, Heidi and Hedy—it’s Benson’s willingness to push boundaries that makes this taut thriller so effective. (Or should that be a “Taunt” thriller?)
In fact, DoubleShot anticipates the cinematic portrayal of a diminished Bond in later films, which have become some of the franchise’s most critically acclaimed entries. The novel’s climax, set in the visceral chaos of a bullfight, turned my vegetarian stomach but kept my heart racing until the final page.
Which brings us to Never Dream of Dying, the finale of the trilogy. Set against the backdrop of the film industry, it certainly appealed to this little film nerd. One of the more entertaining threads sees Bond investigating model-actress Tylyn Mignonne, ostensibly to gather intel on her estranged husband, Léon Essinger, and his Union connections. The greatest danger Bond faces at this point? The ever-present paparazzi—a delightful touch that adds levity to the intrigue.
Benson distinguishes this entry by weaving multiple perspectives into the narrative, including passages from the viewpoint of fellow spy René Mathis. There’s also a poignant full-circle moment with On Her Majesty’s Secret Service, as Bond reunites with Marc-Ange Draco—mob boss, father to Bond’s late wife Tracy, and thus his one-time father-in-law. Their reunion culminates in a twisty double-cross you may not see coming. Even if you do, it’s a cool finale.
Benson feels entirely at home in this space, crafting a narrative that blends Fleming-esque sophistication with a modern edge. While EON Productions seem content creating original Bond stories, albeit at a pace nobody can rightly predict, one has to wonder why they’ve never tapped into the fertile territory of the Union Trilogy for cinematic inspiration. I can completely see these three tales forming the backbone of a new series of Bond films.
Perhaps it’s the scale of Benson’s storytelling that gives The Union Trilogy its added resonance today. Spanning the end of one century and the dawn of the next, it’s shaped as much by cinematic history as by the legacies of Fleming and John Gardner before him. Or perhaps it’s Benson’s exploration of a more vulnerable Bond, delving into his past relationships and even fears, that offers a depth of characterisation that’s more in tune with contemporary audiences—especially in light of the complex portrayals of the Daniel Craig era.
James Bond will return…in The Man with the Red Tattoo.
