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  • William Stark

The Mysterious Benedict Society and Prisoners’ Dilemma by Trenton Lee Stewart: Traps and telepathy

Updated: Jan 4, 2023

3rd book in the Mysterious Benedict Society trilogy (not including prequel The Extraordinary Education of Nicholas Benedict and sequel The Mysterious Benedict Society and the Riddle of Ages)

Overall rating: 8.5/10

Plot: 8/10

Characters: 9.5/10

Difficulty: 3/10

Quality of writing: 8.5/10

Concerning content (language, violence, etc.): minimal

Age level: 10 and up

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In this book, “The Mysterious Benedict Society” must deal once more with the evil genius Ledroptha Curtain and his “Ten Men,” when a blackout darkens the city of Stonetown and the antagonists seek to re-capture the nefarious device “the Whisperer.” Incorporating a plethora of clever riddles and codes, this book’s revolves not only around the protagonists’ attempts to apprehend the evildoers, but also several trials and obstacles to their own friendship, which culminate in an action-packed climax that lovers of mystery and action genres will enjoy.


The plot of this book is similar to that of the second book in the series (The Mysterious Benedict Society and The Perilous Journey), and is based largely on the protagonists unraveling a series of clues to find missing people and track down further information. However, the plot also hinges on conflict between the protagonists, as disputes develop among them and new abilities emerge (Constance Contraire, for example, turns out to be a telepath, prompting an entire subplot after she goes missing). However, these difficulties are ultimately resolved, leaving the protagonists’ friendship stronger than before and demonstrating some excellent examples of loyalty and self-sacrifice.

On the other hand, the plot of this book is probably the least cohesive out of the entire trilogy: it takes quite a while to “get going,” and when it does, its structure is complicated by subplots, which might confuse some readers (is the main plot about looking for Constance? or is it about finding Mr. Curtain? etc.). However, the plot is still quite engaging and overall fun to read, and merits an 8/10 rating.


Stewart keeps the cast of characters mostly the same in this book as in the trilogy’s two previous books, a plus for readers who like a lot of familiar characters. The protagonists, as always, are funny and witty, and engage in bantering conversation that is itself quite amusing to read; the villains are classically ominous, threatening types (that usually threaten more than they act). We get to see the friendships between the protagonists develop quite a bit in this book, as they are tested and divided by various trials (this book exhibits greater development in that regard than the other two, in my mind), and the protagonists demonstrate greater loyalty and selflessness while still remaining the quirky and creative characters that readers will know from previous books. Overall, Stewart’s characters in this book are the same loyal, yet humorous characters that he’s introduced in previous books, while relatively few new characters show up.



This book’s style is not hard (despite the included riddles and codes, Stewart’s writing is very readable), and the plotline is rather straightforward. Furthermore, kids (particularly adventurous ones) will easily sympathize with Stewart’s plucky protagonists, leading to an experience of reading that will (in my experience) make it quite engaging for them and encourage them to keep reading. I remember that I myself read the first book in the trilogy almost in one sitting, I found it so interesting—and the other two books are similar. (3/10)

Quality of writing

The quality of writing in this book is similar to the previous two books: Stewart keeps the story engaging through clever plot twists, action sequences, and amusing characters, while making the style relatively easy to read. The plot of this book is the least direct and linear of the three books in the trilogy, but is still exciting—this should not prove an issue for most readers. Furthermore, this book dives deeper into the themes of friendship and family through tests of the protagonists friendship and a search for the names of the birth parents of the character Constance (an orphan). Overall, this book is well-written and exciting, but not overly difficult or complex in style. (8.5/10)

Concerning content

This book contains no sexual content or language, although scenes involving fighting are relatively frequent (as befits the genre), However, these involve mostly minor injuries of a more humorous and dramatic nature, and are more for effect than otherwise. Consider for example a scene during the climax when two characters are fighting on top of a roof, using assorted weapons including boomerangs, teeth (yes, teeth, although not attached to either character’s mouth), a briefcase, and handkerchiefs soaked in chloroform. Characters crack jokes while fighting, and the overall tone is more lighthearted than one might expect. Granted, more serious injuries do occur, as is the case when a character hurls himself out of an upper-floor window in order to save the protagonists, breaking several bones (this is the same character who broke bones in the previous book), but he is subsequently shown to be recovering in a scene at a later date, and doesn’t seem to mind being hurt as long as he accomplishes his mission (keeping the protagonists safe). Overall, this book contains relatively minor concerning content, and should not be an issue in that regard for most readers.

Age level

This book has an easy-to-read style and an engaging plot, furthermore, the characters are funny and relatable, and the climax provides a satisfying conclusion to the trilogy. Overall, based on these attributes, this book is recommended for ages 10 and up.

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