Rereading Trenton Lee Stewart’s Mysterious Benedict Society Series

After my adventures in Narnia and quest across the universe of Madeleine L’Engle, I ventured back to a (mostly) normal Earth to revisit another childhood favorite of mine: Trenton Lee Stewart’s Mysterious Benedict Society series. Since I read the fourth book when it came out last year, I’ve wanted to reread the whole series. I finally took the opportunity to do so this semester. I read the books in chronological order (reading the prequel first), which I would not recommend unless you’ve read the whole series before.

Trenton Lee Stewart is one of my favorite modern authors. I consider him a master of subtle showing of emotion and writing from the mind of a child. I think his prose is witty and vibrant, and he writes incredible, memorable characters that I would want to be friends with.

Now, for some thoughts on each individual book, in the order I read them:

The Extraordinary Education of Nicholas Benedict is the best out of the series at capturing the pain of orphans and the joy of childhood so well and yet with beautifully subtle moments and emotional beats. Nicholas learning trust is such a powerful and touching theme, and seeing where the wonderful mentor of the Mysterious Benedict Society started makes sense with who we know he becomes. I also appreciate Stewart’s twist on the orphan narrative trope: Nicholas doesn’t get adopted and even denies the chance to have a family, instead embracing a purpose bigger than himself and creating a “found family.” Nicholas’s story is one of hope, and it’s a satisfying standalone story in its own right.

The original trilogy surprised me with how powerful its overarching themes are. I appreciated the profundity of how Stewart explores the clash of good and evil throughout the adventures of the Mysterious Benedict Society. In particular, the emphasis on how the good and the evil use their power and position differently was well-executed. I was also surprised to find the messages of how good comes out of evil and how the bad can make the good feel all the more sweeter – two very complex themes that worked well in the context of a children’s story.

The Mysterious Benedict Society, the book that kicked it all off, took me right back to my childhood when I started rereading it. As an adult, I still found Mr. Curtain’s villainous plot a little nebulous, which I remembered also being a slight problem for me as a kid, but it is still a good book, made better (and more clearer) by its sequels. The Mysterious Benedict Society and the Perilous Journey might be my favorite of the series (though they all are very close in how much I enjoy them). It has the clearest character arcs for the main trio, and each character’s personal journey is beautifully written. The nonstop adventure of this book is full of twists and turns that kept me on my feet even though I’ve read it before. The Mysterious Benedict Society and the Prisoner’s Dilemma starts out a little slow for me, but once the plot picks up, it becomes the most intense and gripping story of the series. Its high stakes and slightly darker encounters with the villains made it especially compelling, though I think the character arcs are a little less defined in this one. Mr. Curtain also borderlines cliché for me; I don’t find him as compelling a villain as the Ten Men who serve him. I also think this book does well as a finale to the trilogy, as it captures so much how the kids have grown as individuals and in their friendship. It is extremely satisfying.

Now, as for The Mysterious Benedict Society and the Riddle of Agesspoilers ahead for this one, by the way, if you haven’t read it yet and care to do so spoiler-free – when I first read it, I loved it. Rereading it after reading the rest of the series, though, took off some of its luster. I still think it’s a good book, and I appreciate getting a glimpse of the Mysterious Benedict Society kids coming of age as a young adult reader who grew up with them. However, I think the plot is forced for the sake of this premise (watching the kids struggle with growing up). By far the strongest element of the book is its exploration of how the Mysterious Benedict Society are navigating the pains of growing up and how their friendships are changing. Some of the beats between the characters as they wrestle through making adult decisions and learning how to navigate their friendships are the best of the series, and they personally resonate with me as I continue with my own growing pains. But the plot itself almost tries too hard to provide a rounded ending, which I think the third book did very well already. The third book didn’t leave any unresolved plot threads, so the book did its best to create conflict as best it could.

Also, maybe slightly unpopular opinion, but I found it slightly unrealistic for the Mysterious Benedict Society to end up staying together again at the end of the book, especially since the third book ends the same way. I think premise of watching the Mysterious Benedict Society growing up might have been better served by the gang splitting up, since that is more reflective of adult reality and would’ve moved me more. I remember thinking the same thing when I read it the first time last year, too. But I’m also a sucker for bittersweet endings, so that observation may be more personal preference than thematic advice.

It was a fun diversion from classes to reread The Mysterious Benedict Society this semester. This series will remain on my shelf for a long, long time, and hopefully I’ll get to read them to my own kids and nieces/nephews someday. I’m going to finish out 2020 by reading some new books, but I hope to swing around to reread Andrew Peterson’s Wingfeather Saga and Tolkien’s The Lord of the Rings in 2021 to round out the rest of my childhood rereading adventures!

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