The best middle grade books starring mobsters, schemers, and thieves

I love the whole Tales from Alcatraz series, but this one is my favorite. The series is about a boy named Moose whose family lives on Alcatraz, the island off the coast of California, home of the famous prison. Moose’s dad is a prison guard. The books are set in the 1930s, when Alcatraz still held prisoners, including notorious mobster Al Capone. The book is funny, yes, but it’s also a really loving portrait of a family with problems. Moose’s older sister has special needs, his mother is going through a depressive episode, and the prisoners are threatening to go on strike. The authentic historical detail helped me visualize the island, the prison, and all of the people. And Moose is a real character in every sense of the word! 

Loot is a really fun book about kids for whom thievery runs in the family. Twelve-year-old March sees his father die during a heist, and now March is on a mission to find the precious stones that will reverse the curse on his family. On the way, he meets the twin sister he never knew he had, and together, they set out to find the jewels. What I love most about this book is that March is kind of an anti-hero. He’s not the all-around good guy that readers find in so many middle grade books. He loves being a thief and wants to carry on his father’s legacy. But, of course, March is a great kid at heart, and I couldn’t help but root for him all the way through this maze of a mystery.

The Artemis Fowl series is so much fun, and readers must start with the first book. Artemis is a genius, a kid-criminal, a true anti-hero who does the wrong things (robbery, kidnapping) for the right reasons (family!). This book has led to an entire industry—a long series, graphic novels, a Disney movie. The book contains fantasy elements, like fairies and trolls, but it moves at the pace of a fun heist story and has some mystery thrown in for good measure. I’ve heard that the movie is trash, but I’ve never watched it. The book is always better than the movie, though, right?

If you love a smart, self-referential book in the mode of A Series of Unfortunate Events, you will love Adam Perry’s book. Right from the beginning, the book speaks directly to the reader with warnings about what’s ahead: monsters and villains and horrible deaths. But instead of being a Stephen King horror novel for the middle grade set, the book has a fairy tale-meets-Thursday Next vibe. The protagonist, Oliver, steals books from the library, but since no one reads anymore, he’s not overly concerned about his thievery. That is, until he steals a book that is also being sought by the Pribbles, two inventors that have devised a set of goggles to steal the book directly from Oliver’s mind. Mayhem and shenanigans ensue, and it’s all just delightful. 

Who doesn’t love a middle school con artist with a heart of gold? Jackson Greene thinks he’s out of the scam business forever, until he believes that the fix is in on the next student council election. The only way he can take down the school bully and student council president candidate, Keith Sinclair, is to pull off the biggest con the school has ever seen. The diverse cast of characters makes this book feel like Ocean’s 11 for tweens. Each kid has his or her own “specialty” and Jackson is the guy who brings them all together. The book also reminded me of the Kiki Strike series, but in a more realistic setting. Could anything like The Great Greene Heist really happen in a middle school? Well, no, but the book is just a great time from beginning to end.