The Great Brain series by John D. Fitzgerald
Most of us are Watsons, not Holmeses; the fish, not the Cat in the Hat; the Beezuses, not the Ramonas. Always the supporting character, never the hero.
I spent the weekend perusing these old childhood favorites about a progressive, brainy Catholic family living in Mormon country at the turn of the century*. John D. Fitzgerald's books are semi-autobiographical reminiscences of his older brother, Tom, otherwise known as the Great Brain. Where Tom is shrewd, crafty, and able to wring a dollar out of most situations, young John is easily outsmarted, usually at the moment he thinks he is being most clever.
Sometimes Tom uses his powers for good, as when he teaches a boy with a wooden leg how to play with the other children, but mostly he spends his time swindling his peers and running mental rings around their parents. For my money, the best book in the series is The Great Brain at the Academy, wherein Tom is sent to a Catholic boarding school in Salt Lake City, and terrorizes a bunch of priests.
If you like...: boyhood tales of young scamps like The Adventures of Tom Sawyer, or stories about charismatic, ingenius leaders as told by their followers, this book is for you.
* Gwen will be amused to learn that whenever a character in the books must go to the city for provisions, they go to Cedar City.