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In 1913, a Chicago publishing house called Reilly & Britton offered a $10,000 prize for the best manuscript submitted to them. About five hundred manuscripts were submitted, and eventually it was announced that Leona Dalrymple (later the author of Jimsy: the Christmas Kid) had won the prize for her novel Diane of the Green Van. She had also submitted another manuscript to the competition, and they were going to publish that, too.

So, is Diane of the Green Van worthy of the prize? Not having seen the other manuscripts, I obviously can’t judge, but this one? Is insane.

Diane Westfall is an heiress with a fondness for the outdoors. She builds — or orders to be built — a gypsy caravan, and plans to spend the year camping, slowly making her way down the east coast to Florida. Then there’s Diane’s cousin Carl, brilliant, dissolute and unpredictable. You know the type. He’s short on cash, and when he finds a mysterious document inside a broken candlestick at Diane’s house, he tries to sell it to the Ruritanian kingdom of Houdania. We don’t find out what the document contains for a long time — there are a lot of things we don’t find out for a long time — but Carl’s letter of inquiry clearly spooks the Houdanians enough that they send over Baron Tregar and a few other characters, one of whom remains unidentified for more than half the book.

Enter Philip Poynter. He’s Carl’s best friend from college, and if they were in closer touch, Carl probably wouldn’t be trying to sell family secrets to the Houdanians, or drinking so heavily. He has also, coincidentally, become Baron Tregar’s secretary. And that’s the last time I’m using the word “coincidence.” From here on out, you can take it for granted.

The Baron sends Philip to suss out Diane’s feelings towards Houdania, which is how he happens to be on hand when someone tries to kill her. Whether because he’s fallen in love with her or because he’s a decent guy and would do the same for anyone, he tries to talk her out of the caravan trip. When she insists on continuing, he hires a hay cart and follows her. Then a third camper joins there procession –a mysterious foreign gentleman who poses as an organ grinder but also shows off his education by ostentatiously dropping volumes of Herodotus on the ground. Three guesses as to what country he comes from.

This is probably the most entertaining part of the book — Diane making her way to Florida, followed by Philip and the organ grinder. The organ grinder is constantly doing silly, pretentious things like writing poems to plants, and Philip is just as reliably trying to take the wind out of his sails by writing poems to bugs. Meanwhile, we drop in on Carl from time to time, helping a friend to stop drinking, and then torturing a foreigner (where is he from? Only three countries feature in this book, and he’s not from Spain).

Then there’s the Seminole girl Diane meets in Florida. She’s persistently referred to as an Indian, in spite of the fact that her dad was white and her mother was half Spanish. When she introduces herself as “Shock-kil-law,” Diane is like, “Oh, that shortens really easily to ‘Keela,’” and the girl is like, “Yeah, that’s what my foster-father says.” She and Diane immediately become best friends.

There’s a masquerade ball, which is attended by practically all of the significant characters, and during which someone is unmasked in more ways than they expected. Then most of