Cover image of "What's the Worst That Could Happen?" by Donald E. Westlake, a caper novel

If you’ve never encountered John Dortmunder and you feel a need to cheer up, immerse yourself in the series of fourteen books about the dubious criminal career of this marvelous character. These stories are among the more than one hundred novels and nonfiction books Donald E. Westlake wrote in a career spanning fifty years. What’s the Worst That Could Happen? is the ninth caper novel in the Dortmunder series. It may be one of the best.

Estimated reading time: 4 minutes

John Dortmunder is “a slope-shouldered defeated-looking fellow in dark clothing and thinning hair, who had an air of such dejection and collapse there seemed no need to point anything at him more threatening than a banana.” He is a New Yorker, a professional burglar with a supportive live-in girlfriend named May and a large circle of criminal friends with a variety of useful skills. Dortmunder “picks things up when people aren’t looking” simply to support himself and May. “All of finance was too much for him. His understanding of economics was, you go out and steal money and use it to buy food. Alternatively, you steal the food. Beyond that, it got too complex.”

The inner circle of Dortmunder’s fraternity includes Andy Kelp (information maven), Stan Murch (getaway driver), and Tiny Bulger, “the mountain shaped something like a man” (intimidating presence).

What’s the Worst That Could Happen? (Dortmunder #9) by Donald E. Westlake ★★★★★

Here, for example, is Tiny speaking to Stan. “I want to thank you. This is a roomy car. I’m not used to roomy in a car. I remember one time I had to make a couple people ride on the roof, I got so cramped in the car.”

“How’d they like that?” Stan asked.

“I never asked them,” Tiny said.

From time to time, whenever Dortmunder has an inspired idea, or simply feels the need to make money, they get together in the back room of the O. J. Bar & Grill on Amsterdam Avenue to plot their next caper. Sometimes Dortmunder sits in the front room, entertained by the spectacularly ignorant dialogue of the regulars who hang out at the bar. Here’s one example of that witty repartée: “[D]own at the other end of the bar the regulars had segued in a natural progression into consideration of cold cures. At the moment, they were trying to decide if the honey was supposed to be spread on the body or injected into a vein.”

Another cockamamie caper novel

In What’s the Worst That Could Happen?, Dortmunder and Gus Brock (“a longtime associate in this and that”) travel to the south shore of Long Island to burgle the second (or third or fourth) home of a billionaire named Max Fairbanks. Fairbanks has declared bankruptcy, and the judge has declared his Long Island home off-limits to him, so Dortmunder and Gus enter without worry. Unfortunately, Max has chosen that night to take his current mistress, Miss September, for fun and frolic at that very house. When Dortmunder heads upstairs to retrieve pillow cases to carry all the loot, he meets Max on the stairway, holding a pistol. Gus escapes, but Dortmunder is left to be arrested by the local police. Then Max makes a very big mistake.

As Dortmunder is handcuffed and held by the two cops, Max announces that the ring Dortmunder is wearing is, in fact, his—and takes it off his finger. This ring was a gift from May, and losing it infuriates Dortmunder. In fact, he is so angry that, after escaping from the police, he single-mindedly sets out to get even with Max—and get the ring back. Thus ensues a series of ever-more-ambitious burglaries ultimately involving two dozen of Dortmunder’s friends and acquaintances in a spectacular heist in Las Vegas.

Will Dortmunder get the ring back? What do you think?

I’ve also reviewed Watch Your Back! at A hilarious novel from Donald E. Westlake, and Get Real, the final novel in the series, at Dortmunder’s last caper, funny to the end. If you crave reading a clever caper novel, you’ll love these books. And check out My 10 favorite funny novels.

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