Considering Westlake: What’s The Worst That Could Happen?

Whats the worst that could happen-westlakeThe adventures of John Archibald Dortmunder (the beleaguered and bewildered crook who hates his middle name and ends up in the oddest escapades) have taken some strange turns (starting in the first volume of the series, in fact). The Hot Rock might have been slender in terms of page count, but it was no less meaty for its short length. Six different crimes in less than two hundred pages and plenty of laughs along the way. It started out as a Richard Stark novel with Parker forced to steal the same thing a bunch of times, but then gave birth to Dortmunder when it got to be too funny. At this point in Westlake’s career, the Parker name was not producing any new works (though that would change within the next two books), so the only regular thief in Westlake’s career was John D.

For the ninth outing with Dortmunder, readers have the chance to see something unusual for this character. He gets to win a lot of times, even though he constantly fails in his stated goal. It is the classic case of a man who is failing in an upward direction. Let’s take a gander under the hood.

The books starts with John getting a present and an opportunity. The present is a ring, a simple little cheap thing from May’s dead uncle. It’s a good luck ring, and as May delicately observes:

“You could use a little luck,” May said.

“Come on, May.”

“Skill, you’ve got,” she hastened to assure him. “Adaptability you’ve got, professionalism you’ve got, good competent partners you’ve got. Luck you could use a little. Try it on.” (9)

Of course, the ring is just the right size. The opportunity is a juicy one: the chance to rob an easy mark. As it so happens, there’s a mansion that is home to no one at the moment. The actual owner is a guy by the name of Max Fairbanks, an international jet setting billionaire who is in the middle of legal proceedings of some note in the States:

“He’s in Chapter Eleven,” Gus Brock said.

“Is this a person,” Dortmunder asked, “or a book?” (16)

Dortmunder’s experience with economics is basic. It does not include an awareness of such convolutions as Chapter Eleven bankruptcy. However, he is no dummy.

Dortmunder shook his head. 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. So he said, “Okay, it’s just one of those cute ways rich guys have to steal from everybody without having to pick locks.” (17)

Regardless of the actual issues Fairbanks is facing, the mansion should be empty. Strike that. No one might be home, but the house is still home to all kinds of expensive toys and goodies. It is a playground for the crook who can get in and out. Of course, this being the world of John Dortmunder, nothing is so simple. As it turns out, the dude in Chapter Eleven is violating the terms of his settlement by occupying the house, at least temporarily, in the company of Miss September, a gal who is most certainly not his wife. Between bouts of adultery flagrante delicto, Dortmunder breaks in and Max Fairbanks catches him (also in flagrante delicto, for those playing at home) and decides to hold him at gunpoint until the cops arrive. In a fit of pique, Fairbanks then decides to lie to the cops when asked if the burglar has stolen anything by claiming Dortmunder’s ring for his own. The crook gets robbed, and the cops go along with it.

Well, nothing steams Dortmunder like this. He escapes from the police, returns to the house to demand his ring back, only to find the place vacated. He robs it for a quarter million in booty (as well as a Lexus) and sets out on a road for revenge. Yes, dear readers, you got that right. He loses a worthless ring, makes off with a quarter million in stolen goods (sure he only makes a dime on the dollar for the stuff from his fence, but it is real money) and he thinks of himself as failing. This will continue throughout What’s The Worst That Could Happen?

The novel is a head-to-head war between Dortmunder and Fairbanks, both men too proud to back down no matter what advantage the other takes. Needless to say, we do not get to see Dortmunder pull so many successful jobs in a row as we do in this book, and yet each time out he fails to achieve his stated goal of getting his damned ring back.

This time around, Dortmunder is not the only one to get some good luck rolling his way either. Andy Kelp finds himself involved with a woman who maybe sees eye to eye with him. It is fun to see Kelp wooing a gal when he obviously has little to no clue about women like her.

Westlake is the master of the comic caper. His crime fiction is a hoot to read, thoroughly enjoyable. The Dortmunder books in general are a great gift to his fans. While not all of them are laugh out loud funny, What’s The Worst That Could Happen? is nevertheless an enjoyable romp with familiar company as they explore terrain that is not quite new but not too familiar either.

As with that first outing, The Hot Rock, we have several crimes occurring here, including a burglary gone bad in the mansion, another one in The City proper, a break in at the Watergate in Washington, DC, and an extended romp in Las Vegas. Although Westlake does not explore these individual crimes with quite the detail as a writer like Lionel White might employ, he manages to keep the tensions high, the humor quirky, and the characters entertaining. Dortmunder and his crew are in full display here. We get a chance to visit with the aforementioned Andy Kelp as well as Stan Murch, Tiny Bulcher and Herman X. We see some new faces in the antagonist roles, the irritating Max Fairbanks and his unsinkable wife Lutetia as well as a variety of mistresses and flunkies. As series books go, the novel is a fun revisit with beloved characters and their weird little world. That is the draw of series, after all, as Westlake well exploited in other series works before this.

At this point in his career, Westlake’s prose is assured. He knows the story he wants to tell and he knows how to write readable, effective sentences. His humor is fast, his wording is witty, and he makes the difficult art of writing funny look downright easy. As we learned in the previous entry, Don’t Ask, John D is not a man to anger. When he wants revenge, he can be almost as mean a son of a bitch as Parker, the star of the Richard Stark penname series. Not as deadly, perhaps, John Dortmunder is a non-violent kind of guy. More passive-aggressive than Parker’s just plain aggressiveness. However, What’s The Worst That Could Happen? continues to show readers that angry side of the set-upon John Dortmunder.

One of the fun additions this time around is the inclusion of divination. The I-Ching is not quite the same poo-pooed class as tarot cards or astrology (which got its day in Westlake via A Jade In Aries). It’s a book of poems, obscure, visionary poems. Fairbanks has a copy, which he calls The Book, and which he consults as necessary. A few passages are presented throughout the text, giving Fairbanks clues about where to go next and what to do about the crook dogging his trail. Of course, readers will have fun seeing Fairbanks’ interpretations and then applying their own with the fuller picture. I can imagine a grinning Westlake flipping through his own copy of The Book, seeing if he might add a twist here, an unexpected turn of events there for his plotting. Authors might be the biggest skeptics about such things as applied to real life, but many of the best novelists see such tools as fun and useful in terms of developing stories and plot twists. After all, plotting is an attempt to apply some sense of order to the randomness of creative impulse.

As series go, the Dortmunder books had an unlikely start—he was originally envisioned as a one book guy, but then he returned again and again—and he would still have a few more adventures waiting in his future. Westlake’s affection for the character as well as his love for the weird and awkward situations he can stick the guy into is evident on just about every page.

What’s The Worst That Could Happen? might not blaze any new trails for the author of the character, but it is a fine, fun read from the master of comic crime fiction. It’s comfortable territory for the writer, comfort reading for the audience, and it manages to play the role of a grand welcome for new readers. As with Wodehouse’s Jeeves and Wooster novels, each of the Dortmunder books stands well on its own. What’s The Worst That Could Happen? is no different in that regard. The novel is a light read that manages to achieve poignancy in occasional moments; this blend is a Westlake specialty.


What’s The Worst That Could Happen? Is available in an eBook edition. Since this novel saw release as a film starring Martin Lawrence and Danny DeVito, there are tons of artifact editions in the world available from secondary sources with a little looking. The whole run of Dortmunder books are available in eBooks, some of them also in paper copies, and they are worth the investment.

Next up in the Considering Westlake reading series is The Ax, a chilling novel that runs closer to horror than the author is perhaps known for (despite the horror elements in Pity Him Afterwards and Sacred Monster). A perfect book to chop up (heh) for Thanksgiving. Grab an overpriced eBook copy, today.


Westlake, Donald E. What’s The Worst that Could Happen? Mysterious Press: 1996.

“Considering Westlake: What’s The Worst That Could Happen?” is copyright © 2019 by Daniel R. Robichaud. Cover image and quotes taken from the Mysterious Press hardcover edition.

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