Discovering Dortmunder: The Road to Ruin


The eleventh Dortmunder story, The Road to Ruin, though frequently funny, was something of a disappointment on first reading, and whilst it improves on closer acquaintance, it’s still one of the weaker efforts in the canon, for much the same reason as Bad News: John Dortmunder, the ingenious planner, simply doesn’t get enough to do.
It’s not the case that Dortmunder and Co are inserting themselves into someone else’s heist, although the job is brought to them from the outside. Once the idea arises, the gang approaches the job in their usual fashion. But the plan Dortmunder devises to achieve their ends is surprisingly simplistic, and its inevitable frustration has none of the usual sparkle and wit Westlake usually brings to the workings of fate and the real world.
The Road to Ruin begins with a double break with tradition. Firstly, Dortmunder is not on a job that’s either failed or, within moments, is about to fail. Indeed, he’s in the apartment he shares with May, watching the 6 o’clock news.
The second breach is that the street-bell rings, and it’s Kelp: the same Andy Kelp who usually lets himself into their apartment so as to spare John or May the trouble of opening the door. Kelp’s being formal today because he’s not heard from Dortmunder in some time, and he’s worried that John has cut him out, is running with another bunch of guys. Dortmunder can reassure him on that: he’s not even pulling single-os at the moment. Things are pretty dead.
Until Anne Marie phones from Kelp’s apartment, which has just been invaded by this guy, giving no name, wants to see Kelp, is prepared to wait. Dortmunder returns with him, to lend moral support, but there’s nothing to fear: the interloper is Kelp’s old buddy, Chester Fallon, a driver.
Chester’s led an interesting life. First, he was a stunt driver for the movies, until he got replaced by CGI, then he used to work driving away from banks, which is how he knows Kelp. After getting parole, he went to work as chauffeur to Monroe Hall, a rich guy who has a great collection of vintage cars, $6,000,000 worth: perfect job, with house, medical benefits and pension thrown in through Hall’s company, SomniTech.
Until Hall was found to be embezzling SomniTech, and pretty much everyone under the sun, in a deeply greedy and omnivorous fashion. So now Monroe Hall is a pariah, unable to leave his estate in Pennsylvania on account of all these people hanging around wanting to have discussions with him about the staggeringly large sums of money they’ve lost. And the cars have been turned over to a charitable foundation in Florida, even though they’re still ‘displayed’ at the impenetrable, security-wrapped Pennsylvania estate.
Except that the Foundation can’t employ ex-cons, so that’s Chester out on his ear; no job, no house and, thanks to SomniTech having been sucked dry, no pension or medical benefits. So now Chester hates Monroe Hall, like everybody who ever meets him, with the exception of his still-loving wife Alicia. Chester would like some revenge. $6,000,000 of vintage cars-worth.
Naturally, after another trip to the O.J. Bar & Grill on Amsterdam Avenue, the regulars are in the midst of another of their endless cross-purpose rambles, Stan Murch and Tiny Bulcher are on board and the gang head for Pennsylvania in another of Kelp’s doctor’s cars – nice and spacious, to suit Tiny – to case the joint. The security is, however, impenetrable. No-one can get in, and whilst Alicia Hall and the cook come out, Monroe Hall doesn’t.
Dortmunder’s solution is surprisingly simple. Hall, being both a pariah, and a man who offends people as easily as you or I click on a blog, is desperately short of staff: the gang will get themselves hired.
This isn’t quite as easy as it sounds, given the no ex-cons barrier, but this is where Anne Marie – who has adapted with surprising smoothness to this unusual life – comes in. Among her friends from her Washington days as a Senator’s daughter is the deliberately anonymous Jim Green, former FBI Agent and specialist at creating unbreakable new identities for people. Green costs too much for the gang to buy four lives off him, and four’s too many for freebies, but he can let them have four existing identities that the recipients no longer use.
The only risk is that if any of the original inhabitants of these identities created any enemies, any revenge might be directed against these temporary users, but it’s probably only a small risk, eh?
(You’re getting ahead of things. Slow down.)
So Monroe Hall gets four new staff simultaneously: Warren Gillette, a carroty-haired chauffeur, Judson Swope, a man-mountain security guard, Frederick Blanchard, a sharp-featured private secretary, and John Rumsey, a hangdog-looking, slope-shouldered butler. (There’s an in-joke here, but you’re going to have to wait for me to get to the right book before I explain it).
Once inside, the plan is, once again, utter simplicity. Tiny is doing the graveyard shift as the new boy, so he’ll open the gate whilst the other three drive the cars off to a handy holding space whilst the gang dicker with the insurance company.
I mean, that’s it. In terms of Dortmunderian ingenuity, this is kindergarten stuff. I could plot a crime novel with this plan, and I don’t even write crime novels.
So the book, which is already reliant on the little details along the way – the best of which being the discovery that Arnie Allbright’s family, who mainly go in for counterfeiting, have staged an intervention and sent Arnie to Club Med on one of them islands, to get his personality cleaned out –  becomes ultra-dependant on the foil. How will this one screw up?
Westlake takes his time getting there. Given the simplicity of the gang’s part in it, the story stretches to encompass lots of other viewpoints. There’s Chester, for one, taking a (hopefully temporary) job as driver to a drunken sales-rep, under constant bombardment by sales-rep jokes. There’s Monroe and Alicia Hall, at different times: he an unthinking, unheeding monster of selfishness, contemptuous and callous of all, she an attractive, intelligent, perceptive woman doomed by the fact she still loves him.
There’s Hall’s personal trainer, Flip Morriscone, trying to get somewhere with a suet pudding of a man, who Hall betrays to the IRS. Henry Cooper, old ‘friend’ of Hall’s and owner of the Employment Agency to whom the gang apply.
And then there’s Mark and Os, and Buddy, Mac and Ace.
These are people who have been wronged by Hall, people who have been stalking the estate, people who want to get hold of Hall, just for a while, for some monetary redress (Hall, though technically making redress for his embezzlements, is in control of substantial, hidden assets offshore). Mark and Os are brokers, privileged men from privileged families, who want to be put back where they were. Buddy, Mac and Ace are union men, trying to get money back for, not directly themselves, but rather the ACWFFA.
These two sets join forces – tentatively, with piles of mistrust on both sides but no actual double-crossing – and with the assistance of Morriscone, they get onto the estate in a horsebox (Hall wants to take up horse riding) and they get off the estate with Hall in the horsebox.
Unfortunately (that word crops up rather often when discussing a Dortmunder story, doesn’t it?), they also have to take the witness to the kidnapping. The butler, John Rumsey.
Now Dortmunder is not unresourceful, as we have seen. Dortmunder escapes from captivity using a chair (he smashes it into the face of the guy coming into his room, and runs). Monroe Hall, however, is even more resourceful, and escapes from the hunting lodge in which they’re being held. Unfortunately (that word again), he doesn’t so much jump from the window as fall out of it. As a consequence, he hits his head, hard, on a head-sized rock. And loses his memory. Permanently.
Including all the passwords and codes to those off-shore holdings.
And everything just drains away like water. Whilst Dortmunder is making his way back to Pennsylvania, Kelp, Murch and Tiny have to watch the Foundation driving all the cars off the estate, to go to Florida, leaving nothing.
Which, sadly, is the feeling this denouement leaves.
As for the amateur conspirators, whose blunderings across Dortmunder’s path have led to this disaster, the fall-out takes different outcomes, with a pleasingly blue collar twist. And Dortmunder and Co. return to New York dogged by the realisation that they have actually spent two days working in a job!
Westlake does throw in one final plot twist, as we near the end of the book. As Jim Green warned, there is indeed an enemy, a foreign assassin no less, seeking the whereabouts of Fred Blanchard. However, this final twist gets untwisted with such perfunctory and unexpected ease, that it just becomes the reddest of red herrings.
Despite all of this, I like the book, and it’s still plenty funny. But I like it because I know Dortmunder and his friends and associates and hangers-on so well, because their skewed perceptions and the slightly surreal atmosphere that surrounds them is comfortable and engaging, because I like hanging around with them.
In that sense, The Road to Ruin is an archetypal late series book, getting by on familiar routines and tropes, but beginning to have some difficulties in finding fresh things for the cast to do. It might have been the point at which the series began to run into the ground, especially as – breaking his inviolable rule of thirty-odd years – Westlake was going to be writing another Dortmunder story immediately after this one.
But The Road to Ruin would prove to be no more than a stumble, as the series would pick up into its final, compressed years.
Strictly speaking, the next Dortmunder book, published later the same year as this novel, is the short story collection, Thieves Dozen, collecting together all the Dortmunder short stories then published. But I’m leaving the short stories until next to last, after we’ve covered all the novels. You’ll have to wait for me to explain that in-joke.

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