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Dortmunder asks the eternal question.
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John Archibald Dortmunder is a fictional character created by Donald E. Westlake, and who is the protagonist of 14 comic novels and 11 short stories published between 1970 and 2009. He first appeared in the novel The Hot Rock, published in 1970.

Dortmunder is a career criminal and a planner; creating schemes for burglaries, assembling a team, and assigning responsibilities. However, Dortmunder's schemes never run as smoothly as he would like them to, and almost always dissolve into a Plethora of Mistakes, followed by Crime After Crime as Dortmunder and his crew have to commit a succession of different crimes while attempting to achieve their original goal (if they haven't lost sight of the original goal altogether).

The fact that something almost always goes wrong with Dortmunder's jobs, in spite of careful planning, has given him the reputation of being jinxed — and despite claiming not to be superstitious, Dortmunder has believed so, too. In fact, Dortmunder gets worried when things go smoothly and seems relieved when something does go wrong. In most novels, Dortmunder's team earn only small amounts of money; the resultant heists, therefore, are only Pyrrhic victories, and the moral for the reader is that Crime Does Not Pay ... at least not very well. However, Dortmunder is not always unlucky, and in some novels and stories he and his crew make out quite well.

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The works in the Dortmunder series are:

Novels:

  1. The Hot Rock
  2. Bank Shot
  3. Jimmy the Kid
  4. Nobody's Perfect
  5. Why Me?
  6. Good Behavior
  7. Drowned Hopes
  8. Don't Ask
  9. What's the Worst That Could Happen?
  10. Bad News
  11. The Road to Ruin
  12. Watch Your Back!
  13. What's So Funny?
  14. Get Real

Shorter Works:

  1. Thieves' Dozen (2004), a collection of ten Dortmunder short stories and one related story.
  2. "Walking Around Money" (2005), a novella in the anthology Transgressions, edited by Ed McBain.

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Tropes in the Dortmunder series:

  • Bavarian Fire Drill: Dortmunder pulls this off brilliantly in What's the Worst That Could Happen?, managing to convince his target's bodyguards to hand the target over to him by faking a fire. (Incidentally, this is one of the few times where A Simple Plan of Dortmunder's runs exactly as he envisaged it.)
  • Born Unlucky: Dortmunder has an uncanny ability to snatch defeat from the jaws of victory by having the most unlikely things go wrong. He actually feels uneasy if everything is going too well on a job.
  • The Caper: Every Dortmunder story is a caper of some variety.
  • Clipboard of Authority: In What's the Worst That Could Happen?, Dortmunder and Kelp are able to gain access to almost every area of the Watergate complex by dressing as engineers and carrying clipboards.
  • Caper Crew: Dortmunder is the Mastermind, Kelp is the Partner In Crime, Murch is the Driver, and Tiny Bulcher is the Muscle.
  • The Casino: In What's the Worst That Could Happen?, the final crime in the escalating series of crimes committed by Dortmunder in his attempts to regain his ring is an Ocean's Eleven style heist on Max Fairbanks' casino in Las Vegas.
  • The Convenient Store Next Door: In one of the short stories, Dortmunder and his crew tunnel into a bank from a nearby building. They emerge in the middle of another bank robbery and become part of hostage situation. They ultimately end up using their tunnel to help the hostages escape.
  • Crime After Crime: Almost all of Dortmunder's schemes end up with the crew having to commit additional crimes due to the original heist not running to plan. The Hot Rock is a classic of this and prompts the client financing Dortmunder's scheme to remark "I've heard of the habitual criminal, of course. But I never dreamed I'd become involved with the habitual CRIME."
  • Criminal Procedural: All the Dortmunder books involve cons, capers, criminals, and gentlemen thieves.
  • Deprogram: Good Behavior, involves the group of criminals having to rescue a young nun from the deprogramming efforts of her corporation-owning father.
  • Double Caper: In The Hot Rock, a team of crooks is hired to steal a valuable emerald. After five separate attempts to get it, all but the last of which fail, they finally get their hands on it — and the diplomat who hired them stiffs them. So they steal it back from him, give it to a rival nation in exchange for a fake version, and wait for him to try to buy it off of them so they can reveal that they sold him a fake.
  • Eat the Evidence: In The Hot Rock, Greenberg is trapped in the museum with the emerald the gang was attempting to steal. He swallows the emerald before the police arrive.
  • Evil Is Petty: In What's the Worst That Could Happen?, Max Fairbanks catches Dortmunder burgling his beach house. Fairbanks hands Dortmunder over to the cops, which Dortmunder regards as a fair cop as he was caught fair and square. But then Fairbanks claims that Dortmunder's ring is actually his and takes it off him. This act of petty vengeance means It's Personal for Dortmunder and kicks off the plot.
  • Go-to Alias: Dortmunder occasionally use the alias "John Diddums" (he claims to anyone who asks that it's Welsh), a name he dislikes but uses involuntarily in circumstances that preclude using his real name. The first time he used it, he started to say 'John Dortmunder', caught himself after say D, and blurted out the first thing to come into his head. He has been stuck with it ever since.
  • Hypno Fool: At one point in The Hot Rock, the crew hires a hypnotist to plant a trigger in a bank guard to help them get the emerald out of a safe deposit box.
  • I Am One of Those, Too: Once, under pressure, Dortmunder claimed his name was "John Diddums," and then started to use it as a regular alias. Whenever people asked about the name that sounds like babytalk, he'd tell them, "It's Welsh," and they'd be embarrassed for questioning it. And then he ran into a British gentleman who remarked, "I know a Diddums family near Caernarvon. Might you be a relative?"
  • Monumental Theft: In Bank Shot, Dortmunder and his crew steal a bank. (It was a temporary branch established in a mobile home, but even so, it shows some serious ambition.)
  • Pity the Kidnapper: Dortmunder and company bite off a lot more than they can chew when they turn their hand to kidnapping in Jimmy the Kid.
  • Plethora of Mistakes: Almost every one of Dortmunder's carefully planned heists run afoul of this.
  • Steal the Surroundings: In Bank Shot, the gang steals an entire bank in order to crack the safe! The bank had temporarily relocated to a trailer while the bank building was being renovated.
  • Sue Donym: When asked for his name, Dortmunder started to say 'John D...' and the hurriedly changed the last name to 'Didums': the first thing that popped into his head. This later becomes his Go-to Alias, despite him hating it, as it always the only alias he can think of when under stress.
  • Tempting Fate: The superstitious Dortmunder should really have known better than to ask "What's the worst that could happen?" before embarking upon a seemingly simple job in What's the Worst That Could Happen?.
  • Walk, Don't Swim: Dortmunder and Kelp plan to do this in an attempt to retrieve a cache of stolen cash from under a lake in Drowned Hopes. It fails as they discover the inherent buoyancy of the human body.
  • What Could Possibly Go Wrong?: What's the Worst That Could Happen? takes its title from an offhand remark Dortmunder makes before he embarks on the initial crime of the novel; burgling an empty house. Needless to say, this crime goes horribly awry and Dortmunder gets arrested. After he escapes, he embarks upon a series of crimes in an attempt to recover the ring that was stolen off him by the householder who caught him. The phrase gets repeated before each of these crimes. Atypically, these crimes are spectacularly successfully and net Dortmunder the biggest profits he ever makes in the books, but he fails to obtain the one thing he actually wants: his ring.


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