Tough Guy; Good Reads – The Ray Dudgeon Novels By Sean Chercover

The Author: Sean Chercover

Sean Chercover worked as a private investigator.

That fact is so frequently raised as the first point in any discussion of Sean Chercover’s books that it may be some kind of an informal, if not contractual, agreement his publishers reached with the reviewers’ guild.

In Chicago, arrangements get worked out like that.1

I am, however, more often in search of a competent author than an effective PI; consequently, this post will be more concerned with Mr. Chercover’s writing than the authenticity of his gumshoedness. As he himself points out,  “I gained enormously from my time working as a PI … but it didn’t teach me how to write.”2

In testimony to Sean Chercover’s writing skills, I offer into evidence the opening lines of his first novel, Big City Bad Blood:3

In the shadows of the John F. Kennedy Expressway, surrounded by warehouses, factories and auto-body shops, stands Villa d’Este, a family-run restaurant that serves generous portions of decidedly untrendy Italian-American food at reasonable prices. The restaurant was there more than thirty years before the expressway slashed the neighborhood in two and I imagine it’ll be there long after the Kennedy collapses under the weight of bureaucratic neglect and political corruption. In Chicago, some things never go out of style.

I paced the restaurant’s black and white checkerboard marble floor, waiting to ask Johnny Greico if he planned to kill my client. I didn’t know how he would take such a question and I decided not to think about it. So I thought about other things.

It’s not “Call me Ishmael,” but it’s certainly effective, efficiently setting the tone, describing the physical and cultural environment, exposing a bit of the narrator-protagonist’s personality, inserting a soupçon of sardonic humor, and precisely positioning a nifty hook to entice the reader to continue.

Not bad for two short paragraphs.

The Books: Big City Bad Blood and Trigger City

Both novels are built around Ray Dudgeon,4 a former journalist turned private investigator who is the center of the action as well as the narrator. Ray Dudgeon is a complex, acutely introspective, ironic detective who is willing to manipulate, mislead, or coerce others for his version of the greater good but is unwilling to deceive himself about his motivation or avoid responsibility for his actions.

He is, in many ways, the less glib, Chicago-style, PI  version of  Mickey Haller, the titular hero of Michael Connelly’s The Lincoln Lawyer, whom I previously described as a

Los Angeles defense attorney whose roster of clients is composed of various lowlifes. He is a bit world weary but still in the game; … He openly attests to being motivated by cash ( “Don’t do the crime if you can’t pay for my time.”) and to being able and willing to play all the angles, although, as we soon find out, he remains true to a deeply ethical core. … His concern that he may have not recognized the innocence of an earlier client becomes intertwined with the current case, resulting in a dilemma which forces Mickey into a battle with many fronts: his ethical responsibilities to his previous and current clients, his concern for his own and his family’s safety, the risks to his personal reputation and livelihood, the cost of adhering to his own moral code, and the threats to his self-image.

Ray inhabits a universe free of superheroes in which everyone demonstrates psychological vulnerabilities, mixed loyalties, and notably imperfect behaviors. Even long standing best friends are not immune to influences other than personal allegiances and are not always stand-up guys.

Ray’s love life fits is congruent with his other relationships. He is desperately in love with a woman who reciprocates his affection but is simultaneously repelled by the violence and moral ambiguity of his work, creating an ongoing tension as he confronts the dilemma of either winning the confidence and love of this woman by giving up the work which has proven his only means of dealing with his demons or losing her forever as he continues his current path.  Ray, of course, is incapable of doing either, a situation neatly placed on display when, In Trigger City, Ray hires his own assistant to maintain surveillance on his then ex-girlfriend’s lover, not in order to intimidate the new man in her life but in hopes of finding a character flaw that would prove he was not good enough for her.

A disappointingly overlooked  element in Ray’s personality profile, at least in the reviews I surveyed, is that he reads. He reads autobiographies (e.g., The Autobiography of Benvenuto Cellini). And novels (e.g., The Book of Ralph). For fun. Left alone to wait for a meeting, he invariably roams through the bookshelves. He makes stops at Powell’s Bookstore, Stuart Brent Books, and Waldenbooks.  In one scene in which he is obsessed with protecting the life of a woman from a chain of violence he himself set in motion, Ray interrupts his internal morality debate when he realizes he may be spending many hours protecting the potential victim and he has nothing to read.5 He immediately takes the time to hit a bookstore to find an interesting volume. (That the book he buys later becomes part of a sequence that ends with Ray killing a man pursuing him through a shopping mall with a knife is, as far as I’m concerned, tangential.) While we also learn about his office decor and his taste in  music, those are routine sections of the standard checklist for fictional detectives. Name a few other hard-boiled PIs with heavy reading habits. If one eliminates the tony Anglophilic group of  cerebral (soft-boiled?) detectives such as Ellery Queen, Philo Vance, Nero Wolfe, Lord Peter Wimsey, and Sherlock Holmes, only Spenser, Jack Taylor, and John Dunning’s Cliff Janeway, the tough Denver cop turned bookstore owner, come immediately to mind.

While the moral and psychological coordinates of Ray Dudgeon’s world may be ambiguous, his geopolitical  field of operations is explicitly Chicago. And, recognizing  a few of the restaurants, streets, and landmarks enriches the reader’s experience.  Those poor souls uninitiated into the nuances of Chicago can, however, rest assured that any local information essential to the plot (e.g., the status of organized crime in Chicago) is provided in the text.6

This is not to say that these books were my perfect read.  My perception, for example, is that Chercover indulges in more violence than needed to advance the story. And, the plot of Trigger City is too dependent on  black ops, mercenaries, private agencies hired to do the government’s dirty work, and too many too-secret, too-powerful government agencies. At some points, I felt as though a change in the direction of the action was less a plot twist driven by the devious aims of a secret government agency than an arbitrary movement rationalized by a new revelation, like a magician pulling the 83rd rabbit from his hat.

Still, those complaints can legitimately be attributed to differences in individual tastes, and, in any case, I end up with a long list of items in the category, mandatory in the book report template favored by my fourth grade teacher, “Why I Like This Book and Think You Will Like It Too,” and a list of negatives that is strikingly shorter.

Heck, I even have a list headed “Could Go Either Way” with a single entry: Gravedigger Peace.

Gravedigger Peace,7 is Ray’s childhood friend  who spent some time dealing out death and destruction in the service of one national agenda or another and who is now redeeming himself by serving as the groundskeeper of a cemetery. In both books, he is presented as the final resort for Ray – the go-to guy when something has to be done, no questions asked. Gravedigger Peace has become the darling of many fans and reviewers.  While I have not yet leapt onto this particular bandwagon, I do like the idea of a sometime sidekick for Ray and even envision  Gravedigger as a sort of dark-side edition of Skink, the recurring character in a number of Hiaasen novels (e.g., Double Whammy, Sick Puppy) who went mad  while  Governor of Florida from dealing with the scummy politicians and businessmen and escaped into the Everglades where he dines on road kill, periodically emerging to punish evil-doers or assist the heroes, tasks always accomplished in the most bizarre manner imaginable.

I end this review by pointing the reader to an Chercover entry From The Outfit, a blog produced by a group of crime writers based in Chicago.  While this is ostensibly one more indication of Chercover’s skills as a writer (a purpose it does serve), I’m actually including this reference because I get off on pieces written by authors who value accuracy, write well, and make me laugh while pointing out violations of reality in less astutely constructed publications and broadcasts. I’ve excerpted a couple of sections from  his treatise on the depiction of gunplay in crime fiction, Egregious Gunplay . . .8 but urge viewers to read the entire post.

3. People do not fly backward through the air when they are shot. They just don’t. So knock it off with the people flying through the air. It’s stupid, no matter how many times you saw it in a Steven Segal movie. Truth is, most people who are shot don’t even know they’re shot, right away. Not only do they not fly backward through the air, most times they don’t even fall down for a while. They’re in shock, and it takes a minute before they realize they’ve been hit. Movie nonsense aside, if a bullet were able to send someone flying backward, then the shooter would also be sent flying by the recoil. Action-reaction. Laws of physics. Get it? Good.

5. Stop “jacking a round into the chamber.” This is the pistol equivalent of “checking your load.” What made you think this was a cool thing for tough guys to do? Oh, yeah, those Steven Segal movies. Right. If your character is a professional (PI, cop, or professional bad guy) then s/he will most likely carry in Condition One. Which means, a round in the chamber, safety on. There’s no reason to jack the slide, since there’s already a round in the chamber. Yes, there are pistols that you don’t carry in this manner, but even then, stop “jacking a round into the chamber” for dramatic effect. You’re driving us crazy with that crap, and it’s a cheap substitute for real tension.

Reading an essay that well done, that convincing, and that entertaining… well, if that isn’t Christmas, I don’t know what is.


Note: Originally posted Dec 8, 2008 at, a predecessor of


  1. This line, as far as I know, is not true. I’m just working on my cynical, tough guy, see things as they really are voice in emulation of Mr. Chercover’s admirably hard boiled tone. []
  2. Trigger City by Sean Chercover by Tasha Alexander at the  International Thriller Writers web site []
  3. This passage is not the epitome of Chercover’s writing; it is, however, well-done, representative of his work in general, and, of special import to one who belatedly decides to post a review and consequently lacks those bookmarks conveniently signaling relevant portions of the book, easy to locate. []
  4. I had written a speculation about Chercover’s choice of an almost Dickensian name for his protagonist yesterday. While doing a final fact check this morning, I found Chercover himself had neatly addressed that exact issue in a post dated yesterday. One can, I suppose, make a prima facie case that the author’s report of his own intentions carries a superior claim to more validity than my guesses on that point. Consequently, I have replaced my explication with the excerpt of the relevant lines from Chercover’s  The Name Game . . . :

    Ray Dudgeon, my series protagonist, went through many names along the way. His penultimate name was Ray Dunbar. Dunbar Road is the street I grew up on. I didn’t like the name Dunbar, but I liked Ray, and I liked the way it sounded with a surname that started with D. I also like names that have independent meaning as words. Spade, Archer, Hammer, Reacher, Strange, Rain . . . all great names that tell us something about the character. So I started flipping through the letter D, in Webster’s dictionary.

    Dudgeon fit my protagonist perfectly, both for its modern meaning and for the archaic meaning, most famously used by William Shakespeare in Macbeth. A few folks have commented that Ray’s name is a bit too clever, but the vast majority of people dig it. And I’ve had email correspondence with a number of real-life Dudgeons as a result, including a real Ray Dudgeon.

    A totally unexpected benefit of using an unusual name.

    The Shakespeare reference, by the way, is to Macbeth soliloquy in Act 2 scene 1, which describes what Macbeth anticipates seeing when he murders Duncan: “I see thee still, and on thy blade and dudgeon gouts of blood, which was not so before.” Since dudgeon, in this context, is the hilt of the dagger, the image is of Duncan’s blood covering not only the blade but also the handle of the dagger. []

  5. As the poster child for abibliophobia, the fear of running out of things to read, I empathize with a fellow sufferer. []
  6. Only after reading both of Mr Chercover’s books did I discover that he is a native of Toronto. Once again, my Canadaphilic inclinations are outed. []
  7. The name, “Gravedigger Peace,” according to The Name Game . . . , is a respectful tip of the fedora to Grave Digger Jones, a brutal Harlem cop featured in the novels of Chester Himes []
  8. For extra fun, compare Chercover’s Egregious Gunplay with Fenimore Cooper’s Literary Offenses, Mark Twain’s evisceration of Cooper’s deranged vision of life on the frontier []