Tag Archives: William ‘Bad Bill’ Bailey

Addendum: 361 Revisited


“This thing about family,  now, he said.  “It’s an important thing with a lot of people.  All kinds of people.  And I’ll tell you a group of people it’s important to, and that’s the people who make up the mob.  Particularly in New York.  You don’t think so?  Hard cold people, you think.  No.  There wasn’t a two-bit gun carrier on the liquor payroll didn’t take his first couple grand and buy his old lady a house.  Brick.  It had to be brick, don’t ask me why.  It’s in the races, national backgrounds, you know what I mean?  Wops at the national level, mikes and kikes at the local level.  Italians and Irish and Jews.  All of them, it’s family family family all the time.  Am I right?”

From 361, by Donald E. Westlake.

I had planned to post my review of Up Your Banners this week, but between rereading the book itself, and researching its background, I fell behind schedule.   And in the process of researching it, I came across an article I wish I had known about when I reviewed 361, last April, because it sheds some light on aspects of what I think is now widely agreed to be Westlake’s best book written under his own name in the first half of the 1960’s, and one of the best crime novels of any era.

It fell along the wayside for a time, I think, because of the notion, still prevalent in some quarters, that Donald E. Westlake wrote comic capers, and his alter-ego Richard Stark wrote hard-boiled heist stories.  It was never that simple, but it was an appealing meme–here’s this guy who writes funny lighthearted criminal romps with sad sack protagonists like Dortmunder, but sometimes he’s this other guy who writes about a cold-blooded killer named Parker.

The implied dichotomy was even turned into a best-selling horror novel by Stephen King, who had named his alter-ego Richard Bachman partly out of homage to Richard Stark, and then borrowed the other half of the name–but it’s hard for me to see how Richard Bachman is any darker or more ‘visceral’ than Stephen King.  He’s just a bit harder to pigeonhole, which I assume was the point.   Westlake is a far better example of a writer doing radically different things under different names, but under his own name he might do almost anything–and he nearly always did it well.

In any event, 361 was hardly ignored when it first came out, even if it was no best-seller.  It was reprinted in many countries, many languages, and inspired some of the most interesting cover art I’ve seen for any book, as well as a variety of new titles (though the original title proved fairly durable).

Mexico and Portugal:


British hardcover and paperback:


French Serie Noire and Italian Giallo:


Japan and Germany:


Finland and Sweden (sharing the same publisher, if not the same title):


Sometimes I don’t know what I’d do without the Official Westlake Blog’s cover galleries.  But please note, every single one of these editions came out in the 1960’s.  This was a forgotten book for quite some time after that, until Hard Case Crime put out the first American paperback edition, which is how I first came to read it, and probably many of you as well.


So now that we’ve all rediscovered the glories of the early hard-boiled Westlake, before the Nephews, before Dortmunder, and quite a long time before The Ax proved beyond all doubt that he could still write the hard stuff under his own name–what do we make of this book, and its odd multi-ethnic pre-Godfather take on organized crime?

Ray Garraty and I have had many discussions here and elsewhere about why Westlake seems determined throughout the 1960’s to not make the mob an exclusively Italian thing.  Italian mobsters do show up (Italian by name only, it often seems), but so do lots of Irishmen, Jews, and some guys with generic ‘American’ names.  I’ve put forth a variety of explanations for this.  Was he trying to avoid offending Italian-American readers, sensitive to the assumption that they were uniquely responsible for racketeering in America?  Was it just a convention of the genre as a whole, going back to the old Warner Brothers gangster pictures that had inspired so many crime writers, Westlake included?

Well, it may not have been any of that.  I now enter into evidence Exhibit A–a New York Times article, dated April 13th, 1980–Donald Westlake: Larceny and Laughter, by Sheldon Bart (himself a novelist).  It was printed right next to a review of Westlake’s latest novel at the time, Castle in the Air, and is mainly devoted to an interview with Westlake (after first mentioning that he was working with Joan Rivers on a script for something entitled A Girl Called Banana). 

The reader of this article is informed about the Westlake/Stark thing, and further told that “His style is bright and zingy and his books abound with clever twists and fast dialogue.”  Well I guess you’re supposed to say stuff like that when you’re interviewing a writer.

Bart kicks off the interview with the usual “Where do you get your ideas from?” sort of question, only it’s got a somewhat odd spin to it–why does Westlake write so much about crime?  I guess Bart never heard of the mystery genre before? Or is this something pre-arranged between them?  Either way, he opens by asking “Was your father a criminal?”  

Now in Bart’s place, I personally would not have gone there, but instead of taking umbrage, Westlake tells a story–I’d copy/paste it, but you can’t do that with the database I found this on, so I’ll just have to type it out.

Sometime before I was born, my father and mother and another couple were in a speakeasy in New York, and a tall skinny man in a shiny black suit came in, followed by two tough-looking guys with their hands in their topcoat pockets.  They headed toward the rear of the place, but as they passed by my parents’ table the skinny man looked at my father and said “Hi Al.”  My father said, “Hi, Bill.”

Bill pulled up a chair, sat down and called for a bottle of champagne for the table, on his tab.  The two guys with him didn’t sit down or look at anybody in particular.  My father didn’t introduce Bill to the others at the table.  Bill and my father talked baseball for a while, my father being a very passionate Giants fan, the Giants being at that time a perfectly respectable Major League baseball team in Upper Manhattan and not a lot of padded psychopaths in a Jersey swamp.  Then the champagne came.  Bill had a taste, and then he got to his feet and said “See you later, Al,” and he and his two friends went away through the door in the back.  My mother said “Who was that?” and my father said, “Bill Bailey.  I’ll tell you about it later.”  But he never did.  Now Bill Bailey was a prominent gangster and bootlegger, Dutch Schultz’s right-hand man who took over the Schultz mob for a while after Dutch was killed.

My mother told me this story after my father was dead, so I couldn’t ask anybody any questions.  Then later on, after my mother died, I found something very curious in a trunk in the basement.  A packed-away trunk is in geological layers, the most recent stuff on top, the oldest on the bottom, and that’s the way it was with this trunk, working on down all the way to my father’s World War I uniform on the bottom.  But then under the uniform, out of proper sequence, were a lot of newspaper clippings about the death of Bill Bailey, which took place in 1931.  It was a strange death; he walked into a hospital, and was admitted, and by midnight he was dead.  The death certificate said advanced pneumonia, but doctors I’ve talked to tell me nobody walks around like a healthy man seven hours before dying of advanced pneumonia.  Anyway, those are the only newspaper clippings my father ever saved, and he went out of his way to  hide them, and that’s all I know about it.  Except that for a while my father was a bookkeeper for a sugar company, and I know the bootleggers needed a lot of sugar in making their booze, so maybe that’s the connection.  Anyway, the mysteriousness of it, the completely impenetrable aura, if that’s what I mean, has occasionally gotten into my books, particularly the early ones.

Hard to say how much research he did into the history of organized crime in response to this–some, certainly–but based on the bit of research I did via Google (hardly an option for him back then), I think we can say that Westlake never made much attempt to master the subject.  William ‘Bad Bill’ Bailey was the right-hand man of Vannie Higgins. Higgins was a bitter rival of Dutch Schultz during the Prohibition era, who exchanged shots with The Dutchman on more than one occasion, and was eventually fatally wounded (perhaps by Schultz’s men), several years before Schultz himself was killed.

There’s not a lot of information about Bill Bailey out there.  That’s him standing (appropriately enough) to the right of Vannie Higgins, in the photo up top–in a dark topcoat–Higgins is in the trench coat.  And before you ask, the song “Won’t You Come Home Bill Bailey” is not about him.  I checked.  That must have been another Bill Bailey.   But if there’s one thing we can know for dead certain, it’s that this Bill Bailey couldn’t have taken over for Dutch Schultz, because he died (of natural causes or otherwise) in 1931, and Schultz was famously (or infamously) murdered on October 24th, 1935.   Westlake wouldn’t have needed Google to find that out.  He didn’t give a damn.  He was writing fiction, not history.

So why all the mob stories?  Because to him, the point of that little anecdote about his dad was that all your parents have secrets, lives they lived before you were even born.  Mostly those secrets stay buried, though if they live long enough, maybe they’ll tell you some of them (my dad’s shared some real corkers with me in the last decade or so–no ganglords so far).  Westlake lost his father when he was still a very young man, his mother not long after, and there were questions he was never going to get to ask them, answers he was never going to find.

He’s writing in a genre where stories about organized crime are de rigeur, but how does he put his own unique spin on them?  His most important literary role model, Dashiell Hammett, wrote mainly from the detective’s point of view–saw criminals only from the outside, though he had the advantage of actually knowing a whole lot of them from his work as a Pinkerton.

His more contemporary influence, Peter Rabe, used mob stories as a way of dissecting character–strong willed, resourceful, but ultimately chaotic individualists, striving for power in an organization, and eventually undone by a combination of hubris and emotional vulnerability.  Psychological case studies, from a future psychology professor.  The only ones who survive are the ones who just give up the game they’re playing before it’s too late, let go of their ambitions, learn how to live for the sake of living.

Westlake probably never made the acquaintance of any real crooks until he started getting fan mail from them, mainly for his Parker novels–in the article I quoted above, he says he got a letter from one guy who was about to start serving a long stretch in prison, and he was hoping Westlake could fill a few holes in his collection of Parker novels, because he wanted to take the whole series into the joint with him.   Westlake doesn’t say if he provided the books–the guy only needed two of them.  I’m guessing Westlake helped him out.

But while he clearly got some ideas from these letters–I see references in that interview to missives he received from criminals that almost certainly inspired Help I Am Being Held Prisoner and Bank Shot–his knowledge of the criminal class remained primarily second-hand.  He maintained a certain distance between himself and his subject material, which was certainly prudent.  And he had to start writing crime novels before he could get fan mail from criminals–361 can’t be based on correspondence he hadn’t received yet.

No, he was mainly working from pre-established fictional models–Hammett, the Gold Medal novelists (Rabe, Jim Thompson, Chester Himes), the Warner Brothers pictures of the 30’s and 40’s.  And many others.  But he’s going to make this old subgenre new and personally relevant, by linking it up to his belated discovery that his father was connected, however peripherally, to the world of organized crime.  As so many Americans were, during Prohibition.  Perhaps the majority, in the sense that most Americans never really accepted the 18th Amendment, went right on drinking what they damn well wanted to drink, and came to admire many of the colorful characters who supplied their illicit hooch.   That goes on to this very day, of course–but never to the same extent seen in the 20’s and early 30’s.

The Italians (chiefly but not entirely Sicilians) were gaining ever-greater power in the gangs of that period, because of the syndicate subculture some of them had brought from the old country, and the fact that it was harder for them to assimilate into the mainstream (the most talented individuals from other groups would more often find other outlets for their talents).

But they were joined by German, Russian, and Eastern European Jews (who also had assimilation issues), the Irish (troublemakers wherever we go), and quite a few poor WASP’s–basically every group that was on the outs with society in some way.   And that’s a lot of people.   And while some members of these groups would fight Italian control, others were quite happy to go along with it, as long as they got their slice of the pie.  The ethnic boundaries were never that clearly drawn, and certainly not back in those days.

At their peak, these racketeers were so politically and socially well-entrenched that Vannie Higgins could land his private plane at a state prison in Washington County, New York–and have a nice public tete-a-tete with the warden there, an old friend of his.  This was widely reported,  and the warden didn’t even lose his job.  You absolutely could not trust the police and many other authority figures of that time, so many were on the payroll.

That’s why Elliot Ness and his men were called The Untouchables–because a cop who couldn’t be bought was such an oddity.  But in the end, the Prohibition mobsters made themselves too visible, too obvious a source of public corruption, and a lot of them went to prison, often on tax evasion charges.

The most important Chicago organization was called The Outfit–and was heavily Italian, but to Westlake that was never the point–the point was that it supplied things people wanted–liquor first, then gambling, prostitution, etc–and was run like a business–and as time went on, a modern corporation.

In 361, you see a war between the old-era Prohibition guys getting out of jail, and the new corporate-style mobsters, who have assimilated more into the mainstream–and learned to keep out of the public eye most of the time.  Ed Ganolese, introduced in The Mercenaries, is the boss of this faction in New York–and Eddie Kapp, the biological father of 361’s protagonist, Ray Kelly, is the old-school boss who takes him down, with Ray’s help.

From this one glimpse into the elder Westlake’s past, we see the genesis of these early books.  Westlake imagining an alternate family history, where his dad had been a smart lawyer who got enmeshed in mob politics, and was good friends with Eddie Kapp.  Westlake himself, who we gather didn’t look much like his dad, could ask himself what if his father was somebody else–what if the mobster buddy was his true genetic forebear–though Ray makes it clear that he considers Willard to be his father either way.

The most powerful emotional moment of the book comes between Ray and Willard Kelly, very early on–Willard meets Ray in the city, after a long separation, and they’ve clearly missed each other a great deal.  “We cried like a couple of women, and kept punching each other to prove we were men.”   It’s hard not to think this is based on a reunion between Westlake and his father after he got out of the Air Force.  And very shortly before Albert Joseph Westlake died.

Westlake had powerful but mixed feelings about his father, and fathers in general–he never forgot the way his father had intervened on his behalf when he was arrested for stealing a microscope at college, pulling every string to get the case squashed, and his record scrubbed clean.   And then, as he wrote in his unpublished memoirs, his father apologized to him for not being able to better provide for him.  Love mingled with gratitude and guilt–always a heady mixture.

And always behind that–in just about every parent-child relationship that ever was–is that underlying realization that comes upon us as as we mature, if we mature–that we never really knew our parents completely.  That they used to be these other people, who will always be strangers to us.  That they had their own identities, completely apart from being ‘mom’ or ‘dad’, which most of us ignored until it was too late.

And the less we know about our parents, the less we know about ourselves.   Many an autobiographical work has been devoted to someone’s quest to better understand his mother or father, in order to achieve self-understanding–the current President of the United States wrote a rather good one.  I wonder if Westlake read it?

So maybe a good alternate title for 361 would be Schemes From My Father–or fathers, plural, since Willard Kelly wasn’t as innocent as he seemed.  We never get to hear Willard’s side of the story–just like Westlake never got to ask his father what his connection to Bill Bailey was.  Some mysteries are never completely solved, even in a mystery novel.  Let alone a blog about mystery novels.

Still, I think I’ve stumbled across a big piece of the puzzle here.  Westlake wrote about organized crime the way he did in the early days because he didn’t see it as this separate exotic world, cut off from the rest of us, the way many others in the genre depicted it as, full of strange codes and foreign rituals–its roots might be foreign, but its genesis was entirely American and familiar–it was made up out of our fathers and uncles and brothers and cousins (and occasionally Nephews).

He knew that perfectly ordinary decent ‘respectable’ people had roots in that world, whether they cared to know it or not.  He went digging for his past in an old trunk in the attic, and he found out some things his father maybe didn’t want him to know–or maybe he did on some level, and that’s why he didn’t just destroy those newspaper clippings.  It’s hard to let go of your past–it’s like turning your back on a part of yourself.

He also wanted to point out that dishonesty was not something unique to criminals–there are other kinds of ‘Outfits’ in the world, many of them quite legal, their methods sometimes even more contemptible.  The corporate world was something he despised on a very deep level, but he also knew it was unavoidable.  He may not have been an employee of any corporation, but he still worked for them.  Publishers, movie studios, etc.  Increasingly all just one big conglomerated mass of mendacity and mediocrity.

To be sure, that was part of the point Mario Puzo later made with The Godfather–the book that at least temporarily made non-Italian mobsters seem quaint and old-fashioned, and that was about the time Westlake started writing more about the mob as a specifically Italian thing.  The fashion had changed, and he’d mainly gotten mafia stories out of his system anyway.  It wasn’t going to be a major thing for him–he was about the independent operators.

And this is a sort of symbolic rebellion against his father, who may not have been any kind of mobster (maybe he and Bailey just knew each other from school or something), but who had been a loyal company man all his life–a cog in a machine, never really getting anywhere, never making it, doing everything he could to see his son got a better shot than he did.  And his son was grateful, but he had to try it his own way–he didn’t think his dad’s way had worked out so well.

At the end of 361, Ray Kelly is alone–his family erased from existence–but he’s his own man.  He’s learned the whole truth about himself, and he can build on that, if he wants.   That’s very much how it was with Westlake himself in the mid-1950’s, with both parents dead, and a younger sister he seems to have never been close to.   Like Ray, Westlake is going to have to make a life for himself–standing on the shoulders of those who came before him.  But free to make his own mistakes, instead of just repeating theirs.

And standing on Albert Westlake’s shoulders, Donald E. Westlake became his own man, never holding a steady job for most of his adult life, making his living a book at a time, which wasn’t an easy way to live, we can be sure.  He was never 100% secure, never had the kind of big seller that makes a writer’s fortune.  But he was free.  Of everything but the past.   Nobody’s ever completely free of that.

Case in point–there was another group involved in organized crime–Kapp, talking about how it takes three generations for the children of poor immigrants to become ‘respectable’, mentions them–

This is about Cheever again.  The Negro.  He wants to be respectable too, same as everybody else.  But he can’t be, and it don’t matter how many generations he’s been here, you see what I mean?  So he’s liable to wind up in the organization.

Already, Westlake was feeling some curiosity about African Americans–they keep turning up in 361, and other novels, but just as minor characters–he’s nibbling around the edges of something.   He’s got some opinions on The Race Question, but he’s not quite ready to share them.

In our next book, he’s going to tell us what he really thinks.

(Addendum to the addendum–I should have checked earlier, but according to the New York Times, William Bailey died of pneumonia on December 1st, 1934–not 1931. Westlake got that wrong too. He still died before Dutch Schultz. Westlake really didn’t give a damn about the fine details of mob history.)


Filed under Donald Westlake novels, Parker Novels