"YOU DON'T KNOW UNTIL YOU'VE DONE IT AND MESSED IT UP.": AN INTERVIEW WITH CITY IN RUINS' DON WINSLOW

Don Winslow has just put and end to his gang lang trilogy as well as his writing career with City In Ruins, that ends with Irish mob soldier in Las Vegas doing his best to put his past behind him as gaming mogul. His ambition to build his dream hotel, brings out out feuds and puts his life and those he loves on the line. The book that covers different plots, genres, and themes, making his swan song a symphony. It was with a heavy heart I asked what might be my last questions to Don.

SCOTT MONTGOMERY: This is the first time you planned a literary project this epic. How did it feel to finish it, particularly as a career capper? 

DON WINSLOW: It took me almost thirty years to complete this trilogy.  I would pick it up, set it down, then pick it up again as time (and confidence) allowed.  I wasn’t sure that I could actually pull it off.  So when I finished the third volume, City In Ruins,  I was looking back at three decades of my life.  My son, now a married adult, was a toddler when I started the project. My career, now much larger than I ever dreamed, was at a standstill. And, of course, I was much younger.  So it was a period of reflection on my life.

S.M.: City In Ruins contains several storylines in different locations with different characters  and locations. There are even different genres like the corporate and courtroom drama. How do you know what strand to place where?

D.W.: You don’t know until you’ve done it and messed it up.  It took a lot of trial and error.  I don’t outline, because I want to remain open to the possibilities of surprises (and there were many).  But basically, after I finish early drafts, I go over the manuscript with the reader in mind.  First, does the sequencing make literal sense?  Is the chronology right, can the reader follow the events.  Then, does it have the rhythm that I want?  Third, does the placement of these various strands make emotional sense, that is, does it lend itself to the impact of feeling that I want?

S.M.: Do you have to construct a character like Danny Ryan or Art Keller who are the center of these sweeping tales?

 D.W.: No. I think it’s the other way around, that the characters shape the tales. I wouldn’t go so far as to say that character is everything, but character is pretty much everything. I don’t try to create characters that fit the tales, but rather, try to get to know the characters so well that their actions become inevitable as an outgrowth of the wants, needs and backgrounds.  If I know the Arts and Dannys well enough, then the choices they make will be the right ones.

S.M.: Did you find anything distinctive with organized crime of the late twentieth century?

 D.W.: Well, it’s changed over the years.  Organized crime (in the US, that is) in the late twentieth century was a shadow of what it was in the mid-century, largely due to the RICO statutes, mandatory sentencing  on drug convictions, and also a generational evolution wherein the smarter sons and grandsons chose to go into legitimate business.  So what you had left was a culture in decline, trying to hold onto what it was once, while knowing that it was on the inevitable decline.  For me, that makes for a fascinating writing opportunity.

S.M.: The books in the trilogy primarily take place in one city in each book. How did you end up choosing Vegas for the finale?

 D.W.: I had to find a place where Danny could build an empire.  It took me an embarrassingly long time to figure out what kind of empire someone in 1990’s America could build. Then the answer seemed obvious – you can build anything you want in Las Vegas if you have the cash.  Also, I was fascinated by this transitional era in the city – when organized crime had been all but been chased out and corporations were taking over to build the mega-hotels.  Las Vegas’s  attempted change of image coincided nicely with Danny’s attempt to change his own life and evolve from the criminal into the ‘legitimate’ world.

S.M.: What have you enjoyed the most about being a professional writer? 

D.W.: The writing itself.  It’s what I’ve wanted to do since I was kid, although life took quite a while to agree with me. I love to write, I love the work, and I’m so grateful to have had it. Then there’s the readers – at the end of the day, the work is about them, isn’t it?  readers have been so wonderful to me (talk about gratitude) and it’s going to be great to get out and thank them in person.