Don Winslow Heads for Retirement With ‘City In Ruins’

The characters of novelist Don Winslow inhabit a corrupt, violent and ego-stoked world that can be both grimy and glittering, alluring and deadly. Whoever is taking part in the action–the deceit and the blood sport–knows it’s a zero-sum game.

This could apply to the men and women in Winslow’s cocaine-cartel fueled trilogy (Power of the Dog, The Cartel, The Border) and it certainly is the case with Danny Ryan, protagonist of the mob-based trilogy that began with City on Fire (2021), continued with City of Dreams (2023) and, wraps up in City in Ruins, out today.

Danny, who started off a small-time gangster in Rhode Island, has risen dramatically in the underworld. He’s killed before and he’ll kill again, reluctantly perhaps, but definitively. He narrowly escaped death on the East Coast, inexplicably went big time in Hollywood and now, in 1986, maybe even more inexplicably, is pushing the envelope in Las Vegas. A billionaire, he has built an empire of casinos and hotels, but this doesn’t exactly delight the already entrenched mob owners. And Danny wants an even bigger piece of the Vegas pie.

As the title of the meticulously plotted new book suggests, things may not end well for Danny, his friends or his enemies. And as any Winslow reader knows, alliances inexorably shift: Friends can become enemies in a flash or maybe in the course of a slow landslide.

City in Ruins is Winslow’s final novel. We emailed with him  in late March.

Not a lot of writers retire–or announce their retirement. I know Philip Roth did, but I can’t think of many. You, of course, have done so. I would think in some ways, it’d be hard to tell the world that it’s full-stop for you, or maybe, it’s freeing. What led you to that place and decision to make it public?

 A confluence of things. First, I think, given what’s been going on in our country, my time and energies are best spent engaged in the fight for democracy, which I believe is under a genuine and dangerous threat.  Then, finishing this trilogy – which is the culmination of thirty years of effort, trial-and-error, and love–felt like an appropriate end to what has been a career far bigger and better than I ever dreamed.

Why make it public? I’m grateful to my readers.  They’ve given me this career, they’ve been so supportive and generous over the years.  I felt I owed it to them to be forthright and honest.  They’ve been with me for this whole wonderful ride and they deserve to know that it’s coming to an end. 

Are you going to miss Danny Ryan (and his pals or foes)? 

Sure.  Listen, as I said, I’ve spent nigh on thirty years with Danny and his family, his crew and his adversaries.  When you write a trilogy like this, you wake up and go to bed with these guys on your mind. I’ve actually grown kind of fond of them.  Maybe what I’ll miss most is their conversations with each other.  

You’ve written seven standalone books, where the story is complete by the end. But also, not just one set of trilogies – the Cartel series – but two. What is it about the trilogy format that so appeals to you? 

In Western culture, we tend to tell, and hear, our stories (whether they be novels, films, or even jokes) in three acts – a beginning, a middle and an end.  That’s sounds obvious, but it really isn’t.  It tends to create a certain kind of structure that I find to be complete, satisfying, even beautiful.  It allows for character development over a period of time that resembles real life (hence the term ‘middle age’, by the way) and a rhythm that readers feel comfortable with.

In Danny’s, there were three distinct phases of his life – his origin story in the mob war of the first book, his wandering years as a fugitive, and then his final act in building an empire. That structure required three separate books – a trilogy – to give both Danny and the reader a little breathing space between the three acts.

In City in Ruins, once again, we find ourselves in a world where friendship, loyalty and betrayal are all in the mix. A Don Winslow signpost, I’d say. And there’s the feeling that whatever loyalty or friendship that might be felt at the onset, or even midpoint, that’s not going to hold by the book’s end. Do you think readers have (or should have) a rooting interest in Danny’s fate? Did you have a rooting interest when writing it? 

I try not to have a rooting interest in any of my protagonists, Danny included, but that’s probably unrealistic. I went on a long journey with Danny – across his life and mine – so if I’m being honest with myself, I suppose I did want it to end well for him. At the end of the day, though, I can’t let that interfere with the inevitable demands of the story.

The loyalty you refer to is an important aspect to Danny.  Classically, a hero must have a ‘tragic flaw’ – the Achilles’ heel, if you will – and if Danny has one, it’s loyalty. His sense of loyalty leads him down tragic paths in all three books, it forces him to make choices that he would otherwise not have made.

Betrayal is certainly a theme in the trilogy, but what make it more interesting is when betrayal is not just a lapse in loyalty but a result of conflicting loyalties. Is a character going to loyal to his own values or to his friends?  To his real family or his crime family? To his past or his future. I love writing about characters faced with those choices. 

I talked to John Irving in 2010 when his novel Twisted River came out and he told me: “Part of the process in writing the book, is I do know the fate of the characters before I start to actually write down the story. I do know the action before I begin, when they meet, when their paths cross again, I know who lives and dies and if they die when and how. There is a certain fatalism. I think that gives a certain melancholy to the accidents that these people will meet with.”

Does this pertain to you? And when you started City on Fire did you have outlines of the following two books somewhere in your head or on a computer screen? 

Yes and no, and I’m not being coy. The trilogy tracks the stories of The Iliad, The Aeneid, The Odyssey and the several Greek tragic dramas as well are some mythological tales.  So I did have an overall sense of where the characters were headed in the arc of their lives.  So certainly, there was fatalism in that the characters in the trilogy are walking toward their, well, fates.

Having said that, I tried to write a story that fully modern, fully contemporary, that could be read an enjoyed with no reference to the classics at all, while at the same time being faithful to the classical themes, stories and characters. So the real challenge was creating the modern equivalents in a way that was credible, interesting and fully human.

I didn’t outline. I don’t like to write down a scheme or a plan because I want to be open to the possibility of surprises.  Sometimes characters will do or say something that I didn’t expect and that will send the story into a different–and better–direction.  

An obvious question perhaps, but how do you get into the right mindset to write books that are so down and dirty and violent? Maybe more specifically, how was the mindset different for Danny Ryan’s story than the Cartel books? Is there a visceral thrill for you writing about the mayhem? And do you get a sense of catharsis yourself when you complete the story’s arc?

I wish there were some catharsis–there’s actually more of a hangover.

Writing violence is a tricky thing–I don’t want to sanitize it but at the same time I don’t want to cross the thin line into a sort of pornography.  More and more, I found myself writing more about the aftermath and consequences of the violence than the acts themselves.  Having said, I write crime novels, and crime often involves violence. There’s no way around that.

In terms of mindset, mine is always the same no matter what I’m writing about at the moment–it’s always to try to see the world through the character’s eyes. 

We know Danny is trying to bury his criminal past, but we also know going in (because it’s you writing), that that may not work out so well. What’s the inexorable pull for him? The power, the money, or it’s just that’s who he is and always has been at his core?

Once you cross the line, it can be hard, if not impossible, to cross back.  Actions have consequences, and they can last a lifetime.  For good or ill, this is the case with Danny. I think that the central question in crime fiction–well, I’ll speak for myself–is how do you try to live decently in an indecent world?  That’s Danny’s struggle.  Once his loyalty, as discussed above, leads him into the mob war, that becomes his life. He spends the rest of it trying to create a decent life for himself and his family, and he realizes that is going to require money and power. But acquiring and retaining that money and power require, in turn, more indecency. 

I’ve read all three books in the Ryan trilogy so I know how one story evolves from the previous one–the cast of characters and backstory–but in reading City in Ruins I also thought, “This would work well for someone just diving in without knowing the backstory.” Was that a consideration in writing this? 

Oh, yeah.  I want any reader to jump into the trilogy at any point and be able to understand it.  That’s a little difficult technically, because you don’t want to bore the reader who started at the beginning with a lot of backstory, but you need to give enough to the new reader so that he or she can understand it. And at the same time, you have to remember that the story and characters are so familiar to you, the writer, that you might assume the same for any reader.  I really have to rely on the editors to give me an objective viewpoint on this. They might tell me ‘a little more here’, ‘a little less here’, and I listen.

Word is that City on Fire is being made into a movie and the other two have been optioned. Austin Butler, of Elvis fame, becomes your Danny.  Can you envision Butler as Danny? How close does his look approximate what you had in your head and on the page? 

That word is true. Sony Pictures is planning on making films of the three books with Austin Butler as Danny. I’m really pleased, and I easily see him as Danny.  He’s a terrific actor. I also just watched Masters of the Air and he’s really smart and down to earth.  Yeah, he’s Danny. 

Did you have any involvement in turning the book into a screenplay or did you sell the rights and step away? What kind of emotional investment do you have the filmmakers “getting it right,” if you will? 

I do have involvement. I usually read the screenplays and give notes, talk to the writers and directors, very often take people to the locations where the books are set.

Absolutely I’m invested in them ‘getting it right’, and I have to say that my experience has been that the filmmakers are invested in that as well. I also know that books and films are two different breeds of cat, with different needs, so I know that there are going to be changes from the book.  What’s important to me is the film retains the spirit of the book and the legitimacy of the characters. 

From what I understand you’ve kept a pretty rigid writing schedule–up early to write for 4 ½ hours, take a long walk, then back at it. Do you ever break from that routine? Are there days where you say, “Fuck it, I just don’t have it in me”–the writing that is?

There are days when I’ve said it (and far worse), but I can’t recall a day when I’ve actually done it. Look, life happens, so there are days when things come up and I have to break from the routine.  But by and large, no–I stay in the harness.

Here’s the thing–this is the life I’ve always wanted. I struggled for years to get the privilege of being a full-time writer. Once I got that, I was going to approach it with respect and gratitude, which meant suiting up and showing up, no matter how I felt on any given day. 

I’m guessing that you have a lot of readers who entered your world late (or late-ish) in the game.  I started with Savages in 2010, then The Cartel and have read the six that followed. You’ve written 23 total. Where would you suggest a relative newcomer go in your catalog if they wanted to dig back? In other words, what do you think the best of your early-mid period work is and why? 

I think your guess is pretty accurate.

Gosh, I don’t know where I’d tell someone to start.  I’m not exactly objective, am I? But if you put a gun to my head, I guess I’d point a new reader to a few of my books that might be considered touchstone–my first, A Cool Breeze on the Underground, then maybe The Power of the Dog or The Cartel, then probably The Force and the first Danny Ryan book, City on Fire.

That’s too hard a question, man. 

You’re 70, with presumably some good years ahead of you. How do you envision yourself spending your time? You have been quoted as calling writing “an addiction.”  Might the tug of writing pull you back into the writing game like Danny Ryan gets sucked back into the world of crime?

 Well, I sure hope that your presumption is right. I don’t know what the future looks like, because it feels like a long way off right now. Look, I’ll probably always write, I just don’t think I’ll publish.