The end: Q&A with Don Winslow on his final book ‘City in Ruins’ and retiring from writing fiction | About Town

After more than 30 years as a fiction author, Don Winslow has retired from his day job of novel writing with the publication of the New York Times best-selling “City in Ruins.”

Fittingly, Winslow’s career comes to a close with the final book in the Danny Ryan trilogy that stretches decades and settings from Rhode Island to Hollywood to Las Vegas. In the final installment Ryan, the former dock worker mobster has turned casino mogul. As he tries to grow the business, his past catches up with him when warring factions are revived. 

It’s a trilogy he started writing shortly after publishing his 1991 debut “A Cool Breeze on the Underground,” yet it didn’t hit shelves until 2022 with “City on Fire” followed by last year’s “City of Dreams.” We spoke last year about that book and Austin Butler signing on to develop them as film adaptions.

Shortly before Winslow’s book was published by Morrow, he received a shipment of his new book for the final time. 

“When the book arrived at the house I had this sudden feeling, and it hadn’t occurred to me it was going to happen, this is the last time I’ll open up that box and see a book. It felt a bit strange,” says Winslow, who has gone through this routine over 20 times in his career. “It took me close to 30 years to write this trilogy, and now it’s all out there. It’s it’s kind of an amazing feeling. It’s exciting, but also a little bittersweet.”

Winslow took part in a Q&A to discuss his final book, life after crime fiction with his political activism and the rise of the Oklahoma City Thunder – his favorite NBA team. 

Let’s talk “City in Ruins,” which I couldn’t put down until I finished it. This trilogy started in Providence with the East Coast mob stuff. You take it to Los Angeles and have him deal with the Hollywood in book two, and then you take it to Vegas to wrap this thing up. It’s an interesting time period in the late 90s for Las Vegas, and our main guy Danny Ryan, he’s chilled out. He’s a business man.

Yeah, he’s a mogul. I very deliberately chose that era in Las Vegas. I didn’t want to do the Bugsy Siegel thing. I didn’t want to do the Tony Spilotro “Casino” era. I wanted this transitional era in which the mob was just about gone but still a little lingering. Corporate America was taking over, and it seemed to me it sort of matched Danny’s life when he’s trying to leave behind his criminal past and go into sort of straight business. So it seemed like the town and the character matched in that area.

So did you coordinate with the folks at the Tropicana in Vegas to close the thing down the day your book comes out? An iconic Vegas casino closes its doors the day your book comes out about closing doors of old casinos and replacing them. How is this possible?

(Laughs) You’re funny, man! No I did not. But you know, it reminded me of when I brought out “The Cartel” and Chapo Guzman escaped from prison the next day. My publisher literally accused my agent of arranging Guzman’s escape. (laughs) I was on tour. I was in DC. It’s my second or third day on tour, and I wake up and my phone is blowing up, which it doesn’t do. What the hell’s happening? Guzman’s escaping! Oh shit! Later I had brunch with (writer and political commentator) George Will. He’s standing out in front of the restaurant where we met in Georgetown, and he just looks at me, smiles and says, “I’ll bet you’ve had a busy morning.”

“City in Ruins” is a great book. There’s so much going on, and you wrapped it up nicely. 

It took me a long time to write that book because I couldn’t figure it out. I couldn’t figure out what would the Empire be that Danny would build? What would the central conflict be because in the “Aeneid,” it’s over a woman, it virtually repeats the Helen of Troy story, which wasn’t going to work and would feel silly and trivial. What I finally figured it out, and it took me years, that the the central conflict would not be over a woman, but over a piece of real estate. Then that’s when the book opened up for me, and I was able to write it. No one’s gonna recognize this, but the name of the hotel in question is the name of the princess who was in contention in the “Aeneid.”

There are so many characters and settings in this book that are intertwined and many carrying over from the previous installments. How did you keep all those characters and such straight for that amount of time? 

It was just trial and error. I had to put the other two books on my desk, and keep referring to them like, what did I do with this guy? Is this guy alive still? Just going back and forth.

The sort of more interesting or difficult challenge was the sequencing of it. When do I cut to Chris in Nebraska? When do I get back to the trial scene and then get back to sort of the mainframe in Vegas? That was the real challenge.

I was interested in those characters, both in the classics and in my version of it. What happened to them after the Trojan War? We think “The Iliad” tells us the whole story of the Trojan War. It doesn’t. Starts in the middle and ends in the middle. To find out what happens you have to read “Aeneid” and the Greek tragic dramas, which is where that trial scene and all of that comes from. It comes from Aeschylus plays and just flat out mythology to find out what happened. I was intrigued to know. Then when I found out what happened I thought it was interesting and wanted to try to get that into my novel. 

This book is now out there. You’ve said repeatedly you’re done writing novels. I’m not alone in being a longtime reader who has grown accustomed to new novels from you over the years. There won’t be anymore Don Winslow new releases after this one on the fiction shelves. Have you taken time to reflect on your career and work and everything you put into it, and now it’s over? 

It’s causing me maybe more reflection than I had anticipated. I’ve done four appearances now on the tour in front of an audience, and they’re all saying the same thing you are. It is making me reflect a little bit on the 30 years of writing and in the struggle to get there.

We’ve joked before I was an overnight success in my 50s. A lot of those years and writing those books I was getting nice reviews and even awards but not selling a lot. I was in that that perfect trap, that perfect catch 22, where publishers say, “Well, you’re not a best-selling writer, so we’re not going to print a lot of books.” “Well, but then I can’t be a best seller.” It’s the perfect catch 22. Then you get labeled a cult writer, and you get told you’re not a best-selling author or you’re not an airport author, you’re not this, you’re not that. I’ve reflected a lot about those days and how different it is now. I’m really grateful for everything I’ve received, but I think that there’s a time when one needs to exit the stage, hopefully gracefully, and make room for other people and move on.

You’re not done working though. There’s your political activism.

There’s that. So yeah between now and November it doesn’t feel like retired. 

It’s the most important election since 1860. I think American democracy is at stake. I think you’re looking at a Neo-fascist movement led by a traitor, who tried to overthrow the United States government. It boggles the mind. It sounds insane when you talk about the nominee of the Republican Party is a man who tried to stage a coup against the government. The Republican Party is ridiculous. There’s nothing left of it. 

I think when you look at the choices we have, there’s a stark choice between a fundamentally decent man and a fundamentally indecent man. There’s a stark choice between a man who believes in democracy and our system of government and a man who doesn’t believe in anything beyond his own nose. It’s a stark choice between an honest man and a crook. Look at what Donald Trump did the other day in screwing his own followers, getting them to buy stock in Truth Social. Now their investments are worth half of what they were the day before.

Now he’s selling Bibles like a third-rate Elmer Gantry. I have concerns of course about anybody who’s in government, but when you look at the actual choice, I don’t think there’s a lot to choose. To me that the choice is very, very clear.

Then there’s your Hollywood deals and adaptations in the works on television and film. Austin Butler is doing firearms training. 

Everything is still on track. That’s all I’m permitted to say at this time. 

There’s also Thunder playoff basketball! You’re a fan of the team that is back on top on in the West after some years of struggles. 

It’s just great! I think we kind of knew it was gonna happen. It was a matter of being patient and supportive, and yeah, I’m stoked. We’ll see what happens. 

So now that you’re done writing, would you be open to other writers taking on your characters or worlds to continue or expand those stories?

I don’t think I would. It’s funny, I’ve never been asked that question before, so I haven’t really considered the possibility. I don’t know why anyone would, but I don’t think I would. But then again never say never.