Like a Greek tragedy: With ‘City in Ruins,’ bestselling crime writer Don Winslow calls it a day

March 30, 2024 5:00 pm • Last Updated: March 29, 2024 1:42 pm

By Rick Koster
Day Arts/Features writer

Don Winslow (Robert Gallagher)

The core group of writers who shaped crime fiction is well established. E.A. Poe, Arthur Conan Doyle and Wilkie Collins begat Agatha Christie, Raymond Chandler, P.D. James, Ross Macdonald and Dashiell Hammett, and now there’s a densely populated modern age wherein the masters would certainly include Don Winslow.

But Winslow might argue we should delve farther back — all the way to the work of such hard-boiled pulpists as Virgil, Homer and Aeschylus.

After all, those were the thematic sources Winslow used for his so-called Danny Ryan trilogy, a remarkable mob-saga-to-the-third-power that includes “City on Fire” (2022) and “City of Dreams” (2023) and now concludes Tuesday when “City in Ruins” hits bookstores.

Movingly, “City in Ruins” is the last novel Winslow will write. He finished most of the Ryan trilogy during COVID and has retired to pursue political activism. A Perryville, Rhode Island native who splits his time between the Ocean State and California, Winslow is on a farewell tour in support of “City in Ruins.”

He appears Thursday at the United Theatre in Westerly and bestselling thriller author/Ocean House proprietor Deborah Goodrich Royce leads the conversation. Bank Square Books co-sponsors the event.

All the way back to Greece

A self-described autodidact who, in the mid-’90s successfully committed seven years to reading all the works on a list of the world’s greatest books, Winslow was overwhelmed by Greek classics, in particular “The Aeneid” and “The Iliad,” which tell the story of the Trojan War.

“And it hit me that they have all the elements of a great gangster novel,” Winslow said. “I couldn’t get it out of my mind, and I frankly became obsessed with transforming it into a modern crime novel.”

Winslow’s trilogy is told through the life of Danny Ryan, whose Greek antecedent is Aeneas. In “City on Fire,” Ryan transforms from a low-level mobster who, during the 1980s turf war between Irish and Italian gangs in Providence, rises to power through unlikely circumstances — only to flee the city in desperation. In “City of Dreams,” Ryan reinvents himself in cunning fashion and becomes a successful Hollywood producer. And in “City in Ruins,” Ryan relocates to Las Vegas with the goal of becoming a casino mogul.

These surface descriptions seem almost soap opera-esque, but that dreadfully undersells Winslow’s literary artistry. These books are wonderfully written, complex and intensely affecting examinations of loyalty, family and power. There are dozens of indelible characters, exotic (and not so exotic) settings, plenty of violence, heartbreak, sex, witty dialogue and plot spins (unless, regarding the latter, you’re fluent in Greek tragedy, and even then you’ll be amazed by how Winslow is true to his source material while simultaneously making it perfectly and irresistibly contemporary).

Along the way

Winslow conceived of the series and wrote the first sentence over 20 years ago. But … didn’t he also write and publish several books since then? Including the eviscerating, brutal and heartbreaking “Border Trilogy” — “The Power of the Dog,” “The Border” and “The Cartel” — about the U.S./Mexican drug wars and the rise of cartels; the genre-smashing “Savages” and the New York City police epic “The Force”?

Why, yes.

The problem was, as Winslow said in a phone interview earlier this week from California, transforming Greek epics into modern times ain’t easy. In the meantime, he had a family to support — which he did through a variety of jobs while he continued to publish wonderful novels that just didn’t sell. Ultimately, he became the first client of screenwriter-turned-agent Shane Salerno’s Story Factory management company, and things quickly turned around.

In addition to serial bestseller status, Winslow now enjoys knowing that actor Austin Butler will play Ryan in the film version of “City on Fire,” “The Border” is in the works as a series for FX, and Oliver Stone directed “Savages” for the big screen.

Here are excerpts from the conversation with Winslow, edited for length and clarity.

Q: The epilogue of “City on Fire” is very bittersweet — not just because it closes out a remarkable trilogy but because it closes your career. Was it emotional writing the end of your last book?

A: In fact I WAS emotional. By the time I wrote the epilogue, I knew I was retiring. It was a bittersweet ending and I thought about a lot of things. I thought about my father’s death and looking back on 30 years of writing. My son was a toddler when I started this trilogy and now he’s a married adult.

Back then, I was a quote/unquote cult writer and very much struggling. People were saying I’d never have my books in airports or be a bestseller. And I thought about a lot of friends, readers, journalists. In a way, then, this is a bit of a homecoming. A wrap, if you will. And I’ll go back to the beach in Rhode Island — at least six months of the year.

Q: I get that the idea was to adhere to the story lines of the Greek tragedies. But you’re also an accomplished pro. At any time, did you have to deal with any real-time plot or character ideas that were really cool — but that would lead you off the original track?

A: They didn’t tug me off track, but I had to supplement and find the modern equivalent of situations and setting so my characters could become fully human and contemporary rather than just representational. Every one of my characters has an analogous character in the Greek stories. It was hard. Who’s Helen of Troy? Who’s Aphrodite?

At a certain point, I went online and took college courses. Twenty-six weeks studying “The Odyssey” and Oresteia and “The Iliad” … I wanted to do this well and have the deepest understanding of the material. Still, I’m glad there were no exams!

Q: Any particularly big roadblocks?

A: Plenty (laughs). But scholars will tell you that Aeneas was devout, and that wasn’t going to work for me in a contemporary setting. What Danny does have as a similar virtue, though, is loyalty, and it leads him continually into problems.

Q: It occurred to me while reading how much geography comes into play. In “City on Fire,” the Italian-Irish mob war in Providence established the entire central conflict. In the second book, Los Angeles and Hollywood are essential, then you close with “City in Ruins” in Las Vegas, the casino capital of the world.

A: Exactly. Providence was easy because it WAS the starting point, and I grew up there. Hollywood was easy because I’ve spent years there. Aeneid gets washed up on the shore of Carthage and sees cave murals in which he and his friends are depicted. And the contemporary equivalent of that is the film business: Danny meets an actor playing himself. Dido becomes the actress Diane.

But I couldn’t figure out the setting for the third book. I knew Danny needed to build an empire, but where and what? He’d done the film empire. Drugs? No, that felt false, and I wasn’t interested in writing about it.

Vegas came out of nowhere. Where can you go and build anything you want if you have the cash? Vegas. They’ve already built pyramids and circuses and Rome and Venice, and the story had already taken me into the post-casino era where the mob has been eclipsed by corporate America and real estate procurement. Perfect — a place where Danny can achieve his empire and leave the past behind.

Q: One problem with that could have been that, as someone with a criminal background, Danny would realistically have almost no chance of getting a casino license. And yet, you pull that off.

A: I had to think about it a lot. I’d written all of the first and most of the second novels somewhat certain that the focus of the last book would be a woman. When the Vegas idea struck, it solved a lot of problems, but then I had to make it believable that someone like Danny could get involved. I did so much research and, in terms of credibility, I was worried that I couldn’t make it work. In the end, I think I did.

Q: I won’t ask if you have a favorite of your books. But are there any moments that spring to mind when you glance back at your career — maybe things that didn’t resonate at the time?

A: It makes sense to reflect, and I have and do. Certainly I think fondly on my first book (1991’s “A Cool Breeze on the Underground”), as one would. I was traveling for work and trying to write. It took me three years. I remember it took six years of real struggle to write “The Power of the Dog,” and when I finished it I had $37 in the bank.

“The Cartel” was the hardest to write. In terms of fun, “The San Diego Zoo,” where a cop has to deal with an armed chimpanzee, made me laugh. And I guess, of course, the last trilogy because it was nearly a 30 year struggle.

Q: Speaking of that, these are litigious times. Given your source material for the Danny Ryan trilogy, have you been contacted by attorneys representing the descendants of Virgil or Homer?

A: (Laughs.) Not yet, but let’s not give them any ideas!