Even Don Winslow's mob characters wouldn't vote for Donald Trump

Self-defined "cult writer" on his final novel (he says!) and his new career as anti-Trump social media agitator

By Andrew O'Hehir

Executive Editor

Published April 6, 2024 1:30PM (EDT)

Don Winslow (Photo illustration by Salon/Eduardo Munoz Alvarez/Getty Images)
Don Winslow (Photo illustration by Salon/Eduardo Munoz Alvarez/Getty Images)

Of arms and the man he sings — no, seriously, he does. Don Winslow's latest novel, "City in Ruins," completes his Danny Ryan trilogy, the saga of a mid-level Irish-American mob soldier from Providence, Rhode Island, who flees across the country to build a new life, first in Hollywood and finally as an empire-builder in Las Vegas. Winslow says the trilogy took 30 years to complete — nearly his entire writing career, in other words — and also says it's his final work of fiction. We'll get to that. All three novels have been published in rapid sequence — the widely acclaimed "City on Fire" in 2022, followed by "City of Dreams" in 2023. They're loosely based, Winslow says, on the real-life gang war that paralyzed Providence in the late 1980s and early '90s, in which nearly 40 people died. (Someone in "City on Fire" observes that Providence tolerates only three religions: Irish Catholicism, Italian Catholicism and the Red Sox.)

But the Ryan trilogy is also based on "The Aeneid," the Homeric knockoff epic by the Latin poet Virgil that turns a minor figure from the tale of the Trojan War into the founder of Rome. Yeah, Winslow is a guy who writes hard-boiled crime fiction full of leggy, tough-talking dolls and guys with $70,000 watches and short, telegraphic sentences. ("First thing you learn in this kind of life: Never get in the car.") But he's also another kind of guy, a historian by training and inclination, as he told me during his recent visit to Salon's New York studio. He's not kidding about "The Aeneid": After our conversation, he sent me the "character key" for the Danny Ryan novels, which runs to three pages. So I could tell you who his cognates are for Achilles, Hector, Helen of Troy, Aphrodite, Odysseus and a whole bunch of others. But Winslow asked me not to share it, and as a character in his fiction might say, he seems like the kind of guy you don't want to cross.

Well, OK, Danny Ryan is Aeneas, the wandering hero of Virgil's epic. That much is obvious. Like the Roman poet, Winslow takes this relatively ordinary figure — a working-class guy with decent intentions, who does bad things for bad people — and turns him into a highly resourceful if not entirely admirable protagonist, as well as a representative symbol of his time and place. Winslow had already become politicized while writing his trilogy about the drug war (beginning with "The Power of the Dog" in 2005), but while he was writing the Danny Ryan books, he says, he couldn't avoid noticing that America was changing, becoming increasingly divided, embittered and polarized.

Winslow is putting his fiction aside, after publishing 26 novels in 33 years, he says, because the times demand it. As a social media activist and anti-Trump propagandist — working in concert with screenwriter and filmmaker Shane Salerno, his close friend — he believes he can reach millions more people, potentially changing hearts and minds and moving the needle of history, than would be possible by spinning more gripping, surprising, economical yarns about men who kill each other. Virgil, I suspect, might disagree. We can't ask him about that, and we can't ask Danny Ryan whether he would have voted for Donald Trump in 2016. A lot of real-life Danny Ryans went down that road like Aeneas entering a really bad version of the underworld, chasing some absence or lack they felt in themselves or in life, and never came back. But Danny's creator stuck up for his boy: Absolutely not, Winslow told me, Danny would have spotted that "punk" miles away. We'll have to take his word for it.

This transcript of our interview has been edited for length and clarity.

I would describe you as one of the signature crime novelists or popular novelists of our age, but I don't know if you even like those labels. We could just say writer.

Writer is good. I've had so many labels and most of them have been negative. They tell me what I'm not. You're not a bestselling author. You're not an airport author. Cult writer was my favorite label over the years.

It's a friendly cult. It's not like the alleged cult associated with someone else with your first name, whom we might talk about later.

We could drop the alleged, I'm comfortable with that.

You say your new novel is your last novel.

It's the truth, actually.

Your new and final novel is “City in Ruins,” which is the conclusion of a trilogy that began with “City on Fire.” I understand you've been working on this trilogy for a long time.

30 years.

That's incredible. What took you so long? 

"You have to go through 10 or 20 bad pages sometimes to get to that one good one."

Just lazy, I guess. No, 23 other books I think, kept me [busy]. To give you a serious answer, it was tough to do. I was trying to take the Greek and Roman classics and use all those characters and stories and themes, but write a completely modern contemporary crime epic because I'm a crime fiction writer; that's my beloved genre. 

It took a while to do that successfully. I failed at it a lot. So I'd set it down, I'd do another book, and then between books I'd go, “Let's pick that up again and try it,” and then I'd fail again. This process repeated itself for three decades.

It’s important to experience failure. Every successful writer has to go through periods of not getting it right.

Yeah, I would say more days than not. I think when you're a young writer it feels crushing, but you get a little experience under your belt, you've done a few laps around that pool, and you realize, yeah, Tuesday I sucked, but I’ll just keep at it. I think you have to go through 10 or 20 bad pages sometimes to get to that one good one.

While reading the first book in the trilogy, “City On Fire,” it actually took me a minute to figure out that it was rooted in mythology. It is a very engrossing story, beginning around 1987 on a beach in Rhode Island, and it took me a minute to be like, “Oh, this is a story about one guy from one gang who steals a somewhat mysterious, beautiful woman from a guy in another gang. This precipitates a devastating and destructive conflict. Where have I heard that story before?”

Well, you might've heard it in this little thing called "The Iliad," but I will tell you that a very similar incident to that happened in New England between the Irish and Italian mobs that launched a 10-year gang war that ended up costing about 40 lives. So, when I read "The Iliad," I already knew this story because it was part of my youth.

In the books, you're following Danny Ryan from Providence, Rhode Island, in the first book, to L.A. in the second, then Vegas, for the third. To some extent, I see the pattern. You could look at Martin Scorsese films and say, “OK, the gangsters tended to go in that direction,” but why those three cities in particular?

Providence, Rhode Island, because that's where I grew up and I wanted a small environment where all of these people knew each other and maybe even [were] related before the war breaks out. That felt ideal because I could just walk out my door and listen and I was there. 

Hollywood, really, and it took me a while because in "The Aeneid" — and Danny Ryan is Aeneas — Aeneas goes into a cave shipwrecked in Carthage and there are murals of the Trojan War. He sees himself, he sees his late wife, his friends, his home. I thought, OK, what's the contemporary equivalent to that? A movie — someone making a movie about basically what's in book one. It just seemed to be fun, frankly, because I've spent some time in Hollywood, to take some of these Rhode Island punks and put them at the craft services table at a Hollywood studio, because they'd be like raccoons. They'd never leave. Free food and all of that. So that was why Hollywood.

"I'm not interested in the morality of it. I'm not trying to be objective. I'm trying to be subjective when I'm typing."

Vegas, same thing. At the last half of "The Aeneid," Aeneas has to build an empire. It’s embarrassing, but it took me years to figure out: What could that empire be in contemporary America? I didn't want to do a drug empire; it felt wrong and nasty. I thought about continuing with a Hollywood empire, but that also felt false and unrealistic. Then it occurred to me, like one of those Eureka moments, where I went, “Well, in Las Vegas, if you have the cash, you can build anything you want.” They have built Rome there, right? Caesar's Palace, Venice, Paris, pirate ships, pyramids, whatever you want. When I hit on that, then book three started to click.

There is a version of social history in these books. How important was that for you in constructing this trilogy?

Pretty important. I think crime writing's a big tent in this room for all kinds of different stuff. I'm a historian by education and by inclination. I love history, which is one thing that's made me hard to label frankly. It has been an issue that I like getting social history in there because to me it's interesting. I often think we underestimate our readers. They think, “OK, it's got to be action, action, action, action, action.” I'm saying it doesn't, necessarily, that we can incorporate these things. 

I was interested in writing about America and about Las Vegas at a particular era, which was when the mob had pretty much faded out and corporate America was taking over. It was the era of the mega hotels and "greed is good," and the bigger the better. To me, that was interesting to write about and I hope it is interesting to read about.

One of the things I appreciate about the way you approached Danny Ryan as a character is that you're not completely on his side. You're not advocating for him, as in the way that a lot of crime fiction would, as the hero. He lives by his own moral code, but you're not necessarily saying it's a good one all the time.

My job is to take the reader into a world that she or he could not necessarily otherwise enter, or maybe help them see a little differently. Because I do have a lot of readers who are criminals — I guess I'm very big in prisons — so to do that, I have to look at the world through that character's eyes. I approach it, I guess, the way maybe a method actor would approach taking a role. I'm not interested in the morality of it. I'm not trying to be objective. I'm trying to be subjective when I'm typing. Now, I might have my own moral opinions about what's going on, but I try not to inject those into that point of view.

There's a technique that you use where you will move even within a chapter or a couple of pages from one character's perspective to another without announcing it. There's no narrative voice informing us that that is happening. You don't have signals on the page the way that some writers do, like, “Now we're in person X's head.” It struck me that you can read it and almost not notice this happening. It must have been difficult or at least interesting to work that out.

Listen, I've never had a writing class, so I don't know what the names of these techniques are. Nobody taught it to me. I think it was kind of instinctual. Again, I'm trying to put the reader into that person's point of view, and what I think is that readers are pretty smart. I don't think we need to hold up a sign that says, “Now we're in Danny's head.” I think if I can do it skillfully enough, we just go there. 

A critic one time said, "Man, you changed the point of view inside of a sentence one time." I said, "Yeah, and if I can find a way to change it inside of a word, I will."

It reminds me in some ways of the classic thing that would happen in 19th-century fiction. Charles Dickens or George Eliot would have this other voice — this hovering UFO — who is announcing everything and making ironic commentary. But you don't do that at all.

I try not to. Sometimes I think of it in film terms, because I think it would be disingenuous for anyone of my generation to say we haven't been influenced by film and television. I'm not trying to write a movie, but sometimes I'll think, “Well, maybe I need an establishing shot here. Maybe I need to back up and get high and look down at the city of Las Vegas or give a background on a character.” But other times, I think, “No, I want an extreme close-up.” Other times I think, “No, I want this to be from the point of view — a film term — of that character.”

Speaking of that, am I correct that there is a TV adaptation of this series in the works?

You're semi-correct. It's a film adaptation. They're making three films.

Oh, fantastic. How much can you tell us about this at this point?

Well, what I can tell you is that Danny Ryan is being played by Austin Butler.

No kidding. That's an interesting choice. 

"I don't want to publish just for the sake of publishing or just for the sake of a paycheck. I'll probably always write. I might just write and never do anything with it."

It's funny. I had just seen "Elvis." My wife and I had just watched the film. Then the next day or the day after, my agent called up and said, "Hey, what do you think about Austin Butler? He wants to do Danny." Oh, yeah, great. Then in the interim, I've been watching “Masters of the Air,” and he's great in that. It’s intense. Tough to watch, but very, very good, as you would expect from that crew. I'm delighted about it. The strike slowed everything down. I think we were supposed to go take these guys out on location last summer, and I think that's going to happen this summer, where I'll take them to the beach that you alluded to that Danny's lying on.

There's a lot of discussion about Rhode Island clam chowder. I was unfamiliar with the Providence versus Boston clam chowder battle.

Yes, which I triggered — much, much to my downfall. I made some snarky remark, I thought off the record, to a reporter at a Boston paper that was printed. The next night I had to be in Boston, but I was asked about that in Germany. It's very serious.

Crime fiction has become cooler and respectable in a way that it wasn’t before. Colson Whitehead and John Banville are two examples of literary novelists who started writing crime books. Should they stay in their lanes?

No. Listen, man, nobody owns the genre. I'd be the last person in the world to try to close the door behind me because the door was closed in front of me for a long time. My attitude is, welcome in; if you can do it well, do it well. Welcome, I'll read it, I'll enjoy it. I hope that you're never going to find me slamming another writer in any way, shape or form.

Well, you've talked about the fact that the genre was, for a long time, dominated by white guys.

Yeah, people like me.

It is a lot more diverse now.

It is, yeah, which is really good. For a long time we were looked down on, which I liked. I had a very literary journalist ask me one time, “As a crime fiction writer, do you feel you live in a literary ghetto?” It was not asked in a particularly friendly tone. I said, “Absolutely, and I love my neighborhood.”

I think it's been a little bit to our benefit because I think you get that slight chip on the shoulder, a little bit of an attitude that I think is useful. I also think that it's been my experience that inside the genre, we tend to be a bit more collegial with each other. We help each other out, it's pretty friendly. You don't see the kind of backbiting and rivalries that I think you see elsewhere.

Now we get to talk about why this is your last novel, after writing 26 of them. Many people will know you from your social media interventions in politics. You and your friend, Shane Salerno, have been doing stuff on social media. It's gotten 300 million views cumulatively. I know you've sold a lot of books, but probably not 300 million.

It's in the 295 million [area] — I don't think I've hit 300. Maybe this afternoon. After this airs, we're way up.

What made you decide to stop writing?

I've been busy on what used to be Twitter — I guess now is X — and doing pretty much daily commentary now for quite a few years, since about 2015. It wasn't a revelation, really. This volume is sort of, I think, the culmination of my life's work. It's something I've been trying to do for 30 years, and I finally completed it, and I hope successfully. I'm not the person to judge that. 

Around the same time, all of this stuff has been happening in this country, what I consider to be correctly considered a neo-fascist movement in America. Those things coming together now and thinking we're seven months away from an election that I think is going to determine what the world looks like for the next era. That my energies, such as they are, I'm not a young guy, are better spent in that fight and I just want to focus on that.

That has to go past the question of this one election, doesn't it? I'm sure you're going to tell me that the problem of this election is critical, but the problem in the country is much bigger than what happens in the first week of November.

Sure. Well, yes and no. I think we need to focus on the first week of November. You know that old saying, “How do you deal with a nest of cobras? You kill the closest one first.” We have to win that. All right, I'm not thinking past that now. OK, let's cross that bridge when we get to that bridge. Right now we have to win that election, period, and that's where my focus is. Then we'll see what the world looks like.

I feel like in our profession, in the journalism that we do in this room and on this website, we've been compelled to think a lot about what the country will be like under a second Trump term: the possible formations that could occur in Congress, how that will change our roles, how that will shape the future of politics. You don't want to cross that rhetorical bridge.

It's not useful right now to me. I'm sure it is to you and what you do. To me, that's not useful right now. I'm focused on the battle, on the fight. I want to win that one. Then let's see where we're at.

So you're really ready to put fiction down now?


You could write 10 or 12 more books.

"He would look at Donald Trump like he'd look at any other punk."

Could. Look, I've had such a much bigger and better career than I ever thought I'd have, than I'd ever dreamed. It's been fantastic and I'm grateful for that, truly. I don't want to push it. I don't want to publish just for the sake of publishing or just for the sake of a paycheck. I'll probably always write. I might just write and never do anything with it. I’ll just write because I want to write this or I want to write that. I love researching, and there's a lot of topics I'm interested in.

I'm never bored. I don't understand how, except for in airports, anyone ever is. There's so much to do, so much to see. I'm not worried about laying on the couch eating potato chips or something.

Obviously you get a lot of feedback on social media, and I'm sure not all of it is positive. How often do you hear the response from people who have read your books and like them, but say, “You communist, go away and stick with what you do.”

Oh, every day. Every day. I call it the “shut up and type” — as opposed to the "shut up and dribble" — factor. Sometimes it gets worse, sometimes a little nastier. Threats.

Have you had actual threats?

Oh, yeah. That's common. Most of these people are physical, as well as moral cowards.

Would Danny Ryan have voted for Trump in 2016?

Absolutely not. I'm telling you, man. No, he would not have. He would not have. Look, Danny is a working-class Rhode Island guy. Right?

You can't tell me that there weren't some working-class Rhode Island guys who went there.

I know them, but not this guy. He would look at Donald Trump like he'd look at any other punk.

By Andrew O'Hehir

Andrew O'Hehir is executive editor of Salon.

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