Don Winslow’s Crusade Against Trump: ‘Do You Want a Narcissistic Sociopath in the White House?’

For crime fiction fans, a new Don Winslow novel is usually a time of joy, but the arrival of the writer’s latest crime opus, City in Ruins, is bittersweet. Winslow, 70, says this is his last book, and he’s going to focus on his online political activism — and the immediate threat of Donald Trump. His viral videos attacking the Republican candidate garner millions of views online, and he plans to keep the campaign going until November and beyond. His vendetta against Trump becoming his day job. 

If Winslow really is ending his career with this Danny Ryan trilogy, he is going out in epic style. The three books are a gangster retelling of some of the foundational texts for literature: The Iliad, The Odyssey, and The Oresteia cycle. The final installment, City in Ruins, is classic Winslow — electric prose, zooming along well above the speed limit but with a deep understanding of the haunted characters at the center of the action. Vengeance, greed, and blood soak the pages but so do love, loss, and a lot of regret. It’s a page-turning saga in every sense. Rolling Stone caught up with the author to ask why he would leave his fans wanting more and what’s next for him as a political activist hell bent on fighting Donald Trump.

Which of the ancient authors did you go back to the most when writing this last book?

Aeschylus. If you take the Orestes cycle, those three plays, that’s a noir fiction plot. Put a trumpet to it and make it black-and-white, and you have a noir movie, right? I wanted to follow all these characters throughout their life cycles. So yeah, Homer, Virgil, obviously, and Aeschylus. 

You have your stand-ins for Aeneas and Odysseus throughout all three books, and then you have the Orestes character. Which one did you gravitate to or feel the most sympathy for?

Probably the kid. Probably Peter Moretti Jr.

Orestes, essentially. 

Exactly. Because he’s so effed up. I can’t imagine what that’s like, because I came from this very stable family. My parents were married forever, my dad was a sailor, my mom was a librarian. But can you imagine? You come home and your mother’s murdered your dad, and the lover who was involved is right there. Again, it’s noir fiction. And he had this twisted thing of “What am I supposed to do?” And he goes to exactly the wrong guy to get the answers.

You can see where Shakespeare got Hamlet from too, right? 

Absolutely. Absolutely. With Gertrude and Laertes and all of that. And I can’t help but think that Shakespeare took some of that plot from Aeschylus. Of the 28 Shakespeare plays that we’re sure he wrote, only one plot is original; that’s The Tempest. And of course, The Godfather, I think famously, is a retelling of Shakespeare’s Henry IV. It’s the exact same story.

You have the very American theme of pushing westward and reinventing yourself, as you go throughout the Ryan series.

Which is also in The Godfather. It’s all over Western literature, that traditionally — if you look at Celtic literature and early English literature and Viking [stories], all of that — the West is where people go to reinvent themselves, and sometimes that reinvention means death. I was very aware of that tradition. But then it’s funny how unaware you can be. I was not aware until I was writing the third book about the parallels to my own life. I headed west to reinvent myself, first leaving Rhode Island at age 17 to go to Nebraska and college, a place I’d never been. And then later on, leaving the East Coast to go to California, where I reinvented myself as a writer. But I laugh about this; I was an overnight success in my fifties. So, I wandered this country for decades trying to find a place to put my feet, trying to support a wife and a toddler. It didn’t occur to me until I was writing book three how much of my own life was in these books.

Do you think you could have written this trilogy as a younger man?

No, I was thirtysomething when I started the Ryan trilogy. Took me 30 years. Listen, I’ve had so much bigger and better a career than I ever thought I would have. It’s ridiculous. Much bigger than my dreams. You develop a certain amount of compassion. These three books are by far my most compassionate books. But it was some struggling years, and I’d written books that were critically acclaimed and I had double-digit dollars in the bank. I mean, I wrote Power of the Dog, which has achieved some sort of recognition, and I was broke. 

OK. But I have to admit to being a little annoyed. Why are you laying down your pen? I want some more books. Opening a Don Winslow novel is one of the highlights of my year. What the hell, man?

Go back and read the old ones.

Do you really just feel like you’ve just tapped out? 

No, I don’t feel tapped out. I don’t. I think there’s a couple of things. One is that having finished this trilogy, it felt like an ending to me and also a homecoming. As I mentioned, I left Rhode Island when I was 17, and writing about Rhode Island again in the Ryan trilogy felt like a wrap. Also: What’s happening in the country, and what’s happened in the country since 2015. I think that my energies are better spent in a fight against, let’s be blunt, Donald Trump.

Anybody who follows you on social media knows that you post video after video attacking Donald Trump — often using his own words and actions. These are Hollywood level-productions, slick, punchy and incredibly damning. But what do you think of the efficacy of your efforts? Obviously half the country’s still enthralled by this guy.

Yeah. Look, I mean, in terms of the efficacy of what I’m doing, we’ve had over 300 million views on those videos. That’s mind-boggling to me. Fifteen million views in just the last three of them. Somebody’s watching. Now, you could say, “Well, yeah. Sure. The people who are already anti-Trump are watching.”

Yeah, that’s my point. Is this kind of sermon to the converted worth it?

Preaching to the converted. But there’s some utility to that. If you motivate our own base, or those people who are not enthused, and say, “Look, here are your stark choices.” You’ve got a guy, and I’m going to be very, very blunt about this, who’s a traitor. A traitor. [Winslow’s voice rises.]. I’m sorry if I’m yelling, but here’s a guy who tried to overthrow the government of the United States.

We all saw Jan. 6.

Exactly. We all saw it. We all heard it. What the hell are we talking about here? And he’s going to be the Republican nominee? And he could win. We have to get organized, and get serious, and get energized — and speak in tough terms. Enough of pussyfooting around this bullshit. Sorry, I don’t mean to get angry, but I am.

You are very worked up …

I am angry. I mean, I sat there watching Jan. 6. I thought about my dad, an old-school Democrat but by no means a liberal, who was on Guadalcanal when he was 18 years old with the Marines. And I thought, I’m almost glad he’s not here to see this. It would break his heart. You’ve got a traitor who could possibly be the next president of the United States. And I don’t think that we’re fully encompassing that concept.

If you didn’t have the success you have had and weren’t walking away from writing, do you think you’d be doing what you’re doing?


But you are alienating a large part of the country. Don’t you have some concern about that? In terms of wanting to sell books?

No, I don’t. I don’t. It doesn’t occur to me, frankly. And listen, my publisher’s been great about it. They’ve never said one word to me along the lines of shut up and type. But no, that doesn’t worry me. If I lose them, I lose them. Listen, look at the stakes. American democracy versus Don Winslow selling a few less books.

But for all the attention you have gotten with the videos, social media is such a double-edged sword. It’s also helped create Trump and all these viral moments with his fans …

Sure. Listen, Clausewitz, the great military historian thinker, said famously that one should always fight a battle on the ground of one’s own choosing. OK. Great, Clausewitz. Thank you very much. We probably could have figured that out on our own. You have to fight the battle where the battle is, and the battle’s on social media now, for good or for ill. Not all of it, but a crucial part of it. And so we might not want to be in that alley, but that’s the alley we’re in, and we better win the fight there. We keep bringing spoons to a knife fight. 

RFK Jr. is going to have a profound impact on this race, perhaps. He’s on the ballot in a few states that could really help Trump win.

Absolutely. Every vote for RFK is a vote for Donald Trump. Let’s not kid ourselves. So, if you’re dissatisfied with Joe Biden, you decide, “Well, RFK is my way.” RFK is not going to be elected president of the United States, for God’s sake. And if you do that, you better do it with your eyes open and say, “OK, I’m going to vote for RFK and put a dictator into the White House.” Because this country will never be the same again.

Isn’t there something about RFK Jr.’s that is troubling about the entire country’s political journey. Being this kind of standard-issue Democrat, doing great work in New York cleaning up the Hudson River, but then falling down these wormholes of conspiracy theories that are just honestly outrageous, unproven, and slightly crazy and dangerous.

Slightly crazy and dangerous? Do we need [an] adverb there? I don’t think so. They’re crazy and they’re dangerous. And OK, you clean up the Hudson River Valley. Does that allow you to get people killed? In terms of vaccines. No, it doesn’t. And does it entitle you to help a wannabe dictator achieve his goals? No, it doesn’t. Listen, man, the RFK assassination was childhood’s end for me. I was brokenhearted, and it started me on the road towards cynicism about American politics. I feel deeply about RFK Sr., but having said that, certainly not enough — not even close to enough — to be in any way supportive or other than completely derogatory about this whack job running for office. Sorry, I’m yelling.

What do you do if Trump wins?

Don’t know. Not going to jump off that bridge until it happens, or unless it happens. Totally focused on November. I’m not focused on December. Listen. We have to win this. There is no losing this.

If you were going to set a doomsday clock, where would you put the time?

Five till midnight. Look what’s happening. We cannot afford to be blasé about this. We were blasé in 2016, weren’t we? Right? I was calling Trump a fascist as early as 2015, and people called me an extremist, a fantasist. “Oh, my God, you’re overreacting. You’re being ridiculous.”

And Trump’s only gotten worse.

Exactly. I thought this was over in 2020. I remember this profound sense of relief. And then Jan. 6 happened, and then all this election-denial bullshit. And the Republican Party, or what once was the Republican Party, continues to kneel on the ground and throw dirt over itself. So, we can’t afford to be complacent. We can’t afford to be blasé. We can’t afford to want the perfect choice, because the choice is going to be stark, and it’s going to be binary. Do you want a fundamentally decent human being in the White House? And Joe Biden is a fundamentally decent human being. Or do you want a narcissistic sociopath in the White House?

There was a Biden rally here in New York, and there were a lot of protesters out there. Is that what you would say to them?

Well, that’s what I would say to them. Look at the choice. It’s what you wanted to say to the Bernie people in 2016, right? They didn’t get behind Clinton. And look what happened. They wanted their perfect choice, and they wanted their own pristine kinds of politics and their high moral stance. Great. Beautiful. Look what happened. Look what we got. Look at the destruction of this country in four years. We’re almost unrecognizable from what we were in 2015.

Given the polls, do you worry that you’re losing ground?
I do. Of course. Listen, I worry all the time. But so what? This is what I say to people a lot. People say, “Well, shouldn’t we be pessimistic? Shouldn’t we be worried?” Yeah, maybe, but so what? What are we supposed to do? Curl up on the couch in a fetal position and let the country go to hell? No. Sometimes our feelings don’t matter. Go ahead and do something.

Some days I think Trump’s going to win, and then other days I look at him and think you just would not want to have the negatives that guy has, starting with all the criminal cases.

More indictments than John Gotti and Al Capone combined. I looked it up. Being a crime writer.

Well, is that one of the reasons that Trump fascinates you so much? He’s like one of the great criminals of all time, right? 

He doesn’t fascinate me, man. I find him extraordinarily tedious. And stupid and annoying. I can’t look at his fat, fucking stupid face. I once referred to him as Mussolini with worse hair and a lesser command of English. Donald Trump should have been dragged out of the White House in handcuffs before the sun set on Jan. 6, and we all know it.


Let’s shift back to writing to end this conversation. What advice would you give a young writer starting out today?

Well, a couple of things. First and most importantly, don’t give up. Don’t give up, ever. Because people are always going to tell you no. People are always going to tell you that you can’t, and you’re going to tell you you can’t. That voice is going to come into your head telling you, you can’t do this. It certainly came into mine, more than once.

The other thing that I try to tell aspiring writers is do the doable. Instead of saying, “I’m going to write my novel this year” — you’re probably not if you frame it that way, because quite understandably, you probably have a job, or two, you have maybe a family, maybe kids, all kinds of other obligations. What I try to tell them is, “Instead of saying, ‘I’m going to write my novel this year,’ say, ‘I’m going to write two pages on Tuesday. I’m going to write two pages a day, or three pages a day.’ Or whatever is realistic for you to do.” Set that goal, but then do it — no matter what.