Crime novelist Don Winslow imagines Trump behind bars — but will it happen?

Donald Trump is essentially a political crime boss. He controls the Republican Party from his palace at Mar-a-Lago where he dispenses favors and collects money and displays of subservience in exchange for his blessing and protection. Like other authoritarian leaders, Trump viewed the presidency — which he is still plotting to regain — as an opportunity to enrich himself, his family and others in his inner circle at the literal expense of the public. As documented by investigative journalists and public watchdog groups, Trump was remarkably successful in that regard.

Trump has no conception of public service or of any obligation to anyone or anything outside his own self-interest. Like other political thugs, Trump is compelled toward violence and causing harm to those he deems the enemy, largely because they refuse to show deference and comply with his wishes. As demonstrated by his regime’s callous and negligent response to the COVID pandemic, Trump has shown that he has no regard for human life.

Throughout his decades in the public eye, Trump has demonstrated gross disdain for the rule of law and basic standards of human decency, compassion, care and concern. He has been credibly accused of sexual assault by numerous women. Like other such leaders, Trump corrupts the people around him. This is true of his inner circle as well as the Republican Party and the followers of his fascist movement. 

Although Joe Biden is now president, America’s democracy crisis shows no signs of ending anytime soon. Too many Americans are still in denial about the existential threat that Donald Trump, his movement and the broader white right pose to the future of the United States.

Don Winslow, the bestselling crime fiction author, activist and truth-teller, is not one of those people. Winslow has used his unique combination of skills, experiences, background, resources and public platform throughout the Age of Trump to sound the alarm about America’s escalating societal and political disaster. His videos about the dangers to democracy embodied by Donald Trump and the Republican Party have been viewed online more than 250 million times.

RELATED: Author Don Winslow: Trump’s administration has “manifested itself” as the coronavirus

Winslow is the author of many bestselling novels, including “Savages” (2010), “The Cartel” (2015), “The Force” (2017), and “The Border” (2019). His work has also been adapted for major Hollywood movies and TV series. His new book, the first in a trilogy, is “City on Fire.”

Winslow recently announced that he is so committed to protecting American democracy from the threat posed by the Trump movement and American fascism that he is retiring from writing — at least for now — and will devote most of his time and energy to that struggle.

In this wide-ranging conversation, Winslow warns that the American people cannot afford fatigue or exhaustion in what will likely be an extended battle for the future of the country. He calls out those public voices he says remain in denial about the harsh reality that Donald Trump and his inner circle will in all likelihood never be prosecuted or punished for their crimes. Winslow also argues that the twin crises posed by the pandemic and Trump’s authoritarian regime have harmed the American people on both a collective and individual level, and that real healing and serious accountability will be necessary if the country is to be made whole and move forward.

Throughout this conversation, Winslow also reflects on his journey as a writer, on how his working-class New England origins have shaped his new novel, and on the importance of family and friends in keeping him grounded amid the trappings of success. At the end of this conversation, he stresses the importance of hope in dark times, arguing that surrender to despair is not an option.

This conversation has been edited for clarity and length.

You and I have spoken on several previous occasions and I’m always struck by your humility. For example, when you say that you have an office you sound genuinely appreciative of that fact. When you’re a writer, or following some other creative path, to say, “I have an office” is really an accomplishment. That’s a little thing for some people but a big thing for the rest of us.

It is a big deal. I was either six or seven published books into my career before I could quit my day jobs. Writing my first six or seven books, I never had an office. I was writing in hotel rooms and on trains and planes, wherever I could sit down. When I first got an office, it was a really heady experience. It was like, wow! I have kind of arrived. I can get up in the morning and walk over here and work and then leave it and go home.

Guess what? Now I have two offices. I have an office in my house where I do a lot of my work. But we rented this old gas station that’s literally a minute walk up the dirt road that sits out on a little highway, the two-lane blacktop in this little town. My wife has the bigger part of it for a studio, and I have the smaller part of it for an office. I put industrial furniture and a heavy punching bag in it. I like it a lot. Then I get to walk a minute back to my house. That physical separation is significant. I can separate work from home.

You don’t come from money. You are a working-class man at heart. For you to be able to say, “I’m a writer with an office,” what would your parents think about that?

I wonder that too. But it’s funny, because in Rhode Island, where I wrote most of the new book, I don’t have an office. I could if I wanted to. I started to write outside on the old front porch, sitting on a futon in front of a coffee table. I was back in Rhode Island to help take care of my mother, who was in her declining years. I start work at 5:30 in the morning and I didn’t want to wake anybody up by banging around the actual house.

I would wake up and go downstairs and make a quiet cup of coffee in the kitchen. I would then sneak out onto the front porch and sit down on this damn futon. At some points during the year, I was literally doing the Bob Cratchit thing, wearing gloves with the tips of the fingers cut out and a scarf. It was cold, and there was no heat out there. When the time came that I could have put an office anywhere in that house, I didn’t. I liked my porch: I was just so used to writing out there. I wrote some pretty good stuff out there and I thought to myself, why change it?

You have your creative voice as a writer and also your political voice as a truth-teller about the Age of Trump and America’s worsening disaster. How do you keep this all together and keep the momentum going?

I work with a colleague on the political matters. I’m not carrying that load myself. In terms of staying grounded, I’ve been married to the same woman for 37 years. If ever I got to the point of just being “the author” and all that comes with that stereotype, it wouldn’t play well at home.

My son is an adult now. Being a parent grounds you, because I don’t care what great literary thoughts you might be having, when your child is a baby, the diaper still needs to be changed. I never shut my door when our child was growing up, ever. If he wanted to come in and go play ball or chat or whatever, I just stopped what I was doing and did that, because that was more important both to me and to him. It’s not hard to stay grounded when you come from blue-collar people. I was an overnight success at 55, so I have far more experience of failure than I do of success. Staying grounded has never been an issue for me.

The Trump regime committed crimes against the United States and the American people on a grand scale. It was really just Grand Theft USA. There is a plague that will kill more than a million people. Fascism is ascendant. There are so many challenges and simultaneous crises. This is a litmus test of our national character, and it’s also a test on a personal level. What have these last few years done to our relationships with each other?

I lost my mom during the pandemic. We couldn’t be with her. We were on the opposite coast and there were no planes, and we would not have been allowed in to see her anyway. There was no funeral. I’ll be 68 in October. I have less time for people in general, but I have more time for the people who really matter to me. It’s a funny thing. The close friends that I’ve had for 50 years are still the same friends. What I’ve taken out of this experience is that I didn’t lose touch with them, but I didn’t spend as much time with them as I wanted because I’ve been so busy.

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The value of those friends is incalculable to me. The time that you spend with people who you care about is the one thing you can’t make any more of. I can always make more money if that became an issue. I know how to do that now. But you can’t make any more time. Once it’s gone, it’s gone. We also don’t know how much time we have. It’s not like you can look at the bank account and know what you have. The very essence of life, which is time, you do not know.

There’s been no closure to this era yet. There have been no consequences for Trump’s crimes.

We have not had any closure or other reckoning, because there have been no consequences. If you look at what Nixon did in Watergate, it’s a misdemeanor compared to what Trump did in and around Jan. 6. 

Clearly, we have not had any closure or other reckoning as a society, because there have been no consequences. If you look at what Nixon did in Watergate, it’s a misdemeanor compared to what Trump did in and around Jan. 6 and at other points throughout his administration. What happened with Nixon? We had nationally televised hearings with people who were sworn in under oath and subpoena. The whole country could watch it. The whole country could see what was being exposed about Nixon’s crimes. You might have different opinions and different feelings about it, but the American people got to watch the hearings.

Nothing like that has happened with Trump. We need an open investigation that reveals to everybody what happened on Jan. 6 and the related events — as if it’s not obvious enough anyway.

These past few years, I think I’ve aged more than at any other time in my life. Part of this is because of the stress of Trumpism and COVID and the losses and the challenges and having to fight this fight for the country’s democracy. What have I learned? I’m probably stronger than I think. I’ve also really learned the value of time and the value of close relationships.

Donald Trump and his inner circle made decisions that led to the preventable deaths of hundreds of thousands of people. Trump and his cabal also tried to overthrow democracy on Jan. 6, 2021. He was prepared to institute martial law, using the Insurrection Act. How do you explain the collective lack of outrage by the American people? I’m disgusted and tired from their apparent lack of care and concern. Should I just lower my expectations?

Lowering your expectations is dangerous and ultimately self-defeating. Please don’t do that. I believe that there are two major elements at work here. One, there are a significant number of people in this country who at the end of the day don’t really believe in democracy. They believe in authoritarianism. They’re comfortable with authoritarianism because it provides easy answers. It also plays into their racial prejudices.

Second, the country is tired. There is mental and emotional fatigue because of the Trump years and COVID. People are just worn out and they don’t want to hear about what Trump did. Many people just want to say, “Oh God, that was in the past. Let’s put it in the past.” People like me and you and some others are saying, “That would be great, but it’s not in the past.” The reason that we need consequences is not so much for retribution. It’s to prevent another Jan. 6 and what Trump did more generally from happening again, which it easily could in 2024.

There is a cadre of vocal people on Twitter and elsewhere, who continue to proclaim that Donald Trump is going to jail, or to insist that there’s more going on with the DOJ and Merrick Garland than the public sees. “Just be patient,” they tell us. You have been very vocal in rebutting such claims. What do you see that those people do not?

People would love to believe that Donald Trump is going to spend time behind bars. I would love to think that. I haven’t seen evidence that we are moving in that direction.

You have to look at the evidence. What has happened? Nothing. People want to believe what they want to believe, and people would love to believe that Trump is going to spend time behind bars. I would love to think that Donald Trump would spend time behind bars. I haven’t seen evidence that we are moving in that direction.

Is it just childish thinking? Do some people ultimately just want to live a life of denial?

It’s wishful thinking. The alternatives are painful. It’s part of our nature as human beings, really as animals, to avoid pain and seek pleasure. Some of these truths are really painful. It’s painful to me. I would love to see Trump behind bars. I wake up every morning hoping to see that headline. But on a rational level, I don’t see it happening.

So many people still believe in these fantasies about American justice, that in the end the good guys always win. What do you think it will do to the American people when they finally understand that Trump and his cabal are walking free, with few if any serious consequences for their crimes?

It would confirm what many people have thought for a long time, and not without reason. You could tell this story about Trump in Hebrew, Latin or Aramaic. If you look at history, there are not very many examples of the rich being held to consequences.

As a crime writer, when you look at this moment with Trump, how do you make sense of this? Could you write it?

It is not interesting to me to write. As the saying goes, organized crime only wished it were as organized as Congress. These are very old stories. Should we be surprised that white-collar crime is far more profitable and effective than other types of crime? It shouldn’t come as a shock.

In a recent interview you observed that John Gotti, the legendary New York crime boss, was the only one in his family who didn’t flip. He was on top, and you can’t snitch down. Donald Trump is a political crime boss. Who does he snitch on?

Trump has nobody to trade. He’ll try, if it comes to that, and the only person he wouldn’t sell out would be Ivanka. Trump would sell out everybody else when it came to it.

What have you learned about human nature from writing about crime? How has that informed your understanding of the Age of Trump and this moment more generally?

We have a capacity for both good and evil that’s unlimited. I’ve seen the best of people and the worst of people. In my 23 years of writing about the Mexican drug cartels, I’ve seen hideous psychopathic sadists and mass slaughter. I’ve also seen the incredible nobility and courage of Mexican women in opposing the cartels, for example. I have no way to explain the courage of Mexican journalists either, 200 of whom were killed in covering the cartels and the drug war.

Human beings have an enormous capacity for nobility and for tremendous evil. Donald Trump is legitimately a deeply evil human being. But I think we have to have some hope that there are more people who will listen to the better angels of their natures and defeat this thing.

We as human beings have this enormous capacity for nobility on the one hand and for tremendous evil on the other. How has that informed this moment in America with Trump and these crises? Donald Trump is legitimately a deeply evil human being. I think he’s a narcissistic sociopath. Trump has gathered around him a group of accomplices who will do just about anything and say just about anything. On the other hand, I think we have to have at least some hope that there are more people who are going to listen to the better angels of their natures and defeat this thing.

What does it mean to be working class and from Providence?

That is what the new book is all about that. I had to go back and learn that language and dialect again. That kind of way of being. For the most part I’ve been out here in California for 30 years. This is an area that almost could not be any more different than working-class New England. Those are our people. Those are my people. My paternal grandfather went to work in a Providence factory when he was 14 and retired as the top salesman at Rhode Island Tool, the same company. My dad took a different path and went off into the Navy. But at the root I come from a New England working-class environment. It completely dominates the writing of “City on Fire.”

I can speak to the Irish and Italian and what we would call “swamp Yankee” working-class experience. It means that you’re gritty. You’re generally pessimistic. I often joke about being Irish and looking forward to our next defeat. I grew up in an era when the fishing industry was on the decline. The factories had gone south. That identity also means having a tremendous sense of loyalty to your peers, family, neighbors, and friends. There is a certain type of hardcore toughness and resilience that I still find there. The outer shell of the New England working class — and the patrician class for that matter — is very tough and hard to penetrate. But once you do there is an incredible soulfulness and sweetness in it.

How are the organized crime families, the Mafia, that you write about in “City on Fire” and the new trilogy similar or different from organized crime in other regions of the country?

If you’re in the New York Mafia, you may or may not know somebody in one of the other families. In New England, everybody knows everybody. So the guys in Providence are going to know the guys in New Haven, who are going to know the guys in Hartford, who are going to know the guys in New Bedford. So it’s a much smaller, much more intimate community than you would find maybe in Chicago or in New York.

What is the role of that type of familiarity in the new book? And why did you have the compulsion to “come back home,” so to speak? 

The intimacy is critical because at the beginning of the book they’re all friends, they’re allies. There is an incident that drives them apart. As for the impulse to come home, I believe that eventually we all do that in one form or another. I physically went home to help take care of my mother, and then I started to fall in love with the place again.

I had reached a point where I was ready and capable of confronting the past and looking at where I grew up and how I grew up in a more objective, maybe mature way. I now am in a space where I have the ability to write about it. The other element is that the history of crime in New England matched pretty nicely with the stories I was reading in the Iliad and the Aeneid, and as a practical matter that worked out really well too.

The new book has been described as the Iliad meets organized crime. How does it feel to hear that comparison? How are you managing the expectations that come with writing an epic?

It’s a commitment, of course. You’re spending years of your working life on a book, and you hope it’s worth it. For me, it was really worth it. I hope it’s worth it to the readers as well who will be spending time with these three books.

Maybe that discipline can stand as a lesson for the American people in this moment of crisis. This disaster is not over. So many Americans are tired and ready to quit, and the fight hasn’t even really started. What message do you have for them?

This is going to sound so simplistic, but the truth is that it is just right, left, right, left — putting one foot in front of the other and then getting up the next day and doing it again. It’s as simple and as boring as that. I wish I had a more inspiring or romantic take on it. I don’t. It is just a matter of saying, maybe today I don’t feel like it, but I’m going to do it anyway.

Is hope a dangerous thing?

No. Perhaps hope can be dangerous in the sense that you can get hurt. That disappointed hope is maybe the most hurtful thing. But what are we supposed to do without hope? Consider a state of hopelessness. What does that mean in a practical way? What do you do? What would we do with all that hopelessness in this country and this world? Do you just lie down? Do you curl up into a fetal ball? Do you kill yourself? What do you do? We have to have hope, even though it’s risky in an emotional sense, because we have to carry on. Otherwise, we just give up. I don’t think that’s a choice.

Read more on our 45th president and the aftermath of Jan. 6:


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