Don Winslow Explains Why He's Trading Crime Novels for Never-Trump Politics

Robert Gallagher

This story was featured in The Must Read, a newsletter in which our editors recommend one can’t-miss GQ story every weekday. Sign up here to get it in your inbox.

This past February, the increasingly legendary crime fiction author Don Winslow announced the publication of “City in Ruins,” the third and final book in his bestselling Danny Ryan series. He also announced that the novel would be his last, and that he was retiring from writing books, to concentrate full-time on political activism of the extremely anti-Donald Trump variety.

This was not entirely unexpected, but it still felt like a surprise. For several years, Winslow and Shane Salerno—his best friend, agent, and co-conspirator—have been making videos pile-driving Trump. Once, Winslow’s thing was writing about the people he’s fond of quoting “Mr. Springsteen” to describe as “the folks in the darkness on the edge of town.” Fighting resurgent MAGA-ism is his thing now.

Unlike a lot of novelists, who engage with social media with the enthusiasm one might bring to picking up something one’s dog left on the sidewalk, Winslow is a big fan. He believes he can reach far more people on social media and YouTube than he could in his old job. “Listen, the videos that we've done have had over 300 million views,” Winslow says. “I don't think I've sold 300 million books.”

Despite this career pivot, Winslow still absolutely classifies himself as a guy who wanted to be a writer his entire life. “My father was an avid reader and my mother was a librarian in this tiny fishing village, Matunuck, Rhode Island,” Winslow said.

Most kids were expected to go into fishing, or, possibly, crime. But between the two of them, Winslow’s parents produced two wildly prolific writers (Winslow’s older sister, Kristine Rolofson, first published in her 30s, and has written more than 40 romance novels). Winslow loathed school—he failed senior English, in fact.

“I got out of high school [because they let] me and a friend of mine, this girl I knew, write a musical based on James Michener's The Fires of Spring,” he says “She wrote the music and we staged it, and it was kind of a local hit. So they let me graduate with a C.”

Winslow was working as a private investigator in New York when he started reading the crime fiction greats: Raymond Chandler, Lawrence Block, the god Elmore Leonard. “If I wrote for 100 years, I'd never write anything as good as Elmore Leonard,” Winslow says. “I was seated near him at an event once and I couldn’t even approach him.”

Drawn in by the balance of plotting and gorgeous-yet-dynamic writing that the best noir can offer, Winslow has forged his own, extremely successful path, with tight, economical prose and canny storytelling that also happens to be ideal for adaptation into various media.

Winslow’s first novel, A Cool Breeze on the Underground, was published in 1991. “For most of my career, I was branded a cult writer, which is just the kiss of death,” Winslow says. After he and Salerno co-created the short-lived NBC TV series UC: Undercover, the two stayed in touch, and eventually the latter decided to represent the former—Winslow was his first client.

Both have become wildly successful; Winslow has written bestseller after bestseller, a run that’s led to film option after film option. His 2010 novel Savages became an Oliver Stone movie two years later. Christopher Storer, creator of The Bear, is set to direct The Winter of Frankie Machine. Chris Hemsworth and Pedro Pascal are attached to Crime 101. Netflix is adapting The Gentlemen’s Hour and The Dawn Patrol. And so on.

Meanwhile, Winslow is on Twitter. His novels take two or three years to write, another year to publish. On social media, that which is discussed on a Tuesday morning is usually discussed by Tuesday lunch. “[Twitter] obviously promotes the books,” he continues, “But more importantly, in terms of this fight against what I consider to be a fascist movement in this country, it's instantly responsive.”

This is the opposite of the path his final novel took. City in Ruins closes out a trilogy centered on Daniel Ryan, Irish-American thug turned Hollywood player turned gazillionaire Las Vegas casino owner. In City in Ruins, Ryan navigates a deadly power struggle between brutal businessmen in the Neon City. Winslow now-famously mapped the series on Virgil’s Aeneid, with Ryan in the title role.

Winslow, now 70, became fascinated with the classics in his 30s. He describes himself as “pretty well grounded in Shakespeare,'' but started hitting used book stores armed with a Great Books list, looking for cheap paperbacks to fill the holes in his knowledge of everything else.

When he read Homer’s Illiad, something clicked. “I was so struck by its similarity to crime fiction,” Winslow says. “It was a Helen of Troy-like incident that sparked a gang war in New England where I grew up.” Winslow locked on to the Aeneid, which takes a minor character from the Iliad and gives him his own epic, a Better Call Saul to Homer’s Breaking Bad.

“There’s nothing original about mapping a contemporary novel on an epic,” Winslow says, “and it took me about 30 years from conception to finish.” But it’s proven incredibly popular; another Winslow adaptation in the works is a film version of the first book of the trilogy, City on Fire, which is set up at Sony with Austin Butler set to star.

Winslow has toggled between crime and politics for a while now. He grew up a working-class Kennedy Democrat, but says he didn’t have much interest in politics until he began researching drug policy for his novels, especially 2015's The Cartel, which James Ellroy called “the War and Peace of dope-war books.”

“The more I learned, the more political I got,” Winslow says. Once you start looking at the drug war, you run into mass incarceration policy, immigration policy, border policy. Winslow got so pissed off, he took out a full-page ad in the Washington Post advocating for the end of the drug war.

This was also around the time a weird hotelier, long-time New York gossip-column fixture and TV game-show host named Donald Trump started making noises about wanting to run for President. A lot of those noises were about Mexicans and immigration, which made Winslow take notice. The more he learned, the more political he got.

“I'm one of the few people who said back in 2015 that he had a path to victory,” Winslow said, “and I was pretty much laughed at. I think he's a total fraud, but he's a persuasive fraud, and obviously managed to convince a significant number of Americans that he was the answer. Between that and the misinformation that was constantly put out and put out by Fox News, he was able to win.” Winslow and Salerno spent much of 2020 posting anti-Trump videos and hitting Twitter. Now that City in Ruins is out the door, he has no plans to stop.

“The most important thing for Americans to know right now,” he almost yells, “is that Trump is a real threat, that there is a fascist movement in this country, that we get organized and unified and tough, and that if we allow Trump to get power again, I think it's going to be a lethal blow to our democracy from which we might never recover.”

Originally Appeared on GQ