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.
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