Thirty-two years later, I asked him how it felt to see his final book poking out over the horizon. Any second thoughts about calling it quits? “Not second thoughts,” said Winslow, “but certainly mixed feelings. You do a certain thing for decades, almost every day, being at my desk at 5:30 a.m. and working until 5:30 in the evening, to produce what I hoped was decent prose. And now, of course, it’s much different.”
Before logging on to our Zoom, I clicked over to the YouTube page of Don Winslow Films to see what sort of content Winslow and Salerno had been cranking out in the relatively placid interregnum between “Stop the Steal” and Trump 2024. Recent videos include “#WhyAreDemocratsAfraidOfMTG,” “#RevolvingDoorOfCrazyRepublicans,” and “#GregAbbottFakeChristian.” But it’s not all storm and stress. There’s also “#GeorgiaNeedsStaceyAbrams,” “#VoteBetoSaveTexas,” and “#VoteForValStopRubio.”
In the meantime, Winslow’s bête noire—who may very well earn the Republican nomination, criminal investigations be damned—is always in his crosshairs, so you can expect more anti-Trump content as well. “The man is such a fake on so many levels,” Winslow told me, “and that’s another thing I’m hoping to do in the next Couple of years, through social media, through the videos that Shane and I make, through my tweets—to expose the obvious truths behind a lot of these myths about him. You know, that he’s not a great businessman. Great businessmen don’t declare six bankruptcies. He’s not some sort of ladies’ man. A ladies’ man’s is not accused of sexual assault and rape and paying hush money to a porn star. He’s not some big macho military guy. He’s a guy who took God knows how many deferments during Vietnam. There’s all this mythology that his base believes, and it’s going to be our job in the coming months and years to pierce those things.”
Some of Winslow’s political output comes with a splash of starpower. A collaboration with Bruce Springsteen—who lent “Streets of Philadelphia” to a video targeting Pennsylvania voters weeks before the 2020 election—got nearly 5 million views in less than 24 hours and, according to Winslow, eventually nipped the heels of 10 million overall. Another, narrated by Jeff Daniels and aimed at Michigan voters, soared past 5 million total views. “The videos have had a far greater impact than I’d ever dreamed,” said Winslow. “We’ve had something like 250 million views just on Twitter alone.” (He’s gunning for a billion.)
I wondered whether this stuff mostly makes noise in the echo chamber of people who are already on Winslow’s side. “Shane and I”—who fund Don Winslow Films out of their own pockets—“are at a phase where we want to try to reach out more to Republicans. I think that might be the next evolution,” said Winslow. “I live on an old ranch, in an area that voted 73% Republican in the last election, surrounded by cowboys, literally. This one cowboy, a neighbor, we’ve known each other for 26 years, and we’ve had many, shall I say, discussions about politics. He was a dyed-in-the-wool Trump supporter. He called me up, probably a month or so ago, out of the blue and said, ‘Hey, Don. I’m done with Trump.’”
What was the cowboy’s final straw?
“He had been thinking about the events of January 6, and about Trump’s reaction to it. That really struck me, because I’ve been stopped on the road, you know, by guys in pickup trucks yelling at me, ‘We don’t like what you write on Twitter,’ and that kind of stuff…. I think there is a constituency now that’s willing to listen. You know, I’m not anti-Republican. I’m not even anti-conservative per se. I’ve been a lifelong Democrat and I hold those values, but I think there are people that we could reach out to and talk to and find some common ground with.” Some of the issues Winslow wants to spotlight in the months ahead? “Joe Manchin’s been a disgrace. The Lauren Boeberts and Marjorie Taylor Greenes of the world have been flirting, at the very least, with treason. There’s immigration, drug policy, women’s reproductive rights. For God’s sake, book burning.” And by the way: “We might move into television spots.”
For Winslow, as with many Americans, Joe Biden’s victory brought a fleeting moment of euphoria (“Spontaneous celebrations broke out in my little town in Rhode Island,” Winslow recalled. “People were driving up and down the street, honking horns. Boats were cruising up and down the beach.”), only to be replaced with horror amid the madness that followed (Rudy Giuliani’s hair dye; Sidney Powell’s Kraken; the QAnon people storming the Capitol; et cetera). Now, with culture wars raging, far-right policy ascendant, and Trump starting to suck up so much of the oxygen again, it can feel like the whole political environment is a bit of a powder keg.
As our chat came to a close, I asked Winslow to gauge his anxiety level. “My anxiety level’s pretty high, but it has been for a long time,” he said. “Anger, I would say, more, perhaps, than anxiety. Having said that, pessimism doesn’t do anything. And listen, I’m obviously not a terribly Pollyanna type, but what do you do if you decide on pessimism? If you give up? Lay down on the couch in a fetal position and wait for democracy to collapse? It’s almost useless to say, well, I’m optimistic or I’m pessimistic. Those are adjectives, and the adjectives don’t really matter. What matters are the verbs.”
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