Frenetic ‘City of Dreams’

I had some dreams when reading Don Winslow’s latest book, City of Dreams. At the beginning, I dreamt I had never started it, in the middle I dreamt it would never end—then at the end, I got a good night’s sleep. 

Like most Winslow, best known for his bloody Mexican drug war trilogy Cartel and the novel that inspired the Oliver Stone–directed Savages, it was alternately skilled and hacky, insightful and infuriating, glib and sincere, gimmicky and pure. Winslow’s writing tends to be drug-like. There are good, clean highs interspersed with regretful lows. The paragraph structure and syntax are speedy, the plot machinations dopey, the story straight edge. It wouldn’t surprise me if Winslow takes Adderall, both from his output and frenetic pace of his writing.

So far, the first two installments of the City trilogy seem more rushed than usual, especially in comparison to his encyclopedic Mexican series. But that comes with the demands of publishing houses for writers of Winslow’s ilk, which rely on increased output to result in occasional gems, as opposed to waiting for one every few years. 

There’s no denying that Winslow’s ambition and output are seemingly infinite, and the fact that he keeps us reading when maybe we shouldn’t, is an accomplishment near in scope. And that’s perhaps more Homerian than the homage itself.

Publishing strategy

Publisher William Morrow’s rollout has been cunningly professional as well, with each book’s date of release set the year before and excerpts from the next book featured at the end of the current one. Why sell one book at a time when you can sell three? 

Winslow knows this dynamic well from Cartel. The first two books were mind-bogglingly detailed masterpieces, and the final one equal parts titillating and frustrating with unnecessarily macabre violence. In between, Winslow briefly dabbled in Manhattan with his heavily New York Post–influenced The Force, soon to be a movie with Matt Damon, a rare East Coast sojourn in a career that sprouted with a Pacific-surf themed San Diego oeuvre. 

This time, Winslow not-so-subtly introduces chapters with quotes from Homer’s The Iliad or Virgil’s Aeneid, as we travel on an odyssey from Providence to Las Vegas, both of which are the weakest passages throughout. The Hollywood segment they literally bookend, however, is masterful, with writing as smooth as the setting that cleverly includes a Hollywood set of Providence, along with both a scathing indictment of both the film industry—it sounds like it’s from experience—and its accompanying stage-parent scene.

There is a lot of “freakin” and “pisser” thrown about as Irish and Italian gangs—who swear in in Sopranos-inflected italics—battle it out, previously with the help of a Black gang responsible for some of Winslow’s cringiest dialogue. But the furiously paced action supersedes both the plotting and dialogue, so, in the end, like in the first installment, I couldn’t stop reading — convenient since Winslow chooses to end with unfortunate depictions of both graphic incest and a stream-of-consciousness mushroom trip.

Flipped crime worlds

While the book jacket touts both The Godfather and The Sopranos as comparisons, the story is transposed from Whitey Bulger’s Departed–era Boston Irish milieu—and even the real-life adventures of the McLaughlin gang’s (worth a Google) move to Providence and Rhode Island’s many beaches, traditionally the purview of the Italian-American Patriarca crime family. This fabulist switcheroo results in a hodgepodge geographic fantasy of hardscrabble southern New England—New Haven, Hartford and Bridgeport get shoutouts—rather than an actual recognizable version of itself.

These literary liberties call to mind another talented producer of contemporary New England pulp, Spenser creator Robert B. Parker, who himself can draw a direct lineage as a Raymond Chandler disciple, though I suspect Winslow would prefer another noirish Boston writer and Parker acolyte, Dennis Lehane, as his hardboiled comparison.

And like with Parker’s Spenser and Jesse Stone novels, it won’t be long before another fast-paced thriller comes on the scene with a Winslow tag. The trilogy’s final title is due out March 19, 2024. But a final plot twist has already surfaced: Winslow is billing it as his last book before retirement. I hope that’s not the case, but, either way, I’ll be waiting for it on my couch with a pillow and a blanket.