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The Odyssey Meets The Departed In This 3-Part Modern Crime Fiction Masterpiece

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Ambrose Tardive is an editor on ScreenRant's Comics team. Over the past two years, he has developed into the internet's foremost authority on The Far Side. Outside of his work for ScreenRant, Ambrose works as an Adjunct English Instructor.

The Odyssey. The Departed. Two legendary Matt Damon movies, released two decades apart. One of the earliest epics to come down through history, and a timeless 21st-century genre masterpiece with few rivals and even fewer equals. Now, imagine combining the two into one story.

That is exactly what author Don Winslow did with his "Danny Ryan Trilogy," a modern gangland retelling of the fall of Troy and the ten years that followed. That's right, Winslow's novels remix The Odyssey, but also The Iliad, and its Roman sequel, The Aeneid.

Winslow synthesizes a career's worth of crime fiction expertise with a deep knowledge of the classics in the "Danny Ryan Trilogy," starting with City on Fire, continuing through City of Dreams, and culminating in City in Ruins.

The City books are must-read crime fiction, from one of the genre's heavy-hitters. What makes them such a remarkable accomplishment, above all else, is that the trilogy is just as enthralling for people who haven't read its ancient antecedents as it is for those who know the myths.

Warning! Implicit and explicit spoilers for the "Danny Ryan Trilogy," The Odyssey, and more ahead!

The "Danny Ryan Trilogy" Is Epic Crime Fiction, Literally, With Its Literary Retelling Of Ancient Myths

City on Fire by Don Winslow, book cover

Don Winslow's "Danny Ryan Trilogy" was published back-to-back-to-back from 2022 through 2024. This and the pacing of the books suggest it was written as one massive tale and chopped up into three digestible installments. For crime fiction fans, the novels are very digestible. Pages fly by, and so do minutes and hours if you're listening to the impeccable audiobook versions narrated by Ari Fliakos.

City on Fire opens in the mid-1980s. The tenuous coexistence of the Italian and Irish Mobs in Providence, Rhode Island is shattered when Winslow's equivalent to Helen of Troy, a woman named Pam, comes between them. The book's protagonist, Danny Ryan, starts out on the periphery of the war to follow. He's married to the boss's daughter, best friends with the heir apparent, but it is only when everything falls to pieces that he steps into his role as a main character.

City of Dreams by Don Winslow book cover

Reflecting the trajectory of the ancient character Aeneas, who fled the destruction of Troy and later became the subject of one of Rome's founding myths. The parallel is clear as day to those who have read the classics (or, their Wikipedia pages). The same goes for Chris Palumbo, the trilogy's Mafioso Odysseus, doomed Irish mobster's daughter Cassie Murphy, and the many other characters transposed from the ancient world.

At the same time, readers who go in unfamiliar with the source material will find the "Danny Ryan Trilogy" has all the twists and turns, brutal character deaths, and moral dilemmas of world-class crime fiction, scratching the same genre itch as The Departed.

Fans Of History & Crime Fiction Alike Should Make Don Winslow's "Danny Ryan" Books High Priority Reads

City in Ruins Don Winslow book cover

If you know the story of Aeneas, or Odysseus, or any of the figures from Homer and Virgil's epics, it's a pleasure reading Don Wislow's "Danny Ryan" novels and seeing how the author maps these archetypes onto his modern mobster characters. The fact that their ancient character arcs translate so effectively to 20th-century organized crime says something about storytelling, and maybe the human condition as a whole.

Modernizations of myths and epics aren't anything new. It is almost as time-honored a creative tradition as epics themselves. Still, Winslow's trilogy is a masterclass in the form. It is also a playbook for writing gripping crime thrillers. Along with Winslow's earlier "Cartel Trilogy," it solidifies the author's reputation as one of the all-time greats of the genre.

And for anyone with Odyssey-fever right now, the "Danny Ryan Trilogy" is a great crime fiction companion piece to Christopher Nolan's epic film adaptation. Especially if readers facecast a young, Departed-era Matt Damon as Ryan, whose storyline fuses two of the actor's greatest roles of his career.

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