Chapter summaries City in Ruins Don Winslow

Chapter Thirty-Seven Summary & Analysis

Spoiler Notice

This discussion reveals the full contents of Chapter Thirty-Seven of City in Ruins by Don Winslow. The page assumes you have already read the chapter or want a complete breakdown of its events and implications.

Summary

Vern Lasky tosses his newspaper aside in disgust after learning that Dan Ryan somehow persuaded Abe Stern to invest in Las Vegas—a move Stern had stubbornly refused for three decades. Connelly immediately insists Ryan must have leveraged mob connections or hidden dirt to flip Stern, much as he claims Ryan did earlier with a man named Stavros on the Lavinia project.

Connelly pushes Vern to approach a specific, unnamed Gaming Control Board member to launch a formal investigation that could strip Ryan of his license. Though the board previously rejected the idea, Connelly believes the right pressure will tip the scales. Vern resists at first, repulsed by the gutter tactics, but his own business calculus takes over. If Ryan’s license falls, Dom Rinaldi and Jerry Kush could tumble next. Tara’s hotel empire would collapse, and Vern could scoop up the wreckage.

After Connelly leaves, Vern wrestles with genuine doubt. He cannot quite convince himself that Ryan is currently mobbed up, even if past connections existed. The real danger, he realizes, is that excavating Ryan’s buried secrets invites a reciprocal dig into his own history—and no Vegas kingpin’s foundation is spotless.

Key Events

Vern reads the Stern news. The newspaper confirms Abe Stern’s sudden, long-resisted investment in Las Vegas through Dan Ryan.
Connelly lays out his theory. He argues Ryan must have mob muscle or compromising material to force Stern’s hand, citing the earlier “flip” of Stavros as precedent.
A board scheme emerges. Connelly proposes approaching a receptive Gaming Control Board member to open an investigation and pull Ryan’s license.
Vern gives the green light. Despite his reluctance, Vern tells Connelly to make the approach, envisioning a cascading collapse that would benefit him.
Vern’s private misgivings surface. Alone, Vern confronts the possibility that Ryan is not currently mob-connected and that plunging into the gutter could expose his own buried skeletons.

Character Development

Vern Lasky: This chapter illuminates Vern’s internal conflict. He publicly endorses a dirty tactic he privately loathes, rationalizing it as a business necessity. The phrase “It’s risky business to be digging up Ryan’s” reveals that Vern’s real fear is a boomerang investigation. He knows he, like Las Vegas itself, is “mostly clean now”—not fully innocent. The admission that “you have skeletons buried in this dirt” personalizes the danger and shows self-awareness beneath the ruthless façade.
Connelly: Doubles down on his role as Vern’s attack dog. He shows no ethical hesitation about wielding innuendo and board politics as weapons. His certainty about Ryan’s mob ties—even absent proof—displays a transactional view of the regulatory system.
Dan Ryan and Abe Stern (off-page): Though absent from the scene, both men are catalysts. Ryan’s alleged strong-arm tactics underscore his resourcefulness and the question marks surrounding his methods. Stern’s reversal signals that even the most resolute outsiders can be pulled into the Vegas orbit under pressure.

Themes, Symbols, or Motifs Evidenced Here

The Domino Theory of Destruction: Vern explicitly frames the takedown as a game of dominoes. Ryan falls, Rinaldi and Kush lose their licenses, Tara’s holdings collapse, and Vern profits. The motif reinforces how interconnected the Vegas power structure is—and how a single well-placed push can trigger an avalanche.
Skeletons and the Fragility of Reputation: The chapter’s central metaphor is archaeological: digging into someone’s past unearths whatever is buried. Vern’s recognition that “we all made our deals, all made our compromises” universalizes the threat. No one survives a thorough excavation.
The Mostly Clean Myth: Vern’s mantra that Vegas is “mostly clean now” echoes the city’s eternal tension between its outlaw origins and corporate rebranding. The qualifier “mostly” leaves room for the dirt that still clings to every established player.
Mob Echoes vs. Present Reality: Connelly’s insistence on “wiseguys” and Vern’s skepticism create ambiguity. The chapter never confirms Ryan’s current mob ties, leaving readers to question whether Connelly is paranoid, manipulative, or accurate.

Why This Chapter Matters

Chapter Thirty-Seven pivots the conflict from business rivalry to institutional warfare. Until now, Vern and Connelly battled Ryan in boardrooms and negotiations. The decision to weaponize the Gaming Control Board raises the stakes to an existential level—licenses, not just deals, are now on the line.

More importantly, the chapter turns Vern into a reluctant gambler who knowingly bets against his own dirty history. His internal monologue foreshadows that Ryan will not be the only casualty if the investigation becomes a two-way street. The chapter plants a ticking clock of reciprocal exposure, adding psychological depth to a man who previously seemed purely calculating.

Study Questions and Answers

Why does Vern ultimately authorize Connelly’s plan despite his ethical reservations? Vern’s decision is driven by pragmatic self-interest. He sees the domino effect clearly: Ryan’s downfall would destabilize Dom Rinaldi and Jerry Kush, forcing them to sell assets, including Tara’s hotels. Vern can “pick up the pieces” and expand his own empire. His resentment toward Ryan also primes him to accept a plan he would otherwise reject.
What does Vern mean when he says Las Vegas is “mostly clean now,” and how does that phrase connect to his personal fears? The phrase acknowledges that while overt mob control has faded, the city’s power structure still rests on past compromises and morally gray deals. Vern applies the same logic to himself—he is law-abiding now but knows his rise involved actions that could destroy him if exposed. The parallel between city and man underscores the novel’s theme that the past cannot be walled off from the present.
How does the chapter use foreshadowing to create tension about the upcoming investigation? Vern’s realization that “Ryan might retaliate with an archaeological dig of his own” directly foreshadows a counterattack. The metaphor of buried skeletons and the warning “you have skeletons buried in this dirt” makes it nearly certain that Vern’s secrets will surface. The tension lies not in whether the investigation will backfire, but how and when the damage will arrive.