State Of The Mob Book

Don Winslow's "Cities In Ruin" novel, and the sanitized Mafia in contemporary literature.

The Mafia’s history with books and film is a long one, let’s just start in 2012. Andrew Dominik’s star studded Killing Them Softly tanked the box office during what at the time seemed like, if not the death knell, certainly an augur for the gangster film’s decline. It was an ultra cynical movie released in an era still high off the fumes of Hope and Change. Not only were there no heroes, which hadn’t been unusual for mob movies since Goodfellas, there were hardly even anti-heroes. Like the George V. Higgins novel it was based on, Cogan’s Trade, criminals had very little interiority and the various beatings and executions contained no passion and no underlying motives beyond business as usual. This was not a story about wise guys and their wounded psyches and fragile egos, but the 2008 financial crisis, as summed up by Brad Pitt’s final line: “America’s not a country, it’s a business. Now fuckin pay me.”

The film underwent some reappraisal by apartment-shackled critics in the shifted climate of 2020 as something of an overlooked gem. No doubt, its dirty, oppressive, vaguely apocalyptic atmosphere was more fitting for this decade than that of its release. Even the unrebuked misogyny of multiple characters, utterings lifted straight from the 1974 source material that would make Christopher Moltisanti blush, managed to evade post MeToo critical scorn. That might be because the film stayed well within the peripheral of its target niche, but it might also be that it so thoroughly robbed the gangster life of even the remotest hedonic aspirational quality that its characters were free to roll around in the sewage in ways even a Scorsese protagonist couldn’t without a firm lecture. If every major mob film from Mean Streets onward was a compounded distancing from The Godfather’s perceived romanticism, Killing Them Softly marks that trajectory’s endpoint.

But what about the literary world? Despite the mafia’s supreme Hollywood reign in the 20th century, and the most critically lauded of them adapted from books, the organized crime novel never found a firm footing on page outside the non-fiction aisle. If the genre slowly chugged along in the 80’s and 90’s through the efforts of writers like Dennis Lehane and Elmore Leonard, what fertile ground could there be for it today? If Ross Barkan’s recent piece is any indicator, probably not much. He notes:

There are numerous polls and studies that tell us men are no longer reading, men are falling behind in school, and men, in this transmogrifying economy, are struggling to adapt. A different sort of literary culture—one not dominated by the affluent and the college-educated—would be interested in these stories. What does male alienation look like? What about consciousness at its most fraught, its most poisoned?

City In Ruins

Which is why I was pleasantly surprised to find that mob fiction is somehow still making its way into book stores. Standing opposite of Killing Them Softly/Cogan’s Trade on the realism spectrum is Don Winslow’s City On Fire trilogy, recently concluded with City In Ruins. The trilogy was advertised as a loose retelling of The Iliad and The Odyssey set in New England criminal underworld of the 1980s and 90s, as a war breaks out between the Italian and Irish mafias. At the center is soon-to-be-played-by-Austin-Butler Danny Ryan, who in less than two years, rises from occasional loan collector to Boss of the Rhode Island Irish mob without a single unvirtuous motive to propel him there.¹ He doesn’t cheat on his wife, he doesn’t raise his voice to his son, he doesn’t lust after status or fancy cars. He’s a “Springsteen guy,” a New England chowderhead; not a single unrelatable bone in his body outside of his love for the Sox. Every crime he commits is a defensive measure in a war he did everything in his power to prevent. Despite much tortured internal monologue about how everyone he loves ends up paying for his sins, he hardly reaches the corruption of Michael Corleone just two hours into The Godfather.

Before this turns into a hatchet job, let me say I devoured these books faster than anything I ever rated five stars on Goodreads. Winslow’s fast pacing, short chapters, and continuously escalating tension is a masterclass in Elmore-Leonard-writing-advice style minimalism. Though hardly more challenging than a James Patterson novel, the writing is not devoid of its poetic flourishes. From the City of Ruins prologue:

Danny watches building come down.

It seems to shiver like a shot animal, then is perfectly still for just an instant, as if it can’t bring itself to acknowledge its death, and then falls down on itself. All that’s left of where the old casino is a tower of dust rising into the air, like a cheesy trick from some lounge-act musician writ large.

“Implosion,” they call it, Danny thinks.

Collapse from the inside.

Aren’t they all, Danny thinks.

If Danny Ryan himself stays a little too noble for readers that like their anti-heroes to be, well, anti-heroic, there’s plenty of unsavory tertiary characters to give this story the grit it needs. Peter Moretti Jr. is the son of deceased of New England crime family boss, Peter Moretti, and his avenges his father’s death by gunning down his unfaithful mother while she’s in her bathrobe. Christopher Palumbo ditches his wife and son to live in Utah with a new woman, only to return nearly a decade later begging his wife to cuckold him so his old crew sees that he’s whipped and doesn’t murder him. Final antagonist, Allie Licata, uses a special prostitution service that allows him to viciously beat their girls into the E.R. There’s enough fights and shootouts to satisfy any fan of the genre. What gets lost in the breezy and aerodynamic prose is the voice and texture that bring this world and its characters alive. Consider, for instance, the following exchange in City In Ruins where the New England mafia debates bringing Chris Palumbo back in the fold. It’s one of the few scenes where bunch of Wiseguys are in a room together:

Finally, Giglione says, “Go wait outside. The men need to talk. We’ll call you in when we’re ready.”

Chris nods head and goes out.

“Fucking kill this fucking fuck,” Marco says.

“Concur,” Marraganza says.

“I agree,” Giglione says. “But not yet. What’s the hurry? The wife’s about tapped out. Let him make some money for us now. “

“He gave us each twenty g’s,” La Favre says, “so there’s probably more where that came from.”

“Chris could always make,” Vacca says.

“You think he means it about not wanting power?” Marraganza asks.

“You think?” asks Marco.

“I’ll prove it,” Giglione says. “Bring him back in.”

Chris comes in.

There’s nothing wrong with this. It’s snappy. It’s natural enough. It moves the scene along. But compare that to the following exchange from George V. Higgins’ Cogan’s Trade, in which Frankie tries to convince Johnny Amato to let his friend Russell, who seems intent on making the worst impression possible, in on a job:

“He clean?” Amato said. “Both you guys clean?”

“Frankie,” Russell said, “you been using something?”

“Shut the fuck up, all right, Russell?” Frankie said. “Yeah. I haven’t had anything but booze since I get out. Not that much booze, either. Mostly beer. I been waiting for the payday, I start in on the VO and other stuff.”

“You’re on pills,” Amato said. “You’re in, you’re on pills. I seen you, don’t forget. You were beating the hell out of them yellowjackets.”

“John,” Frankie said, “the yellowjackets were there. I didn’t see nobody serving no beer. I took what there was. I haven’t had none of that stuff since I was out.”

“How about him?” Amato said.

“Gee, Squirrel,” Russell said, “I wouldn’t take nothing. I, ah, I probably had a couple quarts of Ripple and some grass, and I might’ve had one or two dime bags once or twice, but I just snort them, you know? It’s not like I was using something. I go to Cub Scouts, you know? And they pat you down, there, they start teaching you how to tie them knots and everything.”

“Smack,” Amato said to Frankie. Frankie shrugged. “I ask you to find a guy for me and I got this thing, and all I got to do is do it and we get some very nice money. All I got to do is find two guys that can do a fairly simple thing without fucking it up, and this is the best you can do for me. A fuckin’ junkie. And I’m supposed to just let you guys go in there and you’re gonna go in and once and for all you’re gonna fuck it up, a job that’s never gonna come around again in a million years. I don’t want to have a whole of fun with this thing, you know, because I hadda go out and get a guy that looked all right when I got him and then he goes in and he’s on the fuckin’ nod or something. I want the goddamned money. That’s what I need.”

Famously, there’s very little description in George V. Higgin’s novels, or any text that’s not dialogue. Despite that, you can almost smell the stale beer and cheap cigarettes wafting off these low lives, feel the creak of the dated furniture in the crumby office. Simply observing these people’s conversations is enough to feel like you need a tetanus shot, much like the real-life Boston crooks that Higgins spent long hours listening to on wire recordings. If that excerpt began a few paragraphs earlier or a few paragraphs later, it would be taken down on most other platforms that aren’t Substack. Forget publishing it through a major imprint.

Winslow can be forgiven for not approaching this subject with the same naturalism as Higgins. In fact, given that his aims here are diametrically opposite, one of remythologization rather than demythologization, too much hardboiled realism might have cut the trilogy even shorter of its Homeric aspirations. The problem isn’t that it’s not gritty enough, it’s that it lacks any kind of texture at all. With the minimal scenes and somewhat flat characterization, Winslow’s more heroic take on the genre never fully comes alive, and thus never truly counters the bleaker vision of his contemporaries. I would be lying if I said it bears no resemblance to its influences, however. Winslow dashes from plot point to plot point with the speed of Achilles, in branching storylines that never rejoin, wrapping up too tidily thanks to a level of plot contrivance and authorial intervention that would put the Aesir to shame. If it seems like I was being snarky earlier with the James Patterson comparison, consider the series ultimate climactic scene²:

Licata howls, then moans, then grunts.

His bladder gives out, then his bowels.

He sighs.

His mouth opens.

Danny finds a rag and shoves it into the gas tank.

Lights it and walks away.

He has to get to Ian.

It’s only then he feels the blood flowing down his leg and realizes he’s been shot.

He doesn’t care.

He has to save his son.

God, Danny thinks, please let him live.

If it seems I’m being unfair focusing on one book to represent the state of mafia literature altogether, it’s only because the City On Fire trilogy was not only successful enough for a major adaptation starring Austin Butler, but actually one of the better offerings of this decade so far. Chuck Hogan’s Gangland is slightly grittier but too limited by its biographical mode to carry much narrative heft. John Grisham’s The Boys From Biloxi is an execrably boring legal procedure that drops its crime drama veneer early on. Dennis Lehane’s Small Mercies is the best of the bunch, but I don’t consider it a true mob story as its protagonist is not a mobster or even an amateur criminal. Furthermore, Don Winslow has proven himself capable of writing much richer material within this genre with The Power of the Dog from 2006. While he’s clearly lost some steam, as any author must to declare it their last book, I’m not entirely convinced this latest neutered entry isn’t at least a little bit due to market trepidation.

The Future of Mob Media

Considering these all came out within the last two years, I’d say there’s a healthier demand for this stuff outside the ghettos of Wattpad erotica than a cursory glance through the Amazon bestsellers would indicate. It might be tempting to ascribe the relative tameness of these works compared with its cinematic counterparts to the prudishness of the publishing industry, but let us not forget that the compounding grittiness of the genre from the 90’s to early 2010s was borne of its own kind of moralism: the imperative to not romanticize the lives of criminals. It can be argued that mob fiction will go the way of the cowboy because, like the cowboy, the mobster is now a figure of history rather than the present. The Godfather came out right around the time of RICO, which marked the end of the Mafia’s Golden Age. Nicholas Pileggi’s Wiseguy, the source material for Goodfellas, came out in 1985, the same year as the Commission Trial; the biggest blow to the Five Families in history and one that they never recovered from. It was as if each crippling of Cosa Nostra buried them deeper into the public consciousness, making them a more lucrative source of prestige entertainment. By the time Tony Soprano arrives on the small screen, the real-life mob is a mostly dead horse existing primarily in entertainment. By its third season, the specter of terrorism would usurp what was left of America’s criminal organizations in the anxieties of Americans, and yet, the popularity of The Sopranos only grew. Even today, the show retains a steady relevance churning out new fans and inspiring new clothing items at Express Men³.

Mob fiction works because it’s never just about the mob. Humans tend to organize themselves in pyramids, making the Mafia something of a catch-all microcosm of larger institutions. For this reason, mob fiction will never be all the way irrelevant. And as one of the few genres where the protagonists are the bad guys by default, the psyche of the maladjusted male can be better explored with much less handwringing of the audience. The question is how much of that psyche can we bear to witness; if the current slate of gangster media is anything to go by, not a whole lot.

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1. I’ve never read a synopsis longer than two sentences I didn’t skim, so I didn’t include a proper one here. But you get the idea.

2. Don’t worry about spoilers. I forgot the plot shortly after putting the book down, you will have forgotten it too by the time you pick it up.

3. I mean, I don’t want to give them free advertising but have you seen their latest shirts for men?