IT’S MY GANGSTER BOOK,” Beantown novelist Dennis Lehane told The Boston Globe of his new book, Live by Night. “Since I was a little kid, it was my dream to write a gangster book, and this is it.” And why not? Lehane has set his fiction everywhere from a 1950s mental asylum in the wonderfully creepy Shutter Island to modern-day ruins like the slums in Mystic River. Prohibition-era America seems as excellent a choice as any for his variety of dark tale. Unfortunately, Live by Night is not a prickly, tight Lehanean crime-thriller. Lehane is usually notable for his tautly constructed plots; pull at the threads of any character or deftly positioned detail and a devilish scheme unfolds. But Live by Night is more a sweeping gangster epic than a mob mystery, and it’s hard to believe the whole arc of protagonist Joe Coughlin’s life of crime takes place in just a decade. There’s never a dull moment for Joe, but never a fun, twisty plot to unravel, either.
We first meet nineteen-year-old Joe in 1920s Boston—natch—where he is a fledging criminal who robs a poker game for a local crime boss and is besotted with an honest-to-god moll named Emma. Joe insists he is an “outlaw,” not a “gangster”—though it is clear from the start that this is a distinction without a difference. Emma is, unsurprisingly, a rival crime boss’s gal; she says arch things like, “And what will the gentleman be having with his robbery this morning?” and generally comes across as an icy-hearted bitch: “Nothing about her invited approach. She seemed locked behind her own cold and beautiful face.” Obviously Joe falls madly in love, “sniffing around Emma Gould like a starving dog following the scent of a cook fire,” because “whatever [she] had, he wanted it for breakfast, lunch, dinner, and snacks.” You know the type.
Otherwise, Joe is surrounded by hard, apparently rock-like men—“Dockworkers by the look of them, ship masts for shoulders, rocks for hands”; “Loomis … wiped his own hand with a silk handkerchief, his face a rock.” They all live in a black-market, gangland underworld—hospitable to psychopaths. But Emma is quick to defend such men: “No one’s good, no one’s bad. Everyone’s just trying to make their way. … Stop fucking judging everyone.” Does the lady protest too much? Ignoring this wee red flag, Joe is charmed by Emma’s nuance and sets out to cuckold her shady patron, run off with her, and become an outlaw elsewhere. After, that is, one last job. And when that goes reliably off the rails, making Joe the most wanted man in Boston, our hero is left with a choice: flee and likely escape, or stick to the highly rational plan of meeting Emma at the opening of the newest, biggest, richest hotel in all of Boston (with the police on his trail and the entirety of the mob and the press corps at the launch event).
Here’s the thing: there is something kind of wonderful about an outlaw without a cell phone. When two young lovers make a getaway plan in the 1920s, there is no texting to say, Hey, maybe meet me in a dark alley instead of the red-carpet. There is no convenient way to bail on someone at the last minute. There is only a pure, blind, and wild faith in The Plan. Joe understands this deeply: the choice is not really about escaping or not escaping; it is about losing love or going for it. And so, as terrible and high-risk as it is, Joe takes his shot.
He ends up in coma, thanks to both gangster and police brutality (the latter under the rueful gaze of his—gasp!—well-to-do police captain father), and then jail. In other words, despite the promise of a high-stakes caper, the episode ends with a whimper, not with a bang. Meanwhile Emma is informed that he is dead. But Joe intuits that she is alive, and for the next three hundred or so pages, so does the reader. Though she is almost never mentioned again, one cannot help but know that the entire rest of the novel is a prelude to the resurrection of the disagreeable Emma Gould. After 150 pages and a life-saving and soul-draining jailhouse alliance with the mafioso Maso Pescatore, Joe leaves prison and Boston to run rum for Maso in Tampa for the next 250 pages. Chowder noir, meet sugar noir.
Tampa turns out to be the setting for the best scenes in the novel, including its one great heist. But for the most part Joe hems and haws about his moral place in the world: one moment, he is a cocksure, outlaw businessman; the next, he is a brooding gangster, totally cognizant of all the nastier consequences of his trade (prostitution, drugs, abuse, death). Joe rarely kills anyone himself, though he is more than happy to let his men kill on his behalf—usually when there’s a direct threat from, say, a bootlegging Klansman. Joe has carefully constructed his moral equivalence, you see. After shooting a man who was on the brink of raping and killing his new girlfriend Graciela, Joe serves up this bit of wisdom:
“Do you think I feel bad?” he asked.
“I can’t tell.”
“I don’t,” he said.
“I don’t feel good.”
“You shouldn’t feel that, either.”
“But I don’t feel bad.”
In case we missed it, Joe has a near-verbatim exchange eight pages later, and this repetition is symptomatic of the book’s limitations. Joe’s inner turmoil doesn’t manifest much soul-searching beyond the annoying “outlaw” vs. “gangster” internal debate. “Because the business was illegal, it was, by necessity, dirty.” Got that? Still with me? “And dirty business attracted dirty people.” It is as though Lehane is attempting to imbue Joe with depth by making him seem a little—but not too—conflicted. (Paging Dr. Melfi!) Problem is, Joe’s occasional navel-gazing is nothing compared with, say, the wrenching complexity of Helene McCready in Lehane’s Gone, Baby, Gone. We are told Joe struggles with his place in the world in matter-of-fact exchanges, but we never see it play out. Scene after scene, Joe is nothing more than a charming bad boy bent on excitement, rather than a dangerous criminal with designs on an empire.
As though mirroring the paradoxes of Joe’s consciousness, Lehane gets a bit sloppy late in the novel—and it’s in this sloppiness that the book really falls apart. It is as though Lehane had lost interest in his own book. We have clever Joe, preparing for the impending transition, the repeal of the Eighteenth Amendment: “The first morning alcohol became legal again, they could flip a switch and their operation would arise, gleaming, into the bright new day.” Yet, when that day comes, “Joe had known it could never last, but he still hadn’t been prepared somehow.” Then Joe frets over “starting to live by day, where the swells lived” during a quiet moment, despite a scene just pages earlier in which his men violently gun down a man on his order. Just like the swells!
By the end, Joe finally starts to kind of, sort of get that only killing the really hateful dudes and throwing a bunch of philanthropy at the city of Tampa, doesn’t actually make him a good guy. When the ruthless abuse of women by thugs hits a bit too close to home, Joe knows: “We’re not outlaws. We’re gangsters.” And he goes straight. This is clearly meant to be revelatory, but since this dichotomy has rung false from the jump and since alcohol is legal again anyway, it is not exactly a weighty moment.
And though that certainly should be the end of the novel, the reader is treated to a weird sojourn into Cuba, obviously designed to create an emotional climax that Lehane, in hundreds of pages, has not earned. (And it is nothing if not didactic: “Arcenas … was more the hope of a village than an actual one.” But wait: “Habana … wasn’t simply a place; it was the dream of a place.”) Lehane has done far better. But don’t feel too bad about his failure here: Leonardo DiCaprio’s production company has already bought the movie rights to Live by Night. That’s good. It’s more a movie of a book than an actual novel of one.