100 books like The Gangs of New York

This was one of the first books I read as part of my research about pirates during the Golden Age of Piracy.

It has a bibliography and footnotes, but it reads more like an adventure novel. You can read it for research, entertainment, or both. Everything in this book really happened. It’s one of the best starting points for someone to learn about piracy in the early 1700s.

Nothing beats an author willing to immerse himself into an outlaw world to get their perspective – until that world starts to literally beat the writer. Hunter Thompson’s first book is more of a journalistic work, examining the infamous biker gang from the inside than what would follow (Fear & Loathing in Las Vegas and so on.) He is very much part of the action at riotous parties, on bar stools, and alongside at motorcycle runs, but his first-person narration is an effective tool for revealing the Hell's Angels as independent people and as a fraternal organization. The writer and his subjects willingly project their images of unrepentant criminals. But when Thompson is on the receiving end of a gang beatdown, it’s a reminder that the line between outlaw and citizen can be hazy, and you might not know you’ve crossed it until blood’s being spilled.      

Danny Greene is a bad role model but a great protagonist. A former US Marine and union boss convicted in federal court of embezzling, he transitioned into organized crime by doing enforcement work for the Cleveland Mafia. However, he soon branches out on his own in the most brazen ways possible, incurring the wrath of his former associates. Murders, an extended bombing campaign and Greene’s work supplying intel to federal agents all culminate in a conclusion that has real consequences – the downfall of La Cosa Nostra in Cleaveland in 1977. It’s hard not to empathize with the crazy-brave Greene, standing shirtless in plain sight in front of his headquarters as the Mafia plots his death. When a criminal is this kind of character, it’s easy for a reader to lay polite society aside and immerse inside that world, enough so to root for a bad guy.      

I loved this book because it put me right there in the life, with all the violence, plots, girlfriends, and craziness. Author Nicholas Pileggi is a master of the craft. He drew me in immediately by capturing the voice of Henry Hill; mob associate turned informant.

I learned things I didn’t know–and some things I didn’t want to know–about the life. When I saw Goodfellas, the Martin Scorsese movie based on the book, it all rang true again.

This is a gritty, riveting look at the Irish Mob on New York’s West Side in the 1980s.

The author grabs you by the arm and propels you at breakneck speed through the blood-stained streets and barrooms of Hell’s Kitchen. Along the way, he introduces the reader to a crew of crazy characters that you definitely wouldn’t want to meet in a dark alley.

The parts about the Irish mob’s connections to the Mafia were especially enlightening. It’s a very atmospheric look at a part of the city where I worked as a newspaperman in the decade the book came out (and downed pints in some of those bars.)

This forgotten masterpiece of a memoir by a prosecutor who took on corruption on the docks of New York came out in 1956, two years after that Marlon Brando classic, On the Waterfront.

William Keating, a hard-nosed, relentless, and incorruptible crime-fighter, gives an inside look at the reign of terror imposed on honest, hard-working longshoremen by the gangsters who ran their union.

Keating was by no means anti-labor – at the start of Chapter 2, he mentions that his father was an official in the United Mine Workers, and that his great-grandfather was a prominent Molly Maguire in the hard-coal fields of Pennsylvania. That earned points with me – I come from a long line of Irish American coal miners in that area. 

Murder, gunrunning, drug-dealing, extortion, informers – it’s all there, but it pales in comparison to the tale of how Whitey Bulger, Boston’s pre-eminent Irish gangster, managed to turn an F.B.I. agent from his old neighborhood into a willing ally in the city’s mob wars.

To me, the most fascinating part was the bang-up job that the authors, two Boston Globe reporters, do in chronicling how the Massachusetts State Police were long frustrated in bringing the crime lord to justice because he was being protected from on high.

I loved this one, because I have a buddy who is a retired Massachusetts state cop, and we’d talk about Whitey Bulger on summer vacations, sitting on the beach.

In 1993, a gang of thieves got away with $7 million in a heist at a Brink’s depot in Rochester, N.Y – and the bulk of it has never been recovered.

The cast of characters includes a former I.R.A. man who’d done prison time in Northern Ireland, an activist priest, an ex-cop who became a suspect, and a charismatic prizefighter whose dismembered body was found in Lake Ontario.

I liked this because at the center of it all is the lingering question of whether the missing money ended up with the Irish Republican Army. 

In 2009, after years of writing Easy Rawlins novels set in a past Los Angeles, Walter Mosley began a new series set in contemporary New York. African-American Leonid McGill is a hard PI, with a complex seamy past who aspires to become a better person, despite the pressures of being a husband and family man caught in a near-loveless marriage. The New York in which McGill lives and struggles is the upscale but still gritty descendant of earlier versions of the city in the Mike Hammer novels of Mickey Spillane and the Matthew Scudder novels of Buffalo-born Lawrence Block. It is a land of wealth and culture but danger and deceit.

I’ll bookend this list with what I consider to be a sort of updated take on Larry Clark’s Tulsa. Serbian photog Boogie has published similarly solemn collections on Moscow and war-torn Belgrade. With It’s All Good, he arrived in New York’s most violent neighborhoods circa 2010 to document the hard and often tragic lives of urban youth. Gangsters pointing their guns into the lens or jabbing their veins with needles might not make the most appealing coffee table book, but the photos themselves are even more sublime than anything shot by Clark, making this book a worthy successor.