The best books that give the outlaws a say

Pirates make great bad guys, plundering their way through history as seaborne barbarians. The Republic of Pirates makes you look at infamous figures like Edward "Blackbeard" Teach, "Black Sam" Bellamy, and Charles Vane in new ways. Those pirate ships were incubators for democracy, marked by equal rights for all races and leadership elections. Compared to the slave-trading empires that the pirates attacked, the pirate ships were bastions of freedom before (and in some ways better) the American Revolution canonized them in the Declaration of Independence. It just goes to show, you’re only an outlaw or a rebel if you’re caught or defeated.  

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.      

In the 19th century, the Bowery and the Five Points neighborhoods of Lower Manhattan were twisted warrens of saloons, brothels, opium dens, and gambling houses, home to gangs of criminals like the Plug Uglies, Bowery Boys, and Dead Rabbits. It’s a complex ecosystem but when it comes to lowlifes Herbert Asbury is an extraordinary naturalist. His book covers a bewildering number of hoodlums, scams, bawdyhouses, convictions, and murders, and the sum total makes a larger impression than any one part. (Although highlights include the depictions of the crooked Tammany Hall political leadership and a chilling account of the New York City draft riots of 1863.) When the book was originally published in 1927, the Prohibition-empowered Italian Mafia pretty much ran Lower Manhattan’s crime and the era of these legendary gangs was already a fading memory. Asbury’s tome captured an entire criminal universe that was packed into a few square blocks, now frozen in time for us to examine.  

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.      

Henry Hill’s story is well-captured in the movie Goodfellas, but the movie departs from the true story in crucial ways. Beyond this book’s utility as an extension (and fact check) of the film, Wise Guy stands on its own as one of the best American chronicles of the life of a modern outlaw. It’s steeped in practitioner-level details on organized crime in the 1970s, from street-level scams to the record-breaking Luftansa heist of 1978. The strength of the story is the rise and fall of the disreputable Hill, the lifetime mobster turned informant. The heart of his saga is a morality play – no one in their right mind can read this and want to jump into a career in organized crime.