95 books like Wise Guy

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.

The Valachi Papers, a 1968 book written by Peter Maas, is the life story of Joe Valachi, a former member of the Genovese crime family, who testified in 1963 before a Senate committee, revealing until-then confidential information about the American mafia. The book was made into a film in 1972, starring Charles Bronson as Valachi.

Maas describes in vivid detail Joe Valachi’s initiation into and rise within a mafia family, frequently relying on Valachi’s own gutsy descriptions. Although it is a biography the book has the verve and pace of a thrilling work of fiction. In many ways better than even a well-written novel, The Valachi Papers is an edge-of-your-seat reading experience.

Chicago is where I grew up watching the fascinating interplay between the so-called forces of law and order battle the criminal element. It wasn’t much of a battle unless the law-and-order guys and the crooks found themselves reaching for the same loot. Mike Royko’s book describes very well the interplay. On a personal note, I once worked for one of the Illinois governors who ran as a reform candidate. He ended up going to jail on a fraud scheme.

Elmore Leonard knew the vagaries of the movie business back to front, and he serves them up on a platter of delicious satire in this story about an East Coast loan shark, Chili Palmer, who comes to Los Angeles chasing a deadbeat debtor and winds up in his own fractured fairy tale version of the Hollywood dream.

Chili’s an endearing character, street smart with a unique blend of humility and self-confidence. When his collection job throws him into company with a group of movie people, he sees them and their milieu with clear-eyed objectivity.

Talking to an underworld associate, he says, “The movie business, you can do anything you want because there’s nobody in charge.” Leonard’s mastery of dialogue and character, along with his wit and sly affection for the industry he’s skewering combine to make this book a complete delight. 

The Godfather portrays the classic conflict between loyalty to a family and the desire to escape it for a better life.

Michael is a former marine who wants to stay out of the crime business and have a normal relationship with his girlfriend. But family loyalty trumps principle when his father is attacked, his brother killed, and his wife in Italy murdered. It wonderfully shows his slow fall to unfeeling coldness as the price for avenging his family and protecting their empire.

The book has great and colorful characters, especially Don Corleone. He is fascinating because he offsets his violence with principle and a love for his family.

Dashiell Hammett, more than any other author, created the hardboiled anti-hero. He’s also a damn fine prose writer. I re-read one of his books every year because of this, hoping perhaps to absorb his spare, elegant style. Each sentence is brutally trimmed of any excess and yet resonates with layered meaning. 

Dashiell Hammett himself was a broken hero. He fought in two World Wars for his country and yet was sent to jail by the committee for un-American activities for refusing to name names. He was a communist, who yet, as a young man, worked for the fascist, union-busting Pinkertons.

A complex, troubled individual who created dark and cynical worlds, and none more cynical than that of The Maltese Falcon. Here, we have a femme fatale, a hardboiled detective, gangsters, and conmen, all vying for the titular prize. It is a mean-streets masterpiece. 

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.      

This work came out in the Roaring Twenties, but the gangsters of that decade had nothing on the 19th-century outfits like the Dead Rabbits and the Gas House Gang.

When the dive bars have names like the Tub of Blood and they’re kept in business by the likes of Razor Riley, One-Lung Curran, and Stumpy Malarkey, you can’t go wrong. But to me the most compelling part was Asbury’s account of New York’s horrendous Civil War draft riots.

The Molly Maguires of Pennsylvania were born in opposition to that same draft, after a Protestant Republican allied with the coal industry used conscription to try to rid the coal fields of Irish Catholic Democrats and mine labor activists before a crucial election. 

In this case, I saw the film before I read the book, and if I’m going to call myself an honest man, I’d have to say I enjoyed the film more than the book.

Still, the book struck me as a great read because it embraced and portrayed the extraordinary amount of tension an undercover agent deals with 24/7. I mean, when you’re trying to make an arrest undercover, you’re two people at the same time, but you’d better not mess up and let anyone know you are or it’s game over—and very probably, bang-bang, pal, you’re history.

Add to that being undercover for the FBI and you’re guaranteed a high-stakes conundrum. Which is to say, after reading this book, how could I not have had my book’s character working undercover for what he and his partner Jonas refer to as “the Bureau”?