Book Review: Wiseguy

Book: Wiseguy

Watch Goodfellas.

But actually this was an entertaining read, and after having read it Goodfellas is even a better movie in that it’s based in truth. I often don’t read fiction, but this book felt like a fabricated story in the way that truth is stranger than fiction. I haven’t been engrossed in a story like this for awhile.

Organized crime has always been so interesting to me, in that it represents this shadow government and community with its own set of rules and regulations that exists to skirt the rules of the hierarchical and highly-organized society we live in. There’s an odd duality alluded to in the book - the communities and neighborhoods that the wiseguys inhabit are often clean from petty crimes, order is well maintained, and undisturbed by outsiders or troublemakers, however the wiseguys often bleed their earnings from blue-collar workers and middle-class families in the area via gambling, cons, or robberies and use their influence to run up tabs that will inevitably go delinquent or shutter honest businesses that encroach on their own enterprises. The wiseguys see the working class as “already dead”, people who have given up their potential for real freedom in exchange for a mortgage and 40 hours a week on someone else’s clock, however these are the people that become targets for many of the rackets the wiseguys run. They do a pretty good job of convincing you that they’re got the better end of the deal until you finish the book and realize that these convoluted networks of bookmakers, loan sharkers and shooters eventually implode and everyone ends up dead, in jail, or in witness protection program.

But, the ride is entertaining! It’s truly remarkable how much of a hustler every character in this book is. At every second a scheme is being cooked up, a plan is being executed, and it never stops. The wiseguys skill at making money is only matched by their penchant for spending it. This book is mainly a biography of Henry Hill, who along with his (now divorced) wife Karen, tell the story from their perspectives of how they participated in the New York metropolitan-area organized crime community. They described widely-known schemes like the Boston College point-shaving scandal and highly-lucrative robberies like the Lufthansa heist of six million dollars (today $22m). It’s worth a read and was short enough where I finished it mostly reading during my 30-minute commutes back and forth from work in a week.