The most arresting gangster books

Fitzgerald himself saw the book as a struggle between rich and poor. Bootlegging functions as a backdrop to the corruption of America and its aspiring classes. The narrator, Nick Carraway, escapes the attention of most readers who think the book is about Gatsby, when in fact it is about Nick, who at the outset disapproves of Gatsby and concludes by praising him. I particularly like the irony that Nick and readers of the novel think Gatsby foolish for thinking that you can repeat the past; but in fact, the book proves that you can repeat it. Nick relates his story two years after the events occurred; Tom Buchanan is still reliving his football glories from college; and. most importantly, Gatsby and Daisy resume an affair that began shortly before he went off to war.

Billy Bathgate employs a favorite device of E.L. Doctorow: placing a fictional character in the midst of factual ones. Billy goes to work for Dutch Schultz and, in memorable prose, charts the downfall of Dutch and raises the compelling question of whether Billy betrays Dutch. The epic catalogue that ends the novel is worth every reader's attention for its artistry. At times, I find the writing in this novel almost lyrical. If readers are like me, they want the prose to sing. This book is rife with arias.

The Godfather is a favorite film of American audiences, but the book, unlike the film, raises serious questions about the integration of Italians into the American mainstream. A society within a society, the Italians embrace the gangster life initially as a way of survival and subsequently as a way of gaining wealth. From the first paragraph, Puzo calls attention to the Italians as outsiders, which makes the Don's question all the more important: Why didn't you come to me first (for help)? I find the novel rather philosophical, in an accessible way, when Michael argues that people behave not from principle but from personal motives. His argument is both passionate and moving.

This book relates the story of Legs Diamond, who began as a street urchin working for Arnold Rothstein and then became a major figure among gangsters. Kennedy treats Legs as a mythic figure, larger than life, who was in the 1930s as much of the story as the Great Depression. The narrator, Gorman Marcus, functions as a kind of Nick Carraway, telling the story from an observer point of view. I admire Kennedy's ability to make Legs a likable figure, notwithstanding the corruption and the murderous instincts of the man. If readers want an intelligent gangster story, this is the book for them.

Tough Jews is a short history of Jewish-American gangsters and their Italian colleagues with whom they made common cause. It is here for the first time that we understand why Arnold Rothstein was the most important gangster in America.  Having introduced "organized" into organized crime, he promised underworld figures the help of the famous attorney William Fallon if they landed in trouble and agreed to look after their families if they got sent up the Hudson (to Sing Sing). I am struck by the fact that Cohen makes his history personal, by means of his own contacts with the people who know the inside story of how the Jewish gangsters thrived—or didn't. He sits down with them; he eats with them; and he gets them to remember how it once was in the days of Dutch Schultz, Legs Diamond, and Arnold Rothstein.