Gangsterland: A Tour Through the Dark Heart of Jazz-Age New York City offers a handshake with the era’s most powerful crime bosses, but David Pietrusza suggests you count your fingers afterward. In his new book, he guides readers in and out of Manhattan speakeasies, bordellos, theaters and hotels where infamous bad guys reigned and heinous crimes were committed. At the center of this mobster map is netherworld kingpin, Arnold Rothstein. Nicknamed “The Brain,” Rothstein made the Roaring Twenties roar, writes Pietrusza. The author and historian shares how he immersed himself in this fascinating world.

Guests checking into a luxury suite at the Park Central Hotel on 7^th Avenue today might not realize it was a hotbed for illegal gambling and gangster activity a century earlier. What kind of on-site research did you do for this book in the buildings that still exist? 

A lot of Jazz Age buildings in the West 40s and 50s are now replaced by steel-and-glass office buildings. But a number of sites from my book survive. The Park Central Hotel, the site of not only Arnold Rothstein's 1928 murder but also Albert Anastasia's 1957 slaying, survives. I visited that hotel a few years back and even helped tape a public television episode regarding Rothstein's slaying, trundling down the same stairwell he did as he commenced his blood-drenched one-way trip to the morgue. Most of the surviving private residences I cited are, of course, off limits to researchers. And I'm not sure what one might find there of significance. I was, however, still able to visit some sites such as that fabled old speakeasy, The 21 Club, and its very elaborate hidden Prohibition-era wine cellar. Unfortunately, it closed in late 2020.

The idea for Gangsterland came from a New York City walking tour you led about Rothstein’s Times Square locales of high crimes and misdemeanors. Was there one story that would reliably make your audience gasp? 

Gangsterland's bloody pages are chock full of murders. But the most startling involves the July 1912 slaying of gambler Herman "Beansie" Rosenthal. Rosenthal, like Rothstein, was protected by Tammany boss Big Tim Sullivan and operated a West 40s gambling house. Rosenthal, angry over the amount of graft he had to surrender to a crooked police lieutenant, Charles Becker, squawked to the old New York World — all very publicly and very foolishly. Becker contacted some underworld pals and, before you knew it, Rosenthal was rubbed out in the first drive-by murder in American history, right off Times Square, in front of West 43rd Street's old Metropole Hotel. Becker was encouraged in this by Big Tim himself  —  and the kicker here is that Sullivan was the author of New York's Sullivan Act, the first major gun control statute in U.S. history! Becker became the first police officer to die in the electric chair. 

Rothstein and other men ruled the seedy underbelly of the city. But there were a few women, like bordello operator and racketeer Vivian Gordon, who were able to wield some power on the streets of Gangsterland. Can you talk a little about how women fit into this world? 

Both Vivian Gordon and Buda Godman (mistress of New York Giants owner Charles Stoneham) operated as badger game operators (i.e. sexual blackmailers). Godman also dabbled in jewel robbery. Gordon got rubbed out in The Bronx in February 1931.

Prostitution was more commonplace back then; Manhattan's most notable madam being Polly Adler who later dared to write an autobiography revealing a fair amount of dirty laundry in the bargain. She operated multiple brothels.

Fannie Brice (wife of Arnold Rothstein associate Nicky Arnstein and later of speakeasy operator Billy Rose) and Lillian Lorraine rated as major Broadway stars. Lorraine, at one point in her career, served as a "steerer" to Arnold Rothstein's West 46th Street gambling house.

You write that Rothstein was the mastermind of the modern American drug trade. What remnants of this sordid place and time do you see in our society today?

Well, we've got a larger drug trade today than back in Arnold Rothstein's day. But he was certainly the creator of modern drug trafficking, investing millions in pre-inflation dollars in importing heroin, etc. from both Europe and the Far East. Rothstein was not just involved in the drug trade; it was merely the final step in his crime-ridden path. But narcotics were something newer and bolder and, as far as he was concerned, more permanent. Today, we see drug traffickers also connected to other illegal activities, such as human trafficking. We also see how Prohibition gave way to repeal, and how today, marijuana has joined alcohol in crossing the threshold into government-sanctioned legality.

The names of these guys! Dapper Don Collins, Sammy the Hook, and of course Albany-famed Legs Diamond. Do you have a favorite? 

The 1920s weren't just The Jazz Age and the Golden Age of Sports, they were evidently also the golden age of nicknames.

Arnold Rothstein, being the centerpiece of Gangsterland, appropriately boasts the largest number of nicknames: "The Big Bankroll," "The Brain," "The Big Brain," "The Man Uptown," and "The Man to See."

But I'd say my three favorites from Gangsterland involve Legs Diamond's secondary sobriquet, "The Human Clay Pigeon" (Legs survived a ton of assassination attempts before his fatal one in Albany), Ciro "The Artichoke King" Terranova (he controlled the city’s produce trade), and Ownie "The Killer" Madden (don’t mess with him!).