Q&A with Christian Cipollini, Crime Historian and Author

We’re always thrilled when we can connect with great entrepreneurial minds, especially when they share our obsession with organized crime. Authors, though seriously under-publicized in the entrepreneurial community, are great examples of independent thought leaders who work for themselves. This week kicks off a series of interviews we’re conducting with authors of biographies and historical nonfiction about organized crime. Getting to pick their brains has been a real privilege– we can’t wait to share everything we learn with you.

Christian Cipollini Author of Lucky Luciano Gangland Legends

The Business of Crime sat down with Christian Cipollini, Organized Crime Historian and award winning Author of Lucky Luciano: Mysterious Tales of a Gangland Legend. We were thrilled to connect with Cipollini, and  ask him questions about one of our favorite gangsters; Lucky Luciano.


How did you get into writing about Organized Crime?

[Christian Cipollini] Writing and history had always been interesting to me. However, a penchant for crime history didn’t hit me until I was in my early twenties. I got my love of history from my father, a narcotics cop, who happened to be fascinated by history (mob stuff included of course). I had never really put the two together, and began moonlighting as a freelance author, whereby one thing led to another and I crossed paths with some authors of organized crime books, a couple former law enforcement people, even a former gangster or two… it was then that I decided to revisit the old flame so to speak and write a book.  A long windy road it was.


For those that are new to this…who was Lucky Luciano?

Crime boss Lucky Luciano, a bootlegger during prohibition in New York

Like any public figure or pop culture icon, the infamous American gangsters were dynamic and had multiple sides to their personality. The best way to describe Lucky in a concise manner is to say this – Lucky Luciano was the gangster credited with forming what the world came to know as the ‘Five Families’ of the Mafia.  Now that said, he was not as much a household name as his friend Al Capone. However, Lucky was, for lack of a better term, the number one guy in New York during the 20’s and 30’s.


How did you go about researching for your award winning book, Lucky Luciano: Mysterious Tales of a Gangland Legend?

When my publisher asked if I wanted to contribute a short and sweet book, to a series they were doing called Gangland Mysteries, I said I definitely wanted to do something on Lucky.  I realized there were already dozens of books on the subject, because I had read most of them.  So instead of reinventing the wheel I decided to research in reverse; I started with old press or police photos, read the finer details, then researched further from the tidbits I’d find along the way. I then cross referenced those interesting discoveries, and built individual stand alone chapters that addressed little nuances or lesser known ‘truth is stranger than fiction’ kind of factoids.  For example, Lucky always covered up his arms. Not a big deal, but something I always noticed.  Then I discovered that he had large tattoos on his forearms that he hated later in life and religiously hid from photographers.  From that, I wanted to know exactly what the ink was, and the significance to his story.  A discovery like that then led to myth-busting on how he got his nickname and the permanent scars on his face.  


What stands out about Luciano, as compared to all of the other wise guys you have written about?

First and foremost Lucky Luciano was at the height of his underworld reign during a time when Jewish and Italian gangsters were finally working together. Lucky was part of a larger ensemble of up-and-coming criminal entrepreneurs that pushed this change. From which came the likes of Capone, Lepke Buchalter, Frank Costello, Bugsy Siegel, Meyer Lansky, the Purple Gang’s Burnstein Brothers, and the list goes on.  I don’t care what period of mob history you look at and compare – there is no comparison between the unique and uncanny heyday that existed during his time. Although this was of course short lived, only lasting from 1929 through 1940. I truly believe author Nick Gage characterized Lucky best when he wrote ‘First among equals.’ Indeed, Lucky had a charm, an unmatched entourage of friends and a story that still leaves us a bit in the dark.  


What’s your favorite story about Luciano?

If I had to choose a favorite, I would say my favorite anecdotal tale would be his role in the post-Arnold Rothstein murder drama. I find it so fascinating that all these young mobsters learned from Rothstein, and when their teacher got whacked – they all scurried to reap the rewards of his death.  Lucky, along with drug trafficker George Uffner and Thomas ‘Fatty’ Walsh, a member of the Legs Diamond gang, were the first ones caught looting Rothstein’s offices for documents.  I don’t want to give away more than that but suffice to say the story is completely divulged in my book and further explored in the comic book series.


In the spirit of The Business of Crime, what would you say Luciano could teach aspiring entrepreneurs?

Opportunism is what Lucky and his friends learned, especially from their mentor Arnold Rothstein.  They also understood the laws of supply and demand, and most importantly – to work across dividing lines; they didn’t stick within cultural or ethnic or religious boundaries. They knew everyone could benefit if everyone was onboard.


What can organized crime at large, teach entrepreneurs?

The lessons that can be applied from successful organized crime groups, are that one must truly understand the market or client, and how to streamline the delivery of whatever product/service is creating the profit.  Gangsters had incredible research and development, logistical support, and intraorganizational structure.  They didn’t fly by the seat of their pants and hope for the best; those who did died.


What are you working on next?

I’m currently working on a documentary project with some very esteemed colleagues.  Details will be revealed soon, I promise. Suffice to say – it will be ‘Dope’ :).  Also, the comic book series on Lucky Luciano has been written and turned in for our artist and editor to do their magic.  It’s a four chapter series (chapter one is currently available) and all will be released together in a graphic novel in 2018.  I’m also looking into doing a couple book appearances this fall and winter, and one more super secret television related project that we can talk about in more detail soon.

A huge thank you to Christian Cipollini for doing this interview with us. To say we’re grateful is an understatement. To get access to more of his work, check out his website. Seriously, check it out.

Get Cipollini’s Book on Luciano Now


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The Business of Crime was created by a bunch of crime-obsessed startup junkies. We don’t condone the bad guys, but we do think we can learn something from them. What criminal mastermind’s strategies would you like to hear about next?

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