HBO just released The Penguin, which follows the character from the Batman franchise, who is striving to be a mob boss in Gotham City. The first two episodes have been really good. Collin Farrell, who plays the villainous Oswald ‘Oz’ Cobb, is unrecognizable. He fully embodies the character. While Oz is a fictional mob boss-in-the-making of a fictional crime family. New York has had its fair share of real crime bosses of real crime families over the years. Not to be outdone by Chicago, there are some certified gangsters that operated their criminal enterprises in New York. Here are the 8 most dangerous and infamous.