Chronicled and mythologized in scholarly and popular history books, novels, films, and plays, New York’s Lower East Side in the late 19th and early 20th centuries was overcrowded, and teeming with peddlers, tailors, sweatshops, and barely livable tenement houses. By 1910, an estimated 540,000 Jews resided within the neighborhood’s 1.5 square miles. The poverty, hardships, and daily struggle to survive drove some Jewish immigrants to seek other ways to make a living, even get rich. Hence, the Lower East Side also had a vast collection of crooks, pimps, prostitutes, thieves, pickpockets, gangsters, fraudsters, forgers, arsonists, and hoodlums. Offered here and in future articles are portraits of some of these nefarious characters, who also left their mark on the Lower East Side’s historical legacy.