The First Gangster Kingpin of New York

The Underworld Podcast · Feb 17, 2026 · 1h 3m

Monk Eastman ruled the depraved streets of turn-of-the-century Manhattan with fists and absolutely zero regard for human life, commanding an army of 1,200 thugs who terrorized the Lower East Side. At the height of his power, he was pulling cash from every racket you could think of while rigging elections for Tammany Hall and overseeing street violence so extreme that cops needed reinforcements just to enter his territory. Eastman represented a true transition in the evolution of the underworld, when crime became organized. All that, and he managed to become a war hero too, before the street…