9. Manny Horvitz
Never get into business with a butcher, especially one adept with a knife. Philadelphia gangster Manny Horvitz was regularly seen wearing a bloodied apron and fondling his meat blades, which only added to his menacing cadence. But even when his weapon of choice was a gun, the outcome was no less horrifying. At the end of Season Two, Manny ruthlessly shot and killed Jimmy's wife, Angela Darmody, and her lover Louise in cold blood merely because they were in the wrong place at the wrong time. "Your husband did this to you," Manny sneers at a helpless Angela before taking her life. Early in Season Three, however, Angela's death was avenged by her friend Richard Harrow, who shot Manny squarely in the eye on New Year's Day, 1923.