George Remus - A lawyer who broke the law and became known as “King of the Bootleggers,” Remus even served as the inspiration for F. Scott Fitzgerald’s character Jay Gatsby. By buying bonded whiskey used for medicinal purposes, and then hiring people to hijack it, Remus made $40 million in less than three years, nearly a billion in today’s currency.
Charles Luciano - Charles was widely credited as the father of modern organized crime, splitting the New York mafia into five families. During Prohibition he teamed up with Arnold “The Brain” Rothstein and other members from “Boardwalk Empire.” By 1925 he was making $4 million per year in profit, and he eventually became so powerful that the Office of Naval Intelligence commuted his prison sentence in exchange for Sicilian mafia contacts during World War II.
Al Capone - The original Scarface, Al Capone is probably the most notorious criminal of the Prohibition era. Most famously, he’s responsible for the St. Valentine’s Day Massacre, in which two of his henchmen pretended to be police officers and murdered seven of his rivals. He probably would’ve gotten away with even more crimes, had it not been for being arested for tax invation.
Dean O'brien - A New York-based Irish gangster, Dean O’Banion was crazy enough to steal from Charles Luciano and other more powerful mafia members. That didn’t work out so well for him, he was murdered at his flower shop after ignoring a “back off” from Al Capone about a powerful mafioso’s gambling debt.
William McCoy - He earned the name “the real McCoy,” because his liquor was never diluted. But since it was so high-quality, McCoy made enemies out of both the U.S. government and other bootleggers. Eventually the Coast Guard caught him on his boat, but only after a machine gun firefight.