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There have been some very good choices proposed so far, obviously. I'd have to go with Al Capone out of the ones I've seen, as the person who caused the most economic AND personal devastation.
Lucky Luciano, Carlo Gambino and Anthony Accardo, probably in that order, would be right up therew with Capone. If you ascribe the acts of their entire empires to them, then the amount of murder and misery they caused would far exceed what a Ted Bundy or any other single person could really do in one lifetime, though the individual acts would be "more evil" in the case of a Bundy or Dahmer. More sadistic at least.
And while those guys were a hero to a very small segment of society, I trust it's still in line with Rule #2.
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