"Mad Sam" DeStefano: The Mob’s Marquis de Sade (Part Two)

Oct 14, 2009 - by Allan May - 0 Comments

"Mad Sam" DeStefano

"Mad Sam" DeStefano

The story of a man many consider to be the most vicious in Chicago gangster history.

by Allan May

Charles "Chuckie" Crimaldi worked as a "juice collector" for Sam DeStefano during the 1950s and 1960s. He claims that Sam pioneered "organized" loansharking in Chicago, and, because of his success, he had the permission of Anthony Accardo and Sam Giancana to stay independent. Crimaldi claimed DeStefano "could make loans anyplace in the city irrespective of the jurisdiction allocated to the sharks who came later after Sam had greased the skids."

DeStefano’s independent status was confirmed by Roemer who wrote that Sam once told him that he was never a made guy because he could never submit to the discipline of the outfit. Crimaldi reported that one of Sam’s pastimes was to drive along lonely country roads and look for burial grounds for his future victims. "We could bury a dozen guys there and nobody would ever find a smell of ‘em." He would also go to pig farms and stare at the pigs for as long as an hour contemplating how he would feed his victims to the pigs so he could destroy the "evidence."

When DeStefano was upset his face pinched up and his eyes narrowed. His voice became gravelly and he spoke his words very slowly and punctuated his conversation with the filthiest profanity. In addition, DeStefano’s eyes bulged, his lips drew back to reveal an evil smile, and he would begin to drool. He was a cautious man, almost to the point of being eccentric. He once sent a gold watch, engraved with, "To Bob from Sam" as a gift to a politician who owed him several hundred thousand. He explained his reason for sending the watch this way: "That way, if we have to whack him, everybody’ll think we were friends; and I won’t draw no heat from the dead son-of-a-bitch."

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