developing a reputation for viciousness. When Tony was 18, his actions caught the attention of Sam “Mad Sam” DeStefano.
DeStefano was connected to the Outfit and operated a loan-sharking business. He was known to friend and foe as being completely insane. When he dealt with his enemies, his depravity knew no bounds. Mad Sam preferred to use an ice pick on his victims, but wasn’t above slicing, shooting, or incinerating them, depending on his mood. Although he was unstable, the bosses kept him around; he was a good earner. In addition to being an accomplished torturer and killer, Sam had another talent. He could spot street kids who demonstrated the same capacity for brutality that he had. DeStefano liked what he saw in Tony Spilotro and recruited him as an enforcer; Spilotro accepted.
On January 15, 1961, Tony took a break from his normal activities to marry Nancy Stuart. Born in Milwaukee in 1938, she was living in Chicago when they met. According to John L. Smith’s book Of Rats and Men, while the Spilotros were on their honeymoon in Belgium, Tony was thrown out of the country for possession of burglary tools.
Back in Chicago, Tony continued to work as one of Sam’s heavies until 1962, when he got his big break. On May 15, two minor hoodlums, Billy McCarthy and Jimmy Miraglia, committed a fatal offense. They killed a couple of Outfit-connected guys—the Scalvo brothers—without permission, and they did it in a mob-inhabited residential area that the bosses had declared off-limits for murders. The powers-that-be wanted the culprits found and taken care of. The man who accomplished that task was bound to achieve an elevated status within the Outfit. Allegedly, Mad Sam suggested that Tony take a stab at it.
Opportunity had knocked and Tony wasn’t shy about opening the door. In short order, he and his associates picked up McCarthy, but they still needed the name and location of the other condemned man. Their prisoner declined to cooperate, despite a severe beating. Surely, they thought, an ice pick to the scrotum would loosen the stubborn man’s tongue, but it didn’t. Getting frustrated, Tony decided it was time to quit playing nice and really apply some pressure. For McCarthy, it proved to be an eye-opening experience.
Putting McCarthy’s head in a vise, Tony resumed the questioning. Unfortunately for his victim, Spilotro didn’t allow Fifth Amendment privileges during his interrogation sessions. Each time McCarthy refused to respond, Tony turned the handle on the vise, compressing McCarthy’s skull. He finally obtained a breakthrough when one of McCarthy’s eyeballs popped out. This was too much for the tough and loyal McCarthy to bear; he gave up Miraglia. The bodies of both men were later found in the trunk of an abandoned car in what became known as the M&M Murders. After this successful debut, Tony became a made man in the Outfit.
In 1963, Mad Sam got into a dispute with Leo Foreman, a real estate broker and one of his collectors. Not long after, Spilotro and an associate named Chuck Grimaldi reportedly lured Foreman to the home of Mario DeStefano, Sam’s brother, in Cicero. The two beat Foreman, then dragged him into the cellar, where Mad Sam was waiting. Skipping an exchange of pleasantries, Sam got right down to business. He took a hammer to Foreman’s knees, head, groin, and ribs. Next came twenty ice-pick thrusts, followed by a bullet to the head. The realtor’s battered body was later found in the trunk of an abandoned car.
In 1964, with the heat mounting over the growing number of unsolved homicides in Chicago, the Spilotros spent some time in Miami. They had many friends and acquaintances there, including Frank Rosenthal. In 1966, they adopted their only child, an infant son, Vincent.
As the 1960s came to an end and the ’70s began, the Chicago bosses initiated a cash-skimming operation involving the Las Vegas casinos under their control. They covered themselves by installing a front