While Frank made sure to stay independent of the Outfit, his pal Tony Spilotro was determined to become part of it. He worked as a thief for Outfit-connected crews, and began to develop his reputation as an enforcer when he went to work for a mob associate named Sam DeStefano.
DeStefano, known as “Mad Sam,” was connected to the Outfit and operated a loansharking 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 because he was a good earner. In addition to being an accomplished torturer and killer, Sam reputedly had another talent. He could spot young up-and-comers who had the same capacity for brutality that he had. DeStefano apparently liked what he saw in Tony Spilotro and recruited him to help collect money from delinquent borrowers and assist in other enforcement matters. In that capacity, Tony was allegedly involved in the 1961 murder of a man named William “Action” Jackson.
Jackson was part of Mad Sam’s loansharking operation and apparently became greedy. Sam thought Jackson was skimming money and had to be made an example of. It is believed that Spilotro and tough guy Chuckie Grimaldi, who later turned government witness, were part of the team Sam assigned to the task. According to sources familiar with the case, Jackson was taken prisoner by DeStefano’s men and tortured for two days.
Jackson, who weighed over 300 pounds, was stripped naked and hung on a meat hook. He was beaten, stabbed with ice picks, strips of his skin were peeled off with a razor, and a blow-torch was used on his genitals. The inquisition ended when Jackson’s heart finally gave out. Presumably, the grisly discovery of his mutilated body sent a clear message to any one considering stealing from Mad Sam.
Frank first met Sam DeStefano when he and Tony were in the North Avenue Steak House. Tony was working for Sam and was tight with Sam’s brother Mario. They were sitting at the bar when Sam came over and started talking to Tony. Sam must have been drunk, because he was ranting and raving about future Outfit underboss Jackie Cerone — who was later convicted for skimming money from Las Vegas casinos — and picking on everybody in the place. Frank found Sam to be an obnoxious blowhard and told Tony they had to leave because he couldn’t stand being around him.
Tony apparently didn’t find Mad Sam as offensive as Frank did. He continued to work for him, but took a break in early 1961 to marry Nancy Stuart. The Milwaukee-born Nancy was living in Chicago when they met.
In 1962, Tony allegedly participated in a pair of murders that propelled him to the status of made man in the Outfit. Those killings involved Frank Cullotta and will be addressed in detail later on.
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 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.
So, by the early 1960s, Tony Spilotro — only in his mid-20s — had risen from school bully to a made man in the powerful Chicago Outfit. His reputation as a ruthless enforcer was in place, and some of his best years were still ahead.