Sam DeStefano was born in 1909 in southern Illinois. His family moved to Chicago when he was a teenager, and he started a life of crime. His first act was to rape a female in 1927 at the age of 18 and he was convicted. Soon after, he was convicted for assault with a deadly weapon, extortion, bank robbery, and counterfeiting postage stamps.
Sam soon joined the 42 Gang, which was led by Sam Giancana. He fit right in with the group of thugs, getting involved in their gambling and bootlegging operations. By the 1960s, Sam was a big fish in the gang, having a hand in the group's drug trafficking and loan sharking. His brother, Mario, had joined him in the same gang and they were among the first in Chicago to run loan sharking operations where violence was used to force payments out of debtors.
Unfortunately, Sam was too mentally unstable to serve as a boss, or even under boss, but he still gained much respect within the gang. They used him as a loan collector and hitman without any regrets. His basement was a literal torture chamber, soundproofed and filled with his torture devices. DeStefano's tool of choice in extracting information or payments, or simply having some "fun" was the icepick. He used to stab his victim in the throat, testicles, and torso, with great effect.
A local restaurant owner, Artie Adler, was late on debt payments so DeStefano dragged him into his basement after a week. Unfortunately, stabbing his ice pick into his testicles caused Adler to have a heart attack and die, so DeStefano couldn't collect his debt. He dumped the body in the sewer, where it was preserved by the winter until the spring and found by the sanitation department.
One of his most notorious victims was Peter Cappelletti, who tried to keep $25,000 of Sam's money. Sam caught him and brought him to Sam's brother's restaurant, chaining him to a boiling hot radiator. For three days the man was tortured by various methods, likely enduring unspeakable horrors. On the third day his family was invited to the restaurant for a dinner in his honor. During the meal, Cappelletti was thrown in front of his family bare naked and severely burned, where Sam proceeded to urinate on him. Sam was paid back promptly afterward.
Even when Sam's boss, Giancana, ordered that Sam perform a hit on his younger brother Michael DeStefano, Sam had no problem and did it. Sam was always angry about his brother being a drug addict and took great care to remove all traces of the drugs from his system before dumping the body. When questioned about the hit by police, Sam only laughed uncontrollably.
One time in 1963, Sam got in an argument with a real estate agent and loan collector named Leo Foreman. Sam was thrown out of his office and vowed to get revenge. Foreman was called to the home of Sam's brother Mario, told that Sam wanted to meet him and make up. When Foreman got there, he was taken in the basement where he was restrained by Chucki Crimaldi, Tony Spilotro, and Mario DeStefano. The three beat Foreman's knees, crotch, head, and ribs with a hammer while waiting for Sam. Later, Sam entered the basement in his pajamas, laughing gleefully at Foreman in his injured state. After some fun with the ice pick, reportedly stabbing him 20 times, Same elected to shoot him in the buttocks, while Foreman begged for his life. Finally, the crew finished him off with a butcher knife and cut chunks of flesh from his arms after he was dead.
When the FBI got Crimaldi to testify against the other 3 involved in the Foreman murder, things turned bad for Sam. The last thing the crew wanted was a highly publicized trial, because it would make it hard to bribe the judge. However, Sam was well known for attracting attention to his trials. Oftentimes he would demand to represent himself and speak through a bullhorn during the trial. He often showed up in pajamas, on stretchers, and gave long rants, accusing the prosecution of collaborating with Joseph Stalin.
Therefore, the crew decided to take care of Sam. They told Sam that they had found Crimaldi's safe house and when the day of the hit rolled around, they met Sam at his house. When Sam was in his driveway, Spilotro shot Sam twice with a shotgun, killing him. Thus, Sam "Mad Sam" DeStefano died on April 14, 1973. Mario was still convicted for the Foreman murder, but Spilotro was acquitted.