Samuel “Mad Sam” DeStefano Jr. was born on September 13, 1909, in Streator, Illinois, into a traditional Italian-American immigrant family. His parents, Samuel Sr. and Rosalie DeStefano, arrived in the U.S. in 1903. His father worked as a laborer and later in real estate, while his mother remained a homemaker. The family, with seven children, moved around Illinois due to economic pressures—first to Herrin and later to Chicago’s Little Italy after the Herrin Massacre unrest.

Sam's early life was turbulent. By his teenage years, he was already tangled in gang-related trouble. In 1926, at just 17, he was arrested for escaping jail. By 1927, he was convicted of rape alongside fellow gang member Ralph Orlando for the assault of a 17-year-old girl—DeStefano received a three-year sentence.

He joined the Forty-Two Gang in 1930, where he ran with future Outfit boss Sam Giancana. He delved deep into bootlegging, gambling, and robbery. In 1932, he was wounded in a grocery store robbery, and the following year, convicted for bank robbery in Wisconsin—earning him a 40-year sentence, which was later commuted.

During his time in federal prison, he befriended key Chicago Outfit figures like Paul Ricca and Louis Campagna. Upon release, he worked briefly as a garbage dump foreman for the city, concealing his criminal past. However, by the 1950s, his shadow dealings surged once again.

He invested in real estate and politics, using rental income to bribe officials and judges. DeStefano was a manipulator, exploiting his reputation and connections to “fix” criminal cases. Known for unpredictable behavior and outbursts, he balanced his sadistic tendencies with a sharp mind for influence and intimidation.

DeStefano became infamous not just for loan sharking—but for extreme sadism. He was a high-level enforcer and loan shark for the Chicago Outfit. His brutal methods of extracting payments from debtors turned his basement into a torture chamber. He reportedly charged up to 25% weekly interest and preyed on high-risk debtors, intentionally setting them up to default so he could exact his sick sense of punishment.

In one disturbing case, his associate Peter Cappelletti stole $25,000 and fled to Wisconsin. When caught, he was chained to a radiator and tortured for three days, screaming in pain during a public banquet. The torture ended with DeStefano forcing Cappelletti's family to urinate on his burned body. These acts weren't just discipline—they were psychological warfare to keep his world under control through fear.

In November 1963, DeStefano was violently ejected from Leo Foreman's office after an argument. Later, Foreman was lured to DeStefano’s brother’s house and murdered—allegedly with the involvement of future mob stars Tony Spilotro and Chuck Crimaldi. Another known victim, Arthur Adler, was also tortured and killed under similar conditions.

Despite a string of arrests over the years, DeStefano remained a protected asset of the Outfit because he made them money. Outfit leaders Giancana and Tony Accardo even invested in his operations. But his erratic behavior was growing too risky. FBI agents like William Roemer described his bizarre antics—exposing himself during questioning, urinating in FBI coffee, and shouting rants about Satan and politics. He believed he was framed for rape at 17 and once claimed he could have been President if not for that.

DeStefano’s behavior during court trials worsened. He demanded to represent himself, wore pajamas, shouted through bullhorns, and disrupted proceedings. By 1973, Outfit leaders decided he was a liability. On April 14, 1973, he was gunned down with a shotgun—allegedly by Tony Spilotro—outside his garage in Chicago. He died instantly. No one was brought to justice for his killing. He was buried at Queen of Heaven Cemetery in Hillside, Illinois.