Sam “Mad Sam” DeStefano will become the Chicago Outfit’s most notorious loan shark and sociopathic killer. No less an authority than FBI agent and mob fighter, William F. Roemer, Jr., considered DeStefano to be the worst torture-murderer in the history of the United States. Samuel DeStefano, Jr. was born on September 13, 1909 in Streator, Illinois. Samuel DeStefano, Sr. was a laborer and later had a produce market. He and his wife Rosalie DeStefano (née Brasco), immigrated from Italy to the United States in 1903. Destefano, Sr., would rise in status and later a real estate salesman. Mad Sam’s father was not an Outfit member and would die of natural causes, in 1942, at age 77. His mother, Rosalie, was a housewife, who throughout her life was supported by the contributions of her children. She died in October 1960. In all, the DeStefanos had six children, four sons and two daughters. In the early 1900s the DeStefano family moved to Herrin, Illinois, where Sam Sr. worked in the local coal mine. After the labor-related turmoil surrounding the Herrin Massacre,(this was a coal mine strike and union members killed several strikebreakers), the DeStefano family moved north to Chicago’s Little Italy. By the age of 17, on September 12, 1926, Sam Jr. was arrested in Chicago as a fugitive for breaking out of jail. He became involved in gang activity and in July, 1927, several hundred Westside gang members showed up threatening violence against a police sergeant for arresting DeStefano and shooting DeStefano’s associate Harry Casgrovi. In November 1927, Chicago police arrested DeStefano and another gang member Ralph Orlando on charges of kidnapping and the rape of a 17-year-old girl. DeStefano was found guilty of rape but was sentenced to only three years because the police arrived before DeStefano had actually raped the girl. In 1930, DeStefano joined the infamous Forty-Two Gang. This gang became a conduit for Sam and fellow gang members like future Outfit boss, Salvatore “Sam” Giancana to move up into Al Capone’s Chicago Outfit. The Outfit would hire gang members as beer runners or truck drivers and help fence their booty from various robberies and burglaries. Sam “Momo” Giancana had built a reputation as a skilled wheel man and became the first Forty-Two member to join the Outfit. He eventually became a protégé of Tony “Joe Batters” Accardo and Paul “The Waiter” Ricca. With his induction, Giancana was able to eventually bring a number of his fellow gang members like Mad Sam into the Outfit. Many former Forty-Two members like Joey Aiuppa would go on to rule the Outfit well into the 1970s. Al Capone’s bootlegging and gambling operations brought Mad Sam into the Outfit. In 1932, a policeman shot and wounded him during a grocery store robbery. DeStefano appeared at a hospital on Chicago’s West Side with bullet wounds, which he refused to explain. In 1933, DeStefano got his first taste of the big time when he was was convicted of a Wisconsin bank robbery. The judge sentenced him to 40 years in prison. But after 11 years, the Wisconsin Governor released in him in December 1944. DeStefano got a job in a printing plant but he was soon returning to prison for possessing counterfeit sugar ration stamps. This was an opportune sentence, because while in the Leavenworth Federal Penitentiary, DeStefano became close to Outfit members Paul Ricca and Louis Campagna. DeStefano was released in 1947 and the Outfit helped him obtain a civil service job in Chicago as a garbage dump foreman. By the 1950s, DeStefano became one of the most well known loan shark operators in Chicago. he had cash left over from his Wisconsin bank robbery and he began investing in Chicago real estate. He bought a 24-suite apartment building and used the rent money as legitimate income to bribe local aldermen and other politicians.