Mad Sam DeStefano Chicago Outfit Part 1

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.

DeStefano soon became known as the most successful fixer in Chicago as he bribed city officials, prominent judges, and law enforcement officers. DeStefano often bragged “there wasn’t any case he couldn’t fix. Since that time law enforcement learned that Mad Sam’s fees ranged from $800 for fixing a robbery case to $1,500 for an assault case. Allegedly, DeStefano once fixed a murder case for $20,000. In Chicago where the corruption was so open and notorious, police officers often took arrests directly to mad Sam’s house for their bribe. When they received the bribe and released their suspects, that person would be “put on the juice” to DeStefano in exchange for his assistance.

The political corruption business created the loan sharking business for mad Sam. By the 1960s, DeStefano was a leading Outfit loan shark. His victims included politicians, lawyers and small-time criminals. DeStefano charged 20% to 25% a week in “vig” or interest. These high-risk debtors, such as drug addicts or business men who had already defaulted on previous debts, were often delinquent in making payments. DeStefano reportedly looked forward to dealing with his delinquents. He would bring them to the sound-proof torture chamber he had built in his basement. Other gangsters said the sadistic DeStefano would actually foam at the mouth while torturing his victims. From time to time, DeStefano would also kill debtors who owed him small sums just to scare other debtors into paying their bigger debts.

DeStefano had an unusual practice. In order to provide evidence that his customers/victims were really just friends and not loan shark victims, he would give his loan shark victims presents, such as a gold watch with his name engraved on the back. Then if they ever complained to the police or he had to murder them, he could use the watch as proof of how close he was to the victim and why he could never have harmed him. Under normal circumstances, the Outfit would have distanced itself from DeStefano due to his sadistic, irrational behavior. However, the bosses tolerated DeStefano because he earned them a great deal of money. DeStefano was such a successful earner, most Outfit bosses like Giancana and Tony Accardo invested some of their own money in DeStefano’s loansharking operations.


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3 thoughts on “Mad Sam DeStefano Chicago Outfit Part 1”

  1. Gary, I love your podcast even though you have an accent:-). I’m from the Berwyn/Cicero area. I have all kinds of things. Is there an email or something just between us I can send some pics etc? I’ve never reached out to anyone, you’re the first. I left a few comments on your you tube channel. You’ve commented back.

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