Samuel "Mad Sam" DeStefano, Jr. (1909 - 1973) was an Italian-American mobster, political fixer, loan shark, contract killer, mass murderer, serial killer, serial rapist, businessman, and veteran hitman who became the most powerful, notorious and feared loan shark in America, and one of the deadliest assassins for the Chicago Outfit. DeStefano is considered by the Federal Bureau of Investigation (FBI) to be one of the deadliest criminals of all time. He is unquestionably one of the most murderous gangsters in American history. He was described by the late Chicago-based FBI Supervisory Special Agent Bill Roemer, who investigated the Chicago Outfit for over two decades as "the worst torture-murderer in history" and "one of the most vicious, sadistic and dangerous criminal's who has ever lived."
Samuel DeStefano, Jr. was born in Streator, Illinois, into the Italian-American family of Samuel DeStefano, Sr., and Rosalie DeStefano (née Brasco), both of whom had been born in Italy and had immigrated to the United States in 1903. Destefano, Sr., was a laborer and, later on in life, a grocer and real estate salesman who died of natural causes in 1942, at age 77. 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 seven children, three sons and four daughters. Not long after his birth, Sam DeStefano and his family moved to Herrin, Illinois, where his father worked in the local coal mine. After the labor-related turmoil surrounding the Herrin Massacre, the DeStefano family moved north to Chicago's Little Italy.
One of the earliest reports on DeStefano is from September 12, 1926, when he was arrested in Chicago and turned over to the Niles Police Department as a fugitive for breaking out of jail. On July 1, 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, DeStefano and fellow gang member Ralph Orlando were in court on charges of raping a 17-year-old girl. The prosecution claimed that on August 19, 1927, the girl was forced into an automobile and driven to a garage where she was sexually assaulted by seven men. Orlando and DeStefano were both found guilty of rape; Orlando was sentenced to ten years while DeStefano was sentenced to three. The reason for the lighter sentence was that police arrived before DeStefano had the opportunity to rape the girl.
In 1930, DeStefano joined the Forty-Two Gang, an infamous Chicago street gang led by future Outfit boss, Salvatore "Sam" Giancana, the Forty-Two Gang worked was a powerful street gang and an enforcement arm for the Chicago Outfit, and murdered hundreds of people for the Outfit. DeStefano also worked as an occasional driver and hitman for legendary Chicago kingpin Al Capone. DeStefano soon became involved in bootlegging, extortion, bank robbery, burglary, hijacking, prostitution, and gambling. In 1932, he was wounded by a policeman during a grocery store robbery. In August of that year, DeStefano appeared at a hospital on Chicago's West Side with bullet wounds, which he refused to explain.
In 1933, DeStefano was convicted of a bank robbery in New Lisbon, Wisconsin and sentenced to 40 years in prison. His sentence was commuted by Governor Julius Heil in December 1942 and he was released in December 1944. DeStefano returned to prison in June 1947 for possessing counterfeit sugar ration stamps.
While in Leavenworth Federal Penitentiary in the 1940s DeStefano met Outfit members Paul Ricca and Louis Campagna. Later in 1947, DeStefano was released and obtained a civil service job in Chicago as a garbage dump foreman. In 1952, city officials discovered DeStefano had omitted his criminal record from his Civil Service application; however, they chose not to prosecute him.
He married his wife Jeanie Rose Weldrin in a private New York ceremony in 1932. He was known to be abusive and controlling towards his wife often beating or raping her if she didn’t do exactly as he asked. At one point he kidnapped a man at gun point and forced him to rape Jeanie. They have six children together: their daughters Beanie, Roberta, Alexia and Eljean, and their sons Donald and Bertie. All went into hiding after their father's death.
DeStefano was one of the most powerful and feared mobsters in Chicago, a formidable loan shark and political fixer who reportedly had many cops, judges and politicians in his pocket. Over the years he gained immense political power and his reach and influence extended to prominent politicians, district attorneys, U.S. attorneys, federal judges, city officials, government officials, senators, congressmen, alderman, councilmen, and law enforcement officers. He manipulated the courts, law enforcement and local government in the State of Illinois, fixing hundreds of cases for his fellow Chicago Outfit members. He was infamous for being one of the most dangerous gangsters in America, single-handedly murdering more than 1,000 people on the orders from the Chicago Outfit bosses. He was a prolific, ruthless and much-feared hitman, brutal enforcer, powerful loan shark, vicious killer, and a sadistic psychopath who was widely feared amongst his Outfit associates and was even feared by local law enforcement as well for all of his terrifying reputations as an incredibly dangerous, brutal, bloodthirsty, barbaric and psychotic man who enjoyed brutally torturing people and killing people. DeStefano was so ruthless, dangerous and feared that his rivals and law enforcement were afraid to go after him. He reportedly would murder people's entire families, killing anyone in a heartbeat, and his ruthlessness was not limited to criminals - he didn't hesitate to kill cops, federal agents, judges, lawyers, women or even children. He had an infamous underworld reputation for viciousness, ferocity and sadism. He was notorious for committing brutal murders and inflicting gruesome torture on his victims, killing them slowly and excruciatingly. He committed some of the most unspeakable, brutal and horrific atrocities and murders in American history. He committed murders and atrocities that even had law enforcement petrified. He is considered to be one of the most murderous criminals of all time. DeStefano allegedly killed as many as 3,000 people for his own pleasure and on orders from the Chicago Outfit bosses.
DeStefano was known for being capable for unspeakable and horrific acts of brutal violence, and always tortured his victims for hours and even days before murdering them. DeStefano was a serial rapist as much as he was a cold-blooded killer, he was a notorious rapist, and would often kidnap an attractive young women or multiple women and viciously rape them for a period of a few days for his own personal demented pleasure, and would force them into prostitution or kill them afterwards. Which disgusted many Chicago Outfit members. He would sometimes go to a local bar and publicly rape young pretty women in a bar full of men for the purpose of displaying his immense power, and becuase of his formidable reputation as a brutal hitman and powerful soldier for the Chicago Outfit, no man in the bar did a thing to stop it or called the police, fearing that they would be killed or thier families would be killed. DeStefano's bizzare and psychotic behavior esculated over the years, and even followed him home. When his wife would make him angry in anyway, he would kidnap a man off of the street at gun point and bring him to his house and force his wife to have sex with the man at gun point, and would murder the man afterwards. DeStefano would often go to his farm that he owned and watch the pigs for hours, he always said to his underlings that he bought the farm and pigs just so he can kill people and feed them to the pigs and watch them eat. DeStefano once peed on one of his lawyers for making him angry.
The Devil Himself
DeStefano was allegedly a devil worshipper, and he allegedly prayed to the devil in demonic tounges. He was a sadist, and one of his close associates who worked for him as a hitman Frank Cullotta stated that
"Sam was a killing machine with no soul, he loved and enjoyed savagely and mercilessly torturing people so much that he would foam out of the mouth while doing it and pray to the devil in tongues. He was a homicidal maniac, he was a psychopath and just a very sick and deranged guy, i saw him kill a'lot of people, and i saw him rape a'lot of young women and even teenaged girls, i've seen him physically abuse his wife and mistresses, and i've seen him brutally and horrifically tortured to death hundreds and hundreds of people. Ive never seen anybody in my life so evil, demented, vicious, bloodthirsty, and merciless, he is the epitome of pure evil, if you look up evil on the dictionary his face would be right there, he is the devil himself, and if thats not the devil then i don't know who or what is. They didn't call him "Mad" Sam for nothing, he was the worst of the worst, theres nobody in history of the world that could surpass him when it comes to being a serial killer, nobody could ever surpass him as far as being evil, crazy and vicious. I thought i was bad, i mean i am a killer, i've killed people, i've tortured people, i've killed people for Sam DeStefano on his orders, i've killed on the orders from the Chicago Outfit bosses, but i'm a saint compared to Sam DeStefano. He makes ted bundy look like a girl scout. Sam DeStefano was far more evil and ruthless then every serial killer in the world combined, he was a million times worse than Ted Bundy and Jeffrey Dahmer. He was in my opinion the most evil and ruthless man who has ever lived. He was the worst human being ever, he was an animal, he was pure evil, he was stone-cold evil, he was the worst evil that anybody in the world could ever know or see. He was literally much worse than Satan himself."
DeStefano was well known for being a serial killer, sociopath, loose-cannon, sadist, sexual deviant, rapist, psychopath, and savage, and was widely infamous for being an extremely lethal, cold-blooded and ferocious loan shark who would ruthlessly torture and brutally kill anybody who didnt pay him back his loan money on time. DeStefano was fearless and would go after and kill absolutely anybody if anyone crossed him. It was this reputation as a homicidal maniac and a psychopathic killer that prevented DeStefano from ever being promoted from associate to a made member of the Outfit because the top Outfit bosses thought he was too mentally unstable and unhinged. In the late 1960s, Destefano was regarded by the Federal Bureau of Investigation (FBI) as "one of the deadliest criminal's in the world" and as "the most murderous gangster in America".
Wealth and Power
DeStefano was the Chicago Outfit's most ruthless and feared hitman. Despite DeStefano's extremely violent and saditic nature and his reputation for being a psychotic killer, he was an immense money-maker for the Chicago Outfit, and was raking in hundreds of millions of dollars a year for the Outfit, and controlled a $50 million a year loan sharking operation, and a $300 million a year numbers racket and bookmaking operation. For over two decades, Destefano was a multi-millionaire, and just three years before his death he became a billionaire worth more than a billion dollars. He was an extremely rich and powerful man with immense political reach and powerful friends within the government and law enforcement. DeStefano was making a personal income of over a half a billion dollars a year from loan sharking, drug trafficking, extortion, prostitution, pornography, sex trafficking, bookmaking, numbers and protection racket operations. He had a staggering net worth of roughly $2 billion in 1973 before his death, making him at the time one of the richest gangsters in America (his net worth of $2 billion is equivalent to an estimated $12.4 Billion as of 2019) his immense fortune was left to his wife and children.
DeStefano participated in one of the most brutal and infamous murders in U.S. history, that of William "Action" Jackson. Jackson was a bookmaker and enforcer for the Chicago Outfit who it became rumored was an FBI informant. As a result Jackson was snatched from the streets and brutally tortured to death over the period of four days, at one point being hung by a meat-hook in his rectum, he had a cattle prod used on his genitalia, he was even horrifically burnt all over his body by a blow-torch, ferociously beaten with brass knuckles, he was even viciously stabbed over 113 times with ice picks, and slit his throat with bayonets.
During the early 1950s, DeStefano became one of the most prominent loan shark operators in Chicago. Using stolen money from his days as a bank robber, DeStefano 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.
By the mid-1950s, DeStefano's influence extended to city officials, prominent judges, and law enforcement officers. DeStefano would brag "there wasn't any case he couldn't 'fix,'" and began offering his services accordingly. His fees ranged from $800 for fixing a robbery case to $1,500 for an assault case. DeStefano allegedly fixed a first-degree murder case for $20,000. DeStefano's arrangements became so routine, corrupt police officers would escort suspects to DeStefano's house. After DeStefano paid off the cops, the suspects would be "put on the juice" to DeStefano in exchange for his assistance.
King of Loan Sharking
By the early 1960s, DeStefano was a leading loan shark for the Outfit. DeStefano's loan shark victims included politicians, lawyers and small-time criminals; by the end of the decade, DeStefano was charging 20% to 25% a week in interest. DeStefano would accept very high-risk debtors, such as drug addicts or business men who had already defaulted on previous debts. The reason was simple: DeStefano enjoyed when debtors did not pay on time, since he could then bring them to the sound-proof torture chamber he'd 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 would give his loan shark victims presents, such as a gold watch with his name engraved on the back, so that if he had to kill his victim and the police accused him he could use the watch as proof of how close he was to the victim and why he could never have killed him. He wore thick black rimmed glasses, making people believe he couldn't see without them, when in truth he could see everything that was going on and would take mental notes on how people operated.
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, Giancana and Tony Accardo invested some of their own money in DeStefano's loansharking operations.
Following a negative report in the Chicago Tribune by reporter William Doherty, DeStefano assaulted Doherty, chased him with a gun, threatened his family and finally broke the windows on Doherty's nearby parked car.
Bizarre and psychotic behavior
In January 1950, DeStefano bought a new car, in which police later spotted him driving around with a sign on it, reading "This is a lemon". To make sure everyone would notice it, he also festooned the car with grapefruits. DeStefano's reason for this was because that he thought he had bought a bad car and wanted the world to know it.
In 1962, DeStefano was arrested after he tried to represent Vito Zaccagonini in a forgery trial in Rockford, Illinois. He later demanded the names of all employees in the state's attorney's and sheriff's offices so that they could be called as witnesses at his subsequent trial. During another court date in Rockford, when he was serving as his own lawyer as was his practice, he confused everyone in the courtroom when he approached the jury and asked, "Have you ever seen an elephant?" Moments later, DeStefano suddenly changed his plea to guilty, telling the jury, "something had come to light that I had not known before." The jury found him guilty and fined him $100 for disorderly conduct.
He would say it was his dream in life to own a pig farm so he could feed his victims to the pigs. He even drove to pig farms just to watch them for hours.
According to hitman-turned-informant Charles Crimaldi, DeStefano once forced his wife Anita to take his gun and put the end of the barrel in her mouth, then demanded that she pull the trigger. When she pulled the trigger and the gun didn't go off, DeStefano began to laugh and told her he had removed the bullets. He would tell this story repeatedly to his mob associates for amusement.
FBI Agent William F. Roemer wrote of going to DeStefano's house to question him about mob business, saying that several times, DeStefano would walk down the stairs in his pajamas, exposing himself. Often DeStefano's wife would serve the agents coffee and the agents would comment that the coffee had a unique taste to it. DeStefano would claim that the coffee was made from special Italian coffee beans that his wife brewed. Months later Roemer found out DeStefano had been urinating in the coffee before serving it to the agents. Roemer wrote that he could never drink coffee again.
DeStefano's partner in the drug dealing business was rogue cop Tommy Dorso. Dorso said he once saw DeStefano roll on the floor, with spit running from his mouth, begging Satan to show him mercy and screaming over and over again, "I'm your servant; command me."
Once, while riding in his car, DeStefano saw a man walking down a Chicago street. He forced the man into his car at gunpoint, took the man to his house and forced the man and his own wife to have sex with each other, all for some real or imagined grievance that DeStefano had with his wife. Afterward, the man was so mortified that he would be accused of rape, he went to the nearest police station and reported the incident.
One informant who was close to DeStefano described him as a highly emotional, temperamental individual, extremely egotistical and concerned with his personal appearance. The walls of his home were lined with mirrors and as DeStefano talked to people, he constantly watched his reflection in the mirrors as he walked across the room. He was described as being of such a temperament that he could be crying at one moment and laughing the very next. DeStefano would often state that if he had not been framed for rape at age 17, he would have become President of the United States.
In November 1963, DeStefano had a violent argument with Leo Foreman, a real estate agent and one of DeStefano's "juice-loan" collectors, in Foreman's office. DeStefano was physically ejected by Foreman from his office, and then he went into hiding. Later on, DeStefano underlings Tony Spilotro and Chuck Crimaldi contacted Foreman and said DeStefano wanted to let "bygones be bygones". Foreman was lured to DeStefano's brother's house and was murdered soon after.
In another incident, Peter Cappelletti, a collector for DeStefano, fled Chicago with $25,000 from a loan shark victim. DeStefano's men located Cappelletti in Wisconsin and brought him back to Chicago. DeStefano chained Cappelletti to a radiator and tortured him for three days. While a banquet was going on, Cappelletti was secretly being tortured in the back of the restaurant. "Kill me man, please, I'm on fire!" Cappelletti implored, to which DeStefano replied "Then we need to put the fire out" before having his men drag the severely burned Cappelletti into the dining area and forcing the man's family to urinate on him in unison. Following the banquet, the family quickly paid back the stolen money.
DeStefeno was murdered in 1973 due to a rumor of his becoming a government informant, however the rumor was false, DeStefano was facing a long prison term over an old murder case and it seemed as if he was not in a disposition to do the time. DeStefano was shot-gunned in his garage. It was rumored that Anthony Spilotro DeStefano's former protege and DeStefano's older brother Mario DeStefano were the assailant's, though no one was ever formally charged with the murder. Ironically Spilotro was himself murdered in 1986.
In Popular Society
A fictive version of DeStefano, Mad Sal D'Onofrio, appears in the 1995 James Ellroy novel American Tabloid. Mad Sal is also a loan shark and notorious for his violent ways. He serves as an informant for one of the primary characters, F.B.I. agent Ward Littel. D'Onofrio also meets an early and violent end, though his death occurs in the early 60s setting of the book, not as it occured in reality in 1973.