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MAD SAM DESTEFANO: PRE-EMINENT CLOWN PRINCE OF THE CHICAGO OUTFIT

 [NOTE: This is not a new piece. I wrote this a long time ago when a friend was putting together a true crime podcast. That podcast never came to fruition, which is a shame, but I thought the piece I wrote for it was too interesting to not release into the wild. So here you go. Enjoy, if that's the correct word for it.]

“The mob was full of psychopaths and morons, and keeping order among them was a challenge to the mettle of any boss, be he an elderly don like Paul Ricca, or a power broker like Giancana. Nobody tested the patience and discipline of both men more than Sam DeStefano, a freelance juice-loan operator and terrorist who was the pre-eminent clown prince of the Chicago outfit, a buffoon with no equal . . . DeStefano through the years had somehow gained the favor of Ricca and Giancana, a standing that kept him alive. For nobody made more enemies, or talked louder, than DeStefano, the mad hatter.”

                        --William Brashler, The Don: The Life and Death of Sam Giancana

 

Make no mistake. Samuel “Mad Sam” DeStefano was a scary guy. He carved out a neat little niche for himself as a loan shark by also ensuring that everyone knew he was a sociopath and a lunatic and very unpredictable. One minute you could be having a normal conversation with him, and the next you could have an ice pick in your throat. Or somewhere a lot less pleasant.

 

But where did such a killer come from? Oddly enough, he hails from Streator, IL, where he was one of seven children born to Samuel DeStefano, Sr., and Rosalie Brasco. Streator, now, is a farming community with a dab of city living. Back then it was just a farming community. Not a lot to do there. It’s not a surprise that the family picked up stakes and moved across the state to Herrin in coal country. What happened, then, to make them move to Little Italy in Chicago?

 

The Herrin Massacre, naturally. The miners were on strike, and at first things were amicable, but when the price of coal went up the owner hired scabs to take over. The union boys were upset over this, so they started to shoot at the scabs. The mine had armed guards, so they started killing the miners in retaliation. Add in some strike breakers, and you have more corpses. They even got the superintendent. Twenty of the scabs and strike breakers were killed compared to the three miners. Twenty-three men died over this labor dispute, and not all of them were merely shot. Some were brutally killed.

 

“The only way to free the county of strike breakers is to kill them all off and stop the breed.” Imagine being told that by a striking miner, and you’re a strike breaker. You’ve walked out under a white flag, and then you and your men are attacked. Brutalized. Murdered.

 

“Listen, don’t you go killing these fellows on a public highway. There are too many women and children and witnesses around to do that. Take them over in the woods and give it to them. Kill all you can.” Chilling words. But that’s what they did.

 

“Let’s see how fast you can run between here and Chicago, you damned gutter-bums!” One of the miners said this  as they set loose a bunch of strike breakers at a fence. Keep in mind, Herrin is closer to Springfield than Chicago. If you’re not from Illinois, that’s all the way across the state.

 

Some strike breakers were caught at the fence—a barbed wire fence—and shot. Some were shot trying to escape beyond the fence. One was captured and hanged from a tree. Three of his companions were shot just under his twisting soon-to-be corpse. Some of them were captured and stripped to their unmentionables and forced to crawl to the cemetery. The miners beat and shot and urinated on these men. Townspeople came to taunt these men, and anyone still alive at the end of the trek had their throats cut with a pocket knife. And not even death could stop the abuse. The miners spat on their corpses.

 

The rest of the country wasn’t happy with this. It horrified everyone outside of Herrin. Some compared it to how the Germans in WWI comported themselves with their POWs. President Harding supposedly said, “[It is a] shocking crime [of] barbarity, butchery, rot and madness.” If he didn’t say that, he probably should have.

 

Not a single miner did time for this crime. Arrests were made, but everyone was acquitted. The bodies were buried in unmarked graves, and it took us as long as 2013 to find them. There’s a monument to the dead there now, which eases the sensation of being brutally murdered, no doubt.

 

Mad Sam’s dad was one of those miners. It’s not clear that he took part in the massacre, but Sam wasn’t the only member of the family affected by this crime. His brother, Mario, was also a sadist. This part is speculation, but it seems pretty clear that Mad Sam’s sociopathy began here. Some of his crimes do, in fact, mirror what happened to the strike breakers.

 

The FBI thought of Mad Sam as the most vicious torturer/killer in the history of the US. The mob used him when they needed to send a sadistic message, but even they felt uneasy about using him. He did, after all, murder his own brother, Michael. Charles Crimaldi, a mobster who somehow survived to 2020, claimed Mad Sam was a Satan worshipper. How did it all begin?

 

The first record of him being arrested comes from 1926, but it was because he had escaped from a jail in Niles, so there was at least one crime he committed before that we didn’t know about. Shortly after he was handed back to Niles, his gang showed up threatening to kill anyone who stood in their way of freeing Mad Sam. It’s not clear if this worked, but not long after that Mad Sam got arrested again, this time for kidnapping a woman off the street, taking her to a garage, and—with six other men—sexually assaulting her. She was seventeen. Mad Sam was found guilty and sentenced to three years.

 

Just three years for the sexual assault of a minor.

 

When he got out he joined the Forty-Two Gang. If that sounds familiar, it’s because it was run by the infamous Sam Giancana, who went on to run the mob in Chicago for many decades. It was 1930, so they mostly got up to bootlegging, gambling, women, that kind of thing. Throw in some light robbery, and you get the idea. He was wounded during a grocery store heist. He had several bullet wounds when he showed up at the hospital, and he didn’t feel the need to explain them. It doesn’t seem that he got arrested for that one.

 

(It should be mentioned that by this time he married his girlfriend (Anita) and would have six kids by her. He was very abusive to all of them, especially his wife. For her disobedience, he would often rape her. His kids all went into hiding and refused to come back to the world until after his death.)

 

He did get caught for the next one. In 1933 he tried to rob a bank and got 40 years for it. Think about that. He robbed a bank and got 40 years. He raped a minor and got three years for that. The world had a different set of priorities then.

 

He didn’t serve his whole sentence. The governor inexplicably commuted it in 1944. Not that it mattered. He returned to prison in 1947 for, of all things, having fake sugar ration stamps. (Remember, this was just after WWII.)

 

While in Leavenworth he met Paul Ricca and Louis Campagna, who would help him get in with the mob. He was released the same year and got a job in waste management, like any good li’l mobster. He didn’t tell them about his criminal record, and when they discovered it they got upset but didn’t have him arrested.

 

And then his real life of crime began.

 

It turns out that he managed to steal that money from the bank job, and he used it to set himself up as a loan shark. He also became big in real estate, buying an apartment building which he used to squeeze money out of people. He used that money to bribe people from judges to alderman to anyone in between. He paid off cops to ignore crimes to the point where he used twenty grand to dismiss a Murder One charge. Assault cost $1,500, robbery $800. (Incidentally, he guaranteed acquittal. If it didn’t happen, he would pay for the appeals himself.)

 

What was the vig? 20-25%. That’s insane. But the mob loved it. But he didn’t want people to pay him back. He had a sound-proof basement where he would bring those who couldn’t make the cut where he could torture them to death. Even if the sum was small. Especially if the sum was small. He liked scaring people, and some mobsters claimed he foamed at the mouth while torturing people to death. More on that in a moment.

 

He would often give personalized gifts to people who borrowed from, engraved with his name, to prove to police that he couldn’t have killed them. He liked them. Why else would he give them gifts? The ploy seemed to have worked. He never did time for killing those people. He would also wear super thick glasses to make people think he couldn’t see without them. He could. He wanted people to underestimate him, and they did constantly. Until he killed them.

 

Giancana and other mobsters invested in Mad Sam’s business practices. They didn’t like him, but he made them a lot of money, so why not? Once he even attacked a Chicago Tribune journalist.

 

William Doherty was the writer in question. He wrote something bad about Sam in the paper, so Sam decided to chase him with a gun, threaten his family and then damage property at Doherty’s home.

 

And then there’s Leo Foreman, one of Sam’s collectors. He was technically a real estate agent, but you know how that goes. They had a major argument in Foreman’s office, and Foreman had Sam kicked out forcibly. Realizing with horror the grave mistake he’d just made, Foreman went into hiding. Crimaldi (what a great name for a criminal!) and the infamous Tony Spilotro reached out to Foreman claiming that Sam wanted to “let bygones be bygones” and wanted to see him. It’s kind of like being a prince in the Roman Empire and having the emperor recall you to Milan. Nothing good is going to come of it.

 

Foreman fell for it and was murdered at Sam’s brother, Mario’s, house. Sam’s men softened him up first with a vigorous beating and shooting him in a few non-vital places, and when Sam got to him, he used a hammer on Foreman. His knees, his head, his crotch, his ribs. He stabbed him with his beloved ice pick twenty times. By the time he shot Foreman in the head, Foreman probably took it as a blessing. The whole time he was killing Foreman, Sam kept telling him that he was a blood sacrifice to the devil. When he was done killing him, Sam said, “Look. He’s got a smile on his face. Looks like he was glad to die.”

 

And then there is Peter Cappelletti, yet another of Sam’s collectors. Somehow he messed up worse than Foreman. He ripped Sam off for twenty-five grand and fled to Wisconsin. Sam’s men had no problem finding him, and they brought him back home. Sam chained him to a radiator in the basement of a banquet hall and tortured him for three days. WHILE BANQUETS WERE STILL BEING HELD. But that was no problem. The place was owned by his brother, Mario. At one point he set Cappelletti on fire, and the poor man screamed for them to kill him, to put him out of his misery. “Please!” he cried. “I’m on fire!”

 

“Then we need to put the fire out,” Sam said. He had his men drag him out into the middle of a banquet, where Cappelletti’s family was having dinner. Mad Sam had planned it by inviting them there in the first place and treating them to a meal. He made the family urinate on him at the same time, just to put that fire out.

 

Not surprisingly, the family coughed up the dough.

 

If that’s not crazy enough, he tried to represent Vito Zaccagonini during his forgery trial. There is no evidence that Sam had any knowledge of the law outside of breaking it. He also represented himself several times. His tactics could be described as “shock and awe.” Or more like, “What the hell is this guy doing?” He liked to be brought into court in a wheelchair or on a stretcher. He once asked the jury, “Have you ever seen an elephant?” Then, without any pause, he changed his plea to guilty on the spot. He claimed that “something had come to light that I had not known before.” What was he on trial for? A mere disorderly conduct charge. They fined him a hundred bucks. How’s that for punishment? His courtroom antics at his own trials gained a lot of public attention, especially when he started showing up in his PJs. He liked to ramble his arguments through a bullhorn. There is actually footage of this if you look it up on YouTube.

His victims weren’t limited to people who owed him money. His brother, Michael, had a drugs and gambling problem, and the mob called Sam to get Michael out of their casino. He went out to the there and picked Michael up only to shoot him five times in the head. IN HIS OWN CAR. (Another variation of the story states that he stabbed his brother, probably with an ice pick.) He went to his other brother, Mario’s, place, where he stripped the body down, washed it, put it in another car and left it abandoned on a city street. He then had the nerve to call the police to tell them where Michael could be found.

 

He liked to go to pig farms to watch them at work for hours. He claimed he wanted to own a pig farm so he could feed them his victims Mason Verger-style. He also liked to tell a story, and Crimaldi confirmed it, that he once forced his wife to put a gun in her mouth. He told her to pull the trigger, and when she did, he laughed and told her he’d taken the bullets out. He thought it was an amusing anecdote that his mob buddies would enjoy.

 

Few, if any, did.

 

Famed FBI Agent William F. Roemer wrote a book about his adventures, and Sam played kind of a big role. He said this of Sam: “About this time I got to know Mad Sam DeStefano, the worst torture-murderer in the history of Chicago. He was a sadistic, arrogant, swaggering thug of the worst order, responsible for scores of killings, almost all by his own hands. I had a long series of confrontations with this beast, and looking back I must admit I enjoyed every one.” He visited Sam at his home many times in an attempt to turn him into an informant, and a lot of the time he said that Sam came downstairs in his pajamas with his penis hanging out like it was some kind of accident. Perhaps he did this for the same reason that Lyndon B. Johnson held press conferences while he defecated: intimidation. Roemer always had Sam’s coffee, and it had an odd taste to it. Sam claimed it was due to the “special Italian coffee beans.” Roemer later learned it was actually because Sam had been urinating into it. Roemer said he “could never drink coffee again.”

 

If you follow mob history in Chicago, you might know about a dirty cop by the name of Tommy Dorso. He helped Sam deal drugs back in the day, and he once said that Sam rolled around on the floor, mouth foaming, praying to Satan. “I’m your servant! Command me!” he would howl. Dorso himself said of Sam, “DeStefano is not normal. Mentally, physically or spiritually . . . and he knows it.” Crimaldi had this to add: “[Sam] was convinced that he was indeed Satan’s disciple. When he was in trouble or getting heat . . . he would drop to his knees and pray. The ritual was always preceded by a violent rage during which he would stomp the floor and swear endlessly. He seemed to lose contact with the world around him and his anger propelled him through a series of spasms into some private hell where only he and the devil could enter. On all fours he would smash his fists against the floor in frustration and rage. The drool would pour from his mouth in streams to form frothy puddles beneath his face. His gravelly voice would become a croak so guttural that his words were barely comprehensible. Once he had reached this state, he would pray to the devil.”

 

What would a guy like Mad Sam do in his leisure time, aside from visiting pig farms? One time he saw a Black man walking down the street and forced him into his car at gunpoint. He brought the stranger home (to Sam’s place, not the stranger’s) and forced poor Anita DeStefano to perform oral sex on this man. It destroyed him so badly that he actually fled from the house to the nearest precinct to report what had just happened. When the cops investigated and discovered that Mad Sam was behind the whole thing, nothing really happened to him. Even the police were scared of him.

 

An informant, possibly Crimaldi, also called Sam egomaniacal. His house had a lot of mirrors on the walls, and when he talked to people, he looked at his own reflection instead of at them. He would do the same while simply walking on his own. He could be laughing one moment and crying the next. He also claimed that if he hadn’t been “framed” for rape when he was younger, he could have been the President of the United States.

 

Also in his house, down in a soundproofed basement, he had a torture chamber. A wooden cabinet on the wall contained his favorite weapons: ice picks. He liked to shove them into eyes and crotches, and he did that often. Just ask a man named Artie Adler, who died in just such a way before Mad Sam dumped his body in a sewer drain. The cops found it because the sewer backed up, and sanitation had to unblock it. Since the crime had happened during the winter, Adler’s body was in a block of ice, preserved just like a wooly mammoth’s might be.

 

At one point after this killing, Roemer went to visit Sam, who came down in his PJs with his penis hanging out, as usual. This time Sam went to one of the many mirrors in his living room to hold and admire his penis while talking with Roemer. When Roemer accused Sam of killing Adler, Sam brought his whole family into the room. Sam screamed, “These two gentlemen are FBI agents. They have come out here to accuse me of killing Arthur Adler! I cry out to God up above! If I am guilty of killing Arthur Adler, may God come down, right now, and put cancer in the eyeballs . . . of you and you and you!” Pointing his finger to each of his family members.

 

In 1965 Mad Sam went back to prison, this time for conspiracy. Three to five years. In 1972 he went back to prison yet again, this time for threatening the life of none other than Crimaldi himself. In the very same year he was indicted yet again for illegal possession of firearms by a felon.

 

And then another indictment was handed down, this one for Foreman’s murder. He continued with his courtroom lunacy until finally, after all these years, Tony Accardo, the boss of the Chicago mob, decided that Mad Sam had gone too far. He gave Mad Sam’s own crew permission to whack him.

 

April 14, 1973. On the 1600 N. Sayre Ave. block. Mario Anthony DeStefano, the brother who hosted Foreman’s murder, invited his brother over. Sam went, not suspecting a thing. Never imagining that Spilotro would be there, too, and that Spilotro would shotgun him. He got Sam in the chest with one shot and tore his left arm off with the second. Mad Sam DeStefano died instantly.

 

Another variation of the story is that Mario and Spilotro arrived at Sam’s house, who let them into his garage, at which point Spilotro pulled the shotgun from under his coat. The first shot took off his right arm, and the second exploded his chest. One way or the other, he was finally, irrevocably, dead.

Not surprisingly, no one ever went to trial for it. Everyone in Chicago probably released a big sigh of relief knowing that Sam’s reign of terror was finally over. To quote an unnamed mobster, “[Sam] was sick. Crazy, sick, a sick dog, worse than you can ever think. We didn’t whack him a second too soon.”