crime The Most Gruesome and Terrifying Murders Committed by the Mafia

Phil Gibbons
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Life in the American Mafia typically ends in one of two ways: death or prison. In a perpetual struggle over illegal power and money, murder is practically an occupational hazard. From the very first days of organized crime, mafia hits, brutal assassins, and crime's most horrifying killers underlined the fundamentally violent lifestyle of this uniquely American entity. In a world where violence is practically second nature, these are some of the most brutal killers and gruesome murders associated with the Mafia.

Some of the people on this list are classic gangsters like Al Capone. Others weren't even in the mob, but pissed off the wrong people. In either case, the lesson is clear: stay clear of the mob and definitely don't make a gangster mad. Keep reading below to see some of the most violent murders ever committed by the Mafia.

Roy DeMeo's Gemini Method: An Assembly Line of Murder


Roy DeMeo's Gemini Method:... is listed (or ranked) 1 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: FBI/Wikimedia Commons

Roy DeMeo was a New York based member of the Gambino crime family who ran his own crew of criminals in Brooklyn. This particular group of thugs specialized in murder and contract killings that typically involved dismemberment and the ultimate disappearance of any trace of the victim. Those slated to die would be lured to DeMeo's headquarters, the Gemini Lounge, through the promise of a meeting, drugs, or some other inducement for them to enter the apartment area behind the bar itself.

DeMeo would be surreptitiously waiting for them with a silenced pistol in one hand and a towel in the other. After a point blank shot in the back of the head, DeMeo would carefully wrap the towel around the wound to prevent too much blood from spilling. As quickly as possible, a confederate, usually Chris Rosenberg, would stab the victim in the heart to minimize excessive bleeding. Then the body would be deposited in a bathtub where it would bleed out as much as possible. If a victim was murdered to send a message, they would dump the body publically for all to see. Otherwise, blood would eventually be washed down the drain and DeMeo, a trained butcher, would supervise a quick and efficient dismemberment, with body parts packed in plastic and stuffed in cardboard boxes. Occasionally, a victim's head would be pulverized in the bar's industrial strength trash compactor. The boxes would be included with refuse intended for a large local landfill. 

When Chris Rosenberg murdered several Colombian drug-dealer partners, DeMeo was ordered to kill his associate to avoid a gang war, and he complied, even imposing the Gemini Method on a close friend. It is estimated through court testimony provided by turncoat witnesses that over 200 individuals were murdered by the DeMeo crew in less than a decade.

In January of 1983, DeMeo was killed by his own men, who believed that he would not stand up to inevitable federal and state indictments. The hit was ordered by crime boss, Paul Castellano, who felt DeMeo and his crew were too wild and attracted too much attention with excessive violence, even for the Mafia. DeMeo's entire crew would eventually be convicted of numerous murders and receive life sentences. The landfill was eventually closed and covered over, with law enforcement concluding that searching through thousands of tons of garbage would be fruitless. DeMeo's victims literally disappeared without a trace.

Richard Kuklinski Was Called "The Ice Man" for a Reason


Richard Kuklinski Was Called &... is listed (or ranked) 2 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: YouTube

Richard Kuklinski was known as the "Ice Man," the perfect nickname for a Mafia contract killer who murdered several dozen victims in any number of ingenious ways. At 6' 5" and 275 lbs, Kuklinski was also physically well suited to his chosen vocation. Early in his mid 20s, he began stalking and killing derelicts on Manhattan's West Side. Originally exposed to the Gambino crime family when he was beaten into repaying a debt to an associate of Roy DeMeo, Kuklinski quickly became involved in Gambino pornography bootlegging, collections, and, occasionally, contract murders.

Kuklinski would eventually branch out into financially-based murders involving first scamming a victim and then killing them. His methods were diverse and included stabbing, shooting, blunt force trauma, and even employing cyanide from a spray bottle, an especially difficult method to use. Kuklinski also employed an additional process to thwart investigators. He would freeze his dead victims in an industrial freezer, sometimes for years, before thawing and dumping them, completely obscuring their actual date of death.

This would eventually be Kuklinski's undoing. When he dumped a body in warm weather before completely thawing it, the medical examiner found ice crystals in the lungs of the victim. Dubbed "The Ice Man" by law enforcement, they eventually connected him to the murders of five people, mostly his friends and business associates, and he was sentenced to life in prison in 1988. After appearing on numerous crime documentaries discussing his methods and life, Kuklinski died in prison in 2005.  

Anthony "The Ant" Spilotro's Brutal Ways


Anthony "The Ant" Spil... is listed (or ranked) 3 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: FBI/Wikimedia Commons

Anthony Spilotro was so ruthlessly effective as a Mafia enforcer and killer that, in 1971, he was sent to Las Vegas to oversee the Chicago mob's casino cash skimming and criminal operations in the rapidly expanding gambling mecca. He earned this reputation through his involvement in numerous egregiously violent murders in the Chicago area. Reenacted in the 1995 film Casino, Spilotro and two other gangsters kidnapped Billy McCarthy, another criminal who had murdered two of Spilotro's associates. Spilotro placed McCarthy's head in an industrial vice and demanded the identity of McCarthy's partner, exerting pressure until one of his victim's eyes popped out of his head. McCarthy gave up his partner's name and Spilotro rewarded him by slitting his throat.

When the Outfit suspected that one William "Action" Jackson had turned informer to the feds, he was assigned to Spilotro who tortured him for two days. He was beaten, sliced up with knives and razor blades, burned with a blow torch, had his skin ripped off of his 300 pound frame, and ultimately hung by the rectum with a meat hook until his heart gave out.

Sometimes the Outfit would summon Spilotro from Las Vegas when they had a special need in Chicago. In January, 1978, someone stupidly burgled Chicago mob boss Tony Accardo's house while he was on vacation. Spilotro was assigned to discipline the individuals responsible for this transgression and he quickly identified the professional theft ring involved. In six weeks, he murdered all six men - all died horribly from stab wounds and torture. Spilotro returned to Vegas and Tony Accardo had sent a clear message.  

The 1929 St. Valentine's Day Massacre Was Utterly Ruthless


The 1929 St. Valentine's D... is listed (or ranked) 4 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: Miami Police Department/Wikimedia Commons

Throughout the '20s, Al Capone battled George "Bugs" Moran for control of Chicago's organized crime operations, especially bootlegging and alcohol sales. Moran controlled the predominately Irish North Side neighborhood and had killed two of Capone's Unione Siciliana associates. Capone decided that he needed to completely eliminate Moran and his gang. In a scheme that was elaborately planned for months, Capone's top henchman, "Machine Gun" Jack McGurn, sent four men, two dressed as police officers, into Moran's Clark Street headquarters on the morning of February 14, 1929. Lookouts believed that Moran was already present, in fact they mistook another individual, Albert Weinshank, similar in appearance and dress, for the North Side Gang leader.

The decision to dress two assassins in police uniforms proved to be wise, as gang members grumbled but felt intimidated enough to agree to line up against a wall for what they presumed would be petty arrests. Instead the two men dressed as civilians, opened up with Thompson submachine guns, spraying all seven of Moran's gang with numerous rounds of .45 caliber bullets long after they fell to the ground. The two other killers shot into the pile with blasts from long barrel shotguns, practically obliterating some of the victims. Surprisingly, one of them, Frank Gusenberg, made it to a hospital despite fourteen bullet wounds. He died three hours later.

The only living witness besides the gunmen was "Highball," the gang's German Shepherd watchdog. Moran was fortunate to be running late and was approaching the garage when he spotted the two "policemen" entering the building. He and an associate ducked into a nearby cafe. Al Capone took great pains to be highly visible in Miami, both on February 14th and the day before. No one would ever be tried for the massacre and it essentially ended the competition between Moran and Capone. It also generated tremendous civilian anger and demand that law enforcement get the city under control.

The identities of the killers are still a matter of debate. Capone hit men Giovanni Scalise and Alberto Anselmi (aka The Murder Twins) were almost certainly involved and the machine guns used were eventually traced to Fred "Killer" Burke, a criminal who would die in prison in 1940, serving life for another murder.

Tony Spilotro's Murder Was Depicted Inaccurately, But Was Still Brutal


Tony Spilotro's Murder Was... is listed (or ranked) 5 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: YouTube

In the film Casino, Tony Spilotro was brutally attacked with his brother in a corn field and then both were buried alive. Court testimony would ultimately surface as to what actually happened to Anthony and Michael Spilotro in the real world. In June of 1986, Anthony Spilotro had completely alienated mobsters in Chicago when several of his Las Vegas associates flipped and testified against Spilotro and other Chicago outfit bosses. When boss Joey Aiuppa was sent to prison in the spring of 1986, he ordered that Spilotro be killed, especially because Spilotro himself was under indictment and was no longer producing revenue.

Spilotro and his brother Michael were lured to a home in suburban Chicago, ostensibly so that Michael could be formally elevated to "made" mob status and Anthony could be formally promoted. The outfit reasoned correctly that killing only Anthony would prompt Michael to seek revenge, so both would be killed. On June 14, 1986, Michael Spilotro left his home to meet his brother and head to the meeting but cautioned his wife, "If I'm not back by nine o'clock, it's no good." In court testimony in 1997, Mafia enforcer Nick Calabrese, testified as to what happened to the Spilotro's when they arrived. As they entered the basement, a dozen men were waiting for them. Michael was tackled, a rope placed around his neck, and he was strangled, he was kicked, and he was beaten. Anthony Spilotro attempted to fight off his attackers but was brutally pummeled and literally beaten to death.

A coroner's report indicated that they asphyxiated on their own blood and their bodies were covered from head to toe with bruises and horrific injuries (autopsy photos, caution, disturbing). The bodies were later found in an Indiana cornfield in a botched burial near farmland owned by another Chicago mob boss. The Catholic church refused both Spilotros' funeral services based on their criminal histories. John Fecarotta, the man who botched the Spilotro burial would subsequently be killed by Calabrese as punishment.

Joe E. Lewis Actually Survived a Horrifying Attack


Joe E. Lewis Actually Survived... is listed (or ranked) 6 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo:  Gobonobo/Wikimedia Commons

In 1927, Joe E. Lewis was a top singer and comedian appearing at Chicago's Green Mill Night Club. With his contract about to expire, he accepted a much more lucrative offer to appear at the Rendez-Vous Cafe. One major problem: Al Capone owned a piece of the Green Mill, the Rendez-Vous was a North Side Gang operation. He was warned specifically by Jack McGurn that he should not take the job.

Lewis started working at the Rendez-Vous anyway, he even mocked his former employers and their threats during his act. One week later, at 10:30 in the morning, Lewis received a knock on the door of the hotel room where he lived. Figuring it was a house keeper, he absentmindedly unlocked and opened the door. Three thugs rushed into his room and two began to pistol whip Lewis with handguns while the third took out a long hunting knife and cut Lewis's throat from ear to ear, as well as part of his tongue for good measure. Then they left him to bleed to death.

But, miraculously, Lewis didn't die. It would take two years for him to learn how to speak intelligibly, albeit with a strangely deep voice that became his calling card, and ten years to regain any semblance of a show business career. He became a regular performer in Las Vegas starting in the '40s and became buddies with Rat Packers like Frank Sinatra and Dean Martin. In 1957, a film entitled The Joker Is Wild, starring Sinatra, depicted Lewis's tumultuous life.

Al Capone Beat Two of His Henchmen to Death with Baseball Bats


Al Capone Beat Two of His Henc... is listed (or ranked) 7 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: FBI/Wikimedia Commons

One of the reasons infamous Capone killers, Alberto Anselmi and Giovanni Scalise, are believed to be two of the killers involved in the St. Valentine's Day Massacre was that Scalise bragged that he and his murderous partner were the most powerful men in Chicago. If that was the case, their status didn't last long, most likely because of a lack of discretion. Scalise met openly with individuals plotting against Capone and when rumors of disloyalty got back to "Big Al" he decided to put his two triggermen to a test. He staged an incident where he slapped another gangster, Frank Rio, and the two men immediately attempted to recruit Rio into their ever-thickening plot.

On May 7, Capone responded with typical savagery. He invited Scalisi and Anselmi and their main conspirator, Giuseppe "Hop Toad" Giunta to what was billed as a laudatory event in their honor. It was to take place in a private room at a mob casino in Hammond, IN. Initially a sumptuous banquet was served and the guests of honor enjoyed all of the food, alcohol, and positive attention. Well after midnight, Capone suddenly stood up from his seat at the head of the table, no longer proposing toasts to his guests but now brandishing a baseball bat. As he began to rage at the three traitors, telling them that he knew everything about their plot, men lead by McGurn, used wire to tie Scalisi, Anselmi and Giunta into their seats.

Capone, starting with Anselmi, then methodically beat each man savagely about the head, shoulders and arms. When Scalisi, having watched his partner's beating, began to plead hysterically for mercy, Capone became even more visibly enraged, his blows even more savage. Giunta was the last to go, then the barely living men were finally untied and tossed on the floor where McGurn put three .45 slugs into each man's head, with the barely conscious Scalise lifting a hand and getting his pinky torn off by a bullet to the eye (caution, disturbing photo). The bodies were dumped in Hammond and when police brought them to the morgue, the medical examiner called them the worst corpses he had ever seen, with every bone in the upper part of each men's body and face crushed or broken.

Machine Gun Jack McGurn Got His in the End


Machine Gun Jack McGurn Got Hi... is listed (or ranked) 8 on the list The Most Gruesome and Terrifying Murders Committed by the Mafia
Photo: Chicago Crime Scenes/flickr/CC-BY-NC 2.0

The St. Valentine's Day Massacre was the high water mark of Al Capone's crime career. Following this event, he would be harassed by law enforcement and arrested for petty crimes wherever he went. In May of 1929, he was arrested in Philadelphia for illegal weapons possession (a handgun) and sentenced to a year in jail, which he would serve in luxury at the infamous Eastern State Penitentiary. In 1931, he would ultimately be jailed for a much longer time period in federal prison for income tax evasion. These circumstances would greatly affect Jack McGurn, who owed his reputation and ability to intimidate other mobsters through his status as Al Capone's top enforcer.

With Capone out of the picture, McGurn was quickly shunned by other Outfit criminals, who disliked the arrogant bully. He was personally told by Capone's successor, Frank Nitti, that he was through in Chicago. McGurn had accumulated a great deal of money and even owned a golf course and attempted a living as a professional golfer. He lived with his wife, Louise Rolfe (aka The Blonde Alibi because she testified that McGurn had spent all of February 14, 1929 with her in a hotel room). He divorced his first wife and married Rolfe to prevent further testimony, quashing any prosecution for the Valentine's Day Massacre in the process.

By 1936, the depression had greatly reduced McGurn's financial fortunes and he survived by freelancing small rackets on his own, without the permission of Nitti. On February 14, 1936, McGurn went to a neighborhood bowling alley where he had been frequently spending time in the evenings. A worker there handed him a Valentine's card that had been left anonymously. After midnight, three hoodlums entered the bowling alley, drew handguns, and told everyone in the building to freeze. McGurn froze, too, thinking he was about to be robbed. Instead, the three men shot him to death. As had been his habit, they put a coin in one of his hands. Technically, it was early on February 15, but McGurn came within minutes of dying seven years to the day after the St. Valentine's Day Massacre. Police recovered the card which had a cartoon of a couple and the greeting:

"You've lost your job; you've lost your dough; Your jewels and cars and handsome houses! But things could still be worse, you know...At least you haven't lost your trousas."

McGurn's murder remains unsolved to this day.