When it comes to the Mafia, these hitmen are the stuff of legends. The things you see in the movies is basically what these guys experienced in their day-to-day lives. And these weren’t just any “ordinary” hitmen – they were hired to carry out the most gruesome acts for the sake of sending a message.
There’s only one thing these hitmen require for the job, and that’s cash. Of all the hitmen in Mafia history, the following are the most prolific, having made fortunes doing the dirty work. And for some of them, they didn’t stop even after they were caught and became FBI informants. In fact, one of them was so unique in his method that he got away with over 200 murders in the mid-1900s.
This one’s not for the faint of heart…
Roy DeMeo: The Butcher
Portrayed in Boss of Bosses (2001) by Michael A. Miranda and in The Iceman: The True Story of a Cold-Blooded Killer (2012) by Ray Liotta.
Roy DeMeo created what would be dubbed the “Gemini Method,” where his victims were dismembered and packaged into boxes.
Roy DeMeo was born in New York City to working-class Italian parents in 1940. Just as he graduated high school (which says more for him than others in his profession), he became a loan shark. But it was his time as a butcher’s assistant that introduced him to his true calling.
The Gambino Family Poached Him
At the butcher’s shop, DeMeo perfected a form of dismemberment that the Mafia clearly needed. In 1966, while working as a loan shark for the Lucchese crime family, DeMeo was approached by Gambino family associate Anthony Gaggi.
Gaggi promised DeMeo a heck of a lot more money if he came to work for him and his boss, Paul Castellano. DeMeo took the offer and formed his own crew, expanding his horizons to a car theft and drug trafficking. He committed his first hit in 1973.
It All Happened in the Gemini Lounge
DeMeo and Gaggi were extorting adult film mogul Paul Rothenberg, who was being questioned by the police about all kinds of suspicious payments. Gaggi ordered the hit on Rothenberg, and DeMeo carried out the deed. He led the man down a Long Island alleyway and shot him in the head. (You know, classic.)
DeMeo started to realize that his butcher days could come in handy – he could eliminate any trace of his enemies. He refined his method and named it after the Gemini Lounge, a bar he owned. His method was mad, and it ran like a well-oiled machine.
It Gets Gory…
His targets would be led into the back room of his club and shot in the head with a silenced gun. The “Gemini Method” wasn’t a one-person kind of job; it required one member of the crew to quickly wrap a towel around the bullet wound as another member stabbed the victim in the heart to stop the blood flow.
The body would then be dragged to a bathtub, where DeMeo carried out all his butcher expertise before packing the body into boxes and sending it to a local garbage dump. DeMeo committed over 200 murders throughout the ‘70s until it all came to an end.
The End of the Road for the Butcher
DeMeo’s hitman career came to a halt when the FBI managed to close in on the Gambino family in the ‘80s. By that point, big boss Castellano saw DeMeo as a loose end. What does that mean? It was the end of the road for the butcher.
Castellano ordered none other than Gaggi to take out his own man. DeMeo was found dead on January 10, 1983. But the butcher didn’t suffer the same demise as his victims. His was riddled with bullets (no less) and stuffed into the trunk of his own car.
Richard Kuklinski: The Iceman
Portrayed in The Iceman: The True Story of a Cold-Blooded Killer (2012) by Michael Shannon.
Richard Kuklinski worked for multiple crime families, including the Genoveses, the DeCavalcantes, and the Gambinos. He was a large man, standing at 6’ 5” and weighing 300 pounds.
But it was his method of murder that really made an impact on his victims, who only knew him as “The Iceman.” Kuklinski was born in 1935 in Jersey City. Unsurprisingly, his father was a violent drunk who beat him and his brother so badly that his brother actually died.
He Was Hired by Roy DeMeo
Kuklinski’s first hit occurred not long after that. The boy took his rage out on a bully, whom he beat to death. Kuklinski’s temper took him on killing sprees across New York City as an adult. Eventually, he caught the watchful eye of the Mafia.
None other than loan shark Roy DeMeo was the man who hired Kuklinski to force the debtors to pay up. The Genovese family liked what they saw and made him their primary hitman, while the DeCavalcante family took him on for specific hits.
A Jack of All Weapons
Kuklinski’s method involved removing the identifiable parts of the body, like the teeth and fingers. That way, the authorities couldn’t trace his victims. His nickname−The Iceman−came from the fact that he tended to freeze the bodies, which prevented experts from assessing their time of death.
There were other victims, though, who were simply thrown off bridges or down mineshafts. Kuklinski used all kinds of weapons, like guns, ice picks, grenades, crossbows, and chainsaws. His favorite? A nasal spray bottle full of cyanide.
A Father to Three Private-Schooled Kids
Kuklinski confessed to taking out between 100 and 200 people, claiming he took the life of the one and only Jimmy Hoffa. What might be even more remarkable is the fact that the cold-blooded hitman was a family man.
He was a father to three children who attended private schools and went to Disneyland on vacations on his bread-winning budget. Believe it or not, he would regularly serve as an usher at his local church and would hold neighborhood barbecues.
Caught by the Wire
He was deadly, but Kuklinski never killed women or children. Nonetheless, all things come to an end, and his came at the hands of the ATF in 1986. He was captured by authorities thanks to fellow Mafia man Phil Solimene, who was wearing a wire.
Solimene got Kuklinski to agree to a murder-for-hire. He was then convicted of six first-degree murders and was serving consecutive life sentences when he died in prison in 2006 of an incurable inflammation of the blood vessels.
Abe Reles: Kid Twist
Portrayed in Murder, Inc. (1960) by Peter Falk.
Murder Inc. isn’t just some aptly titled gangster flick from the ‘60s; it’s the group’s actual name that made up some of the most notorious Mafia criminals in American history. Murder, Inc. was an organized crime group that ran Manhattan between 1929 and 1941.
Bugsy Siegel and Meyer Lansky founded the group that provided paying customers with hitmen. The guarantee? That these contract killings wouldn’t be traced back. Where does Abe Reles come in? Well, he was the main hitter.
He Made Enemies With the Shapiro Brothers
Born in Brooklyn in 1906, Abe Reles was a school dropout. He would steal from local billiard halls and candy shops before getting arrested for the first time at the age of 15 for stealing gum. If his four-month sentence did anything, it made him more of a criminal.
Reles started working for the Shapiro brothers, known for running the racket in Brooklyn. It wasn’t before long that he was arrested again, and the brothers’ lack of help infuriated him. Soon enough, Reles and the Shapiros became enemies.
Ah, the Good ‘Ole Icepick
Reles’ preferred method was jamming an icepick into his victim’s brain through the right ear. The crazed individual once killed a parking lot attendant for taking too long to return his car. The Shapiros attacked Reles’ girlfriend, and by that time, he had already been hired by Lansky as a Murder, Inc. hitman.
With Lansky on his side, Reles got his revenge. Irving Shapiro was shot to death in the street, and his brother Meyer was shot at point-blank range. William, the third brother, was buried alive.
He Ratted Out Murder Inc.
Reles was arrested for the Shapiro murders in 1940 and then implicated in several other homicides. To avoid the inevitable death penalty, he decided to turn against Murder, Inc. Reles gave prosecutors heaps of information on dozens of bodies and was able to implicate his associates.
While awaiting trial, Reles was protected by 18 NYPD officers who stood guard in 24-hour shifts outside his Half-Moon Hotel room (Room 623) on Coney Island while awaiting trial. In 1941, Reles fell to his death from his hotel room window. Ropes found in the room suggested that he died trying to escape.
Sammy Gravano: Sammy the Bull
Portrayed in Witness to the Mob (1998) by Nicholas Turturro.
Salvatore “Sammy” Gravano didn’t just become the most notorious Mafia hitman of all time; he was also one of the most infamous rats.
But before he was forced to break the code of silence and became a witness for the FBI against Gambino boss John Gotti, Gravano earned the nickname “Sammy the Bull.” Born in 1945 in Brooklyn, Gravano caught the Mafia’s attention when he was just ten years old. Local wise guys saw the boy take on two older bullies who stole his bike.
From Colombo to Gambino
The gangsters noted that the young Gravano fought “like a little bull.” Once the kid dropped out of high school and finished a tour in Vietnam, he joined the mob. He was first hired by the Colombo family and tasked with a string of robberies.
By 1970, he graduated to murder when his bosses ordered him to take out a colleague who was being disloyal. Gravano’s quick rise up the ranks started causing internal tension, and so he was given to the Gambino family in 1976.
Making Enemies With the Boss
Gravano was so cold-hearted that he even murdered his own brother-in-law when it was discovered that he had a serious drug problem. And the police could only find one of his hands. Gravano did more than just kill; he was a loan shark who made millions in the wildly corrupt construction industry.
He also opened his own club in Bensonhurst, Brooklyn. By 1982, things started going downhill when his boss, Paul Castellano, sold the club to local drug dealer Frank Fiala. Gravano was enraged and took it out on Fiala and had his crew kill him.
He Ratted Out John Gotti
Obviously, Castellano and Gravano became enemies, and it all came to a head in 1985. Gravano met with then-underboss John Gotti to discuss taking out a hit on Castellano. The hit took place on December 16, 1985, at the Sparks Steak House in Manhattan. Gravano served as Gotti’s muscle in the following years until both men were arrested on racketeering charges in 1990.
When Gravano heard that Gotti was plotting to pin the murders on him, Gravano agreed to testify against his boss. He ultimately revealed that Gotti ordered 10 of the 19 murders he committed. Gotti was then sentenced to life in prison. Gravano received a reduced sentence of five years.
Gregory Scarpa: The Grim Reaper
Portrayed in Scarpa (2020) by Sylvester Stallone.
1964’s “Mississippi Burning” murders left the FBI rushing for answers. Civil Rights activists James Chaney, Andrew Goodman, and Michael Schwerner were nowhere to be found after being killed by the KKK.
The good news (I guess?) was that the Feds had arrested Gregory Scarpa of the Colombo crime family two years prior. Scarpa, who earned the name “Grim Reaper” for being such a prolific hitman, agreed to work undercover and was tasked with solving the case using the tactics he picked up as a hitman.
On a Mission to Find the Bodies
Scarpa was born in 1928 in New York City and introduced to the Mafia in the ‘50s by his older brother Salvatore. He did everything from loan sharking to extortion to drug trafficking to murder. He rose up in the Colombo family ranks and became a captain.
He dressed nicely and owned properties in multiple states. Responsible for over 50 murders, he still never failed to miss family dinners. When he was sent to Mississippi and given a gun, he was on a mission to find the activists’ bodies.
A Three-Decade Tenure With the FBI
Scarpa kidnapped a Klansman and shoved a gun in his mouth. The answers then came quickly. Once he recovered the bodies, Scarpa returned to New York. Naturally, his 30-year tenure for the FBI was a controversial one. After the famed KKK case, Scarpa’s later work for the FBI involved solving petty crimes.
In 1992, the former hitman shot a man who apparently threatened his son. Scarpa was then sentenced to life in prison and could no longer work for the FBI. In 1994, within a year of his incarceration, he died behind bars.
Harry Strauss: Pittsburgh Phil
Hitman Harry Strauss was like Abe Reles in that he spearheaded the operations of Murder, Inc. He was born in 1909 in Brooklyn and got arrested a total of 17 times before he even reached his mid-20s. But he never lived to see 32.
Nicknamed “Pittsburgh Phil” or “Pep,” Mafia historians believe Strauss took out nearly 500 people. And it was because he was one of the most trusted hitmen in organized crime, getting sent routinely on contract killings across the country. Also, like Reles, Strauss preferred to use an icepick.
He Was (a Bit Too) Proud
Strauss used other weapons, though, like an ax, which he used to hack a man to death in a movie theater. His targets were almost entirely informers or gangsters who disrespected Murder, Inc. What might be the most chilling part is just how much pride Strauss took in his job.
He dressed to the nines and would often accept jobs seemingly for the pleasure of the kill. After a contract killing, he would typically stay in town an extra day just to see how his work would be chronicled in the local newspapers.
He Was Sent to the Chair
In the 1930s, Strauss was carrying out assaults, robberies, and drug deals. He was arrested multiple times but never convicted until he was found guilty of a homicide that sent him and hitman Martin “Bugsy” Goldstein to the chair.
Reles was an informant by then, leading to Strauss’ arrest for the murder of Irving “Puggy” Feinstein and five others. Strauss tried to fake insanity in the courtroom as well as on death row. Nonetheless, both Strauss and Goldstein were executed on June 12, 1941.
Harry Millman: The Purple Gangster
Harry Millman was a member of a crime group called the Purple Gang in the 1920s that took on Al Capone’s operations during the Prohibition. Millman and his gang were notorious for their brutality. They made things so hard for Capone that he arranged accommodation with them.
Strauss was in high demand since he could arrive from out of town and be a mystery to the local police. Millman went head-to-head with Joseph Bommarito, the street boss of the Detroit Partnership. At a Detroit bar, Millman severely gashed Bommarito across his face, after which he started calling him Scarface. Millman then became the target. Eventually, Millman was taken out by Harry Strauss.
Thomas Pitera: Tommy Karate
Thomas Pitera earned his “Tommy Karate” nickname because he was well-trained in martial arts. Born in 1954 in Brooklyn, Pitera was raised by first-generation Italian immigrants. By his 40th birthday, he was a suspect in 60 murders for the Bonanno crime family.
Pitera was a soldier for the family before he became the captain of his own crew. Aside from killing on order from his boss, Pitera took pleasure in his hits, usually keeping trophies, like wedding rings, as personal souvenirs.
He Was an “Animal”
If Pitera suspected anyone – be it, friends or other crew members – of knowing too much, he killed them. “Tommy was a psychopath, an animal,” Jim Hunt, assistant special agent in charge of the New York DEA, stated.
“He’d walk into a social club, and the guys would all turn to face him. No one wanted their back to Tommy Pitera.” Hunt was the one who arrested Pitera in 1990, but it took three years of investigation and several dead bodies, including that of a woman named Phyllis Burdi.
He’s Still Serving Time in Kentucky
There was one time when Pitera took a killing too far, even in the eyes of the Mafia. According to Frank Gangi, an associate who later turned on Pitera, he saw Pitera take a bath with the corpse of an informant whom he dismembered.
Ironically, Pitera was arrested for drunk driving, after which Gangi requested to speak to a detective about his associate. Gangi told the authorities the locations of Pitera’s victims. Tommy Karate was then convicted of six first-degree murders in 1992 and sentenced to life in prison. He is still serving time in a prison in Kentucky.
Anthony Casso: The Gaspipe
Portrayed in Gotti (2018) by Andrew Fiscella.
Anthony Casso was a loan shark before he joined the Lucchese family. He made his way up the crime ladder, becoming an underboss. He was christened the “Gaspipe” after his outlaw father’s favorite weapon.
Casso was one of the most extreme hitmen in all of New York’s five crime families, having killed over 36 people. Born in 1942 in Brooklyn, Casso had the Mafia in his blood. His grandfather was a captain in the Genovese family. His criminal father tried straightening him out but to no avail.
He Bribed the NYPD
Casso was a teenager when he joined the South Brooklyn Boys gang. Later, he was poached by the Lucchese family. One investigator referred to Casso as “a ruthless, homicidal maniac who enjoyed killing,” but the mobster had the help of the NYPD.
He would bribe officers Louis Eppolito and Stephen Caracappa with $4,000 per month, deploying them as hitmen while also getting tips about potential informants. Casso served for the Lucchese family in the ‘80s, when he rose to second in command.
He Became a Rat Himself
Even when Casso was indicted on 67 counts in 1990, he didn’t stop plotting and conspiring to murder. He even targeted a federal prosecutor and a federal judge in 1992 and 1993. The hitman had so much hate for police informants (aka rats) that he attempted to kill Patricia Cappazola in 1992, the sister of informant Peter Chiodo.
Both she and her brother barely survived the attempts on their lives. By 1993, the Feds had enough to charge Casso with racketeering charges. It was then that Casso became a rat himself.
455 Years in Prison
Casso gave the authorities information in court the next year but only ratted out Eppolito and Caracappa — the police officers he bribed, whose status wasn’t covered by the Mafia’s code of silence. That way, he could still look at himself in the mirror, so to speak.
Casso ultimately pleaded guilty to 72 counts of racketeering, extortion, and first-degree murder. He was sentenced to 455 years in prison but died in 2020 at the age of 78 from Covid-related issues.
Joe Barboza: The Animal
Joseph Barboza was so ruthless that he once chewed a man’s cheek off, leading people to call him “The Animal.” Historically, he became the first member of the Witness Protection Program when the mob wars hit a peak in the ‘60s.
Still, he continued killing, with over 26 hits under his belt. Born in 1932 in New Bedford, Massachusetts, Barboza came from Portuguese heritage but always wanted to join La Cosa Nostra – the Italians. He was never formally accepted by the group. Instead, he became an enforcer for the New England Mafia.
From the Ring to the Slammer
Barboza started out as a professional heavyweight boxer, but his temper and burglaries sent him to jail several times during the ‘50s. His time in the Mafia only began in 1961, after meeting Boston’s mafiosos in prison.
“I’d stab guys after 14 weeks who still continued to hide,” Barboza said in 1970. “You know, I stabbed them in the face. I stabbed them in the legs. I stabbed them in the arms. I stabbed them in the chest. You understand?” (Yeah, we get it.)
The First Member of the Witness Protection Program
Things took a turn in 1966 when Barboza was arrested on gun charges, and his boss refused to put up his bail. In fact, Raymond Patriarca killed anyone who offered to. The FBI swooped in and offered Barboza immunity and a new life in San Francisco – but only if he gave up Patriarca.
So, Patriarca was indicted in 1970 and sentenced to 10 years in prison. It was soon discovered that Barboza ratted out his boss and six associates, which is why he was put into witness protection – given a new identity and a culinary job in Santa Rosa, California. In the end, Barboza’s body was discovered in the streets of San Francisco in 1976.
Charles V. Harrelson: Woody’s Dad
Did you know that Woody Harrelson’s father was a legit hitman? Yeah, I didn’t either. It was less for the Mafia than it was for business people who simply wanted people gone. To Woody (and his two brothers), the “contract killer” father was still “Dad,” despite the fact they didn’t see him much since he was often in prison.
Woody vividly remembers the moment he realized his dad was a criminal. “I was 11 or 12 when I heard his name mentioned on a car radio,” the actor recalled. He was listening to the radio when he heard about his father.
An Expert “Card Mechanic”
The radio “was talking about Charles V. Harrelson and his trial for murder and blah blah blah.” Woody sat there, thinking, “There can’t be another Charles V. Harrelson. It was a “wild realization,” he said.
Mrs. Harrelson knew what her husband did for a living and never spoke negatively about him to her sons. Charles was born in 1938 in Lovelady, Texas, and served in the Navy as a sonar man. He was also a professional gambler – an “expert card mechanic” is what he would call himself.
Hired by a Carpet Salesman
He was first tried in 1968 in Houston for the murder of Alan Berg, a carpet salesman. Charles alleged that a rival carpet salesman, Frank DiMaria, hired him to do it. Although he was let off at that time, another case, decades later, wasn’t as kind to him.
Charles was tried again for the 1968 shooting of Texas grain dealer Sam Degelia. He was hired by Degelia’s business partner, who wanted his life insurance check. The trial resulted in a deadlocked jury, leading Charles to wait three years in jail for a retrial.
Out of Prison, Back in Court
According to a correctional officer, Charles retained his money and status while behind bars. The 1973 retrial found him guilty; he was sentenced to 15 years in prison but served five (for good behavior). By 1981, he was back in court.
Charles was tried again and given two life sentences for the murder of district judge John H. Wood. Remarkably, it was the first murder of an American judge in the 20th century. Wood had been checking a flat tire outside his home when Charles shot him in the back.
Only the “Deserving” Were Hit
Because it was the first of its kind, it turned into the biggest FBI investigation (outside of the JFK assassination). Texas Rangers eventually tipped the FBI about Charles being a potential suspect. Charles was arrested in 1980 when he was a fugitive on weapons charges.
Charles later stated that he never killed anyone who “was undeserving.” He was caught in a manic six-hour standoff with the police before ultimately being arrested and sentenced to two life sentences. If you ask Woody, it wasn’t a fair trial.
He’s Not a Saint, But…
“I‘m not saying my father’s a saint, but I think he’s innocent of that,” Woody declared. None of the Harrelson sons thought of their dad as guilty, despite knowing their father’s character and profession.
“I think he probably didn’t kill Judge Wood,” Brett Harrelson said in a podcast covering the case. “But I think the state had to find somebody, and I think he would have been the easiest one to convict.” The eldest brother, Jordan, is a bit more resigned: “Do I believe he did it? Do I believe he could have done it? Yes. Yes.”
A Couple Million
As for Woody, he admitted to having spent “a couple million” trying to free his father. “I tried for years to get him out. To get him a new trial,” he explained. Why? Because, as he said, he was “just being a son trying to help his dad.”
By the way, Woody believes his father was a secret CIA operative. Charles passed away in prison in 2007 at the age of 68. Luckily for both Woody and his father, they were able to bond and reconcile before his passing.