Pittsburgh Phil Strauss

Top 10 Killers In The Mafia

What mobster had the most hits to their credit?

  • Roy DeMeo 100 – 250 kills
  • Harry “Pittsburgh Phil” Strauss 100 – 200 kills
  • Albert Anastasia 100 – 175 kills
  • Joey Testa 75 – 150 killings
  • Anthony Senter 75 – 150 killings
  • Joe “Mad Dog” Sullivan 60 – 100 killings
  • Tommy “Karate” Pitera 50 – 100 killings
  • Maurizio “Ice Eyes” Avola 40 – 80 killings
  • Jimmy Coonan 25 – 40 killings
  • Joe “The Animal” Barboza 20 – 35 killings

Roy DeMeo 

This man is widely believed to have killed over 200 victims personally. Demeo killed both on contract hits, and as an enforcer for the Gambino Crime family in the 70’s and early 80’s. His methods were varied but most of the time the victims were shot, drained of blood, chopped up and dropped off at the Fountain Avenue Dump in Brooklyn.

Demeo had a bar named the Gemini Lounge with an apartment behind it. This is where he and his crew did a good majority of their hits. It became a very organized process. First Roy would quickly shoot the victim, often times with a silencer to avoid detection. Then his protege Chris Rosenberg would emerge in his underwear with a knife and quickly stab the victim in the heart. The idea was to stop the heart from pumping blood.

This is when the real work began, the body would be hung upside down in the tub for a couple hours to drain the blood out. After all the blood is down the drain, they would saw the body up right there in the tub, or lay it out on a tarp. Roy DeMeo, Rosenberg, Joey Testa and Anthony Senter all took part in the actual cutting. Roy was a former apprentice butcher who enjoyed showing his boys the tricks of the trade, he even took pride in how neatly his packages were pieced up because of his experience.

It’s absolutely disturbing that a DeMeo cousin Joseph “Dracula” Guglielmo actually lived in this apartment for years while this was going on. He seemingly took showers in this tub that had been used to butcher human beings on a weekly basis. There must have been many times that Dracula couldn’t take a shower because the bathroom had a current operation going on.  

Eventually, the ultra violent DeMeo Crew began to cannibalize itself one member at a time. Roy, Chris and the boys killed crew member Danny Grillo. Rosenberg gloated about killing Grillo but little did he know that he would be next to go. After botching a drug rip-off and using DeMeo’s name, Chris had stepped over the line and Roy was ordered to kill him.

By the early 1980’s, the crew had killed well over 250 people and finally the heat of law enforcement came down. Roy was in real trouble after a stolen car theft ring was busted. His crew were stealing cars which were then sent overseas, and lots of money was kicked upstairs to his bosses, Nino Gaggi and Paul Castellano.

There was simply too much heat around Roy and Paul Castellano decided he had to go. The job was given to Nino Gaggi who brought the Gemini Twins Joey Testa and Anthony Senter in to help do the job. Roy’s bullet riddled and frozen body was found stuffed in his trunk under a chandelier in January 1983.

Harry “Pittsburgh Phil” Strauss

Pittsburg Phil was the go to guy for Murder Incorporated when they wanted someone swiftly eliminated. Strauss was always eager and willing to do a job and Murder Inc. had unlimited work for him. He was paid weekly just to be available and then picked up an extra couple thousand per hit. As a contract killer was how Pittsburg Phil and most of his friends lived their entire adult lives.

And Strauss was sent out to do many killings around the country. When discussing his number of killings, the variation gets wild. Strauss, some say, killed at least 500 people. The majority of historians say that the real number is somewhere around 100. He would take a train to another city with no weapons, sometimes he’d have a picture and other times just an address and description.

There he would stalk his prey before finishing them at the most opportune moment. His specialty weapon was an icepick and he’s also used an axe but he generally used what was available since it was the 1930s. At least one time he axed a man to death in the middle of a movie theater. He often stayed in town an extra day so he could get a copy of the next day’s paper, where he could read the headlines about his deed.

Pittsburg Phil was a good looking ladies man who had dated many beautiful women. He even dated the world famous sex symbol Jean Harlot for a while. Harry’s true passion however, was killing for profit. He worked for the Jewish section of Murder Inc., run by Lepke Buchalter. Abe Reles, Mendy Weiss and Bugsy Goldstein were his partners in crime.

One of the most heinous methods of killing that this crew did was their method of choking victims to death. They’d tie a victim from his ankles to his neck while his legs were bent backward. As the victim struggled, they’d painfully choke themselves to death. Strauss was a big fan of this punishment and used it often on people who gave him a struggle in the process.

The fortunes of Strauss and his Murder Inc. partners would take a turn for the worse after the deflection of Abe “Kid Twist” Reles. Reles was able to connect Strauss and the others to a slew of unsolved killings. One by one, seven Murder Inc. members would be sent to the electric chair. Lepke Buchalter would become the first and only mob boss ever to be executed. Strauss himself was executed by “Ol Sparky” in Sing Sing prison on June 12, 1941.

Albert Anastasia

What separates Anastasia from the rest on this list is the fact that he became the boss of the most powerful crime family in the country. He killed his way right up to the top.  What was the Vincent Mangano family would become the Anastasia family, which would eventually become the Gambino family. He was one of the most powerful gangsters for over 30 years from the 20’s through the 50’s.

Albert had his first known kill at 19 years old when he bludgeoned and beat a man named George Turino to death on the docks. He was convicted of the murder and sent to death row in Sing Sing. After a well connected mobster in prison talked to his boss Lucky Luciano about the tough as nails young kid Albert, soon a retrial was ordered. The original witnesses were murdered and went missing which led to Anastasia being set free. He was now under Luciano’s wing.

This classic was written by prosecutor Burton Turkus Murder Inc. The Inside Story Of The Syndicate Killing Machine Available on Amazon

He would soon be climbing the mafia ranks alongside other legends like Frank Costello and Joe Adonis. Albert was involved in various murders during his twenties but he was just getting started. Lucky was making maneuvers to put himself at the top of the New York mafia, and in 1931 he did just that with the help of his young assassin Albert Anastasia. Anastasia participated in the murders of both Joe “The Boss” Masseria and Salvatore Maranzano, the two leaders of warring factions that ran New York.  

The national crime Syndicate was born shortly afterwards, headed by Lucky of course. For the Syndicate to be effective, it needed a strong enforcement arm that resolved disputes and eliminated threats. Albert took over this portion of the Syndicate and it became known as Murder Incorporated. He had a stable of killers on call at all times and his partner Lepke Buchalter had an equally powerful group of Jewish shooters including Abe “Kid Twist” Reles and Harry “Pittsburg Phil” Strauss.

It was at this point that Albert mostly transitioned to sending out contracts. He had been personally involved in dozens of murders himself, but now he could sit back and give orders. And there were contracts coming from the Syndicate every week, sometimes every day. Albert would usually assign who he wanted to do the deed. If this list was about facilitating murders, Anastasia and Lepke Buchalter would rank 1st and 2nd.

Murder Inc. ran like a fine oiled machine for years, smoothly and quietly eliminating any problems. The most famous hit they did was the one on notorious gangster Dutch Schultz. Albert made the call to Midnight Roses’ Candy Store and then the team would go to work.

The Gemini Twins

Joey Testa and Anthony Senter were the best of friends since the age of 10. They later became known as the Gemini twins because they were always together hanging out at their boss Roy DeMeo’s bar, the Gemini Lounge. They took part in almost all of the killings that took place in the apartment behind the bar. They were also very much into the victim dismemberment that the DeMeo Crew was known for.

Joey and Anthony were there for just about every killing and dismemberment that took place in the apartment behind the Gemini. Law enforcement experts have said that more than 100 individuals were lured to their deaths in the apartment. They each had their own “tool kits” that they would bring, consisting of different knives and other devices used to cut a body apart.

When he angered some Cuban drug traffickers, crew member Chris Rosenberg was killed by Roy and the twins. Chris had been a longtime friend of the twins but they didn’t hesitate to take him out. A few years later, Roy DeMeo himself got in hot water with his Gambino bosses. When it was decided that Roy would be killed, the job went to the twins who symbolically put a bullet behind each of Roy’s ears.

After the murders and disbandment of the DeMeo Crew, the Gemini twins shifted their alliances over from the Gambinos to the Lucchese crime family under Anthony “Gaspipe” Casso. They had done their duty by killing Roy, but were essentially dismissed afterward. By 1989, both Testa and Senter were finally behind bars for their role in DeMeo’s stolen car ring and various murders.

Joe “Mad Dog” Sullivan

Joe Sullivan was possibly the most brazen and fearless hitman in modern history. There was no contract that Mad Dog was afraid to take on. When the mafia needed a piece of work done, they could always count on the ruthless Sullivan. He did lots of jobs for the Genovese Family in particular. 

In 1976, he was hired to wipe out the hierarchy of the west side Irish mob who were battling the Genovese Family for profits on the new Javits Convention Center project. Sullivan took out a couple of Irish boss Mickey Spillane’s top lieutenants. In the case of Eddie “The Butcher” Cummisky, Sullivan blew him away in a west side bar one afternoon.

He also killed Spillane associate Tom “The Greek” Kapatos. Cummisky and Kapatos were both experienced killers themselves. But Sullivan had no hesitation about going into enemy territory to kill his victims. He would take risks that no one else was willing to take. This goes back to when he was only 12 years old doing robberies. 

A few years later, Sullivan was hired to kill Philadelphia capo Anthony Caponigro. ”Tony Bananas” crime was an unsanctioned hit on family boss Angelo Bruno. The killing of Caponigro was a commission sanctioned hit, and Sullivan was the man they chose for the job. He was battered and had money stuffed in his mouth and anus when he was found, a message was sent.

Joe’s luck would soon run out as he was convicted of three separate murders and given life sentences for each. He sat down for an interview for a documentary much later, in which he opened up about his life as a hitman. The man who had led multiple prison breaks and been a career killer passed away of natural causes in 2017. 

Tommy “Karate” Pitera

Tommy Pitera was a kid who grew up idolizing Bruce Lee. He took up karate at the age of 12 and was a natural. Within a short time, Pitera was a very skilled martial artist. He won various striking competitions over the next several years and spent over 2 years in Tokyo, Japan training under some of the world’s greatest karate instructors, sharpening his skills.

One thing the martial arts did not do was put Pitera on a positive path in his personal life. He became a tough guy enforcer for the Bonanno Family when he returned to New York. Pitera was known for really enjoying the beatings he would put on people who owed the Bonannos money. Tommy Karate showed no mercy on the streets, and impressed his bosses in doing so.

His sadistic behavior went way beyond beatings, Pitera became a virtual monster in every facet. He soon started doing killings for the Bonannos. He was a soldier in the crew of Bonanno capo Anthony “Old Man” Spero. The crew loansharked, sold drugs, extorted businesses and individuals, shook down other drug dealers and did contract killings. 

When the Gambino Family was looking to have Wilfred “Willie Boy” Johnson killed, they called on Tommy Pitera as outside help. Willie Boy had been exposed in court as an informant and his boss John Gotti wanted him dead. Pitera ambushed Johnson outside his home on August 29, 1988 as he left for work. Pitera would later be charged with, but acquitted of this murder.

What really leaves a chill about Pitera was his method of body disposal. He would cut his victims up into several pieces and then bag and bury the body parts. After his partner Frank Gangi flipped, he was able to lead police to a mafia graveyard in Staten Island. They were able to find 6 bodies which were neatly wrapped in plastic or put in suitcases. 

When Pitera was in court being handed a life sentence, he turned and gave a grin and a thumbs up to the reporters in the room. He had been convicted of the 6 murders. One of the murders was the heinous killing of Phyllis Burdie, who was a friend of Pitera’s girlfriend who died of an overdose. He then dismembered her and buried her parts.

Maurizio “Ice Eyes” Avola

Born in Catania in 1962, this hitman killed an estimated 80 victims for the Santapaolo family of the Sicilian mafia. In fact he was actually convicted of killing 43 people and confessed to killing over 70. There’s not a lot of information about him online but he deserved his spot on this list.

Maurizio Avola was arrested after a murder in 1993. Avola shared later on that there was a plot to target former New York governor Mario Cuomo. They planned to do it in a broad daylight ambush. They eventually called the hit off when Cuomo came with an army of bodyguards and a bulletproof car to travel in.

Ice Eyes Avola would have been a good fit with the DeMeo Crew or Murder Inc. In some ways, he was even worse because he would kill anybody, including politicians and journalists. The intent with these murders was to terrorize the community into silence and submission.

Despite his participation in dozens of murders, Avola is actually going to be a free man again very soon. Staring at a life sentence, he decided to cooperate with authorities and agreed to testify against the Sicilian mafia. Avola knew that the bosses were likely to have him killed.

A hundred men were convicted because of Avola’s testimony. He’s done a few interviews over the years where he has been candid about his crimes. He recounts the time he was ordered to kill a close friend and has recurring nightmares about the incident.

Jimmy Coonan

Jimmy Coonan is a ruthless Hell’s Kitchen Irish mobster. When he was growing up, a man named Mickey Spillane was the long time boss of the local mob. Spillane shook down his father’s accounting business, pistol whipped John Coonan and held him for ransom. Jimmy was a teenager at the time and the incident had a lasting effect on him. He swore if it was the last thing he would do, he would get revenge on Spillane.

Jimmy was a feared young thug as a teenager, once caving a guy’s face in and giving him 60 stitches. He set his sights on taking over the entire west side, and decided he would eliminate anyone who got in his way. One of the local guys who crossed Coonan and paid for it was Paddy Dugan, who killed his best friend Dennis Curley. Curley was a friend of both Jimmy and another vicious gangster named Eddy “The Butcher” Cummisky.

Coonan and Cummisky killed and then dismembered Dugan. In a move that was designed to scare everyone, they cut Paddy’s genitals off and put them in a milk jug. Then they proceeded to bar hop around Hell’s Kitchen showing random people, wanting the word to get spread around. Multiple witnesses said that Coonan and Eddy both got drunk at a bar after hours with the head propped up on top of the bar.

Spillane was #1 on Jimmy’s hit list and he tried for years to kill him. Coonan had some good fortune on his side though. Spillane in 1976 attempted to block the Genovese family from getting a large piece of the construction kickbacks on the Javitz Convention Center project, which was in the millions. The Italians weren’t scared of Mickey Spillane, they considered him a mere nuisance.

It was Roy DeMeo who killed Spillane which let Jimmy take over the entire West side of Manhattan. Roy, the most prolific mob killer of all time, became a mentor to Jimmy. When Jimmy and his crew murdered connected loan shark Ruby Stein, Coonan found himself in hot water with the Gambinos. It was Roy who not only covered for Coonan, but established Jimmy as an official associate of the Gambino family.

Coonan would rack up dozens of hits on his way up and during his reign as Westies boss. One time he killed a man named Harold “Whitey” Whitehead at a bar in a spur of the moment rage. Whitey had called the cops a few years before on Jimmy’s brother. When Coonan saw Whitey and 3 others head out to smoke a joint, he stalked them out and shot Whitehead in front of all the witnesses. Jimmy then ordered those witnesses to help carry off the body. Then they all went back in the bar and kept drinking.

Joe “The Animal” Barboza

Before Whitey Bulger, there was Joe “The Animal” Barboza who terrorized his victims in the streets of Boston. Joe is estimated to have killed 26 or more people from the late 50’s through the early 70’s. He was an enforcer for Buddy McLean during the McLean vs. McLaughlin street war of the 1960’s, this war took the lives of over 60 men.

Barboza was responsible for many of the murders that took place during the war, including those of Stevie and Connie Hughes. The Hughes brothers were the main killers from the McLaughlin side and Barboza killed them both in 1966. His enemies and his loanshark victims were terrified of the Animal. More than once, he bit chunks out of a debtors’ face off as punishment.

After the war finally died down, Barboza continued on as a freelance hitman. His services were available to anyone who could pay the price. He often did work for the Italian mafia based out of Providence, RI. Joe Barboza was Portuguese but still had illusions that he could one day become a made man in the Italian mafia. The New England mafia was led by Raymond Patriarca.

After his arrest, Joe quickly found out that the Italian mobsters decided that they were done with The Animal. He had sent two of his henchmen to various social clubs to pick up donations for his bail, the two men ended up getting killed and robbed of the money they did raise. When word got to Barboza, he was sick with rage and decided to flip.

The Animal proved to be one of the most controversial government witnesses ever. He testified against Patriarca and others, getting several men put in prison for the rest of their lives. Unfortunately for the FBI, Barboza was later exposed as a liar. He blamed murders that he and his crew did on other men that he had disputes with.

The FBI would later lose a one hundred million dollar class action lawsuit over the deception. Barboza would go into the witness protection program and be moved to San Francisco. After revealing his real identity to a friend there, word got back to the Boston gangsters where Barboza was. A hitman was dispatched and the ruthless killer Barboza was gunned down and killed in 1974.