February 10th, 2002. Ramon Arellano Felix walks through a Mazatlán Carnival crowd hunting his biggest rival. Then his own underling calls his name. He turns. The bullets are already on the way. These are the 12 times cartel bosses and mob kingpins were killed by their own bodyguards and sicarios.
But he was ruthless. I can tell you firsthand that he didn’t have a conscience. Everybody knew he’d kill you for just looking at him wrong. He was a stone cold killer. For nearly two decades, Ramon Arellano Felix was the most feared enforcer in Mexico. He led the assassination wing of the Tijuana Cartel alongside his brothers.
The FBI put him on the 10 most wanted fugitives list in 1997. And then, in early 2002, he made one mistake. He trusted the wrong man. By that point, El Chapo Guzmán had escaped a Mexican prison and joined forces with Ismael “El Mayo” Zambada to wipe out the Arellano Felix organization.
The two Sinaloa bosses had a long list of grievances. Friends killed, family members executed. They wanted Ramon dead. So they reached inside his own cartel. The man they turned was Carlos Terrazas Lizárraga, one of Ramon’s trusted underlings. According to journalist Anabel Hernández, Sinaloa kidnapped Terrazas’ sister to force his cooperation.
Then they fed him a story to pass up the chain. “El Mayo” Zambada, Terrazas told his boss, was attending the Mazatlán Carnival with only two bodyguards. A perfect kill shot at the most powerful man in Mexico. Ramon took the bait. February 10th, 2002, he and his personal bodyguard “Alhambra” were slipped into the Carnival crowd carrying pistols scanning for Zambada.
Torrado walked alongside them. He was supposed to cover their escape. Instead, he shouted Ramon’s name. Ramon turned. Two Sinaloa gunmen came up behind him. The shots came fast. Ramon and his bodyguard collapsed on the sidewalk among the carnival floats. He was 37 years old. The Mexican government covered the entire operation as a routine traffic stop gone wrong.
They claimed a local cop had shot Ramon after Ramon shot him first. That story held for years. The truth only emerged later, in pieces, through informants and journalists. El Mayo’s brother explained it years afterward. “My brother told me Chapo was going to help him kill Ramon in Mazatlán,” he said. “He had to.
Ramon was too dangerous to leave alive.” Less than a month later, Ramon’s brother, Benjamin, was arrested. The Tijuana cartel never recovered. He died on an empty stomach. And because it happened that way, the theory is the biggest mafia rubout of the decade took place with considerable help from inside the dead mobster’s family.
And the Godfather of the Gambino family, his appearance in court every day, and the preoccupation with his defense were bad for business. Experts say his associates may very well have decided Big Paul was more trouble than he was worth. December 16th, 1985, 5:30 in the evening. Paul Castellano pulls up to Sparks Steak House on East 46th Street in Manhattan, expecting a quiet dinner with his lieutenants.
He doesn’t know it yet, but the meeting was set up by his own capo to kill him. Castellano was the boss of the Gambino crime family. He had taken over from Carlo Gambino in 1976. He ran the family like a CEO. Meat distribution, construction, trucking. He banned his soldiers from dealing drugs under penalty of death.
That ban infuriated a Queens-based capo named John Gotti, whose crew was deep into heroin. Gotti knew that the moment Castellano found out about the drug operation, he was dead. So, Gotti decided to strike first, but he needed someone inside Castellano’s inner circle. He got one. Capo Frank DeCicco, a man Castellano had personally promoted and trusted, agreed to flip.
DeCicco set up the Sparks meeting and tipped Gotti to the time, the place, and the seating arrangement. When Castellano stepped out of his black Lincoln onto 46th Street, four shooters in trench coats and Russian fur hats were already waiting. Their names were Salvatore Scala, Vincent Artuso, Edward Lino, and John Carneglia.
They opened fire as Castellano and his underboss bodyguard, Thomas Bilotti, walked toward the restaurant entrance. Gotti and his number two, Sammy Gravano, watched from a parked Lincoln across the street coordinating the entire hit by walkie-talkie. Castellano died on the pavement. Bilotti died next to him. The famous photograph from that night, Big Paul lying beside his car, his shoes off the curb, became the most iconic image in American Mafia history.
Gotti became boss within 2 weeks. The commission, the ruling council of the five families, never approved the hit. And 5 months later, Frank DeCicco, the inside man who had sold Castellano out, climbed into his car in Brooklyn, a car bomb tore him apart on the street. Gotti was eventually convicted of ordering Castellano’s murder.
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He died in federal prison in 2002. Wilbur Varela was the last great kingpin of Colombian cocaine, a former police sergeant who switched sides. He took over the Norte del Valle cartel in 2002. The US Department of Justice estimated his organization had shipped over 500 metric tons of cocaine worth more than 10 billion dollars.
They put a 5 million dollar bounty on his head. By 2008, Varela was hiding in the mountains of Venezuela, paying off Venezuelan generals and politicians to stay alive. He had already survived a cartel civil war that killed an estimated 1,000 people. He thought he was untouchable in his mountain cabin in Merida. He was wrong.
His own two top lieutenants, Diego Restrepo and Comba, had cut a deal with rival drug lord Daniel “El Loco” Barrera. Barrera wanted Varela’s eastern Colombian smuggling routes. The two lieutenants wanted everything else. The night of January 29th, 2008, Varela was sleeping at the Fresh Air Cabin Resort on the outskirts of Merida.
His personal bodyguard, known only as El Grasoso, the greasy one, slept in the next room. His driver, Goyo, was sent out before dawn to buy breakfast. When Goyo returned an hour later, he saw the bullet holes in the cabin door. He didn’t stop. He didn’t go inside. He turned the car around and ran.
Inside the cabin, Varela was already dead. El Grasoso, his bodyguard, was dead beside him. Varela had been traveling under a false identity. It took Venezuelan forensics 32 fingerprint points to confirm the body in the morgue was actually the most wanted man in Colombia. The Colombian newspaper El Tiempo ran the headline that summed it all up.
Al Capo Varela lo mató su gente. The capo was killed by his own people. Rastrojo and Comba took the western routes. Loco Barrera took the eastern ones. Varela’s son was murdered the following year. Within 5 years, every man involved in his death would be in US federal prison or in the ground. 1:00 on a Thursday afternoon in downtown Ciudad Juarez, over the border of El Paso, Texas.
Assassins gunned down a victim outside a crowded shopping mall, and their rifle fire also caused a line of other cars to crash. Some bosses see the betrayal coming. Rafael Aguilar Guajardo did not. He was a former federal police commander in Mexico’s notorious DFS intelligence agency. After Pablo Acosta died in 1987, Aguilar co-founded what would become the Juarez Cartel.
He brought in a younger lieutenant to handle operations. The lieutenant’s name was Amado Carrillo Fuentes. For 5 years, Carrillo Fuentes quietly built his own network inside Aguilar’s organization. He cultivated his own contacts in the Mexican military. He developed his own smuggling routes. He waited. By 1993, Aguilar Guajardo was a fugitive with $100 million in seized assets and a federal warrant on his head.
2 days before he died, he allegedly threatened to expose his high-level government contacts if he wasn’t protected. That was the wrong threat to make. April 12th, 1993, Easter weekend, Aguilar Guajardo was vacationing with 15 members of his family at the Hyatt Cancun Caribe.
They had spent the day on a submarine tour of the reef. That evening, he walked out of Gypsy’s restaurant on Cancun’s tourist strip with his wife and 11-year-old son. Gunmen opened up from across the boulevard with automatic weapons. The bullets tore through the patio. Aguilar Guajardo and an American tourist died on the sidewalk.
His wife and son were both wounded. Carrillo Fuentes took over the Juarez cartel within 48 hours. He became known as El Señor de los Cielos, the lord of the skies, because he smuggled cocaine in his own fleet of Boeing 727s. He lasted 4 years. In 1997, hiding from a Mexican manhunt, Carrillo Fuentes checked into a private hospital in Mexico City for plastic surgery to change his face.
He died on the operating table. The two surgeons were later found dead, their bodies discarded along a highway in oil drums. The Juarez cartel survived all of it. It’s still operates today. Witnesses said it was a gangland-style killing. Four heavily armed men wearing ski masks opened fire with automatic weapons.
In addition to murdering Galante and his associate Nino Coppola, the killers also murdered the restaurant’s owner and wounded his 17-year-old son. Carmine “the Cigar” Galante was an old-school mafia killer. Law enforcement linked him to between 80 and 100 murders going back to 1926. After his release from federal prison in 1974, he tried to take over the Bonanno crime family and seize the entire New York heroin market for himself.
He imported Sicilian gunmen called Zips to staff his crew. He told everyone he was untouchable. The commission of the five families decided he was finished. The plan ran through Galante’s own personal Sicilian bodyguards, Cesare Bonventre and Baldo Amato. According to the Mob Museum’s reporting, the two Zips didn’t hesitate.
They were offered promotions in a bigger cut of the family’s drug rackets. They served their own boss up for execution. July 12th, 1979. Galante was having lunch on the patio of Joe and Mary’s Italian-American restaurant in Bushwick. His cousin Giuseppe Turano owned the place. Capo Leonard Coppola sat at the table. Bonventre and Amato flanked Galante on either side. They were his protection.
At about 2:45 in the afternoon, three masked gunmen walked through the restaurant. Bonventre and Amato sat completely still. They didn’t reach for their weapons. They didn’t shout a warning. Shotgun and pistol fire ripped through the patio. Galante died at the table. Turano died next to him.
Coppola died in his chair. The famous New York Post photograph from the scene showed Galante on his back, his cigar still clenched in his teeth. Bonventre and Amato survived without a scratch. They were both promoted to capo positions inside the Bonanno family as their reward. Bonventre lasted five years before he was murdered in 1984.
Amato is currently serving a life sentence on an unrelated double murder conviction. Only one of the three masked shooters, Bruno Indelicato, was ever convicted for the Galante hit. He went down at the 1986 Mafia Commission trial. Did you know Roy DeMeo? Of course I know. See, there’s a line with everything in life. There’s a line.
I think he crossed the line from a hit guy and became a serial killer. Some of the sea stories end with a boss killed by men he barely knew. This one ends with Roy DeMeo killed by the man who raised him in the mob. DeMeo ran the most prolific killing crew in American Mafia history.
The Mob Museum estimates he and his crew participated in more than 200 murders. They operated out of the Gemini Lounge in Brooklyn. By 1982, the federal noose was tightening. A former associate named Vito Arena had flipped to the FBI. DeMeo received a second federal grand jury subpoena. Paul Castellano, who would himself be murdered 3 years later, became convinced DeMeo would crack and bring the entire family down.
Castellano gave the contract to DeMeo’s lifelong mentor. The man’s name was Anthony Nino Gaggi. Gaggi was the Gambino capo who had recruited DeMeo into the mob back in 1965. He had vouched for him for nearly two decades. He had treated him like a son. Gaggi took the contract anyway. January 10th, 1983.
DeMeo was lured to Patrick Testa’s auto body shop in Brooklyn for what he thought was a routine sit-down. The Testa brothers worked the front of the shop. DeMeo walked in, took off his coat, and turned to face Nino. He realized what was about to happen too late. The Mob Museum’s account of the killing is exact.
“No sooner had DeMeo removed his jacket,” the report reads, “than Nino opened fire.” DeMeo’s own crew, the men he had trained, the men who had killed beside him for years, watched it happen without lifting a finger. 10 days later, ice fishermen at the Varuna Boat Club in Sheepshead Bay popped the trunk of an abandoned Cadillac. The car was DeMeo’s.
The partially frozen body inside was DeMeo’s. He had been killed by his own family in the most literal sense. Gaggi went to federal prison 3 years later on an unrelated murder conviction. He died there in 1988. Holmar Prison. New York’s Anti-Crime Committee says that killer for Murder Incorporated has been a January hermit for more than a month in his heavily guarded home at Fort Lee, New Jersey.
The committee says Anastasia has double-crossed his underworld bosses. Albert Anastasia was called the Lord High Executioner of Murder Incorporated. He ran the killing arm of the American Mafia in the 1930s and 1940s. The unit was credited with hundreds of contract murders. By 1957, he was the boss of what would eventually become the Gambino crime family. That made him a problem.
His underboss, Carlo Gambino, had been quietly conspiring with Vito Genovese to take him out. Anastasia had alienated Meyer Lansky and Santo Trafficante by trying to push into Havana casinos. The hit needed his personal bodyguard, a man named Anthony Coppola, to step aside. October 25th, 1957. Anastasia was driven from his mansion in Fort Lee, New Jersey, to the Park Sheraton Hotel on West 56th Street and 7th Avenue in Manhattan.
His chauffeur parked the car in the underground garage and walked outside. According to multiple historical accounts, his bodyguard, Coppola, also stepped away from his post moments before the attack. Whether Coppola was actively complicit or merely conveniently absent has never been resolved.
But the timing told its own story. Anastasia walked alone into Grasso’s barber shop inside the hotel. He took chair number four. He leaned back. A hot towel went over his face. Two masked gunmen walked in seconds later. They fired 10 shots. Anastasia, towel still draped over his face, rose disoriented from the chair. He stumbled forward and lunged at the reflections of his attackers in the barber shop mirror.
He died on the tiled floor. The shooters were never officially identified. Years later, Joe Gallo, the Brooklyn capo, was alleged to have bragged to his crew that you could just call the five of them the barbershop quintet. Carlo Gambino, the inside man underboss who had set the whole thing in motion, became boss of the family that would forever bear his name.
He ran it for the next two decades. He died of natural causes in his own bed in 1976. Some of the most chilling betrayals in Mafia history come from the homeland. The Sicilian Mafia ran its insider purges with a kind of cold theater you rarely see in America. Rosario Riccobono was the boss of the Partanna Mondello Cosca and a member of the Sicilian Mafia Commission.
During the Second Mafia War, he switched sides to support the Corleonesi, the brutal rural faction led by Toto Riina. He helped lure Bontade and Inzerillo loyalists to their deaths. But Riina didn’t trust a man who had already betrayed once, so he decided the entire Riccobono organization had to be liquidated, not just Riccobono, every man around him. November 30th, 1982.
Riccobono and roughly eight of his most trusted men were invited to a feast at Michele Greco’s country estate in the Ciaculli district of Palermo, another commission member’s house, a friendly meal among allies. Riccobono brought his bodyguards. He sat down. He ate. He drank. After the meal, Riccobono did what he always did.
He fell asleep in his chair for an after-dinner nap. That was the signal. According to multiple Sicilian Mafia pentiti who later testified, each of Riccobono’s men was separated from the others during dessert. Each was strangled by the man sitting next to him at the table. The bodyguards never had a chance to fight back because their bodyguards were the men strangling them.
Pino Greco, Michele Greco’s enforcer, personally garroted Riccobono in his chair. Riccobono never woke up. The bodies were dissolved in acid in a barn behind the estate. None were ever found. Riccobono’s brother, Vito, was decapitated days later inside his own car. The Riccobono Cosca simply ceased to exist within a single afternoon.
Riina consolidated total control over the Sicilian Mafia. It became one of the cleanest insider hits in Mafia history, in part because there were no survivors and no bodies. There was just an empty afternoon and a missing Cosca. Hundreds of homeless peasants stood in line to receive handouts of cash, not from a relief worker, but from a drug boss, the most violent of the Colombian drug bosses, Gonzalo Rodriguez.
In a few hours, Rodriguez, guarded by the national police, personally handed out almost $200,000 using a small amount of his billions in cocaine profits to make himself a beloved figure with people who may not know much. He was nicknamed El Mexicano because of his obsession with Mexican ranchero culture. He was one of the four founding partners of the Medellín Cartel alongside Pablo Escobar and the Ochoa brothers.
Forbes magazine named him a billionaire in 1988. José Gonzalo Rodríguez Gacha ran the Cartel’s enforcement squads. He financed the original right-wing death squads in Colombia. He waged a private war against the Cali Cartel that killed hundreds of civilians. By December 1989, every law enforcement agency in two countries was hunting him.
He had 25 bodyguards at any given time. He moved constantly. He hid in safe houses in Cartagena and Tolu. The Colombian Search Bloc could never get close enough. The breakthrough came from inside. A man known as El Navegante, the navigator, was a member of Gacha’s organization.
Multiple Colombian sources allege he was actually an informant for the rival Cali Cartel planted years earlier inside Gacha’s inner circle. He fed Colombian authorities Gacha’s exact location. December 15th, 1989. Two Colombian Search Bloc helicopters dropped onto a coastal property between Coveñas and Tolu. Gacha, his teenage son Freddy, and three bodyguards bailed out of a red pickup truck and ran toward a banana plantation.
Search Bloc gunners opened up with 50 caliber machine guns from the helicopters. Freddy and two bodyguards went down first. Gacha and the last bodyguard tried to keep running. They were both cut down in the field. Colombia celebrated in the streets. Pablo Escobar, watching the news from his Medellín compound, understood instantly what had happened.
The informant inside Gacha’s cartel had been operational for a long time. The state had reached over 25 of Gacha’s bodyguards and pulled them out. Escobar escalated his war against the Colombian government within hours. He would be hunted down himself three years later. Joe Masseria was called Joe the Boss because he wanted to be the boss of everything.
He was one of the two warring kings of the Castellammarese War in early 1930s New York. He treated his street captains as cannon fodder while collecting a fortune in tribute from every borough. His right-hand man was a young Sicilian named Charles Luciano. People were starting to call him lucky.
Lucky Luciano had been quietly negotiating with Masseria’s rival, Salvatore Maranzano. The deal was simple. Kill Masseria, end the war, take his rackets. Luciano lined up his best gunmen, Vito Genovese, Albert Anastasia, Joe Adonis, Bugsy Siegel. April 15th, 1931. Luciano invited Masseria to lunch at Nuova Villa Tammaro on West 15th Street in Coney Island. They ate, they drank.
After the meal, they started a card game. Then Luciano excused himself and walked to the bathroom. Four gunmen came through the restaurant door less than a minute later. Genovese, Anastasia, Adonis, and Siegel. They walked straight to the back table. They emptied their guns into Joe the Boss.
The famous detail from the New York Daily News, and historians still debate whether it ever actually happened, was that Masseria died with the ace of spades, the death card, still clutched in his bejeweled hand. What is not in dispute is that Masseria’s own bodyguards had mysteriously vanished from the restaurant before the gunmen arrived. They had been bought off.
They had been waved away. Luciano had reached inside Masseria’s security detail and turned every man in it. When Luciano walked out of the bathroom, Joe the Boss was dead in his chair. The Castellammarese War was over. Maranzano took the New York rackets. Luciano took Masseria’s family.
Five months later, Luciano would do the exact same thing to Maranzano. Salvatore Maranzano declared himself capo di tutti capi, boss of all bosses, the moment Masseria’s body hit the floor. He restructured the New York Mafia into the five families in 1931. Then he made the mistake of trying to be the only boss above all of them.
He had a list of men he wanted dead. Lucky Luciano was at the top. By September 1931, Maranzano had hired the freelance killer Vincent “Mad Dog” Coll to murder Luciano. But Tommy Lucchese, a Luciano ally embedded inside Maranzano’s organization, tipped Lucky off. Luciano had to move first.
The plan was almost surgical. Maranzano was expecting an audit from the Internal Revenue say or vice. He had told his own bodyguards to come to his Park Avenue office unarmed, so they couldn’t be charged with weapons offenses during the inspection. September 10th, 1931. Four men in suits walked into Maranzano’s ninth floor office at 230 Park Avenue.
They identified themselves as IRS agents. They flashed badges. Maranzano’s now unarmed bodyguards were lined up against the wall and disarmed completely. The four men were not from the IRS. They had been recruited through Meyer Lansky, Bugsy Siegel, and Carlo Gambino specifically because their faces would be unknown to anyone in Maranzano’s organization.
Tommy Lucchese stepped forward and pointed at Maranzano, so the hit team would know which man was the target. They pinned Maranzano against the wall. They stabbed him. Then they shot him. The murder kicked off what came to be called the Night of the Sicilian Vespers. Across the country, dozens of Maranzano allies were killed in coordinated hits that same evening.
Luciano abolished the title of boss of all bosses. He created the Commission. He restructured the American Mafia into what it would remain for the next 90 years. Masseria and Maranzano. Two bosses killed by their inner circles in five months. 50 years ago the Chicago mob was much more powerful than it is today. And then something happened to attract attention around the world.
Good evening. Sam Momo Giancana, the Chicago crime syndicate chieftain recently named in a reported CIA mafia plot to assassinate Fidel Castro, has been shot to death. Federal, state, and local law enforcement authorities say the killing late last night at the 65-year-old Giancana’s suburban Oak Park home looks like an underworld execution.
The last man on our list wasn’t killed by the men he commanded. He was killed by the men who had quietly replaced him. Sam Momo Giancana ran the Chicago outfit through the 1950s and into the 1960s. He brokered the alleged Cook County vote rigging that helped John F. Kennedy win the 1960 election.
He shared a girlfriend with President Kennedy. He worked with the CIA on at least one plot to assassinate Fidel Castro. By 1975, current outfit boss Tony Accardo had grown nervous. Giancana was scheduled to testify the very next morning, June 20th, before the U.S. Senate Church Committee. The committee was investigating CIA assassination plots.
Senate staffers were already in Chicago. They were planning to escort Giancana to Washington at sunrise. Accardo decided that the flight was not going to happen. The night of June 19th, 1975, Giancana was alone in the basement kitchen of his Oak Park, Illinois home. He was frying sausage, escarole, and beans for a late dinner.
The FBI surveillance team that was supposed to watch his house that night had been pulled off the detail. There was no forced entry to the home. That meant Giancana had let his killer in himself. The killer used a silenced .22 caliber pistol. Giancana was shot once in the back of the head while standing at the stove.
Six more shots followed. The FBI’s working theory, later confirmed by Outfit informant Nicholas Calabrese, was that Accardo had ordered the hit. The triggerman was widely believed to be Giancana’s long-time aid and driver, Dominic Butch Blasi. Blasi was the last person seen with him. The case remains officially unsolved.
Nobody was ever charged. Giancana never testified to the Senate. The CIA secrets and the Outfit’s stayed buried. The man at the stove never knew he had cooked his last meal. 12 men, 12 organizations, one pattern. In nearly every case, the boss wasn’t taken down by police, by rivals, or by federal agents.
He was taken down by the very people he paid to keep him alive. The bodyguard who stepped away, the lieutenant who set the meeting, the mentor who pulled the trigger, the aid who let the killer in through the kitchen door. The lesson of organized crime, at every level, in every country, in every decade, is brutally consistent.
The day you stop being useful to the people around you is the day you become a liability. And in this world, liabilities are erased, not by your enemies, but by your friends.
