April 13th, 1991. Bay 29th Street, Bensonhurst, Brooklyn. 7:45 in the evening. A big man steps out of his house in the fading light and walks toward his 1991 Lincoln Town Car.

He is 47 years old, six-foot-three, 230 pounds of South Brooklyn muscle. For more than a decade he has been one of the most feared men in New York organized crime. He has survived shootings, arrests, and the internal mob politics that chewed lesser men to pieces. He has killed for his boss.

He has protected his boss with his own body. He has driven his boss through the streets of New York for years while federal agents photographed them from parked vans. He thought the worst was behind him. He was six feet from his car when he heard the footsteps.

He never heard the shots. Frank Lasterino opened up with a . 380 automatic and didn’t stop until the magazine was empty. Twice in the head, five times in the torso—seven rounds.

Bobby Boriello dropped beside his own car on his own street and bled out on the asphalt of his driveway while his two-year-old son sat in the kitchen inside, and his wife Susan came running out of the house to find her husband of seventeen years facedown and full of holes. The paramedics arrived in minutes. They could do nothing. Bobby Boriello was pronounced dead on the scene.

This was not just another mob killing. Bobby Boriello was John Gotti’s man—his driver, his bodyguard, his closest personal protector for years. If you wanted to get to the Dapper Don, you had to get through Bobby first. Everyone in New York knew it.

So when Bobby went down in that driveway, the whole underworld asked the same question: who was powerful enough, crazy enough, and well-connected enough to touch John Gotti’s personal bodyguard? The rumor on the street for years was that Gotti himself had ordered it—that Bobby had tried to step back from the life and paid the ultimate price for wanting out. The real story is more complicated, more sinister, and it involves something no one in the entire history of American organized crime had ever managed before: a murder arranged using two active-duty New York City Police Department detectives as the hired scouts for the hit. Bobby Boriello was born on March 31st, 1944, in South Brooklyn—not the gentrified Brooklyn of today.

The Brooklyn of the 1940s and 1950s was a place where neighborhood boundaries were drawn in blood. Each block had its loyalties, each corner had its bosses, and the streets of South Brooklyn were owned by organized crime. Not just one family, either. The Gambinos, the Genoveses, the Colombos—all of them had roots in the same neighborhoods, the same parishes, the same social clubs.

A kid growing up in South Brooklyn in the 1950s didn’t have to look far to find men who seemed to have everything: money, respect, power. Bobby Boriello saw all of it up close. His younger brother, Stevie, was tight with the Gallo brothers—Joey “Crazy Joe” Gallo, Albert, and the whole crew that ran rackets out of Carroll Gardens and Red Hook. These were serious men, violent men, and Bobby, the bigger and physically more imposing of the two brothers, gravitated naturally toward the enforcer’s role.

He became feared on the streets before he was even formally associated with any family. By his early twenties, he was working as muscle for the Gallo gang, and between 1967 and 1972 he was arrested six times: weapons, assault, larceny, gambling. The police knew exactly who he was and what he was doing. But knowing and proving are two different things in Brooklyn, and Bobby Boriello kept walking out of precinct houses and back onto the streets.

In the aftermath of Crazy Joe Gallo’s murder at Umberto’s Clam House on April 7th, 1972, the Gallo crew’s power began to fracture. Stevie Boriello helped preserve what rackets he could in South Brooklyn. Bobby, meanwhile, was drifting toward a different orbit—the Gambino family, the most powerful crime organization in the United States. The man who would transform Bobby Boriello’s life was coming up at the same time through the same streets.

John Gotti, at that point a capo running operations out of the Bergin Hunt and Fish Club in Ozone Park, Queens, was exactly the kind of boss a man like Bobby could respect. Gotti dressed sharp. He talked sharp. He rewarded loyalty.

He punished disloyalty. He ran a tight operation. And somewhere in the late 1970s and early 1980s, as Gotti’s profile inside the Gambino family grew, Bobby Boriello became his man—not just an associate, not just another soldier orbiting the boss. Bobby became Gotti’s driver and bodyguard, the man sitting in the front seat, the man who got out first when the car stopped, the man who stood between the boss and whatever was waiting outside.

In organized crime, that position comes with certain unspoken truths. You are trusted completely or you don’t last a week. You know everything because you are everywhere. And you are permanently linked to the boss’s fate in ways that cannot be undone.

Bobby and Gotti spent weekends together on Long Island. They gambled together. They attended shows by singer Jay Black, a childhood friend of Gotti’s. They were photographed together dozens of times by FBI surveillance teams who made careers out of cataloging the Gambino family’s social arrangements.

Bobby wasn’t just an employee. He was, in the fullest sense of the word available to men in that world, a friend. In the late 1980s, Boriello was formally made a full member of the Gambino crime family. His induction ceremony took place on December 24th, 1988, in an apartment on Mulberry Street in Manhattan, in the home of Joe Butch Corrao’s mother.

The men led into that apartment that evening read like a Gambino family who’s who: John Gotti Jr. , Dominic Pizzonia, Craig DePalma, Nicholas Losurdo, and Bobby Boriello. The oath was administered by Salvatore “Sammy the Bull” Gravano and Pasquale Conte. These weren’t minor ceremonies.

Being made in the Gambino family in the late 1980s, with Gotti as boss, meant you had arrived at the center of American organized crime. But being close to Gotti didn’t just mean sharing the good times. It meant sharing the risk. Boriello’s crew ran trucking, construction, and loan-sharking operations across Manhattan, Queens, Staten Island, and South Brooklyn.

He associated with serious men—Angelo Ruggiero, Anthony Anastasio. The crew had a significant stake in strip clubs up and down the East Coast through a fixer named Steve Kaplan, who paid tribute to both Bobby and Junior Gotti for the privilege of operating without interference. The operation generated significant money, and Bobby was aggressive about protecting it. On one occasion, he opened fire on a Genovese associate named Frank Geritano in broad daylight on a Brooklyn street.

That kind of recklessness might have gotten another man killed immediately, but Bobby had enough juice with Gotti that the families negotiated a settlement rather than go to war over it. Then came October 4th, 1990. John Gotti had a problem. A Gambino family soldier named Louis DiBono had secured a lucrative contract to install fireproofing foam on the infrastructure of the Twin Towers at the World Trade Center.

That was serious money, and DiBono had been dodging Gotti’s summonses, refusing to come in and account for himself. In the mafia, that kind of disrespect has one solution. Gotti gave the contract to Bobby. Bobby carried it out.

Louis DiBono was shot dead on October 4th, 1990, in a parking garage at the World Trade Center. After DiBono’s death, Sammy Gravano took over the construction business. One man disappeared. The money moved.

Nobody asked questions. Remember this name: Anthony “Gaspipe” Casso. He’ll become very important in the next few minutes. By late 1990, Bobby Boriello had been elevated to acting capo of Junior Gotti’s crew.

He was running his rackets from his Brooklyn social club on Sackett Street. He was one of the most powerful men in the Gambino family. And in December 1990, John Gotti himself was indicted on federal charges and taken off the street. Gotti set up a five-man ruling panel to run the family while he fought his case.

Junior Gotti was on that panel, and Bobby Boriello, as acting capo, held a position of real authority in a suddenly leaderless crime family. On the surface, this was the peak. Forty-seven years old, a made capo in America’s most powerful mob family, running his own crew. Gotti’s personal protector, elevated to one of the family’s operational leaders.

But something that had happened back in December 1985 was still sending deadly reverberations through New York’s organized crime world six years later. On December 16th, 1985, Gambino family boss Paul Castellano and his underboss Tommy Bilotti were shot dead outside Sparks Steakhouse at 210 East 46th Street in Midtown Manhattan. The hit was orchestrated by John Gotti. It was a brilliant, audacious power grab, but it was also unsanctioned—no vote, no Commission approval.

Gotti killed the boss and took the throne because he could. A Gambino informant named Dominic Lofaro later identified Bobby Boriello as one of the men involved in the Castellano operation. That detail mattered enormously. Because some of the other New York families, particularly the Lucchese family, had been closely aligned with Castellano.

And the Lucchese underboss, Anthony “Gaspipe” Casso, did not forget slights. He didn’t forget them, and he didn’t let them go. Casso had a list. Bobby Boriello was on it.

Anthony Salvatore Casso, born May 21st, 1942, in South Brooklyn, was arguably the most homicidal figure in the entire New York mob during the 1980s. He ordered murders with the casual frequency of other men ordering lunch. He was eventually charged with fifteen murders and pleaded guilty to racketeering, extortion, and murder while cooperating with the government. Prosecutors estimated his total body count at closer to one hundred.

Casso didn’t just want to win his wars. He wanted the other side to stop existing entirely. And Casso had a weapon no one else in the mafia had. Two of them.

Louis Eppolito and Steven Caracappa were active-duty New York City Police Department detectives. Eppolito was physically imposing, a former bodybuilder who had written a book about his own mob family connections. Caracappa was quieter, methodical, the kind of cop who spent his career inside major case squads tracking organized crime homicides. By any external measure, they were serious police officers.

They were also on Gaspipe Casso’s payroll at $4,000 per month. Starting around 1986, Eppolito and Caracappa began feeding Casso confidential NYPD intelligence. They pulled files. They identified informants.

They provided addresses and vehicle registrations. They facilitated multiple murders. Casso used them the way a military commander uses reconnaissance assets: find the target, confirm the location, let the shooters do the rest. By early 1991, Casso had decided Bobby Boriello had to go.

The trigger was an audio cassette. Eppolito and Caracappa had provided Casso with a recording in which Bobby Boriello could be heard repeatedly threatening Casso and his family. Whether that recording was made through NYPD surveillance or other means is disputed. But its contents were not in dispute.

Boriello had said things on that tape that Casso considered a death sentence. Before the shooters were dispatched, Eppolito took on a different role. He needed to confirm that the family had actually moved into their new home in Bensonhurst. So he drove to Bay 29th Street himself—in uniform—and knocked on the door.

Susan Boriello answered. She described what happened years later to the New York Post. A big detective pushed his jacket back to show his badge and his gun, asked if Bobby Boriello lived there. And when she said her husband wasn’t home, he said he’d be back and drove away.

He never came back. He had what he needed. The address was confirmed. The package was delivered to Casso.

The contract was placed with Lucchese captain Frank “Big Frank” Lino. Lasterino was a serious operator, described in court documents as fierce—a man who got things done without noise or fuss. He did not miss. April 13th, 1991.

Bobby had spent the afternoon at Aqueduct Racetrack. He came home in the evening. Susan was in the kitchen with their two-year-old son, Bobby Jr. Patrick, their eleven-year-old, was out at the movies.

Bobby stepped out of his car and walked toward the house. That’s when Lasterino stepped out of the shadows. Seven rounds—twice in the head, five times in the torso. Bobby Boriello went down beside his Lincoln Town Car and didn’t get up.

Susan heard yelling. She thought it was a neighbor arguing with Bobby about the driveway again—the same fight they’d had a dozen times before. She stepped outside. She saw her husband facedown.

She scooped up Bobby Jr. She called 911. She collapsed when the police told her he was dead. Gotti got the news in jail.

He was furious. He sent word that his son Stevie Boriello had permission to avenge Bobby’s death and had the full backing of the Gambino family. He also ordered family representatives to meet with the Genovese family leadership about Geritano, the man Bobby had shot at years earlier. Gotti wanted every loose end sealed.

But for fourteen years, nobody could tell Susan Boriello who actually pulled the trigger or why. That changed in March 2005. DEA and FBI agents arrested Louis Eppolito and Steven Caracappa in Las Vegas, where both men had retired and were living comfortable lives. The federal indictment against them was one of the most extraordinary documents in the history of American law enforcement: eight murders, two attempted murders, murder conspiracy, obstruction of justice, drug distribution, money laundering.

The two detectives who were supposed to protect New York City had spent years operating as contract killers for the Lucchese crime family. Bobby Boriello’s murder was named in the original indictment. Prosecutors described how Eppolito and Caracappa accepted the contract to locate Boriello and verified his address. Eventually, for trial purposes, prosecutors pared the indictment down, and the Boriello murder was not among the counts taken to verdict.

But the evidence of the mob cops’ role in setting up the hit was documented in federal court filings and confirmed by cooperating witnesses. Susan Boriello found out what happened in 2005, fourteen years after burying her husband. When she saw Eppolito’s picture in the newspaper, she recognized him immediately—the big detective who had knocked on her door, who had shown his badge and his gun, and asked if her husband was home. She called prosecutors.

Her father, who had been there the night Bobby was killed and had been interviewed by detectives, also recognized Caracappa as the cop who had questioned him at the crime scene. The men who came to investigate the murder of Bobby Boriello were the men who had helped arrange it. Eppolito and Caracappa were convicted on all counts in 2006. A federal judge sentenced both men to life in prison plus eighty years and fined each more than $4 million.

Anthony “Gaspipe” Casso, the man who ordered the hit, had turned federal informant in 1994. He eventually pleaded guilty to seventy crimes, including racketeering, extortion, and fifteen murders. A judge sentenced him to 455 years in prison. He died in custody on December 15th, 2020.

Frank Lasterino, the man who pulled the trigger seven times in that Bensonhurst driveway, eventually pleaded guilty to multiple murders and racketeering charges. Stevie Boriello, Bobby’s brother, remained active in the Gambino family in Brooklyn and Staten Island for years after his brother’s death. John Gotti was convicted on April 2nd, 1992—five murders, conspiracy to commit murder, racketeering, tax evasion, illegal gambling, extortion. He received a sentence of life in prison with no possibility of parole.

He was diagnosed with throat cancer in 1998 and died at the United States Medical Center for Federal Prisoners on June 10th, 2002. He never walked free.