Under the ovens at 27 Prince Street, customers lined up for slices of pizza the way they had since 1959. Above their heads, the small, plain shop front in the heart of New York’s Little Italy did its ordinary business, crowded with a counter, a few tables, and the smell of baking dough. Below their feet was a different room entirely: a low basement with whitewashed walls, a dirt floor, and old tree trunks propping up the ceiling. According to the testimony of a former mafia boss, that basement was where the real business happened.

Not pizza. Heroin. The shop was called Ray’s Pizza. The man who opened it was Ralph Cuomo, known as Rafi.

And one of the men who tried to do business with his crew was a Lucchese family gangster named Alonse D’Arco, who would one day become the highest-ranking member of his family to testify for the government. D’Arco’s first attempt at a heroin deal with that crew went wrong. His second went worse. The buyer turned out to be a federal drug agent, and D’Arco went to prison.

Years later, investigators would plant listening devices inside the same pizzeria, and federal agents would arrest its owner on charges of running a narcotics network from the shop where tourists bought their lunch. How did a neighborhood pizzeria, a place people lined up for, hide a drug operation for decades? And what finally pulled the business out of the basement and into a courtroom? The version most people know is a legend: the pizza parlor as a mob front, the kind of thing said about half the restaurants in Little Italy.

Most of those stories have nothing behind them. This one does. It comes from the account of D’Arco himself, from investigators who bugged the shop, and from an arrest at the counter decades after it opened. But it is narrower than the legend.

And in places, the record is thinner than the story people tell. Start with the man who owned it. First, the street itself. Prince Street ran through the old heart of Little Italy, a few blocks of tenements, social clubs, and churches where Italian immigrants had settled since the late 1800s.

Old St. Patrick’s Cathedral stood at the corner of Prince and Mott. By the 1950s, the neighborhood was shrinking as families moved out to Brooklyn, Queens, and the suburbs, but the social clubs stayed. So did the men who used them.

On a block like this, everyone knew which storefronts were just storefronts and which ones were something more. Almost nobody said it out loud. Ralph Cuomo had been to prison before he ever sold a slice. According to the book Mob Boss, written by journalists Jerry Capeci and Tom Robbins with D’Arco’s cooperation, Cuomo served a stretch for armed robbery.

When he came out in 1959, he opened a pizzeria on Prince Street and called it Ray. The name would become one of the most argued-over names in New York food. Over the following decades, dozens of pizzerias across the city called themselves Ray’s, Famous Ray’s, Original Ray’s, and every variation in between, and the owners fought over who had the right to it. Restaurant critics and tourists argued for years about which Ray’s was the first and which was the best.

The shop on Prince Street had a strong claim to being the original. To most New Yorkers, the name meant cheap, good pizza on Prince Street. According to Capeci and Robbins, it also meant something else. Cuomo was connected to the Lucchese crime family, one of New York’s five Mafia families, through a family of brothers named DePalma.

There were three of them: Joseph, known as Joe Beck; Charles, known as Charlie Brody; and Peter, known as Petey Beck. The book says Charlie DePalma married Ralph Cuomo’s sister. The DePalmas, it says, were the supply. The Lucchese family took its name from Gaetano Lucchese, known as Tommy, who ran it from the early 1950s until his death in 1967.

Under him, the family grew rich from the garment district, from trucking, and from the airports, especially what became Kennedy Airport. It was a family that liked to present itself as businesslike and quiet. Its leaders publicly forbade narcotics. Privately, crews connected to the family were deep in the trade, and the DePalma brothers, according to the book, were among them.

And according to that account, the business ran most nights in the basement directly under the ovens. Picture the arrangement. Upstairs, a counter, a cash register, a line of customers, the smell of baking dough. Downstairs, a low, unfinished room with a dirt floor where drugs and money could change hands out of sight, while the noise of an ordinary pizza shop covered everything above.

Next door, the book says, was a social club that served as headquarters for what became known as the Prince Street Crew. It is important to say exactly where this description comes from. It is drawn from Mob Boss, from D’Arco’s own account, and the authors’ reporting. No court ever issued a ruling describing the basement.

But other parts of the story are on the record, and they line up with it. The heroin business that ran through Little Italy in those decades was enormous and dangerous. In the 1950s and 1960s, much of the heroin reaching New York came through the old French Connection route, from Turkey through Marseille. Mafia families that publicly claimed to forbid drug dealing quietly profited from it through crews that kept their distance from the bosses.

Accounts of Ralph Cuomo’s career say he was convicted in a heroin case in 1969. The details of that case vary from source to source, including the amount of heroin involved. What is clear is that the arrest did not end the pizzeria. Ray’s stayed open, the line at the counter kept moving, and the basement, according to the book, kept doing its other job.

To understand how the operation finally cracked, follow Alonse D’Arco. D’Arco was born in Brooklyn in 1932 and spent his life in the Lucchese family. He was a soldier, later a captain, and he worked the businesses the family worked, including the ones it pretended not to touch. He ran restaurants, he ran crews, and at one point, according to his own account and Mob Boss, he tried to go into the heroin trade with the men around Ray.

The first deal, the book says, was a failure. The heroin his side received was rejected by customers as worthless. The second deal was a disaster of a different kind. The buyer D’Arco’s side was dealing with turned out to be an undercover federal drug agent.

D’Arco was convicted in a heroin case in 1983. According to the historian Selwyn Raab, he received a four-year sentence and was paroled in 1986. The detail about the undercover buyer comes from the book, and the exact court records of that case have not been located. Prison did not end D’Arco’s career in the family.

It advanced it. After his parole in 1986, he returned to the Lucchese family and kept rising. He became a captain. And in 1991, when the family’s boss, Vic Amuso, and his underboss, Anthony Casso, went into hiding to avoid arrest, Amuso chose D’Arco to run the family day-to-day as acting boss.

The man whose heroin deal had once collapsed in front of a federal agent was now at the top of the organization the DePalmas belonged to. Here is the part of the story that did not make the pizzeria famous but made it dangerous. The men who sold heroin out of Little Italy did not only sell it to strangers. According to Mob Boss, D’Arco discovered that his own children were using heroin, and he turned against the DePalmas, the family he associated with the drug.

That detail matters because it explains what the business really was. It was not a clever trick behind a pizza counter. It was a supply line that reached into the same streets and the same families as the men who ran it. This is the trap built into every Mafia drug operation.

The families claimed a rule against narcotics because drugs brought long prison sentences, and long prison sentences made men talk. But the money was too large to give up. So the business was pushed down into crews, into back rooms, into basements where the bosses could pretend not to know. The rule did not stop the drugs.

It only decided who would take the blame. By the late 1980s, investigators were paying attention to Prince Street. According to Capeci and Robbins, the Manhattan District Attorney’s Office planted listening devices in the pizzeria during an investigation in 1989. Other accounts say the office bugged the shop more than once.

Customers who came in for a slice had no idea that at times the shop itself was being recorded. Then the story of the man who knew the most changed direction. In September 1991, Alonse D’Arco was the acting boss of the Lucchese family. The family’s official leaders, Vic Amuso and Anthony Casso, were in hiding and running the family through a campaign of fear and murder.

D’Arco became convinced that he was about to be killed by his own family. He walked into an FBI office and began cooperating with the government. According to his own account, the moment came at a meeting at the Kimberly Hotel in Manhattan. He noticed that one of the men in the room was carrying a gun under his clothes.

At a meeting where nobody should have needed one, D’Arco believed the meeting was a setup for his own murder. He left, and within days he was talking to the FBI. He became one of the most important Mafia witnesses of his era, the highest-ranking member of the Lucchese family to turn. He testified in trial after trial.

Among the men he helped convict was Vincent Gigante, the boss of the Genovese family, who for years had pretended to be mentally ill to avoid prosecution. D’Arco’s testimony helped prove that the man who wandered Greenwich Village in a bathrobe was in fact running one of the most powerful crime families in the country. And years later, he told his story in detail to the authors of Mob Boss, including the story of the basement on Prince Street. Ask the question again now, with the people laid out.

How did a pizza shop hide a heroin business for so long? Because it did not look like it was hiding anything. It sold real pizza to real customers every day. The business underneath it depended on the most ordinary thing in New York: a busy little shop that nobody thought twice about.

And the business did not end with D’Arco’s defection. That is worth pausing on. By the early 1990s, the most important witness against the Lucchese family had personal knowledge of the crew around Ray’s. Investigators had been inside the shop with recording devices.

And yet, the counter stayed open, the oven stayed hot, and according to what came next, the business underneath kept going. A pizzeria is hard to shut down. It has a lease, a license, employees, and customers. Unless someone is caught in the act, it is just a pizzeria.

In October 1995, federal drug agents arrested Ralph Cuomo. According to published accounts, he was charged with running a narcotics network from the premises of Ray’s. He pleaded guilty and was sentenced to four years in prison. Some accounts placed the start of his prison term in 1998.

That was more than thirty-five years after he had opened the shop. Ray’s was not the only pizzeria in New York tied to heroin. In fact, it was not even the biggest such case. In the late 1970s and early 1980s, the FBI investigated a network of Sicilian Mafia figures who used pizzerias across the United States as fronts and meeting places in a heroin pipeline from Sicily.

The case became known as the Pizza Connection. Investigators estimated that the network moved heroin worth about $1. 65 billion. The New York base of that operation was not a pizzeria at all.

It was a bakery on Knickerbocker Avenue in Brooklyn, run by a man named Salvatore Catalano. FBI agents watched it on video from the attic of a house across the street. Over the course of the investigation, agents ran 93 wiretaps. Coded calls to pay phones in Queens and on Long Island were traced all the way to Brazil and toward a former boss of the Sicilian Mafia named Gaetano Badalamenti.

The investigation was led on the government side by the United States Attorney in Manhattan, Rudolph Giuliani, and by prosecutors including Lewis Freeh, who would later become director of the FBI. Their most important witness was Tommaso Buscetta, a Sicilian mobster who had broken with the Mafia after many of his relatives were murdered and who explained to an American jury how the Sicilian organization worked from the inside. The money was as revealing as the drugs. Investigators followed millions of dollars in small bills, cash that had to be turned into something a bank would accept.

Some of it was carried into New York brokerage houses in bags and boxes and deposited in accounts that moved it overseas. A pizzeria made that kind of cash look natural. A shop that takes in small bills all day can explain a great deal of money, as long as nobody counts the slices. One of the pizzeria owners in the network, Pietro Alfano, ran a pizza shop in the small town of Oregon, Illinois.

In April 1984, he flew to Madrid. On April 8, 1984, Spanish police arrested him there, along with Badalamenti. The next day, agents arrested dozens of suspects across the United States. The trial that followed was one of the longest criminal trials in American history.

It began on September 30, 1985, and ended on March 2, 1987. Eighteen defendants were convicted. Badalamenti was sentenced to 45 years. So was Catalano.

During the trial, one defendant, Gaetano Mazzara, was murdered, and Pietro Alfano was shot on a street in Greenwich Village. He survived. The Pizza Connection was about a network that stretched from Sicily to small-town America. Ray’s was about one shop on one street.

But both cases rested on the same idea: a pizzeria is a business where cash comes in all day, where strangers come and go, and where nobody asks questions. And there was a third case that made the confusion worse. In September 1994, federal agents and New York police broke up a Sicilian drug ring based at a different pizzeria, called Famous Ray’s Original Pizza on Third Avenue. Twenty-nine people were arrested in the United States and 74 in Italy.

That case had nothing to do with Prince Street. But to anyone reading the headlines, it sounded like the same place. On Prince Street, the end came slowly. Ralph Cuomo died in 2008.

D’Arco, the witness, outlived him. He died in 2019, more than 25 years after he had first walked away from his family and into the protection of the government. Three years later, in 2011, the original Ray’s Pizza at 27 Prince Street closed. Reports at the time said the building was sold for about $5.

9 million. The counter where people had bought slices for more than 50 years was gone, and so was the basement under the ovens. Here is the answer to the question, and it is narrower than the legend and colder than the official record. Ray’s Pizza did not hide a heroin business behind a clever disguise.

It hid it behind the plainest thing in New York: real pizza, real customers, a real line at the counter. According to the account of the man who knew the crew best, the drugs moved below the floor while the shop above did exactly what it appeared to do. The legend says the pizza was a front. The record suggests something more uncomfortable.

The pizza was real. The business underneath it was real, too. And for most of 36 years, nobody upstairs had any reason to know the difference. The people in line were never the audience for the disguise.

The disguise was for the police. And for a long time, it worked. That is the reversal at the heart of this story. The man whose account put the basement on the record was not a detective or a prosecutor.

He was a mobster who had tried to buy heroin from that crew himself, whose deal ended with a federal agent, and who later learned that the drug had reached his own family. The business that was built to stay invisible was exposed by one of its own customers.